6-Bromo-1H-benzimidazol-2-amine

Name: 6-Bromo-1H-benzimidazol-2-amine
Brand: ChemScene
Availability: InStock
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CAS No. 791595-74-9
Cat. No. CS-B1190
Purity≥96%
MDL No.MFCD06659788

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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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6-Bromo-1H-benzimidazol-2-amine|CS-B1190

Structure of 791595-74-9

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General Information

CAS No. 791595-74-9
Cat. No. CS-B1190
Purity ≥96%
MDL No. MFCD06659788
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₆BrN₃
Molecular Weight 212.05
Synonym(s) 2-Amino-5-bromobenzimidazole; 5-Bromo-1H-benzimidazol-2-amine; 5-Bromo-1H-benzo[d]imidazol-2-amine; 6-bromo-1H-benzo[d]imidazol-2-amine
SMILES NC1=NC2=CC=C(Br)C=C2N1

Description

6-Bromo-1H-benzimidazol-2-amine features a bromine substituent at the 6-position and an amino group at the 2-position of the benzimidazole core, enabling direct functionalization in C–N coupling reactions. This electron-deficient heterocycle integrates readily into bioactive scaffolds and serves as a key intermediate in medicinal chemistry and materials synthesis.

Application

6-Bromo-1H-benzimidazol-2-amine serves as a versatile building block for the synthesis of bioactive heterocycles, enabling direct functionalization at the 2-position via palladium-catalyzed cross-coupling reactions. Its bromine substituent provides high reactivity in Suzuki, Stille, and Negishi transformations, while the primary amine facilitates derivatization or incorporation into peptide-like scaffolds. The compound exhibits excellent bench stability and is readily purified by recrystallization, making it ideal for iterative medicinal chemistry campaigns and API intermediate development.

Synthesis

Route1
- 506-68-3
- In-stock
  
  1575-37-7
- ~92%
- In-stock
  
  791595-74-9
References
- BLACKWELL, Helen; Frei, Reto; Breitbach, Anthony; Lynn, David M.; Broderick, Adam H. Patent: US2013/136782 A1, 2013 ; Location in patent: Paragraph 0216; 0217 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06,GHS08
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335-H361
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

TPSA 54.7
LogP 1.9076
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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6-Bromo-1H-benzimidazol-2-amine

CAS No. 791595-74-9

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