2-Chloro-5-nitro-1H-imidazole

Name: 2-Chloro-5-nitro-1H-imidazole
Brand: ChemScene
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CAS No. 57531-37-0
Cat. No. CS-W018201
Purity≥97%
MDL No.MFCD08705680

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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+
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2-Chloro-5-nitro-1H-imidazole|CS-W018201

Structure of 57531-37-0

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Description

2-chloro-5-nitro-1H-imidazole features a fused five-membered ring bearing chlorine and nitro groups at adjacent positions, conferring high electrophilicity and stability under standard conditions. This configuration enables direct coupling in cross-coupling reactions and facilitates incorporation into bioactive scaffolds requiring electron-deficient heterocycles.

Application

2-Chloro-5-nitro-1H-imidazole serves as a versatile building block for the synthesis of functionalized imidazole scaffolds, enabling direct substitution at C2 and electrophilic functionalization at C4. Its dual electron-withdrawing groups enhance regioselective reactivity in palladium-catalyzed couplings and nucleophilic aromatic substitution reactions. The compound exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and API intermediate development.

General Information

CAS No. 57531-37-0
Cat. No. CS-W018201
Purity ≥97%
MDL No. MFCD08705680
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃H₂ClN₃O₂
Molecular Weight 147.52
Synonym(s) 2-Chloro-4-nitro-1H-imidazole
SMILES O=[N+](C1=CN=C(Cl)N1)[O-]

Computational Chemistry Data

TPSA 71.82
LogP 0.9713
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

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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Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

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2-Chloro-5-nitro-1H-imidazole

CAS No. 57531-37-0

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