phenyln.

Brit.

/ˈfiːnʌɪl/,

/ˈfɛnʌɪl/,

/ˈfiːn(ɪ)l/,

/ˈfɛn(ɪ)l/, U.S.

/ˈfɛn(ə)l/,

/ˈfin(ə)l/

Forms: 1800s phenyle, 1800s– phenyl.

Origin: Formed within English, by derivation; modelled on a French lexical item. Etymons: phene n., -yl suffix.

Etymology: < phene n. + -yl suffix, after French phényle (A. Laurent 1841, in Ann. de Chim. et de Physique 3 195); compare earlier chlorophényle (A. Laurent 1837, in Ann. de Chim. et de Physique 66 315).

Chemistry.

The hydrocarbon radical present in phenol and other derivatives of benzene; the group or radical —C₆H₅, derived from benzene by the loss of one hydrogen atom. Cf. benzyl n. at benzo- comb. form 1.

ΘΚΠ

the world > matter > chemistry > organic chemistry > organic radicals > [noun] > monovalent radicals

phenyl1849

acetyl1864

tetrahydrofurfuryl1928

ribityl1935

hydroxymethyl1937

tosyl1938

phosphatidyl1941

1849 Q. Jrnl. Chem. Soc. 1 247 The presence..of carbolic acid in the tar has been confirmed by Laurent, who has analysed and described it under the name of hydrated oxide of phenyle (phenole, C₁₂H₅O, HO).

1850 C. G. B. Daubeny Introd. Atomic Theory (ed. 2) viii. 238 A compound radical called phenyle, a name given by Laurent to the supposed base of the volatile liquid, obtained by compressing oil gas, which was first examined by Faraday, and denominated by him benzole.

1857 W. A. Miller Elements Chem. III. 563 Compounds..have been formed, which appear to contain oxide of phenyl in combination with acids.

1880 E. Cleminshaw tr. C. A. Wurtz Atomic Theory 220 Phenyl..wants but one atom of hydrogen to become benzene.

1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) xxi. 390 Aniline..may be regarded..as ammonia in which a hydrogen atom is replaced by phenyl.

1992 New Scientist 12 Dec. 16/1 R is a hydrocarbon group, such as phenyl or methyl.

Compounds

C1.

a. General attributive and appositive, esp. in phenyl group, phenyl radical.

ΚΠ

1850 Philos. Trans. (Royal Soc.) 140 127 We may hope moreover to form the imidogen- and nitrile-terms of these radicals, in the phenyl-series for instance.

1866 W. Odling Lect. Animal Chem. 123 This relationship of salicic and phenyl compounds.

1869 Proc. Royal Soc. 18 126 In the one case substitution occurs in the phenyl group, in the other in the lateral group.

1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) xxvi. 484 The compound first formed..is thus transformed into mono-sodium salicylate by the exchange of the ·CO·ONa group with the ortho-hydrogen atom of the phenyl radical.

1947 Nucleonics Dec. 51/1 The classical approach of Knoop, in which entire molecules (fatty acids) were labeled with phenyl groups.

1991 J. M. G. Cowie Polymers (BNC) (ed. 2) 297 Examination of the polymer structures suggests that the relaxation in the glass could involve libration of the phenyl ring.

1991 D. T. Sawyer Oxygen Chem. vii. 179 The trace amounts of trapped phenyl radical..are consistent with the reaction sequence.

b. Forming the systematic, semi-systematic, or trivial names of organic compounds containing one or more phenyl groups, as phenyl carbonate, phenyl cyanide, phenyl phosphate.Recorded earliest in phenyl alcohol n., phenylamine n. at Compounds 2.Also with locant.In systematic substitution nomenclature phenyl is now normally written as one word with the item to which it is prefixed. Two-word names are used chiefly in functional class nomenclature, where the second (or final) word is a class term, as of an acid or acid derivative, oxygen or carbonyl compound, halide or pseudohalide, etc. In later systematic use, therefore, there is usually a semantic difference between the two forms, as between phenyl acetate (the phenyl ester of acetic acid) and phenylacetate (a salt or ester of phenylacetic acid), although this rule of chemical nomenclature is not always applied consistently.

ΚΠ

1869 G. Fownes Man. Elem. Chem. 650 Phenyl hydrogen carbonate, or acid phenyl carbonate..is identical with salicyclic acid.

1869 G. Fownes Man. Elem. Chem. 683 Sulphobenzoic acid..is produced by the action of sulphuric oxide on benzoic acid; also..by that of fuming sulphuric acid on benzonitrile or phenyl cyanide.

1872 H. Watts Dict. Chem. VI. 918 Phenyl phosphates.

1924 J. B. Cohen Pract. Org. Chem. (ed. 3) 255 Repeat the same reaction with phenol, taking 1 gram of each substance, and separate the solid phenyl benzoate.

1955 B. C. L. Kemp Elem. Org. Chem. (new ed.) xxiv. 305 Benzonitrile or phenyl cyanide, is best prepared from aniline by means of diazotization followed by the Sandmeyer Reaction.

1977 J. March Adv. Org. Chem. (ed. 2) x. 428 α-Phenyl thioaldehydes and thioketones can be gem-dialkylated by the following procedure.

1999 Proc. National Acad. Sci. U.S.A. 96 11125/2 Phenyl phosphate, a phosphotyrosine mimic, competed weakly at millimolar concentrations.

C2.

phenylacetamide n. = acetanilide n.

ΘΚΠ

the world > matter > chemistry > organic chemistry > organic compounds > [noun] > aniline > derivatives > anilides

phenylamide1851

phenylacetamide1863

1863 Proc. Royal Soc. 1862–3 12 640 This substance..may be more readily prepared by a similar treatment of other less difficultly obtainable phenylamides, such as phenylacetamide.

1955 B. C. L. Kemp Elem. Org. Chem. (new ed.) x. 157 Formation of phenylacetamide (acetanilide) on addition of acetyl chloride to aniline—vigorous reaction.

