733520
1-Cyanobenzimidazole
96%
Synonym(s):
N-Cyanobenzimidazole
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About This Item
Empirical Formula (Hill Notation):
C8H5N3
CAS Number:
Molecular Weight:
143.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
96%
Form:
solid
InChI
1S/C8H5N3/c9-5-11-6-10-7-3-1-2-4-8(7)11/h1-4,6H
SMILES string
N#Cn1cnc2ccccc12
InChI key
SGCJHVTWXFWDOD-UHFFFAOYSA-N
assay
96%
form
solid
reaction suitability
reaction type: C-C Bond Formation
mp
98-106 °C
Quality Level
Related Categories
Application
1-Cyanobenzimidazole can be used:
- To prepare alkyl benzimidazole-1-carboximidates and 1H-benzimidazole-1-carbohydrazonamide by reacting with aliphatic alcohols and excess of hydrazine, respectively.
- As an electrophilic cyanating reagent in cyanation reactions including aryl and heteroaryl Grignard reagents.
Reacant for:
- Electrophilic aromatic substitution reactions
- Electrophilic cyanation of aryl and heteroaryl Grignard reagents
- Hydrolysis in alkalyne solutions
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Transnitrilation from dimethylmalononitrile to aryl grignard and lithium reagents: A practical method for aryl nitrile synthesis
Reeves JT, et al.
Journal of the American Chemical Society, 137(29), 9481-9488 (2015)
1H-Benzimidazole-1-carbohydrazonamide
Sokolov AV, et al.
Acta Crystallographica Section E, Structure Reports Online, 62(8), o3209-o3210 (2006)
New strategies and applications using electrophilic cyanide-transfer reagents under transition metal-free conditions
Schorgenhumer J and Waser M
Organic Chemistry Frontiers : An International Journal of Organic Chemistry / Royal Society of Chemistry, 3(11), 1535-1540 (2016)
A Convenient Synthesis of Benzonitriles via Electrophilic Cyanation with N-Cyanobenzimidazole
Anbarasan P, et al.
Chemistry?A European Journal , 16(16), 4725-4728 (2010)
Reactions of 1-cyanoimidazole and 1-cyanobenzimidazole with aliphatic alcohols
Purygin PP, et al.
Russ. J. Gen. Chem., 72(8), 1286-1288 (2002)
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