Ethyl 2-bromothiazole-5-carboxylate Chemical Properties

Melting point:

60-61 °C(Solv: ligroine (8032-32-4))

Boiling point:

216-217 °C (lit.)

Density 

1.581 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5530(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

-0.98±0.10(Predicted)

form 

clear liquid

color 

Light orange to Yellow to Green

Water Solubility 

Miscible is water.

InChI

InChI=1S/C6H6BrNO2S/c1-2-10-5(9)4-3-8-6(7)11-4/h3H,2H2,1H3

InChIKey

KTYIFXLNIMPSKI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

41731-83-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

3

Hazard Note 

Harmful/Keep Cold

HS Code 

29341000

MSDS

• Language:English Provider:SigmaAldrich

Ethyl 2-bromothiazole-5-carboxylate Usage And Synthesis

Uses

Ethyl 2-bromothiazole-5-carboxylate is used in medicine, pharmaceutical intermediate

Synthesis

General procedure for the synthesis of ethyl 2-bromothiazole-5-carboxylate from ethyl 2-aminothiazole-5-carboxylate: to a stirred solution of ethyl 2-aminothiazole-5-carboxylate (10.0 g, 46.45 mmol, Combi block) in 48% hydrobromic acid (75 mL) at 0 °C, sodium nitrite (4.80 g, 50 mL) dissolved in water (50 mL) was added dropwise. 69.68 mmol) solution. The reaction mixture was continued to be stirred at 0 °C for 15 min. Subsequently, a 48% hydrobromic acid (75 mL) solution of copper(I) bromide (6.66 g, 46.45 mmol) was added dropwise at 0°C. The resulting reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (200 mL), washed sequentially with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification of the crude product by fast chromatography (100% chloroform) afforded ethyl 2-bromothiazole-5-carboxylate as a yellow liquid in 50% yield (5.5 g).LCMS (Method A): 235.9 (M + H), retention time 3.85 min, purity 98.6% (max).1H NMR (400 MHz, DMSO-d6): δ 8.16 (s, 1H ), 4.38 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H).

References

[1] Patent: WO2014/159234, 2014, A1. Location in patent: Page/Page column 87; 88
[2] Patent: WO2016/30443, 2016, A1. Location in patent: Page/Page column 118-119
[3] Patent: WO2017/144637, 2017, A1. Location in patent: Page/Page column 52; 53
[4] Patent: WO2017/144635, 2017, A1. Location in patent: Page/Page column 46; 47
[5] Journal of the American Chemical Society, 2008, vol. 130, # 28, p. 9089 - 9098

Ethyl 2-bromothiazole-5-carboxylate(41731-83-3)Related Product Information

• RESMETHRIN
• 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester
• Fosthiazate
• 2-Bromo-5-thiazolecarboxylic acid
• Ethyl acetate
• Benzothiazole
• Ethyl acrylate
• Ethyl bromodifluoroacetate
• Ethanol
• 2-Mercaptobenzothiazole
• Ethyl pyruvate
• 2-Bromothiazole
• Methylchloroisothiazolinone/methylisothiazolinone mixture (MCIT/MIT)
• ISOXADIFEN-ETHYL
• Ethyl bromoacetate
• Ethyl cyanoacetate
• Ethyl formate
• Ethylparaben