Thiazole

Structural formula
General
Surname	Thiazole
other names	1,3-thiazole
Molecular formula	C 3 H 3 NS
Brief description	colorless to yellow liquid
External identifiers / databases
EC number	206-021-3
ECHA InfoCard	100.005.475
PubChem	9256
Wikidata	Q413426
properties
Molar mass	85.12 g mol −1
Physical state	liquid
density	1.20 g cm −3
boiling point	117-118 ° C
pK s value	2.44 (the conjugate ; acid BH + , 20 ° C)
solubility	Slightly soluble in water, soluble in ethanol
Refractive index	1.5365-1.5395
safety instructions
H and P phrases	H: 226-302-315-318-335
	P: 261-280-305 + 351 + 338
Toxicological data	983 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Thiazole is a chemical compound from the group of heterocyclic compounds or heteroaromatics . It consists of a five-membered ring made up of three carbon atoms and one sulfur or nitrogen atom each , which is used as a basic structure in many derived organic compounds. It is a colorless to pale yellow liquid with a pyridine-like odor. Substituted derivatives of thiazole are called thiazoles . Its isomer is isothiazole ( 1,2-thiazole ), where the sulfur atom is next to nitrogen.

Extraction and presentation

The reaction of monochloroacetaldehyde with thioformamide yields thiazole. The oxidation of substituted 3- thiazolines (produced by the Asinger reaction ) with elemental sulfur gives analogously substituted thiazoles.

properties

Physical Properties

Thiazole is miscible with water, alcohol and ether.

Chemical properties

Thiazoles are a group of organic compounds (similar to azoles ) which contain thiazole as a functional group . For example, vitamin B ₁ , penicillin , epothilone , clomethiazole and luciferins (which belong to the group of benzothiazoles ) contain thiazole or hydrogenated derivatives of thiazole as a structural element. Thiazoles can be prepared by a Hurd-Mori reaction . Dyes in this group are designated with a Color Index in the range from 49000 to 49399. Thiazole salts are used as catalysts in the Stetter reaction and the benzoin condensation .

use

Thiazole is used as a raw material in the manufacture of fungicides , pharmaceuticals and dyes .

Web links

Thiazol Derivative (English) ( Memento from August 22, 2013 in the Internet Archive )
Spectrum of thiazole

Individual evidence

↑ Data thiazole at AlfaAesar, accessed on 9 March 2010 ( PDF )(JavaScript required) .
↑ ^a ^b ^c Entry on thiazole at ChemBlink , accessed on February 25, 2011.
↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
↑ data sheet at Goods Company (English) .
↑ ^a ^b Data sheet Thiazole from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
↑ Thiazole data sheet (PDF) from Fisher Scientific , accessed February 13, 2014.

↑ Heribert Offermanns and Friedrich Asinger : Syntheses with ketones, sulfur and ammonia or amines and chemical behavior of the reaction products, Westdeutscher Verlag , Cologne and Opladen, 1966.

[alfa-1] Data thiazole at AlfaAesar, accessed on 9 March 2010 ( PDF )(JavaScript required) .

[chemblink-2] Entry on thiazole at ChemBlink , accessed on February 25, 2011.

[CRC-3] CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .

[4] ta sheet at Goods Company (English) .

[Sigma-5] Data sheet Thiazole from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).

[6] Thiazole data sheet (PDF) from Fisher Scientific , accessed February 13, 2014.

[Offermanns-7] Heribert Offermanns and Friedrich Asinger : Syntheses with ketones, sulfur and ammonia or amines and chemical behavior of the reaction products, Westdeutscher Verlag , Cologne and Opladen, 1966.