Ethyl 2-bromothiazole-4-carboxylate Chemical Properties

Melting point:

67-71 °C

Boiling point:

154°C/13mmHg(lit.)

Density 

1.654±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

powder to crystal

pka

-1.50±0.10(Predicted)

color 

White to Almost white

Sensitive 

Moisture & Light Sensitive

InChI

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

InChIKey

CNHISCQPKKGDPO-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

100367-77-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

WGK Germany 

2

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29341000

Ethyl 2-bromothiazole-4-carboxylate Usage And Synthesis

Chemical Properties

White solid

Uses

Ethyl 2-bromothiazole-4-carboxylate is an essential organic reagent that can be used as a building block for the synthesis of many organic compounds, such as 4-Thiazolecarboxylic acid, Ethyl thiazole-4-carboxylate， 2-Bromothiazole-4-carboxylic acid and so on.

Synthesis

Ethyl 2-aminothiazole-4-carboxylate (100 g, 581 mmol) and copper(II) bromide (195 g, 871 mmol) were dissolved in acetonitrile (1000 ml) at 0 °C. Subsequently, tert-butyl nitrite (104 ml, 871 mmol) was added slowly and dropwise. The reaction mixture was gradually warmed to room temperature and stirred continuously for 12 hours. After completion of the reaction, the reaction mixture was diluted with a mixture of ethyl acetate (1000 ml) and water (3000 ml) and the pH was adjusted to 2 with 1 N hydrochloric acid.The organic and aqueous layers were separated, and the aqueous layer was extracted three times with ethyl acetate (500 ml). All organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by recrystallization from hexane to give pure ethyl 2-bromothiazole-4-carboxylate (115 g, 84% yield). The product was confirmed by 1H-NMR (400 MHz, DMSO-d6): δ 8.52 (s, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.29 (t, J=7.1 Hz, 3H). Mass spectral analysis showed m/z 235.90 [M+1].

References

[1] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 2766 - 2775
[2] Zh. Obshch. Khim., 2017, vol. 87, # 12, p. 1947 - 1956,10
[3] Patent: WO2018/193387, 2018, A1. Location in patent: Page/Page column 92
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 2, p. 533 - 536
[5] Patent: US6468979, 2002, B1

Ethyl 2-bromothiazole-4-carboxylate(100367-77-9)Related Product Information

• RESMETHRIN
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• Benzocaine
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• ISOXADIFEN-ETHYL
• 2-Ethoxyethanol
• Ethyl acetate
• 2-Bromothiazole
• Ethylparaben
• Ethanol
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• Trinexapac-ethyl
• METHYL 2-BROMOTHIAZOLE-4-CARBOXYLATE
• Ethyl 2-aminothiazole-4-carboxylate hydrochloride
• Ethyl 2-amino-1,3-thiazole-4-carboxylate
• 2,5-DIBROMO-THIAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• Diethyl ether