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Sigma-Aldrich

2-Chlorobenzimidazole

98%

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About This Item

Empirical Formula (Hill Notation):
C7H5ClN2
CAS Number:
4857-06-1
Molecular Weight:
152.58
EC Number:
225-453-3
MDL number:
MFCD00051944
UNSPSC Code:
12352100
eCl@ss:
32151902
PubChem Substance ID:
24881379
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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’.

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?A facile and green synthesis of N-substituted-2-chlorobenzimidazoles?
Rao S.S, et al.
Der Pharma Chemica, 5(06), 69- 72 (2013)
?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)

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