592277

Sigma-Aldrich

2-Chlorobenzimidazole

98%

Empirical Formula (Hill Notation):
C7H5ClN2
CAS Number:
Molecular Weight:
152.58
EC Number:
MDL number:
eCl@ss:
32151902
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

207-211 °C (lit.)

SMILES string

Clc1nc2ccccc2[nH]1

InChI

1S/C7H5ClN2/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H,(H,9,10)

InChI key

AYPSHJCKSDNETA-UHFFFAOYSA-N

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General description

2-Chlorobenzimidazole can be synthesized by reacting benzimidazole-2-one with phosphoryl chloride in the presence of phenol.

Application

2-Chlorobenzimidazole can be used to synthesize the following:
  • 1-methyl-2-chlorobenzimidazole via reaction with dimethyl sulfate
  • 1-ethyl-2-chlorobenzimidazole via reaction with diethyl sulfate
  • 1-benzyl-2-chlorobenzimidazole via reaction with benzyl chloride
  • 2-chloro-4,5,6,7-tetrabromobenzimidazole via bromination with bromine
It may be used as a building block to synthesize 4-amino-6-benzimidazole-pyrimidines.

Packaging

5, 25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

?Polyhalogenobenzimidazoles: Synthesis and Their InhibitoryActivity against Casein Kinases?
Andrzejewska M, et al.
Bioorganic & Medicinal Chemistry, 11(18), 3997- 4002 (2003)
?Discovery of pyrimidine benzimidazoles as Src-family selective Lck inhibitors. Part II?
Zhang G, et al.
Bioorganic & Medicinal Chemistry, 19(23), 6691-6695 (2009)
?A facile and green synthesis of N-substituted-2-chlorobenzimidazoles?
Rao S.S, et al.
Der Pharma Chemica, 5(06), 69- 72 (2013)

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