1998 Jrnl. Molecular Biol. 284 463 Studies have shown that the enzyme [sc. penicillin acylase] is specific for hydrolysis of phenylacetamide derivatives.

phenylacetate n. (a) a salt or ester of phenylacetic acid; (b) (usually in form phenyl acetate) the phenyl ester of acetic acid, a colourless, fragrant liquid, CH₃COOC₆H₅, used as a solvent.

ΚΠ

1873 F. W. Clarke Constants of Nature I. 168 (table) Methyl phenylacetate.

1915 Proc. National Acad. Sci. U.S.A. 1 141 Glycine, glutamic acid, and aspartic acid exerted hydrolytic actions on..phenyl acetate, ethyl butyrate, [etc.].

1965 J. R. Dyer Applic. Absorption Spectroscopy Org. Compounds iii. 43 The position of absorption of normal aliphatic esters (methyl phenylacetate.., 5.73 μ, 1745 cm⁻¹).

1991 D. T. Sawyer Oxygen Chem. vii. 172 This conclusion is supported by the products that are observed in the gas-phase reaction of O₂⁻· with phenyl acetate and phenyl benzoate.

phenylacetic adj. [quot. 1870 refers to a paper apparently read in 1869 to German learned society by a Dr Zinke, but this has not been traced] phenylacetic acid, a white, crystalline acid with a sweet odour, C₆H₅CH₂COOH, used in chemical synthesis and perfume manufacture.

ΚΠ

1870 Nature 20 Jan. 322/1 He [sc. Zinke] has obtained phenyl-acetic acid from Monochloroacetic acid.

1885 E. Klein Micro-org. 73 Antiseptics, such as carbolic acid..strong solutions of phenyl-propionic acid and phenyl-acetic acid.

1975 F. Kennett Hist. Perfume ix. 184 Phenylacetic acid..is used to add a trace of civet, or honey, to a perfume.

phenylacetylene n. an oily liquid, C₆H₅C≡CH, made into polymers esp. in the form of thin films.

ΚΠ

1870 Nature 19 May 55/2 We also find here the discovery of the first acetylene of the aromatic series, by Glaser in acetenylbenzol or phenylacetylene.

1940 Jrnl. Amer. Chem. Soc. 62 48/1 Several attempts to add acetic acid to phenylacetylene under various conditions failed to give this product.

1993 Sci. News 10 Apr. 239/2 To synthesize the new molecule, the team used a carbon-based building block called phenylacetylene.

† phenyl alcohol n. Obsolete = phenol n. 1.

ΚΠ

1850 A. W. Hofmann in Philos. Trans. (Royal Soc.) 140 98 I had hoped that this conversion might be effected by the action of phenyl-alcohol on aniline.

1871 Manufacturer & Builder June 137/3 Phenyl alcohol is a creosote, made from coal-tar, as the ordinary creosote is made from wood-tar.

phenylamide n. a derivative of aniline, an anilide; (formerly also) †aniline (obsolete).

ΘΚΠ

the world > matter > chemistry > organic chemistry > organic compounds > [noun] > aniline > derivatives > anilides

phenylamide1851

phenylacetamide1863

1851 W. Gregory in Monthly Jrnl. Med. Sci. June 576 Phenylamide (Aniline) = N,HHPh.

1863 H. Watts Dict. Chem. I. 295 Anilides, syn[onym] of Phenylamides.

1868 M. Reimann On Aniline & its Derivatives 13 This mode of producing aniline led the discoverer to consider it an amide of the organic radical phenyl..and to call it phenylamide.

1937 Chem. Rev. 20 440 Kraus and Bien..state that it is impossible to prepare disodium phenylamide, C₆H₅NNa₂, by treating monosodium anilide with sodium amide in liquid ammonia.

1993 Plant Dis. 77 1242/1 The phenylamides, metalaxyl, ofurace, and oxadixyl, significantly inhibited growth of Picryptogea.

phenylamine n. a compound with an amino group bonded directly to a benzene ring; spec. aniline.

ΘΚΠ

the world > matter > chemistry > organic chemistry > organic compounds > [noun] > aniline

crystallin1833

aniline1850

phenylamine1850

kyanol1855

phenylia1857

1850 Philos. Trans. (Royal Soc.) 140 112 (table) Phenylamine.

1880 Jrnl. Soc. Arts 16 Apr. 442/1 The earliest violets obtained by artificial means were those produced by the action of pure aniline, or phenylamine, on roseine.

1936 S. A. Waksman Humus ii. 17 Other substances, however, like phenylamines, naphthylamines, and alkaloids, exert a decided toxic effect upon plant growth.

1995 School Sci. Rev. June 65/2 Examination of the resonance forms explains the greater reactivity of phenylamine towards electrophiles than benzene.

phenylarsonic adj. phenylarsonic acid, a toxic, colourless, crystalline acid, C₆H₅AsO(OH)₂, derivatives of which are used as trypanocides; a derivative of this.

ΘΚΠ

the world > matter > chemistry > organic chemistry > organic acids > [noun] > phenolic acids, named

benzoic acid1791

oil of spiraea1842

toluic acid1857

itatartaric acid1872

aspirin1899

phenylarsonic acid1905

tar acid1909

pteroic acid1946

1905 Amer. Chem. Jrnl. 33 104 The reduction takes place with equal ease in the aromatic series, monophenyl arsine..being obtained from phenyl arsonic acid.

1937 Thorpe's Dict. Appl. Chem. (ed. 4) I. 488/1 The introduction of an amino group into the para-position in phenylarsonic acid decreases its toxicity and increases its trypanocidal activity.

1959 Times 7 Dec. (Agric. Suppl.) p. vii/1 So far as arsenicals are concerned, two phenylarsonic acids have received attention [as growth stimulants for poultry].

1991 Biochemistry 30 3739 The complex with hapten has been modeled by docking the small-molecule crystal structure of phenylarsonic acid into the structure of the native Fab.

phenyl blue n. a dark blue dye which is a phenylimide derivative of a quinone.

