2-Chloro-6-methoxy-1H-benzimidazole

Name: 2-Chloro-6-methoxy-1H-benzimidazole
Brand: ChemScene
Availability: InStock
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CAS No. 15965-54-5
Cat. No. CS-0062004
Purity≥97%
MDL No.None

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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-6-methoxy-1H-benzimidazole|CS-0062004

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General Information

CAS No. 15965-54-5
Cat. No. CS-0062004
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇ClN₂O
Molecular Weight 182.61
Synonym(s) 2-Chloro-5-methoxybenzimidazole
SMILES COC1=CC2=C(C=C1)N=C(Cl)N2

Description

2-Chloro-6-methoxy-1H-benzimidazole integrates a chlorine atom at the 2-position and a methoxy group at the 6-position, conferring enhanced electron-withdrawing character and improved solubility in polar organic solvents. This scaffold serves as a key building block in medicinal chemistry, particularly for targeting kinase pathways and modulating receptor activity.

Application

2-Chloro-6-methoxy-1H-benzimidazole serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its ortho-chloro group exhibits high reactivity in Suzuki, Stille, and Buchwald–Hartwig transformations, while the methoxy substituent enhances solubility and modulates electronic properties. The benzimidazole core provides metabolic stability and favorable binding interactions in target-directed synthesis. This compound offers excellent bench stability, straightforward purification, and compatibility with diverse reaction conditions, making it ideal for rapid scaffold diversification in API development.

Synthesis

Route1
- In-stock
  
  2080-75-3
- ~%
- In-stock
  
  15965-54-5
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 3 p. 719 - 723
Route2
- 102-51-2
- ~%
- In-stock
  
  15965-54-5
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 3 p. 719 - 723

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 37.91
LogP 2.2249
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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2-Chloro-6-methoxy-1H-benzimidazole

CAS No. 15965-54-5

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