5-Bromo-3-methylpyrazin-2-amine

Name: 5-Bromo-3-methylpyrazin-2-amine
Brand: ChemScene
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CAS No. 74290-67-8
Cat. No. CS-W019817
Purity≥96%
MDL No.MFCD08705773

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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+
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5-Bromo-3-methylpyrazin-2-amine|CS-W019817

Structure of 74290-67-8

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General Information

CAS No. 74290-67-8
Cat. No. CS-W019817
Purity ≥96%
MDL No. MFCD08705773
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₆BrN₃
Molecular Weight 188.03
Synonym(s) 5-Bromo-3-methyl-2-pyrazinamine; 2-Amino-5-bromo-3-methylpyrazine; 5-Bromo-3-methylpyrazin-2-amine; 5-BROMO-3-METHYLPYRAZIN-2-YLAMINE
SMILES NC1=NC=C(Br)N=C1C

Description

5-Bromo-3-methylpyrazin-2-amine features a bromine substituent at the 5-position and a methyl group at the 3-position on a pyrazine core, enabling selective functionalization in heterocyclic synthesis. This electron-deficient scaffold integrates readily into pharmaceutical intermediates and ligand frameworks, offering enhanced reactivity in palladium-catalyzed couplings.

Application

5-Bromo-3-methylpyrazin-2-amine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its bromine substituent. The pyrazine core provides a rigid, electron-deficient heterocyclic scaffold with enhanced metabolic stability. Its methyl and amino groups offer orthogonal functionalization sites, facilitating downstream derivatization. The compound exhibits good bench stability and is compatible with standard purification techniques, making it well-suited for iterative synthesis campaigns in API development.

Synthesis

Route1
- In-stock
  
  19838-08-5
- ~82%
- In-stock
  
  74290-67-8
References
- Sato, Nobuhiro Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 143 - 147

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 51.8
LogP 1.12972
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazine compounds

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5-Bromo-3-methylpyrazin-2-amine

CAS No. 74290-67-8

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