6126. 4-Methyl-5-thiazoleethanol

Nomenclature

CAS number: 137-00-8
5-Hydroxyethyl-4-methylthiazole; 5-(2-hydroxyethyl)-4-methylthiazole; 4-methyl-5-(β-hydroxyethyl)thiazole.
C6H9NOS; mol wt 143.21.
C 50.32%, H 6.33%, N 9.78%, O 11.17%, S 22.39%.

Description and references

The thiazole moiety of thiamine (vitamin B1). Several syntheses, e.g., by condensing thioformamide with bromoacetopropanol: Buchman, J. Am. Chem. Soc. 58, 1803 (1936); or with γ,γ-dichloro-γ,γ-diacetodipropyl ether: Stein, Stevens, FR 945198 and GB 641426 (1947 and 1950 to Merck & Co.); Londergan, Schmitz, US 2654760 (1953 to du Pont).

Chemical structure

Properties

Oily, viscous liquid. d424 1.196. Characteristic disagreeable odor of thiazole compds, becoming somewhat pleasant at extreme dilutions and imparting a nut-like flavor. bp7 135°; bp3 123-124°; bp1 103°. Sol in alcohol, ether, benzene, chloroform. Very sol in water.

Derivative

Hydrochloride.
C6H9NOS.HCl; mol wt 179.67.
C 40.11%, H 5.61%, N 7.80%, O 8.90%, S 17.85%, Cl 19.73%.

Properties

Hygroscopic crystals, sol in water, alcohol.

Use

Intermediate in the synthesis of vitamin B1.