9718. 2,4,6-Trimethylpyridine

Nomenclature

CAS number: 108-75-8
γ-Collidine; sym-collidine; 2,4,6-collidine; α,γ,α′-collidine.
C8H11N; mol wt 121.18.
C 79.29%, H 9.15%, N 11.56%.

Description and references

Found in small amts in coal tar, in shale oil. Produced commercially from coal tar to some extent; also produced by the Hantzsch pyridine synthesis: Hantzsch, Ann. 215, 1 (1882); Mosher in Heterocyclic Compounds vol. 1, R. C. Elderfield, Ed., (John Wiley, New York, 1950) pp 462-472; from acetone and ammonia: Mosher in Kirk-Othmer Encyclopedia of Chemical Technology vol. 11 (New York, 1953) p 287, cf. Dürkopf, Ber. 21, 2713 (1888); from paraldehyde, acetone, ammonium acetate, and ammonia water: DE 349267; Frdl. 14, 539; from 3,5-dimethyl-2-cyclohexen-1-one, ammonium acetate, and ammonia water: Frank, Meikle, J. Am. Chem. Soc. 72, 4184 (1950).

Chemical structure

Properties

Liquid. Aromatic odor. d416.4 0.9191; d422.1 0.9166 (commercial grade: d15.515.5 0.920-0.935, approx 7.74 lbs/gal). mp 46°. bp762 170.5°; bp760 171°; bp31 65°; bp2.7 10°. nD25 1.4959; nD22.1 1.49770. pKa (25°): 6.69. Flash pt 136°F. Dielectric constant at 22° = 6.6 (λ = 70 cm). More sol in cold water than in hot water: 20.8 g/100 ml at 6°; 3.5 g/100 ml at 20°; 1.8 g/100 ml at 100°. Miscible with ether. Sol in methanol, ethanol, chloroform, benzene, toluene, dil acids.