4-BROMOFURAN-2-CARBOXYLICACID Chemical Properties

Melting point:

115-127 ºC

Boiling point:

284 ºC

Density 

1.891

Flash point:

125 ºC

storage temp. 

2-8°C

pka

2.91±0.15(Predicted)

Appearance

Off-white to yellow Solid

InChI

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

InChIKey

QALYBHRYGIXHOF-UHFFFAOYSA-N

SMILES

O1C=C(Br)C=C1C(O)=O

Safety Information

HS Code 

2932190090

4-BROMOFURAN-2-CARBOXYLICACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-bromo-2-furancarboxylic acid from 4,5-dibromo-2-furoic acid: 10.0 g (37.1 mmol) of 4,5-dibromofuran-2-carboxylic acid was dissolved in a 7.3% aqueous ammonia solution and the reaction system was cooled down to 0°C. The reaction was carried out by adding 2.54 g (38.9 mmol) of zinc powder. Under vigorous stirring conditions, 2.54 g (38.9 mmol) of zinc powder was added in batches and the reaction temperature was controlled not to exceed 7 °C. The reaction mixture was continued to be stirred at 0 °C for 10 min. Subsequently, the pH was adjusted to acidic by dropwise addition of aqueous hydrochloric acid. The resulting suspension was extracted with ethyl acetate, the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford 7.27 g (99% yield) of 4-bromo-2-furancarboxylic acid. The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-d6): δ = 13.5 (s, 1H, COOH), 8.17 (s, 1H, furan cyclic H), 7.40 (s, 1H, furan cyclic H). LC-MS analysis (Method 1): retention time Rt = 1.52 min; mass spectrum (ESI positive ion mode): m/z = 191 [M+ H]+.

References

[1] Patent: US2012/22059, 2012, A1. Location in patent: Page/Page column 10-11
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 407 - 416
[3] Patent: EP2236500, 2010, A1. Location in patent: Page/Page column 49
[4] Patent: EP2441457, 2012, A1. Location in patent: Page/Page column 31
[5] Patent: TWI530497, 2016, B. Location in patent: Page/Page column 61

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