2,5-Dibromo-4-nitro-1H-imidazole

Name: 2,5-Dibromo-4-nitro-1H-imidazole
Brand: ChemScene
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CAS No. 6154-30-9
Cat. No. CS-0060033
Purity≥98%
MDL No.MFCD11877989

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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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2,5-Dibromo-4-nitro-1H-imidazole|CS-0060033

Structure of 6154-30-9

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Description

2,5-Dibromo-4-nitro-1H-imidazole features a rigid imidazole core bearing two bromine substituents and a nitro group at the 4-position, enabling efficient coupling in cross-coupling reactions. The electron-deficient nature of the ring enhances reactivity in palladium-catalyzed transformations, while the bench-stable crystalline form simplifies handling and storage.

Application

2,5-Dibromo-4-nitro-1H-imidazole serves as a versatile building block for heterocyclic synthesis, enabling direct functionalization at C2 and C5 positions via palladium-catalyzed cross-coupling reactions. The nitro group at C4 provides a handle for selective reduction or substitution, while the dibromo substitution pattern ensures high reactivity in iterative coupling sequences. Its bench-stable crystalline form facilitates handling and purification, making it ideal for constructing complex imidazole-based scaffolds in medicinal chemistry and materials science applications.

General Information

CAS No. 6154-30-9
Cat. No. CS-0060033
Purity ≥98%
MDL No. MFCD11877989
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃HBr₂N₃O₂
Molecular Weight 270.87
Synonym(s) 2,4-Dibromo-5-nitro-1H-imidazole
SMILES C1(=C(NC(=N1)Br)[N+](=O)[O-])Br

Computational Chemistry Data

TPSA 71.82
LogP 1.8429
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Safety Information

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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 Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

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2,5-Dibromo-4-nitro-1H-imidazole

CAS No. 6154-30-9

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