| Identification | More | [Name]
2-AMINO-5-NITRO-1H-BENZIMIDAZOLE | [CAS]
6232-92-4 | [Synonyms]
2-AMINO-5-NITRO-1H-BENZIMIDAZOLE
2-AMINO-6-NITROBENZIMIDAZOLE
1H-Benzimidazol-2-amine,5-nitro-(9CI)
2-Amino-5-nitro-benzimidazole
2-amine-5-nitro-1H-benzimidazole | [Molecular Formula]
C7H6N4O2 | [MDL Number]
MFCD06659794 | [Molecular Weight]
178.15 | [MOL File]
6232-92-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
222-223 °C (decomp) | [Boiling point ]
478.5±37.0 °C(Predicted) | [density ]
1.631±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
9.63±0.10(Predicted) | [color ]
White to Yellow to Orange | [CAS DataBase Reference]
6232-92-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Synthesis]
4-Nitrophthalimide (1.4 g, 9.1 mmol) was suspended in an aqueous solution (30 mL) of cyanogen bromide (0.97 g, 9.2 mmol) and heated to reflux for 7 hr. Upon completion of the reaction, the reaction mixture was cooled and neutralized with 25% NH4OH solution to pH 10-11. Subsequently, the precipitate formed was collected by filtration, washed with water, dried over air, and finally recrystallized from hot water to give 2-amino-6-nitrobenzimidazole as orange-yellow shiny crystals. Yield: 1.28 g (91.4%); Melting point: 245-247 °C. 1H NMR (400 MHz, DMSO-d6, δ ppm): 8.10 (d, 1H, J = 2.2 Hz, ArH), 7.90 (dd, 1H, J = 8.70, 2.2 Hz, ArH), 7.20 (d, 1H, J = 8.7 Hz, ArH). 6.90 (s, 2H, NH2). 13C NMR (400 MHz, DMSO-d6, δ ppm): 158.91, 139.92, 136.67, 116.50, 111.16, 106.16. IR (KBr, cm-1): 3514, 3457 (NH stretching vibration), 3092 (aromatic CH stretching vibration), 1658 (C=NH stretching vibration), 1658 (C=NH stretching vibration). ), 1658 (C=N ring stretching vibration), 1587, 1507 (skeletal vibrational bands), 1421 (asymmetric N=O stretching vibration), 1471 (NH shear vibration), 1336 (symmetric N=O stretching vibration), 876 (NH wobble vibration).MS (+ESI-QTOF): m/z calculated value C7H6N4O2 [M+H]+ 179.14, measured value 179.1 (100%). | [References]
[1] European Journal of Medicinal Chemistry, 1990, vol. 25, # 4, p. 309 - 319
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 663 - 674
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 21, p. 5226 - 5229
[4] Bioorganic Chemistry, 2018, vol. 80, p. 24 - 35
[5] Patent: EP1674466, 2006, A1. Location in patent: Page/Page column 25 |
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