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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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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