| Identification | Back Directory | [Name]
(1H-BENZOIMIDAZOL-2-YL)-ACETIC ACID | [CAS]
13570-08-6 | [Synonyms]
NSC 525202
AKOS BBS-00002502
RARECHEM AK ML 0141
CHEMBRDG-BB 4400292
IFLAB-BB F1727-0259
2-BENZIMIDAZOLEACETIC ACID
Benzimidazole-2-acetic acid
2-Benzimidazolylacetic acid
2-(Carboxymethyl)benzimidazole
1H-Benzimidazole-2-acetic acid
1H-BENZIMIDAZOL-2-YLACETIC ACID
2-(2-Benzoimidazolyl)acetic Acid
Acetic acid, 2-benzimidazol-2-yl-
1H-Benzimidazole-2-aceticacid(9CI)
(1H-BENZOIMIDAZOL-2-YL)-ACETIC ACID
2-(1H-benzimidazol-2-yl)acetic acid
2-(1H-benzimidazol-2-yl)ethanoic acid
2-(1H-benzimidazol-3-ium-2-yl)acetate
2-(1H-benzimidazol-3-ium-2-yl)ethanoate
2-(1H-benzo[d]imidazol-2-yl)acetic acid
2-(1H-1H-benzo[d]iMidazol-2-yl)-acetic acid
1H-benzimidazol-2-ylacetic acid(SALTDATA: FREE) | [Molecular Formula]
C9H8N2O2 | [MDL Number]
MFCD01102656 | [MOL File]
13570-08-6.mol | [Molecular Weight]
176.17 |
| Chemical Properties | Back Directory | [Melting point ]
116 °C | [Boiling point ]
498.3±28.0 °C(Predicted) | [density ]
1.437±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [pka]
1.54±0.30(Predicted) | [Appearance]
Light yellow to light brown Solid |
| Hazard Information | Back Directory | [Uses]
(1h-Benzoimidazol-2-yl)-acetic Acid is a useful intermediate for the synthesis of benzisothiazole/benzimidazole derivatives with acidic groups that exhibits numerous pharmacological properties. | [Synthesis Reference(s)]
Journal of Medicinal Chemistry, 36, p. 1746, 1993 DOI: 10.1021/jm00064a008 | [Synthesis]
General procedure for the synthesis of benzimidazole-2-acetic acid from 2-cyanomethylbenzimidazole: A mixture of 1 g of 2-cyanomethylbenzimidazole (3a-b) with 2 ml of 37% aqueous hydrochloric acid in the presence of 1 ml of benzenesulphonic acid was heated and stirred under reflux conditions for 4-5 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ether (3 x 30 ml), followed by removal of solvent by distillation under reduced pressure to afford the target products benzimidazole-2-acetic acid (4a-b).
4.3.1. 1H-benzimidazole-2-acetic acid (4a, C9H8N2O2) was a green solid, hygroscopic, with a yield of 81% and a melting point of 240-242 °C; TLC Rf value of 0.42 [unfolding reagent ratio of toluene: ethyl acetate: formic acid (5:4:1)]; IR spectra (KBr, cm^-1 ): 3624 (O-H telescoping vibration) 3230 (N-H stretching vibration), 1722 (C=O stretching vibration); 1H NMR (300MHz, DMSO-d6) δ (ppm): 3.64 (single peak, 2H, CH2COOH), 7.58 (double peaks, 2H, J=7.5,0.9Hz, H-5,6 on benzimidazole ring), 7.92 (double peaks, 2H, J=7.5 Hz, H-4,7 on the benzimidazole ring), 10.59 (broad peak, 1H, COOH), 12.03 (broad peak, 1H, NH).13C NMR (75 MHz, DMSO-d6) δ (ppm): 164.20, 152.20, 131.95, 128.32, 122.50, 48.40. Calculated values for elemental analysis (%) : C, 61.36; H, 4.58; N, 15.90; measured values (%): C, 61.33; H, 4.56; N, 15.92. | [References]
[1] Patent: US5792768, 1998, A
[2] Farmaco, 2002, vol. 57, # 5, p. 363 - 367
[3] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 853 - 869
[4] Journal of Medicinal Chemistry, 1993, vol. 36, # 12, p. 1746 - 1753
[5] Patent: WO2017/68089, 2017, A2. Location in patent: Page/Page column 243 |
|
|