| Identification | Back Directory | [Name]
2,3-Dihydro-1-benzofuran-2-carboxylic acid | [CAS]
1914-60-9 | [Synonyms]
AKOS BBS-00006837
2,3-Dihydro-2-benzofurancarboxylic Acid
2,3-DIHYDRO-BENZOFURAN-2-CARBOXYLIC ACID
2,3-dihydro-1-benzofuran-2-carboxylicaci
2-Benzofurancarboxylic acid, 2,3-dihydro-
2,3-DIHYDRO-1-BENZOFURAN-2-CARBOXYLIC ACID
2,3-Dihydro-1-Benzofurane-2-CarboxylicAcid
2,3-Dihydrobenzo[b]furan-2-carboxylic acid
(2-methyl-3-imidazo[1,2-a]pyridinyl)methanol
2,3-Dihydro-1-benzofuran-2-carboxylic acid, 2-Carboxy-2,3-dihydrobenzo[b]furan | [Molecular Formula]
C9H8O3 | [MDL Number]
MFCD03086168 | [MOL File]
1914-60-9.mol | [Molecular Weight]
164.16 |
| Chemical Properties | Back Directory | [Melting point ]
116-118 | [Boiling point ]
340.5±31.0 °C(Predicted) | [density ]
1.347±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
3.17±0.20(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
This compound is the starting material in the synthesis of (dihydro)benzofuran-2-carboxylic acid N-(substituted)phenylamide derivatives as anticancer agents. | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 24, p. 495, 1987 DOI: 10.1002/jhet.5570240236 | [Synthesis]
a) Synthesis of (R,S)-2,3-dihydro-benzofuran-2-carboxylic acid (54a): commercially available benzofuran-2-carboxylic acid (Aldrich Chemical Company, 27 g, 167.7 mmol) was dissolved in ethyl acetate (300 mL). The hydrogenation reaction was catalyzed by 10% Pd/C (20 g) at 65-70 psi hydrogen pressure for 2 days. Upon completion of the reaction, the catalyst was removed by filtration and the solvent was evaporated. A solvent mixture of ethyl acetate-hexane (1:6) was added to the residue for recrystallization. Filtration afforded benzodihydrofuran-2-carboxylic acid as a crystalline solid (20.23 g, 74% yield). Melting point: 116-117 °C. 1H NMR (300 MHz, CDCl3) δ: 11.05 (brs, 1H), 7.17 (m, 2H), 6.91 (m, 2H), 5.24 (dd, 1H), 3.63 (dd, 1H), 3.42 (dd, 1H). | [References]
[1] Patent: US2005/54630, 2005, A1. Location in patent: Page/Page column 42
[2] Justus Liebigs Annalen der Chemie, 1883, vol. 216, p. 169
[3] Chemische Berichte, 1906, vol. 39, p. 496
[4] Farmaco, 1998, vol. 53, # 12, p. 764 - 772
[5] Patent: US2008/200540, 2008, A1. Location in patent: Page/Page column 18 |
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