ΚΠ

1894 Lancet 29 Sept. 734/2 The stains easily reducible by Löffler's bacilli are phenyl blue, iodine green, malachite green, and one or two others.

1946 Jrnl. Aesthetics & Art Crit. 4 211 (table) Phenyl Blue.

1999 Re: Back to the Bladder in alt.fan.cecil-adams (Usenet newsgroup) 26 Oct. If you're asking about phenyl blue, or phenophthalene [sic], a fun chemical with which any first year chemistry student is familiar, then the answer is ASAP.

† phenyl brown n. Obsolete = phenicin n.

ΘΚΠ

the world > life > biology > substance > pigment > [noun] > plant pigments > brown

phyllophaein1858

fucoxanthin1873

phenyl brown1875

phaeophyll1890

the world > matter > chemistry > organic chemistry > organic compounds > [noun] > other organic compounds > others

fat1539

nitromannite1857

friction-powder1864

nitramidin1866

nitroform1866

phenyl brown1875

ketide1907

tetryl1909

cyclonite1923

pentryl1933

the world > matter > colour > named colours > brown or brownness > colouring matter > [noun] > stains

ferretto1662

walnut1709

Venetian brownc1791

phenyl brown1875

Bismarck brown1885

vesuvin1885

walnut-juice1912

1875 H. Watts Dict. Chem.: 2nd Suppl. 945 The explosive character of the phenyl-brown is..due to the dinitrophenol.

1891 R. Routledge Discov. & Inventions 19th Cent. (ed. 8) 658 Colours derived from Phenol. Browns. Picrate of ammonia. Isopurpurate of potash. Phenyl brown, phenicienne.

phenyl ether n. (a) an ether in which one of the groups attached to the oxygen atom is phenyl; (formerly) an ester in which a phenyl group replaces the acid hydrogen atom; (b) diphenyl ether, (C₆H₅)₂O, a liquid used in organic synthesis.

ΚΠ

1890 J. Cagney tr. R. von Jaksch Clin. Diagnosis vii. 286 The exhibition of salol (phenyl-æther of salicylic acid [Ger. Salicylphenoläther]).

1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) xxiv. 437 Phenyl ether, diphenyl oxide, (C₆H₅)₂O, is formed when phenol is heated with ZnCl₂ or AlCl₃.

1939 Jrnl. Amer. Chem. Soc. 61 109/2 Phenyl ether was not metalated by triphenylmethylsodium.

1960 F. G. Mann & B. C. Saunders Pract. Org. Chem. (ed. 4) ii. 186 Phenetole (ethyl phenyl ether) is the main product.

1986 Arch. Microbiol. 144 55 [A] bacterium is described which cleaves the phenylether bonds of methoxylated aromatic substrates to give the corresponding hydroxy aromatic derivatives and mixed volatile fatty acids.

phenylethylamine n. an aminoethyl derivative of benzene, spec.(in full 2-phenylethylamine) a liquid, C₆H₅CH₂CHNH₂, which occurs naturally in the brain as a neuromodulator.

ΚΠ

1875 Jrnl. Chem. Soc. 28 1025 Phenylethylamine, C₆H₅·C₂H₄·NH₂, is formed by the action of nascent hydrogen on benzyl cyanide.

1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) liv. 811 The following synthetical methods have been adopted:... Phenylethylamine from benzylcyanide is benzoylated and then nitrated.

1964 N. Weiner in G. Pincus et al. Hormones IV. viii. 435 It had been assumed that phenylethylamines..exerted their sympathomimetic actions by a direct mechanism identical to that of epinephrine and norepinephrine.

1995 Minnesota Monthly Feb. 81/2 Scientists..thought they'd discovered the secret to chocolate's appeal: that the combination of caffeine and a chemical called phenylethylamine (thought to induce ‘feelings of falling in love’) had a serious embrace on some people's constitutions.

phenylglycol n. a low-melting solid or oily liquid, C₆H₅CH(OH)CH₂OH, also called styrene glycol.

ΚΠ

1862 A. W. Hofmann in Proc. Royal Soc. 11 524 The action of nitrous acid upon aniline furnishing phenyl-alcohol,..there is some hope of meeting, in the analogous decomposition of phenylene-diamine with the diatomic phenylene-alcohol (phenyl-glycol).

1926 Jrnl. Amer. Chem. Soc. 48 1070 Phenylglycine is tasteless and phenylglycol is bitter.

1990 Exper. Pathol. 39 195 Measurement of the concentration of the produced phenylglycol (1-phenyl-1,2-ethandiol)..is described.

phenylhydrazine n. a colourless liquid, C₆H₅NHNH₂, used as a reagent and in organic synthesis.

ΚΠ

1883 Science 20 July 85/1 The action of phenylhydrazine upon ketones seems to be analogous to that of hydroxylamine.

1949 R. Livingston in J. Franck & W. E. Loomis Photosynthesis in Plants vii. 183 If oxygen is present the photosensitized auto-oxidation of phenylhydrazine occurs in preference to the oxidation by methyl red.

1991 D. T. Sawyer Oxygen Chem. vii. 179 The reaction of O₂⁻· with methylhydrazine is analogous to that for phenylhydrazine with methane the major product.

phenylhydrazone n. [after German Phenylhydrazon (O. Rudolph 1888, in Ann. der Chem. u. Pharm. 248 99)] any of a class of compounds formed by condensation of an aldehyde or ketone with phenylhydrazine, which are typically crystalline solids and are used to characterize the parent aldehyde or ketone.

ΘΚΠ

the world > matter > chemistry > organic chemistry > aldehydes or alkanals > [noun] > aldehyde derivatives

acetal1838

hydramide1865

phenylhydrazone1888

hemi-acetal1893

formal1900

1888 Jrnl. Chem. Soc. 54 934 Mannose..is obtained by dissolving the above phenylhydrazone in four parts of hydrochloric acid..cooled with ice and salt.

1966 McGraw-Hill Encycl. Sci. & Technol. (rev. ed.) VII. 62/2 When the starting material is the phenylhydrazone of acetone, the product is 2-methylindole.

