2-CHLOROTHIAZOLE-5-CARBONITRILE

2-CHLOROTHIAZOLE-5-CARBONITRILE Property

Melting point:

47-49°

Boiling point:

291.1±32.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

Flash point:

104℃

storage temp. 

-20°C

pka

-2.28±0.10(Predicted)

form 

solid

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C4HClN2S/c5-4-7-2-3(1-6)8-4/h2H

InChIKey

BAFLVXULMMAKMM-UHFFFAOYSA-N

SMILES

S1C(C#N)=CN=C1Cl

Safety

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2934100090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

2-CHLOROTHIAZOLE-5-CARBONITRILE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-chlorothiazole-5-carbonitrile using 2-amino-5-cyano thiazole as starting material: 3.4 g (27 mmol) of 2-amino-5-cyano thiazole (Example 43) was homogeneously dispersed in 100 mL of acetonitrile with 5.1 g (30 mmol) of copper chloride dihydrate. Under vigorous stirring conditions, 5.7 mL of an acetonitrile solution of isoamyl nitrite was slowly added dropwise over a period of 30 minutes, and the reaction was continued for 10 hours after completion of the dropwise addition. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate and filtered to remove insoluble impurities. The organic phase was concentrated and purified by column chromatography to give 2.6 g of the target product (67% yield) as a liquid. The liquid precipitated needle-like crystals upon standing, with a melting point of 54-57 °C. 13C NMR (CDCl3, ppm) data were as follows: 108.16, 110.41, 150.59, 157.36; mass spectrometry (EI) showed the molecular ion peak m/z of 144.1 (M+).

References

[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6363 - 6372
[2] Patent: EP2039686, 2009, A1. Location in patent: Page/Page column 32-33
[3] Patent: US2010/87448, 2010, A1. Location in patent: Page/Page column 22
[4] Patent: US2004/23978, 2004, A1. Location in patent: Page/Page column 13
[5] Patent: US2004/23980, 2004, A1. Location in patent: Page/Page column 13