2-Chloro-5-iodo-1H-benzo[d]imidazole

Name: 2-Chloro-5-iodo-1H-benzo[d]imidazole
Brand: ChemScene
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CAS No. 256518-97-5
Cat. No. CS-0039519
Molecule weight278.48
Purity≥95%
MDL No.MFCD11044655

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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+
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2-Chloro-5-iodo-1H-benzo[d]imidazole|CS-0039519

Structure of 256518-97-5

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General Information

CAS No. 256518-97-5
Cat. No. CS-0039519
Purity ≥95%
MDL No. MFCD11044655
Storage -20°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄ClIN₂
Molecular Weight 278.48
Synonym(s) 1H-BENZIMIDAZOLE, 2-CHLORO-5-IODO-
SMILES IC1=CC=C2N=C(Cl)NC2=C1

Description

2-Chloro-5-iodo-1H-benzo[d]imidazole features a fused bicyclic core with orthogonal halogen substituents enabling selective cross-coupling. The electron-deficient imidazole ring facilitates palladium-catalyzed reactions, while the chlorine and iodine positions allow sequential functionalization. This scaffold delivers high reactivity under standard coupling conditions, offering efficient access to complex heterocyclic architectures in medicinal chemistry and materials science applications.

Application

2-Chloro-5-iodo-1H-benzo[d]imidazole serves as a versatile building block for heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The chloro and iodo substituents allow sequential functionalization, with the iodo group exhibiting high reactivity in Suzuki, Stille, and Negishi couplings. Bench-stable and readily purified by recrystallization, it functions effectively in constructing biologically relevant imidazole scaffolds under standard reaction conditions.

Synthesis

Route1
- 40644-14-2
- ~%
- In-stock
  
  256518-97-5
References
- US6166011 A1, ;
Route2
- In-stock
  
  256519-10-5
- ~%
- In-stock
  
  256519-11-6
- In-stock
  
  256518-97-5
References
- US6166011 A1, ;

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 28.68
LogP 2.8209
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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2-Chloro-5-iodo-1H-benzo[d]imidazole

CAS No. 256518-97-5

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