1981 J. W. Buttle et al. Chem. (ed. 4) xxiii. 519 Phenylhydrazine forms phenylhydrazones by condensation, but these are not the ultimate products.

phenylimide n. (also N-phenylimide) an imide containing the divalent group C₆H₅N^/_\\ or a substituted form of it.

ΚΠ

1866 H. Watts Dict. Chem. IV. 419 Phenylimides or Anils, tertiary monamides..which..may be regarded as aniline in which 2 atoms of H[ydrogen] are replaced by a diatomic radicle: e.g. C₆H₅·(C₄H₄O₂)″·N, phenyl-succinimide.

1908 Jrnl. Amer. Chem. Soc. 30 1890 Aniline is practically without action on the [phthal-m-nitrophenylamidic] acid after 35 minutes, at 65°, in presence of benzene, but at 100°..about 31 per cent. of the phenylimide is produced.

1991 Pesticide Biochem. & Physiol. 40 135/1 These facts suggest that the mode of PPO [protoporphyrinogen oxidase] inhibition by N-phenylimide may be different from that of diphenylether herbicides.

2003 Amer. Jrnl. Industr. Med. 44 627 Exposure to nitro-derivatives and phenylimides among fungicides, hydrocarbon derivatives and insecticide oils among insecticides, and the herbicide amides.

phenylpropiolic adj. phenylpropiolic acid, a colourless, crystalline acid, C₆H₅C≡CCOOH, related to phenylacetylene.

ΚΠ

1872 H. Watts Dict. Chem. VI. 962 Phenyl-propiolic Acid. C₉H₆O₂..related to phenyl-propionic acid in the same manner as stearolic to stearic acid... It crystallises from water or from carbon bisulphide in long white silky needles melting at 136°–137°.

1938 Chem. Rev. 23 220 Similar reactions are those between phenyl azide and acetylene, and between hydrazoic acid and phenylpropiolic acid.

1999 Jrnl. Org. Chem. 64 6896/1 Aqueous bromination of phenylpropiolic acid afforded 11–18% of 1-bromophenyl acetylene among other products.

phenylsulphuric adj. now rare = phenolsulphuric adj. at phenol n. Compounds 3.

ΚΠ

1868 H. Watts Dict. Chem. V. 627 Phenylsulphuric acid may be obtained by evaporation in a vacuum over oil of vitriol, in slender needle-shaped crystals.

1933 S. W. Cole Pract. Physiol. Chem. (ed. 9) xiii. 295 (caption) Phenylsulphuric acid.

phenylthiocarbamide n. a white, crystalline solid, NH₂CSNHC₆H₅, which has a bitter taste to people possessing a certain dominant gene and is tasteless to those lacking it.

ΘΚΠ

the world > matter > chemistry > organic chemistry > substances from animals or humans > urea > [noun] > derivatives > phenylthiourea

phenylthiocarbamide1889

phenylthiourea1896

1879 Jrnl. Chem. Soc. 36 804 Mono- and di-phenylthiocarbamide..are soluble in caustic soda or potash.]

1889 Science 29 Mar. 234/1 The highly refracting liquid phenyl thiocarbamide appears to be specially suitable for experiments on this subject [sc. mapping electrical lines of force].

1932 Proc. National Acad. Sci. U.S.A. 18 121 The heredity differences between people in their taste perceptions of phenyl thio carbamide are not so simple as the preceding paragraph might lead one to suppose.

1995 Guardian 27 Apr. (OnLine section) 12/2 Bartoshuk's experiments..involve testing people for taste blindness to PTC (phenylthiocarbamide) and its chemical relative PROP (6-n-propylthiouracil).

phenylthiourea n. = phenylthiocarbamide n.

ΘΚΠ

the world > matter > chemistry > organic chemistry > substances from animals or humans > urea > [noun] > derivatives > phenylthiourea

phenylthiocarbamide1889

phenylthiourea1896

1896 Jrnl. Chem. Soc. 69 857 If dilute hydrochloric acid be now added to the clear solution, a white solid at once separates, which..forms white prisms..consisting of phenylthiourea.

1959 Listener 3 Dec. 968/2 People who can taste phenylthiourea seem to be slightly more liable to get one form of thyroid disease and slightly less liable to get another.

2000 Proc. National Acad. Sci. U.S.A. 97 2618/2 Treatment of E[leutherodactylus] martinicensis with the goitrogen phenylthiourea (PTU) inhibited tail resorption.

phenylurea n. a crystalline solid, C₆H₅NHCONH, many of whose derivatives are used as pesticides and herbicides.

ΘΚΠ

the world > matter > chemistry > organic chemistry > substances from animals or humans > urea > [noun] > derivatives

uramil1839

dialuramide1857

phenylurea1857

ureide1857

violantin1866

violuric acid1866

biuret1869

1857 W. A. Miller Elements Chem. III. 616 Phenyl-urea (carbanilamide).

1941 Q. Rev. Biol. 16 183/2 Narcotics such as..phenylurea, propionitrile, and valeronitrile inhibit reversibly the respiration of erythrocytes.

1999 New Scientist 23 Jan. 21/1 Isoproturon, the most widely used phenylurea herbicide, used by wheat and barley farmers to control blackgrass, may also pose a hazard to fish.

Derivatives

† phenylous adj. Obsolete phenylous acid = phenol n. 1.

ΘΚΠ

the world > matter > chemistry > organic chemistry > hydrocarbons > [noun] > benzene derivatives > phenols

carbolic acid1835

phenol1849

phenic acid1852

phenylous acid1852

phenylic acid1853

phenol1857

phlorol1868

THC1968

1852 Chem. Gaz. 10 136 St. Evre suspected a connexion between his acid and phenic acid (phenole, phenylous acid), C¹²H⁶O².

1873 Amer. Cycl. III. 768/1 Carbolic acid (synonymes, carbon oil acid..phenylous acid..), a chemical substance now largely employed in medicine and the arts.

