3-Bromofuran-2-carboxylic acid Chemical Properties

Melting point:

127-129 °C

Boiling point:

278.0±25.0 °C(Predicted)

Density 

1.891±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

soluble in Chloroform, DCM, Ethyl Acetate

form 

Solid

pka

2.77±0.20(Predicted)

color 

Light Brown

InChI

InChI=1S/C5H3BrO3/c6-3-1-2-9-4(3)5(7)8/h1-2H,(H,7,8)

InChIKey

UZBGSJZFBUOJNE-UHFFFAOYSA-N

SMILES

O1C=CC(Br)=C1C(O)=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-26-36/37/39

HS Code 

2932190090

3-Bromofuran-2-carboxylic acid Usage And Synthesis

Uses

3-Bromo-2-furoic Acid is an intermediate in the synthesis of selective α4β2 nicotinic acetylcholine receptor agonists used for the treatment of cognitive disorders.

Synthesis

General procedure for the synthesis of 3-bromofuran-2-carboxylic acid from 3-bromofuran-2-carbaldehyde: A) To a solution of tert-butanol (250 mL) containing 3-bromofuran-2-carboxaldehyde (25.0 g) and 2-methyl-2-butene (45.4 mL) was added slowly and dropwise at room temperature a mixed solution prepared from 80% sodium chlorite (40.5 g) and sodium dihydrogen phosphate (51.5 g) in water (350 mL). The reaction mixture was stirred overnight and acidified by the addition of 1 M hydrochloric acid (300 mL), followed by extraction with ethyl acetate. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (5/1, v/v) and recrystallized from the target product 3-bromofuran-2-carboxylic acid (20.3 g) by hexane/ethyl acetate solvent mixture. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 6.66 (1H, d, J=1.9 Hz), 7.58 (1H, d, J=1.9 Hz).

References

[1] Patent: US2013/137675, 2013, A1. Location in patent: Paragraph 0598

3-Bromofuran-2-carboxylic acid(14903-90-3)Related Product Information

• 3-BROMO-2-FORMYLFURAN
• 2-Furoic acid
• tert-butyl 3-bromo-2-furoate
• 3-Bromofuran
• 3-Bromo-2-methylfuran
• 3-Bromofuran-2-carboxylic acid