| Identification | More | [Name]
4-Azabenzimidazole | [CAS]
273-21-2 | [Synonyms]
1 H-IMIDAZO[4,5-B]PYRIDINE
4-AZABENZIMIDAZOLE
TIMTEC-BB SBB004292
1-deazapurine
3,4-diazaindole
7-azabenzimidazole
pyrido(2,3-d)imidazole
4-AZABENZIMIDAZOLE 99%
Imidazo(4,5-b)pyridine
4-Aza-1H-benzimidazole
4H-Imidazo[4,5-b]pyridine | [EINECS(EC#)]
205-987-3 | [Molecular Formula]
C6H5N3 | [MDL Number]
MFCD00005579 | [Molecular Weight]
119.12 | [MOL File]
273-21-2.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to light brown powder | [Melting point ]
148-151 °C (lit.) | [Boiling point ]
140-150°C/0.1mm | [density ]
1.2058 (rough estimate) | [refractive index ]
1.5589 (estimate) | [Fp ]
140-150°C/0.1mm | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Soluble in dimethylformamide. | [form ]
powder | [pka]
8.46±0.20(Predicted) | [BRN ]
2600 | [InChI]
1S/C6H5N3/c1-2-5-6(7-3-1)9-4-8-5/h1-4H,(H,7,8,9) | [InChIKey]
GAMYYCRTACQSBR-UHFFFAOYSA-N | [SMILES]
c1cnc2nc[nH]c2c1 | [CAS DataBase Reference]
273-21-2(CAS DataBase Reference) | [EPA Substance Registry System]
273-21-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
NJ5108000
| [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
mouse,LD50,intraperitoneal,> 200mg/kg (200mg/kg),Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963. |
| Hazard Information | Back Directory | [Chemical Properties]
yellow to light brown powder | [Uses]
4-Azabenzimidazole is used in the preparation of imidazo[4,5-b]pyridine 4-oxide. It is also used as a reagent to prepare benzoylmethyl-substituted azoles which are inhibitors of nitric oxide synthase with antioxidant properties. | [Definition]
ChEBI: The [4,5-b]-fused isomer of imidazopyridine. | [Synthesis]
The general procedure for the synthesis of 4-azabenzimidazole from 2,3-diaminopyridine and triethyl orthoformate was as follows: to evaluate the catalytic performance of different γ-Fe2O3@SiO2-HA catalysts, a catalytic amount of γ-Fe2O3@SiO2-HA (2.5 mol%) was added to a glass flask containing 1.2 mmol of triethyl orthoformate and stirred at room temperature for 15 minutes. Subsequently, 2 mmol of 2,3-diaminopyridine was added to the reaction mixture and the reaction was continued until a predetermined time was reached. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a solvent mixture of hexane and ethyl acetate (ratio 4:1 or 7:3 for diamines). Upon completion of the reaction, 5 mL of dichloromethane (ethyl acetate was used for entries 8 and 9) was added to the mixture, followed by separation of the catalyst by an external magnet for subsequent use. Finally, the resulting solution was concentrated on a rotary evaporator to give the purified 4-azabenzimidazole solid product. | [References]
[1] Asian Journal of Chemistry, 2013, vol. 25, # 6, p. 3446 - 3448
[2] Journal of Molecular Structure, 2012, vol. 1027, p. 156 - 161 |
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