2-Bromo-5-thiazolecarboxylic acid Chemical Properties

Melting point:

182 °C (dec.)

Boiling point:

350.0±15.0 °C(Predicted)

Density 

2.062±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.52±0.10(Predicted)

form 

Crystalline Powder

color 

White to off-white

InChI

InChI=1S/C4H2BrNO2S/c5-4-6-1-2(9-4)3(7)8/h1H,(H,7,8)

InChIKey

BESGTWHUMYHYEQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

54045-76-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29341000

2-Bromo-5-thiazolecarboxylic acid Usage And Synthesis

Chemical Properties

White to brown solid

Uses

2-Bromothiazole-5-carboxylic acid is used as a reagent to synthesize azole-based protein kinase B inhibitors, some of which have anti-cancer properties.

Synthesis

General procedure for the synthesis of 2-bromothiazole-5-carboxylic acid from ethyl 2-bromothiazole-5-carboxylate: an aqueous solution (100 mL) of sodium hydroxide (4.1 g, 102 mmol) was added slowly and dropwise at 0 °C to a solution of tetrahydrofuran (THF, 100 mL) of ethyl 2-bromothiazole-5-carboxylate (20 g, 84.7 mmol). The reaction mixture was stirred continuously at 10 °C for 1 hour. Subsequently, the reaction mixture was neutralized with 6 M hydrochloric acid and extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-bromothiazole-5-carboxylic acid (17.7 g, 100% yield) as a yellow solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6) with chemical shift δ 8.21 (s, 1H).

References

[1] Patent: WO2015/116663, 2015, A1. Location in patent: Paragraph 0103
[2] Patent: US2011/92475, 2011, A1. Location in patent: Page/Page column 14
[3] Helvetica Chimica Acta, 1954, vol. 37, p. 2057,2064
[4] Patent: US6066639, 2000, A

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