This entry has been updated (OED Third Edition, December 2005; most recently modified version published online March 2022).

单词	phenyl
释义	phenyln. Brit. /ˈfiːnʌɪl/, /ˈfɛnʌɪl/, /ˈfiːn(ɪ)l/, /ˈfɛn(ɪ)l/, U.S. /ˈfɛn(ə)l/, /ˈfin(ə)l/ Forms: 1800s phenyle, 1800s– phenyl. Origin: Formed within English, by derivation; modelled on a French lexical item. Etymons: phene n., -yl suffix. Etymology: < phene n. + -yl suffix, after French phényle (A. Laurent 1841, in Ann. de Chim. et de Physique 3 195); compare earlier chlorophényle (A. Laurent 1837, in Ann. de Chim. et de Physique 66 315). Chemistry. The hydrocarbon radical present in phenol and other derivatives of benzene; the group or radical —C₆H₅, derived from benzene by the loss of one hydrogen atom. Cf. benzyl n. at benzo- comb. form 1. ΘΚΠ the world > matter > chemistry > organic chemistry > organic radicals > [noun] > monovalent radicals phenyl1849 acetyl1864 tetrahydrofurfuryl1928 ribityl1935 hydroxymethyl1937 tosyl1938 phosphatidyl1941 1849 Q. Jrnl. Chem. Soc. 1 247 The presence..of carbolic acid in the tar has been confirmed by Laurent, who has analysed and described it under the name of hydrated oxide of phenyle (phenole, C₁₂H₅O, HO). 1850 C. G. B. Daubeny Introd. Atomic Theory (ed. 2) viii. 238 A compound radical called phenyle, a name given by Laurent to the supposed base of the volatile liquid, obtained by compressing oil gas, which was first examined by Faraday, and denominated by him benzole. 1857 W. A. Miller Elements Chem. III. 563 Compounds..have been formed, which appear to contain oxide of phenyl in combination with acids. 1880 E. Cleminshaw tr. C. A. Wurtz Atomic Theory 220 Phenyl..wants but one atom of hydrogen to become benzene. 1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) xxi. 390 Aniline..may be regarded..as ammonia in which a hydrogen atom is replaced by phenyl. 1992 New Scientist 12 Dec. 16/1 R is a hydrocarbon group, such as phenyl or methyl. Compounds C1. a. General attributive and appositive, esp. in phenyl group, phenyl radical. ΚΠ 1850 Philos. Trans. (Royal Soc.) 140 127 We may hope moreover to form the imidogen- and nitrile-terms of these radicals, in the phenyl-series for instance. 1866 W. Odling Lect. Animal Chem. 123 This relationship of salicic and phenyl compounds. 1869 Proc. Royal Soc. 18 126 In the one case substitution occurs in the phenyl group, in the other in the lateral group. 1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) xxvi. 484 The compound first formed..is thus transformed into mono-sodium salicylate by the exchange of the ·CO·ONa group with the ortho-hydrogen atom of the phenyl radical. 1947 Nucleonics Dec. 51/1 The classical approach of Knoop, in which entire molecules (fatty acids) were labeled with phenyl groups. 1991 J. M. G. Cowie Polymers (BNC) (ed. 2) 297 Examination of the polymer structures suggests that the relaxation in the glass could involve libration of the phenyl ring. 1991 D. T. Sawyer Oxygen Chem. vii. 179 The trace amounts of trapped phenyl radical..are consistent with the reaction sequence. b. Forming the systematic, semi-systematic, or trivial names of organic compounds containing one or more phenyl groups, as phenyl carbonate, phenyl cyanide, phenyl phosphate.Recorded earliest in phenyl alcohol n., phenylamine n. at Compounds 2.Also with locant.In systematic substitution nomenclature phenyl is now normally written as one word with the item to which it is prefixed. Two-word names are used chiefly in functional class nomenclature, where the second (or final) word is a class term, as of an acid or acid derivative, oxygen or carbonyl compound, halide or pseudohalide, etc. In later systematic use, therefore, there is usually a semantic difference between the two forms, as between phenyl acetate (the phenyl ester of acetic acid) and phenylacetate (a salt or ester of phenylacetic acid), although this rule of chemical nomenclature is not always applied consistently. ΚΠ 1869 G. Fownes Man. Elem. Chem. 650 Phenyl hydrogen carbonate, or acid phenyl carbonate..is identical with salicyclic acid. 1869 G. Fownes Man. Elem. Chem. 683 Sulphobenzoic acid..is produced by the action of sulphuric oxide on benzoic acid; also..by that of fuming sulphuric acid on benzonitrile or phenyl cyanide. 1872 H. Watts Dict. Chem. VI. 918 Phenyl phosphates. 1924 J. B. Cohen Pract. Org. Chem. (ed. 3) 255 Repeat the same reaction with phenol, taking 1 gram of each substance, and separate the solid phenyl benzoate. 1955 B. C. L. Kemp Elem. Org. Chem. (new ed.) xxiv. 305 Benzonitrile or phenyl cyanide, is best prepared from aniline by means of diazotization followed by the Sandmeyer Reaction. 1977 J. March Adv. Org. Chem. (ed. 2) x. 428 α-Phenyl thioaldehydes and thioketones can be gem-dialkylated by the following procedure. 1999 Proc. National Acad. Sci. U.S.A. 96 11125/2 Phenyl phosphate, a phosphotyrosine mimic, competed weakly at millimolar concentrations. C2. phenylacetamide n. = acetanilide n. ΘΚΠ the world > matter > chemistry > organic chemistry > organic compounds > [noun] > aniline > derivatives > anilides phenylamide1851 phenylacetamide1863 1863 Proc. Royal Soc. 1862–3 12 640 This substance..may be more readily prepared by a similar treatment of other less difficultly obtainable phenylamides, such as phenylacetamide. 