Basic information
- Standard SMILES
c1cnc2nc[nH]c2c1- InChIKey
GAMYYCRTACQSBR-UHFFFAOYSA-N- Molecular formula
- C6H5N3
- Average molar mass
- 119.12 g/mol
- Monoisotopic mass
- 119.04834716
Overview
4-azabenzimidazole is the [4,5-b]-fused isomer of imidazopyridine.
Names & identifiers
- Preferred name
- Imidazo(4,5-b)pyridine
- IUPAC
- 1H-imidazo[4,5-b]pyridine
- English name
- 4-Azabenzimidazole
- Molecular formula
- C6H5N3
- Molecular weight
- 119.12
Names & synonyms
1H-Imidazo[4,5-b]pyridine273-21-21-Deazapurine3,4-Diazaindole7-Azabenzimidazole1H-Imidazo(4,5-b)pyridineImidazo(4,5-b)pyridineImidazo[4,5-b]pyridineDTXSID9075375RefChem:79746DTXCID0037653205-987-3
Show more names
PBTFL44TIMTEC-BB SBB0042924-AZABENZIMIDAZOLE 99%
3H-Imidazo[4,5-b]pyridine4-Azabenzimidazole170245-18-84H-Imidazo[4,5-b]pyridine170245-19-9imidazopyridinePyrido(2,3-d)imidazoleazabenzimidazole
Database identifiers
- CAS
273-21-2- PubChem CID
- 67504
- DTXSID
DTXSID9075375- ChEMBL
CHEMBL4476663- ChEBI
CHEBI:59952- EC Number
- 205-987-3
- Nikkaji
- J193.696D
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 41.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 104
Experimental & physicochemical properties
LogP0.3
Physicochemical properties
- Melting point
- 148 · 148-151 °C (lit.)
- Boiling point
- 140 · 140-150°C/0.1mm
- Density
- 1.2058 · 1.2058 (rough estimate)
- refractive index
- 1.5589 · 1.5589 (estimate)
- Flash point
- 140 · 140-150°C/0.1mm
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Soluble in dimethylformamide.
- form
- powder
- pka
- 8.46 · 8.46±0.20(Predicted)
- Appearance
- Off-white to light brown Solid
- BRN
- 2600 · 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 · 273-21-2(CAS DataBase Reference)
- EPA Substance Registry System
- 1 H-Imidazo[4,5-b]pyridine · 1H-Imidazo[4,5-b]pyridine (273-21-2)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- RTECS
- 5108000 · NJ5108000
- HS Code
- 2933998090 · 2933998090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 · mouse,LD50,intraperitoneal,> 200mg/kg (200mg/kg),Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963.
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (98.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 69 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information1H-Imidazo4,5-bpyridine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (98.6%)
Safety data
- wgk
- 3
- rtecs
- NJ5108000
- hs_code
- 2933998090
- Toxicity
- mouse,LD50,intraperitoneal,> 200mg/kg (200mg/kg),Journal of Medicinal Chemistry. Vol. 6, Pg. 480, 1963.
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Uses4-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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: The [4,5-b]-fused isomer of imidazopyridine.
Related reactions
30 records
Linked notes
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