Skip to Content
Merck
All Photos(3)

Documents

733520

Sigma-Aldrich

1-Cyanobenzimidazole

96%

Synonym(s):

N-Cyanobenzimidazole

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C8H5N3
CAS Number:
31892-41-8
Molecular Weight:
143.15
MDL number:
MFCD18252669
UNSPSC Code:
12352005
PubChem Substance ID:
329764825
NACRES:
NA.22

Quality Level

100

Assay

96%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

98-106 °C

SMILES string

N#Cn1cnc2ccccc12

InChI

1S/C8H5N3/c9-5-11-6-10-7-3-1-2-4-8(7)11/h1-4,6H

InChI key

SGCJHVTWXFWDOD-UHFFFAOYSA-N

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

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H315,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
1H-Benzimidazole-1-carbohydrazonamide
Sokolov AV, et al.
Acta Crystallographica Section E, Structure Reports Online, 62(8), o3209-o3210 (2006)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service