1955 B. C. L. Kemp Elem. Org. Chem. (new ed.) x. 157 Formation of phenylacetamide (acetanilide) on addition of acetyl chloride to aniline—vigorous reaction. 1998 Jrnl. Molecular Biol. 284 463 Studies have shown that the enzyme [sc. penicillin acylase] is specific for hydrolysis of phenylacetamide derivatives. phenylacetate n. (a) a salt or ester of phenylacetic acid; (b) (usually in form phenyl acetate) the phenyl ester of acetic acid, a colourless, fragrant liquid, CH₃COOC₆H₅, used as a solvent. ΚΠ 1873 F. W. Clarke Constants of Nature I. 168 (table) Methyl phenylacetate. 1915 Proc. National Acad. Sci. U.S.A. 1 141 Glycine, glutamic acid, and aspartic acid exerted hydrolytic actions on..phenyl acetate, ethyl butyrate, [etc.]. 1965 J. R. Dyer Applic. Absorption Spectroscopy Org. Compounds iii. 43 The position of absorption of normal aliphatic esters (methyl phenylacetate.., 5.73 μ, 1745 cm⁻¹). 1991 D. T. Sawyer Oxygen Chem. vii. 172 This conclusion is supported by the products that are observed in the gas-phase reaction of O₂⁻· with phenyl acetate and phenyl benzoate. phenylacetic adj. [quot. 1870 refers to a paper apparently read in 1869 to German learned society by a Dr Zinke, but this has not been traced] phenylacetic acid, a white, crystalline acid with a sweet odour, C₆H₅CH₂COOH, used in chemical synthesis and perfume manufacture. ΚΠ 1870 Nature 20 Jan. 322/1 He [sc. Zinke] has obtained phenyl-acetic acid from Monochloroacetic acid. 1885 E. Klein Micro-org. 73 Antiseptics, such as carbolic acid..strong solutions of phenyl-propionic acid and phenyl-acetic acid. 1975 F. Kennett Hist. Perfume ix. 184 Phenylacetic acid..is used to add a trace of civet, or honey, to a perfume. phenylacetylene n. an oily liquid, C₆H₅C≡CH, made into polymers esp. in the form of thin films. ΚΠ 1870 Nature 19 May 55/2 We also find here the discovery of the first acetylene of the aromatic series, by Glaser in acetenylbenzol or phenylacetylene. 1940 Jrnl. Amer. Chem. Soc. 62 48/1 Several attempts to add acetic acid to phenylacetylene under various conditions failed to give this product. 1993 Sci. News 10 Apr. 239/2 To synthesize the new molecule, the team used a carbon-based building block called phenylacetylene. † phenyl alcohol n. Obsolete = phenol n. 1. ΚΠ 1850 A. W. Hofmann in Philos. Trans. (Royal Soc.) 140 98 I had hoped that this conversion might be effected by the action of phenyl-alcohol on aniline. 1871 Manufacturer & Builder June 137/3 Phenyl alcohol is a creosote, made from coal-tar, as the ordinary creosote is made from wood-tar. phenylamide n. a derivative of aniline, an anilide; (formerly also) †aniline (obsolete). ΘΚΠ the world > matter > chemistry > organic chemistry > organic compounds > [noun] > aniline > derivatives > anilides phenylamide1851 phenylacetamide1863 1851 W. Gregory in Monthly Jrnl. Med. Sci. June 576 Phenylamide (Aniline) = N,HHPh. 1863 H. Watts Dict. Chem. I. 295 Anilides, syn[onym] of Phenylamides. 1868 M. Reimann On Aniline & its Derivatives 13 This mode of producing aniline led the discoverer to consider it an amide of the organic radical phenyl..and to call it phenylamide. 1937 Chem. Rev. 20 440 Kraus and Bien..state that it is impossible to prepare disodium phenylamide, C₆H₅NNa₂, by treating monosodium anilide with sodium amide in liquid ammonia. 1993 Plant Dis. 77 1242/1 The phenylamides, metalaxyl, ofurace, and oxadixyl, significantly inhibited growth of Picryptogea. phenylamine n. a compound with an amino group bonded directly to a benzene ring; spec. aniline. ΘΚΠ the world > matter > chemistry > organic chemistry > organic compounds > [noun] > aniline crystallin1833 aniline1850 phenylamine1850 kyanol1855 phenylia1857 1850 Philos. Trans. (Royal Soc.) 140 112 (table) Phenylamine. 1880 Jrnl. Soc. Arts 16 Apr. 442/1 The earliest violets obtained by artificial means were those produced by the action of pure aniline, or phenylamine, on roseine. 1936 S. A. Waksman Humus ii. 17 Other substances, however, like phenylamines, naphthylamines, and alkaloids, exert a decided toxic effect upon plant growth. 1995 School Sci. Rev. June 65/2 Examination of the resonance forms explains the greater reactivity of phenylamine towards electrophiles than benzene. phenylarsonic adj. phenylarsonic acid, a toxic, colourless, crystalline acid, C₆H₅AsO(OH)₂, derivatives of which are used as trypanocides; a derivative of this. ΘΚΠ the world > matter > chemistry > organic chemistry > organic acids > [noun] > phenolic acids, named benzoic acid1791 oil of spiraea1842 toluic acid1857 itatartaric acid1872 aspirin1899 phenylarsonic acid1905 tar acid1909 pteroic acid1946 1905 Amer. Chem. Jrnl. 33 104 The reduction takes place with equal ease in the aromatic series, monophenyl arsine..being obtained from phenyl arsonic acid. 1937 Thorpe's Dict. Appl. Chem. (ed. 4) I. 488/1 The introduction of an amino group into the para-position in phenylarsonic acid decreases its toxicity and increases its trypanocidal activity. 1959 Times 7 Dec. (Agric. Suppl.) p. vii/1 So far as arsenicals are concerned, two phenylarsonic acids have received attention [as growth stimulants for poultry]. 1991 Biochemistry 30 3739 The complex with hapten has been modeled by docking the small-molecule crystal structure of phenylarsonic acid into the structure of the native Fab. phenyl blue n. a dark blue dye which is a phenylimide derivative of a quinone. ΚΠ 1894 Lancet 29 Sept. 734/2 The stains easily reducible by Löffler's bacilli are phenyl blue, iodine green, malachite green, and one or two others. 