2-BROMO-3-THIOPHENECARBOXYLIC ACID Chemical Properties

Melting point:

178-182 °C(lit.)

Boiling point:

313.2±27.0 °C(Predicted)

Density 

1.923±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

3?+-.0.20(Predicted)

form 

Crystalline Powder

color 

White to tan

InChIKey

RVSXMPCELBYUSF-UHFFFAOYSA-N

CAS DataBase Reference

24287-95-4

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26

WGK Germany 

3

HS Code 

29309099

2-BROMO-3-THIOPHENECARBOXYLIC ACID Usage And Synthesis

Application

2-Bromo-3-thiophenecarboxylic acid is an organic synthesis intermediate and a pharmaceutical intermediate that can be used in laboratory research and development processes as well as in chemical and pharmaceutical synthesis.

Chemical Properties

Light yellow crystalline powder

Synthesis

General procedure for the synthesis of 2-bromo-3-thiophenecarboxylic acid from 3-thiophenecarboxylic acid: 3-thiophenecarboxylic acid (2.00 g, 15.6 mmol) and anhydrous tetrahydrofuran (THF; 30 mL) were added to a pre oven-dried 100 mL round bottom flask. The reaction system was cooled to -78.0 °C and a 2.50 M hexane solution of n-butyllithium (12.6 mL, 31.5 mmol) was added slowly and dropwise under nitrogen protection. The reaction mixture was stirred at -78.0 °C for 30 min before adding bromine (0.86 mL, 16.4 mmol) dropwise. Stirring was continued at -78.0 °C for 1 h. The reaction system was then slowly warmed to room temperature. After stirring overnight, dilute 1M HCl solution (50.0 mL) was added to quench the reaction, followed by concentration of the reaction solution. The resulting mixture was extracted with ether and water and the organic layer was dried with anhydrous Na2SO4. The product was recrystallized twice by H2O/ether mixed solvent to give pale yellow needle-like crystals of 2-bromo-3-thiophenecarboxylic acid (2.13 g, 66.0% yield). The structure of the product was confirmed by 1H NMR (500 MHz, DMSO-d6): δ 7.63-7.62 (d, J=5.8 Hz, 1H), 7.32-7.31 (d, J=5.8 Hz, 1H).

References

[1] Journal of Organic Chemistry, 2002, vol. 67, # 20, p. 6931 - 6937
[2] Polymer, 2018, vol. 146, p. 142 - 150
[3] Patent: CN106588868, 2017, A. Location in patent: Paragraph 0025-0029; 0043; 0053-0055

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