| Identification | Back Directory | [Name]
5-Bromo-1H-benzimidazole | [CAS]
4887-88-1 | [Synonyms]
5-BROMOBENZIMIDAZOLE
6-Bromobenzimidazole
6-Bromobenzimidazole>
5-BROMO-1H-BENZIMIDAZOLE
5-BROMO-1H-BENZOIMIDAZOLE
1H-BenziMidazole, 6-broMo-
5-broMo-1H-1,3-benzodiazole
6-BroMo-1H-benziMidazole 97%
5-Bromo-1H-benzimidazole 98%
6-bromo-1H-benzo[d]imidazole
5-BROMO-1H-BENZO[D]IMIDAZOLE
1H-Benzimidazole,5-bromo-(9CI)
6-bromo-1H-benzimidazole(SALTDATA: FREE) | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD00160001 | [MOL File]
4887-88-1.mol | [Molecular Weight]
197.03 |
| Chemical Properties | Back Directory | [Melting point ]
130 °C | [Boiling point ]
417.4±18.0 °C(Predicted) | [density ]
1.770±0.06 g/cm3(Predicted) | [storage temp. ]
Room temperature. | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
11.19±0.30(Predicted) | [color ]
White to Yellow to Orange | [InChI]
InChI=1S/C7H5BrN2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,(H,9,10) | [InChIKey]
GEDVWGDBMPJNEV-UHFFFAOYSA-N | [SMILES]
C1NC2=CC(Br)=CC=C2N=1 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white powder | [Uses]
5-Bromo-1H-benzimidazole is a key intermediate in the synthesis of various organic compounds, especially in the fields of medicine and chemical research. | [Synthesis]
Step 87a: Synthesis of tert-butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate (compound 0601-187)
To a solution of 4-bromo-1,2-benzenediamine (3 g, 16 mmol) in N,N-dimethylformamide (DMF, 22 mL) was added trimethyl orthoformate (44 mL), which was subsequently concentrated. Concentrated hydrochloric acid (1.5 mL) was added and the reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was diluted with deionized water (200 mL) and the pH was adjusted to 7 with saturated aqueous sodium bicarbonate. the reaction mixture was extracted with ethyl acetate (200 mL) and the organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 5-bromo-1H-benzo[d]imidazole (3.25 g, 100%) as an off-white solid. lc-MS (mass spectrum): m/z 197 [M + H]+. 1H NMR (400 MHz, DMSO-d6) δ 7.33 (t, J = 8.8 Hz, 1H), 7.55 (dd, J1 = 7.6 Hz, J2 = 40 Hz, 1H), 7.79 (d, J = 47.2 Hz, 1H), 8.26 (s, 1H), 12.61 (d, J = 25.6 Hz, 1H ). | [References]
[1] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 228
[2] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0580; 0581
[3] Patent: JP2015/187145, 2015, A. Location in patent: Paragraph 0493
[4] Patent: US2009/326029, 2009, A1. Location in patent: Page/Page column 33 |
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