1946 Jrnl. Aesthetics & Art Crit. 4 211 (table) Phenyl Blue. 1999 Re: Back to the Bladder in alt.fan.cecil-adams (Usenet newsgroup) 26 Oct. If you're asking about phenyl blue, or phenophthalene [sic], a fun chemical with which any first year chemistry student is familiar, then the answer is ASAP. † phenyl brown n. Obsolete = phenicin n. ΘΚΠ the world > life > biology > substance > pigment > [noun] > plant pigments > brown phyllophaein1858 fucoxanthin1873 phenyl brown1875 phaeophyll1890 the world > matter > chemistry > organic chemistry > organic compounds > [noun] > other organic compounds > others fat1539 nitromannite1857 friction-powder1864 nitramidin1866 nitroform1866 phenyl brown1875 ketide1907 tetryl1909 cyclonite1923 pentryl1933 the world > matter > colour > named colours > brown or brownness > colouring matter > [noun] > stains ferretto1662 walnut1709 Venetian brownc1791 phenyl brown1875 Bismarck brown1885 vesuvin1885 walnut-juice1912 1875 H. Watts Dict. Chem.: 2nd Suppl. 945 The explosive character of the phenyl-brown is..due to the dinitrophenol. 1891 R. Routledge Discov. & Inventions 19th Cent. (ed. 8) 658 Colours derived from Phenol. Browns. Picrate of ammonia. Isopurpurate of potash. Phenyl brown, phenicienne. phenyl ether n. (a) an ether in which one of the groups attached to the oxygen atom is phenyl; (formerly) an ester in which a phenyl group replaces the acid hydrogen atom; (b) diphenyl ether, (C₆H₅)₂O, a liquid used in organic synthesis. ΚΠ 1890 J. Cagney tr. R. von Jaksch Clin. Diagnosis vii. 286 The exhibition of salol (phenyl-æther of salicylic acid [Ger. Salicylphenoläther]). 1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) xxiv. 437 Phenyl ether, diphenyl oxide, (C₆H₅)₂O, is formed when phenol is heated with ZnCl₂ or AlCl₃. 1939 Jrnl. Amer. Chem. Soc. 61 109/2 Phenyl ether was not metalated by triphenylmethylsodium. 1960 F. G. Mann & B. C. Saunders Pract. Org. Chem. (ed. 4) ii. 186 Phenetole (ethyl phenyl ether) is the main product. 1986 Arch. Microbiol. 144 55 [A] bacterium is described which cleaves the phenylether bonds of methoxylated aromatic substrates to give the corresponding hydroxy aromatic derivatives and mixed volatile fatty acids. phenylethylamine n. an aminoethyl derivative of benzene, spec.(in full 2-phenylethylamine) a liquid, C₆H₅CH₂CHNH₂, which occurs naturally in the brain as a neuromodulator. ΚΠ 1875 Jrnl. Chem. Soc. 28 1025 Phenylethylamine, C₆H₅·C₂H₄·NH₂, is formed by the action of nascent hydrogen on benzyl cyanide. 1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) liv. 811 The following synthetical methods have been adopted:... Phenylethylamine from benzylcyanide is benzoylated and then nitrated. 1964 N. Weiner in G. Pincus et al. Hormones IV. viii. 435 It had been assumed that phenylethylamines..exerted their sympathomimetic actions by a direct mechanism identical to that of epinephrine and norepinephrine. 1995 Minnesota Monthly Feb. 81/2 Scientists..thought they'd discovered the secret to chocolate's appeal: that the combination of caffeine and a chemical called phenylethylamine (thought to induce ‘feelings of falling in love’) had a serious embrace on some people's constitutions. phenylglycol n. a low-melting solid or oily liquid, C₆H₅CH(OH)CH₂OH, also called styrene glycol. ΚΠ 1862 A. W. Hofmann in Proc. Royal Soc. 11 524 The action of nitrous acid upon aniline furnishing phenyl-alcohol,..there is some hope of meeting, in the analogous decomposition of phenylene-diamine with the diatomic phenylene-alcohol (phenyl-glycol). 1926 Jrnl. Amer. Chem. Soc. 48 1070 Phenylglycine is tasteless and phenylglycol is bitter. 1990 Exper. Pathol. 39 195 Measurement of the concentration of the produced phenylglycol (1-phenyl-1,2-ethandiol)..is described. phenylhydrazine n. a colourless liquid, C₆H₅NHNH₂, used as a reagent and in organic synthesis. ΚΠ 1883 Science 20 July 85/1 The action of phenylhydrazine upon ketones seems to be analogous to that of hydroxylamine. 1949 R. Livingston in J. Franck & W. E. Loomis Photosynthesis in Plants vii. 183 If oxygen is present the photosensitized auto-oxidation of phenylhydrazine occurs in preference to the oxidation by methyl red. 1991 D. T. Sawyer Oxygen Chem. vii. 179 The reaction of O₂⁻· with methylhydrazine is analogous to that for phenylhydrazine with methane the major product. phenylhydrazone n. [after German Phenylhydrazon (O. Rudolph 1888, in Ann. der Chem. u. Pharm. 248 99)] any of a class of compounds formed by condensation of an aldehyde or ketone with phenylhydrazine, which are typically crystalline solids and are used to characterize the parent aldehyde or ketone. ΘΚΠ the world > matter > chemistry > organic chemistry > aldehydes or alkanals > [noun] > aldehyde derivatives acetal1838 hydramide1865 phenylhydrazone1888 hemi-acetal1893 formal1900 1888 Jrnl. Chem. Soc. 54 934 Mannose..is obtained by dissolving the above phenylhydrazone in four parts of hydrochloric acid..cooled with ice and salt. 1966 McGraw-Hill Encycl. Sci. & Technol. (rev. ed.) VII. 62/2 When the starting material is the phenylhydrazone of acetone, the product is 2-methylindole. 