2-Chloro-1-methyl-1H-imidazole

Name: 2-Chloro-1-methyl-1H-imidazole
Brand: ChemScene
Availability: InStock
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CAS No. 253453-91-7
Cat. No. CS-0101166
Purity≥98%
MDL No.MFCD02179531

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2-Chloro-1-methyl-1H-imidazole|CS-0101166

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General Information

CAS No. 253453-91-7
Cat. No. CS-0101166
Purity ≥98%
MDL No. MFCD02179531
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₅ClN₂
Molecular Weight 116.55
Synonym(s) Azathioprine Impurity 10
SMILES CN1C=CN=C1Cl

Description

2-Chloro-1-methyl-1H-imidazole is a bench-stable, moisture-tolerant heterocyclic reagent featuring a reactive chlorine atom at the 2-position. This electrophilic site enables efficient coupling in nucleophilic substitution reactions, particularly in the synthesis of imidazolium salts and functionalized pharmaceutical intermediates. The methyl group enhances solubility in polar organic solvents while stabilizing the imidazole core under standard handling conditions.

Application

2-Chloro-1-methyl-1H-imidazole serves as a versatile electrophilic imidazole reagent, enabling efficient N-alkylation and heterocycle functionalization under mild conditions. Its bench-stable nature and compatibility with diverse nucleophiles facilitate rapid access to substituted imidazoles, making it a practical building block for medicinal chemistry and catalytic synthesis workflows.

Synthesis

Route1
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- ~81%
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References
- Jones, Todd K.; Mani, Neelakandha Patent: US2005/250948 A1, 2005 ; Location in patent: Page/Page column 41 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 17.82
LogP 1.0735
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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2-Chloro-1-methyl-1H-imidazole

CAS No. 253453-91-7

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