6-Iodo-1H-benzo[d]imidazole

Name: 6-Iodo-1H-benzo[d]imidazole
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CAS No. 78597-27-0
Cat. No. CS-W006895
Molecule weight244.03
Purity≥97%
MDL No.MFCD13185224

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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General Information

CAS No. 78597-27-0
Cat. No. CS-W006895
Purity ≥97%
MDL No. MFCD13185224
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅IN₂
Molecular Weight 244.03
Synonym(s) 5-IODO-1H-BENZIMIDAZOLE
SMILES IC1=CC2=C(C=C1)N=CN2

Description

6-Iodo-1H-benzo[d]imidazole features a reactive iodine handle at the 6-position, enabling efficient coupling in cross-coupling reactions. The imidazole core provides a rigid, electron-rich platform ideal for medicinal chemistry and materials applications. This bench-stable compound integrates readily into complex molecular architectures under standard conditions.

Application

6-Iodo-1H-benzo[d]imidazole serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for the construction of biaryl scaffolds. Its iodine moiety facilitates efficient functionalization under standard Suzuki, Stille, or Negishi conditions, while the imidazole core provides moderate basicity and hydrogen-bonding capability. The compound exhibits good bench stability and is readily purified by crystallization or flash chromatography, making it well-suited for iterative synthesis workflows and API intermediate development.

Synthesis

Route1
- 64-18-6
- In-stock
  
  20691-72-9
- ~87%
- In-stock
  
  78597-27-0
References
- Hanan, Emily J.; Chan, Bryan K.; Estrada, Anthony A.; Shore, Daniel G.; Lyssikatos, Joseph P. Synlett, 2010 , # 18 p. 2759 - 2764

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 28.68
LogP 2.1675
H_Acceptors 1
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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6-Iodo-1H-benzo[d]imidazole

CAS No. 78597-27-0

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