mesityln.
/ˈmɛsᵻtɪl/, /ˈmɛsᵻtʌɪl/, U.S. /ˈmɛsəˌtɪl/, /ˈmɛsəd(ə)l/ Chemistry.
1.
a. A hydrocarbon radical of which acetone was supposed to be the hydroxide. Now historical except in mesityl oxide n. at sense 1b. Usually attributive.
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the world > matter > chemistry > organic chemistry > hydrocarbons > [noun] > hydrocarbon radicals > others
mesityl1838
carbyl1840
melissyl1852
neopentyl1876
oleoyl1903
1838 R. J. Kane in Trans. Royal Irish Acad. (1839) 18 Science 101 Assuming a radical analogous to ethyl, we have..Mesityl.
1842 T. Graham Elements Chem. iii. ii. 797 Oxide of mesityle, C6H5O (Kane)... Chloride of mesityle, C6H5Cl (Kane).
1844 G. Fownes Man. Elem. Chem. 408 Dr. Kane has described a number of other compounds formed by the action of acids, and other chemical agents, on acetone, from which the existence of an organic salt-basyle, containing C6H5, has been inferred, and to which the name of mesityle has been given.
1850 Q. Jrnl. Chem. Soc. 2 105 The extreme instability of the mesityl compounds, at once distinguishes this group of bodies from the derivatives of the regular alcohols.
1855 H. Watts tr. L. Gmelin Hand-bk. Chem. IX. 27 Chloride of Mesityl.
1879 H. Watts Dict. Chem. (new ed.) I. 27 Acetone was regarded by Kane as an alcohol..containing the radicle C3H5, which he called mesityl.
b. mesityl oxide n. a colourless, oily liquid ketone with a sweet aroma, used as a solvent esp. for resins, gums, and cellulose derivatives.Chemical name: 4-methyl-3-penten-2-one; CH3COCH=C(CH3)2.
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the world > matter > chemistry > organic chemistry > ketones > [noun] > used as solvents
mesityl oxide1868
methyl ethyl ketone1876
methyl isobutyl ketone1888
MEK1930
hexone1938
1838 R. J. Kane in Trans. Royal Irish Acad. (1839) 18 Science 101 Oxide of mesityl.]
1868 H. B. Jones & H. Watts Fownes's Man. Elem. Chem. (ed. 10) 827 This compound, called mesityl chloride, is converted by alcoholic potash into mesityl oxide, (C3H5)20: 2C3H5Cl + 2KOH = 2KCl + OH2 + (C3H5)20.
1877 H. Watts Fownes's Man. Chem. (ed. 12) II. 263 On dilution with water an oily liquid is obtained, consisting of mesityl oxide and phorone, which may be separated by fractional distillation.
1896 Jrnl. Chem. Soc. 70 i. 343 Mesityl oxide semicarbazone melts at 156°.
1922 J. J. Sudborough Bernthsen's Text-bk. Org. Chem. (new ed.) v. 141 Acetone [is], by the action of many reagents..converted, with elimination of water, into mesityl oxide, C6H10O, phorone, C9H14O, or mesitylene, C9H12, according to the conditions.
1973 H. M. Stanley in E. G. Hancock Propylene i. 9 The Shell Oil Company..in 1937–8 commenced the manufacture of acetone derivatives, including diacetone alcohol, mesityl oxide and methylisobutyl ketone.
1994 Proc. National Acad. Sci. U.S.A. 91 12027 Mesityl oxide at a concentration of 20 μM was used as an electrically neutral marker.
2. A cyclic hydrocarbon group or radical derived from mesitylene, either (CH3)2C6H3CH2— (3,5-dimethylbenzyl) or (now usually) spec.(CH3)3C6H3— (2,4,6-trimethylphenyl). Usually attributive or as a formative element in chemical names.
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the world > matter > chemistry > organic chemistry > hydrocarbons > [noun] > cyclic hydrocarbons > others
heveëne1838
menthene1838
carotene1861
stilbene1868
mesityl1879
naphthene1884
tetramethylene1885
hexamethylene1887
pentamethylene1887
irene1894
pregnane1932
adamantane1933
aldrin1949
sterane1951
norbornane1952
1879 H. Watts Dict. Chem. (new ed.) VI. 301 Mesityl sulphydrate, C9H11SH, is easily formed by treating the sulphochloride [of mesitylene] with zinc and sulphuric acid.
1906 H. F. Morley & M. M. P. Muir Watts' Dict. Chem. III. 232 Mesityl,..More recently it has been employed to denote both s-dimethyl-benzyl and s-trimethyl-phenyl.
1950 E. R. Alexander Princ. Ionic Org. Reactions ix. 186 Ethyl isobutyrate can be made to condense with itself in the presence of sodium triphenylmethyl or mesityl magnesium bromide.
1976 A. Streitwieser & C. H. Heathcock Introd. Org. Chem. xxx. 891 Derivatives of toluene, cumene, the xylenes, and mesitylene, where the additional subsitituent is attached to the ring, may be named by using the prefixes tolyl-, cumenyl-, xylyl-, or mesityl-.
1984 Science 14 Sept. 1110/1 Mesityl, 2,4,6-trimethylphenyl, hereafter abbreviated Mes.
1984 Science 14 Sept. 1111/2 The other two mesityl groups are nearly coplanar with the mean plane of the silicon and attached carbon atoms... These two mesityl rings are arranged so that conjugation between their π systems and the Si=Si bond is possible.
1992 Organometallics 11 1076/2 This distortion appears to be a common feature in compounds bearing the mesityl ligand.
This entry has been updated (OED Third Edition, September 2001; most recently modified version published online March 2022).
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n.1838