Benzofuran-5-carboxylic acid Chemical Properties

Melting point:

189-190°C

Boiling point:

325.6±15.0 °C(Predicted)

Density 

1.363±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

solid

pka

4.06±0.30(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C9H6O3/c10-9(11)7-1-2-8-6(5-7)3-4-12-8/h1-5H,(H,10,11)

InChIKey

GTWXSZIQNTUNKR-UHFFFAOYSA-N

SMILES

O1C2=CC=C(C(O)=O)C=C2C=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

HS Code 

2932990090

Benzofuran-5-carboxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Synthesis

General procedure for the synthesis of 1-benzofuran-5-carboxylic acid from methyl benzofuran-5-carboxylate: Methyl benzofuran-5-carboxylate (1.3 g, 7.38 mmol) was dissolved in methanol (51 mL), 5% aqueous sodium hydroxide solution (41 mL) was added, and the mixture was stirred. The reaction mixture was heated to 65 °C and kept at this temperature for 4 hours. After completion of the reaction, the mixture was cooled to room temperature and the methanol was removed by distillation under reduced pressure. The remaining aqueous phase was extracted with dichloromethane and the organic phase was discarded. The aqueous phase was acidified with concentrated hydrochloric acid to pH=1 and then extracted with chloroform. The organic phases were combined, washed with deionized water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 1.2 g (98% yield) of 1-benzofuran-5-carboxylic acid as a white solid.1H NMR (400 MHz, DMSO-d6) δ 12.9, 8.30, 8.11, 7.92, 7.69, 7.09.

References

[1] Patent: US2003/232853, 2003, A1. Location in patent: Page 37
[2] Patent: WO2004/39815, 2004, A2. Location in patent: Page 70
[3] Patent: WO2017/155909, 2017, A1. Location in patent: Paragraph 0182
[4] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105

Benzofuran-5-carboxylic acid(90721-27-0)Related Product Information

• Benzofuran-5-carboxylic acid
• METHYL-7-BROMO-1-BENZOFURAN-2-CARBOXYLATE
• 7-BROMO-1-BENZOFURAN-2-CARBOXYLICACID
• 2,3-Dihydro-1-benzofuran-7-carboxylic acid
• ETHYL 3-AMINOBENZOFURAN-2-CARBOXYLATE
• 5-NITROBENZOFURAN-2-CARBOXYLIC ACID
• 4-Benzofurancarboxylic Acid
• 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBOXYLIC ACID
• ETHYL 5-NITROBENZOFURAN-2-CARBOXYLATE
• 2,3-Dihydrobenzo[b]furan-5-carboxylic acid
• methyl 4-amino-4,5,6,7-tetrahydrobenzofuran-3-carboxylate hydrochloride
• 4-BENZOFURANCARBOXYLICACIDMETHYLESTER
• 2,7-Dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid
• Methyl 3-methyl-2-benzofurancarboxylate
• 7-Methoxybenzofuran-2-carboxylic acid
• ETHYL BENZOFUROXAN-5-CARBOXYLATE
• 2,3-BENZOFURAN-2-CARBOXYLIC ACID,BENZOFURAN-2-CARBOXYLIC ACID,1-BENZOFURAN-2-CARBOXYLIC ACID
• 5-CHLORO-BENZOFURAN-2-CARBOXYLIC ACID ETHYL ESTER