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90721-27-0

90721-27-0 Structure

90721-27-0 Structure
IdentificationBack Directory
[Name]

1-BENZOFURAN-5-CARBOXYLIC ACID
[CAS]

90721-27-0
[Synonyms]

RARECHEM AL BE 1369
5-Benzofurancarboxylic acid
1-benzofunan-5-carboxylic acid
1-BENZOFURAN-5-CARBOXYLIC ACID
Benzo[b]furan-5-carboxylic acid
1-Benzofuran-5-carboxylic acid, 5-Carboxybenzo[b]furan
[Molecular Formula]

C9H6O3
[MDL Number]

MFCD01006742
[MOL File]

90721-27-0.mol
[Molecular Weight]

162.14
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystal powde
[Melting point ]

189-190°C
[Boiling point ]

325.6±15.0 °C(Predicted)
[density ]

1.363±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[form ]

solid
[pka]

4.06±0.30(Predicted)
[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
Hazard InformationBack Directory
[Chemical Properties]

white to light yellow crystal powde
[Synthesis]

Methyl Benzofuran-5-carboxylate

108763-47-9

Benzofuran-5-carboxylic acid

90721-27-0

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
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P271-P280
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-37/39
[HS Code ]

2932990090
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Spectrum DetailBack Directory
[Spectrum Detail]

Benzofuran-5-carboxylic acid(90721-27-0)1HNMR
Benzofuran-5-carboxylic acid(90721-27-0)1HNMR
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