2-Chloro-7-nitro-1H-benzo[d]imidazole

Name: 2-Chloro-7-nitro-1H-benzo[d]imidazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 15965-55-6
Cat. No. CS-0155821
Purity≥98%
MDL No.MFCD22562504

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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-Chloro-7-nitro-1H-benzo[d]imidazole|CS-0155821

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General Information

CAS No. 15965-55-6
Cat. No. CS-0155821
Purity ≥98%
MDL No. MFCD22562504
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₄ClN₃O₂
Molecular Weight 197.58
Synonym(s) 2-Chloro-4-nitro-1H-benzimidazole
SMILES C1=CC2=C(C(=C1)[N+](=O)[O-])NC(=N2)Cl

Description

2-Chloro-7-nitro-1H-benzo[d]imidazole features a fused bicyclic core with complementary electron-deficient character, enabling efficient coupling in cross-coupling transformations. The ortho-chloro and para-nitro substituents provide orthogonal reactivity for sequential functionalization, while the bench-stable imidazole scaffold ensures reliable handling under standard conditions.

Application

2-Chloro-7-nitro-1H-benzo[d]imidazole serves as a versatile building block in heterocyclic synthesis, enabling efficient construction of bioactive scaffolds. Its orthogonal functionalization profile—combining electrophilic chlorine and strongly electron-withdrawing nitro groups—facilitates palladium-catalyzed cross-coupling and directed metallation. The compound exhibits excellent bench stability and compatibility with standard purification protocols, making it well-suited for medicinal chemistry campaigns and process-scale applications.

Synthesis

Route1
- In-stock
  
  85330-50-3
- ~%
- In-stock
  
  15965-55-6
References
- ACESION PHARMA ApS; SØRENSEN, Ulrik, Svane; GRUNNET, Morten; BENTZEN, Bo, Hjorth; CHRISTOPHERSEN, Palle; DINESS, Jonas, Goldin; SKIBSBYE, Lasse; STRØBÆK, Dorte Patent: WO2013/104577 A1, 2013 ; Location in patent: Page/Page column 14-15; 17-18 ;
Route2
- In-stock
  
  3694-52-8
- ~%
- In-stock
  
  15965-55-6
References
- ACESION PHARMA ApS; SØRENSEN, Ulrik, Svane; GRUNNET, Morten; BENTZEN, Bo, Hjorth; CHRISTOPHERSEN, Palle; DINESS, Jonas, Goldin; SKIBSBYE, Lasse; STRØBÆK, Dorte Patent: WO2013/104577 A1, 2013 ;

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

Quality Control

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Computational Chemistry Data

TPSA 71.82
LogP 2.1245
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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2-Chloro-7-nitro-1H-benzo[d]imidazole

CAS No. 15965-55-6

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