| Identification | Back Directory | [Name]
benzofuran-4-carboxylic acid | [CAS]
166599-84-4 | [Synonyms]
4-BENZOFURANCARBOXYLICACID
1-benzofuran-4-carboxylicaci
benzofuran-4-carboxylic acid
1-Benzofuran-4-carboxylic acid
1-benzofurane-4-carboxylic acid
4-Benzofurancarboxylic Acid ISO 9001：2015 REACH | [Molecular Formula]
C9H6O3 | [MDL Number]
MFCD10000600 | [MOL File]
166599-84-4.mol | [Molecular Weight]
162.142 |
| Chemical Properties | Back Directory | [Boiling point ]
326℃ | [density ]
1.363 | [Fp ]
151℃ | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
3.19±0.10(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C9H6O3/c10-9(11)7-2-1-3-8-6(7)4-5-12-8/h1-5H,(H,10,11) | [InChIKey]
WFAPIZKLEVLUMX-UHFFFAOYSA-N | [SMILES]
O1C2=CC=CC(C(O)=O)=C2C=C1 |
| Hazard Information | Back Directory | [Uses]
4-Benzofurancarboxylic Acid is a benzofuran derivative used in the preparation of dual orexin 1 and orexin 2 receptor antagonist which are useful for the treatment of sleep disorders. | [Synthesis]
General procedure for the synthesis of benzofuran-4-carboxylic acid from methyl benzofuran-4-carboxylate: a solution of LiOH (1.44 g, 34.3 mmol) in water (20 mL) was added to a mixture of THF (20 mL) and MeOH (20 mL) of methyl benzofuran-4-carboxylate (2.02 g, 11.4 mmol) and the reaction was stirred at room temperature for 16 The reaction was stirred for 16 hours at room temperature. After completion of the reaction, the solvent was removed by evaporation. The residue was dissolved in water (50 mL) and acidified with concentrated HCl to pH < 2. The precipitate was collected by filtration and dried to afford benzofuran-4-carboxylic acid (1.83 g, 99% yield). The product was characterized by 1H NMR (DMSO-d6): δ 13.10 (s, 1H), 8.14 (d, J = 2.1 Hz, 1H), 7.85-7.91 (m, 2H), 7.43 (t, J = 7.9 Hz, 1H), 7.33 (dd, J = 2.1, 1.0 Hz, 1H). Mass spectrum measured value: [M-H]? = 161.1. | [References]
[1] Patent: WO2017/155909, 2017, A1. Location in patent: Paragraph 0190
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105 |
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