2-(Aminomethyl)-4-bromoaniline

Name: 2-(Aminomethyl)-4-bromoaniline
Brand: ChemScene
Availability: InStock
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CAS No. 771583-12-1
Cat. No. CS-0188432
Purity≥98%
MDL No.None

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2-(Aminomethyl)-4-bromoaniline|CS-0188432

Structure of 771583-12-1

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General Information

CAS No. 771583-12-1
Cat. No. CS-0188432
Purity ≥98%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₉BrN₂
Molecular Weight 201.06
Synonym(s) 2-AMinoMethyl-4-broMophenylaMine
SMILES C1=C(C=C(CN)C(=C1)N)Br

Description

2-(Aminomethyl)-4-bromoaniline serves as a key bifunctional building block for conjugate addition and amide coupling reactions. The pendant primary amine enables direct derivatization, while the bromo group facilitates transition-metal-catalyzed cross-coupling. This dual functionality supports rapid assembly of complex architectures in medicinal chemistry and materials science.

Application

2-(Aminomethyl)-4-bromoaniline serves as a versatile building block in medicinal chemistry, enabling the construction of substituted anilines and heterocyclic scaffolds. Its ortho-bromo and primary amine functionalities offer orthogonal reactivity for cross-coupling, nucleophilic substitution, and cyclization reactions. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis and process development workflows.

Synthesis

Route1
- In-stock
  
  39263-32-6
- ~83%
- In-stock
  
  771583-12-1
References
- Primik, Michael F.; Goeschl, Simone; Jakupec, Michael A.; Roller, Alexander; Keppler, Bernhard K.; Arion, Vladimir B. Inorganic Chemistry, 2010 , vol. 49, # 23 p. 11084 - 11095

Safety Information

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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 52.04
LogP 1.49
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2-(Aminomethyl)-4-bromoaniline

CAS No. 771583-12-1

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