2-Bromo-4-nitroimidazole

Name: 2-Bromo-4-nitroimidazole
Brand: ChemScene
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CAS No. 65902-59-2
Cat. No. CS-D0919
Purity≥97%
MDL No.MFCD09038915

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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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Description

2-Bromo-4-nitroimidazole is a halogenated imidazole featuring a nitro group at the para position, offering enhanced electrophilicity and stability under standard conditions. This electron-deficient heterocycle facilitates selective coupling reactions in synthetic medicinal chemistry and serves as a key intermediate for bioactive compound development.

Application

2-Bromo-4-nitroimidazole serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the 2-position via palladium-catalyzed cross-coupling reactions. Its bromine moiety exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the nitro group provides strong electron-withdrawing character that stabilizes adjacent intermediates. The compound demonstrates excellent bench stability and facilitates efficient purification, making it well-suited for iterative synthesis of bioactive imidazole derivatives and pharmaceutical scaffolds.

General Information

CAS No. 65902-59-2
Cat. No. CS-D0919
Purity ≥97%
MDL No. MFCD09038915
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃H₂BrN₃O₂
Molecular Weight 191.97
Synonym(s) 2-Bromo-5-nitro-1H-imidazole
SMILES O=[N+](C1=CNC(Br)=N1)[O-]

Computational Chemistry Data

TPSA 71.82
LogP 1.0804
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
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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2-Bromo-4-nitroimidazole

CAS No. 65902-59-2

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