ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE

ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE Property

Melting point:

65-69 °C(lit.)

Boiling point:

287.1±20.0 °C(Predicted)

Density 

1.573±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

-0.10±0.10(Predicted)

color 

Light yellow to Brown

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C7H8BrNO2S/c1-3-11-6(10)5-4(2)9-7(8)12-5/h3H2,1-2H3

InChIKey

CFBIOWPDDZPIDP-UHFFFAOYSA-N

SMILES

S1C(C(OCC)=O)=C(C)N=C1Br

Safety

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-36

RIDADR 

1759

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29341000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ETHYL 2-BROMO-4-METHYL-1,3-THIAZOLE-5-CARBOXYLATE Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

It finds its application in the preparation of thiazole-4- and -5-carboxylates, and an infrared study of their rotational isomers and in the discovery of thiazolylpyridinone SCD1 inhibitors with preferential liver distribution and reduced mechanism-based adverse effects.

Synthesis

General procedure for the synthesis of ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate from ethyl 2-amino-4-methylthiazole-5-carboxylate: first, 2-methyl-1-nitro-propyl-propene (28.2 mL, 2.1 eq.) was dissolved in acetonitrile (700 mL) and the solution was cooled to 0 °C. Subsequently, bromo-trimethyl-silane (32 mL , 2.1 eq.). The reaction mixture was maintained at 0°C. Next, ethyl 2-amino-4-methyl-thiazole-5-carboxylate (18.6 g, 0.1 mol) was added to an acetonitrile/ethyl acetate (75/25) solution. After the dropwise addition was completed, the reaction mixture continued to be kept at 0°C. The mixture was warmed to room temperature and stirred for 24 hours. After completion of the reaction, the solvent was removed by evaporation and water was added. The product was extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated. Finally, purification by fast chromatography using dichloromethane as eluent gave ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate as a yellow solid (21.74 g, 87 mmol, 87% yield); GC/MS analysis: [M+] C7H8BrNO2S 250.

References

[1] Patent: WO2004/6923, 2004, A1. Location in patent: Page/Page column 38
[2] Patent: WO2004/6924, 2004, A1. Location in patent: Page/Page column 31-32
[3] Patent: WO2004/7493, 2004, A1. Location in patent: Page 24-25
[4] Patent: EP2518054, 2012, A1. Location in patent: Page/Page column 53
[5] Patent: WO2008/47109, 2008, A1. Location in patent: Page/Page column 38