1981 J. W. Buttle et al. Chem. (ed. 4) xxiii. 519 Phenylhydrazine forms phenylhydrazones by condensation, but these are not the ultimate products. phenylimide n. (also N-phenylimide) an imide containing the divalent group C₆H₅N^/_\\ or a substituted form of it. ΚΠ 1866 H. Watts Dict. Chem. IV. 419 Phenylimides or Anils, tertiary monamides..which..may be regarded as aniline in which 2 atoms of H[ydrogen] are replaced by a diatomic radicle: e.g. C₆H₅·(C₄H₄O₂)″·N, phenyl-succinimide. 1908 Jrnl. Amer. Chem. Soc. 30 1890 Aniline is practically without action on the [phthal-m-nitrophenylamidic] acid after 35 minutes, at 65°, in presence of benzene, but at 100°..about 31 per cent. of the phenylimide is produced. 1991 Pesticide Biochem. & Physiol. 40 135/1 These facts suggest that the mode of PPO [protoporphyrinogen oxidase] inhibition by N-phenylimide may be different from that of diphenylether herbicides. 2003 Amer. Jrnl. Industr. Med. 44 627 Exposure to nitro-derivatives and phenylimides among fungicides, hydrocarbon derivatives and insecticide oils among insecticides, and the herbicide amides. phenylpropiolic adj. phenylpropiolic acid, a colourless, crystalline acid, C₆H₅C≡CCOOH, related to phenylacetylene. ΚΠ 1872 H. Watts Dict. Chem. VI. 962 Phenyl-propiolic Acid. C₉H₆O₂..related to phenyl-propionic acid in the same manner as stearolic to stearic acid... It crystallises from water or from carbon bisulphide in long white silky needles melting at 136°–137°. 1938 Chem. Rev. 23 220 Similar reactions are those between phenyl azide and acetylene, and between hydrazoic acid and phenylpropiolic acid. 1999 Jrnl. Org. Chem. 64 6896/1 Aqueous bromination of phenylpropiolic acid afforded 11–18% of 1-bromophenyl acetylene among other products. phenylsulphuric adj. now rare = phenolsulphuric adj. at phenol n. Compounds 3. ΚΠ 1868 H. Watts Dict. Chem. V. 627 Phenylsulphuric acid may be obtained by evaporation in a vacuum over oil of vitriol, in slender needle-shaped crystals. 1933 S. W. Cole Pract. Physiol. Chem. (ed. 9) xiii. 295 (caption) Phenylsulphuric acid. phenylthiocarbamide n. a white, crystalline solid, NH₂CSNHC₆H₅, which has a bitter taste to people possessing a certain dominant gene and is tasteless to those lacking it. ΘΚΠ the world > matter > chemistry > organic chemistry > substances from animals or humans > urea > [noun] > derivatives > phenylthiourea phenylthiocarbamide1889 phenylthiourea1896 1879 Jrnl. Chem. Soc. 36 804 Mono- and di-phenylthiocarbamide..are soluble in caustic soda or potash.] 1889 Science 29 Mar. 234/1 The highly refracting liquid phenyl thiocarbamide appears to be specially suitable for experiments on this subject [sc. mapping electrical lines of force]. 1932 Proc. National Acad. Sci. U.S.A. 18 121 The heredity differences between people in their taste perceptions of phenyl thio carbamide are not so simple as the preceding paragraph might lead one to suppose. 1995 Guardian 27 Apr. (OnLine section) 12/2 Bartoshuk's experiments..involve testing people for taste blindness to PTC (phenylthiocarbamide) and its chemical relative PROP (6-n-propylthiouracil). phenylthiourea n. = phenylthiocarbamide n. ΘΚΠ the world > matter > chemistry > organic chemistry > substances from animals or humans > urea > [noun] > derivatives > phenylthiourea phenylthiocarbamide1889 phenylthiourea1896 1896 Jrnl. Chem. Soc. 69 857 If dilute hydrochloric acid be now added to the clear solution, a white solid at once separates, which..forms white prisms..consisting of phenylthiourea. 1959 Listener 3 Dec. 968/2 People who can taste phenylthiourea seem to be slightly more liable to get one form of thyroid disease and slightly less liable to get another. 2000 Proc. National Acad. Sci. U.S.A. 97 2618/2 Treatment of E[leutherodactylus] martinicensis with the goitrogen phenylthiourea (PTU) inhibited tail resorption. phenylurea n. a crystalline solid, C₆H₅NHCONH, many of whose derivatives are used as pesticides and herbicides. ΘΚΠ the world > matter > chemistry > organic chemistry > substances from animals or humans > urea > [noun] > derivatives uramil1839 dialuramide1857 phenylurea1857 ureide1857 violantin1866 violuric acid1866 biuret1869 1857 W. A. Miller Elements Chem. III. 616 Phenyl-urea (carbanilamide). 1941 Q. Rev. Biol. 16 183/2 Narcotics such as..phenylurea, propionitrile, and valeronitrile inhibit reversibly the respiration of erythrocytes. 1999 New Scientist 23 Jan. 21/1 Isoproturon, the most widely used phenylurea herbicide, used by wheat and barley farmers to control blackgrass, may also pose a hazard to fish. Derivatives † phenylous adj. Obsolete phenylous acid = phenol n. 1. ΘΚΠ the world > matter > chemistry > organic chemistry > hydrocarbons > [noun] > benzene derivatives > phenols carbolic acid1835 phenol1849 phenic acid1852 phenylous acid1852 phenylic acid1853 phenol1857 phlorol1868 THC1968 1852 Chem. Gaz. 10 136 St. Evre suspected a connexion between his acid and phenic acid (phenole, phenylous acid), C¹²H⁶O². 1873 Amer. Cycl. III. 768/1 Carbolic acid (synonymes, carbon oil acid..phenylous acid..), a chemical substance now largely employed in medicine and the arts. This entry has been updated (OED Third Edition, December 2005; most recently modified version published online March 2022). < n.1849
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