5-bromothiophene-3-carboxylic acid Chemical Properties

Melting point:

140-144°C

Boiling point:

318.9±27.0 °C(Predicted)

Density 

1.923±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

3.82±0.10(Predicted)

color 

Off-white

InChI

InChI=1S/C5H3BrO2S/c6-4-1-3(2-9-4)5(7)8/h1-2H,(H,7,8)

InChIKey

YCNXGPMGMAKDPM-UHFFFAOYSA-N

SMILES

C1SC(Br)=CC=1C(O)=O

CAS DataBase Reference

100523-84-0

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2934999090

5-bromothiophene-3-carboxylic acid Usage And Synthesis

Chemical Properties

White to off-white powder

Synthesis

(d) Synthesis of 5-bromo-3-thiophenecarboxylic acid: a glacial acetic acid solution of bromine was prepared by dissolving 16 g of Br2 (0.1 mol) in 200 ml of glacial acetic acid. This solution was slowly added dropwise to 100 ml of glacial acetic acid solution containing 3-thiophenecarboxylic acid (12.8 g; 0.1 mol). The reaction mixture was stirred at room temperature for 20 minutes. Upon completion of the reaction, the mixture was poured into a vessel containing water and ice to quench the reaction and promote precipitation of the product. The resulting white precipitate was collected by filtration and washed with water to remove residual glacial acetic acid. Finally, the product was purified by recrystallization from water to give 5-bromo-3-thiophenecarboxylic acid in 70% yield.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 11, p. 1460 - 1462
[2] Patent: US4767758, 1988, A
[3] Journal of Materials Chemistry C, 2018, vol. 6, # 14, p. 3731 - 3742
[4] Chemistry of Materials, 2010, vol. 22, # 19, p. 5617 - 5624
[5] Angewandte Chemie - International Edition, 2018, vol. 57, # 26, p. 7714 - 7718

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