Methyl 2-amino-5-bromonicotinate

Name: Methyl 2-amino-5-bromonicotinate
Brand: ChemScene
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CAS No. 50735-34-7
Cat. No. CS-W003197
Purity≥95%
MDL No.MFCD04117787

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Methyl 2-amino-5-bromonicotinate|CS-W003197

Structure of 50735-34-7

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General Information

CAS No. 50735-34-7
Cat. No. CS-W003197
Purity ≥95%
MDL No. MFCD04117787
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₇BrN₂O₂
Molecular Weight 231.05
Synonym(s) Methyl 2-amino-5-bromopyridine-3-carboxylate, 2-Amino-5-bromo-3-(methoxycarbonyl)pyridine
SMILES O=C(C1=CC(Br)=CN=C1N)OC

Description

Methyl 2-amino-5-bromonicotinate features a brominated pyridine core with complementary amino and ester functionalities, enabling direct incorporation into heterocyclic scaffolds. The para-bromine facilitates palladium-catalyzed cross-coupling reactions, while the ortho-amino group offers nucleophilic reactivity for derivatization under mild conditions. This bench-stable intermediate supports efficient access to bioactive nitrogen heterocycles in medicinal chemistry campaigns.

Application

Methyl 2-amino-5-bromonicotinate serves as a versatile building block in medicinal chemistry and synthetic organic chemistry. Its dual functionality—readily oxidizable amine and electrophilic bromide—enables sequential functionalization via Pd-catalyzed cross-coupling, nucleophilic substitution, and directed metalation. The methyl ester group facilitates derivatization or hydrolysis to the corresponding acid, while the ortho-amino and meta-bromo substituents provide orthogonal reactivity for scaffold diversification. This compound exhibits excellent bench stability and is compatible with standard purification techniques, making it ideal for high-throughput synthesis of heterocyclic libraries and API intermediates.

Synthesis

Route1
- In-stock
  
  52833-94-0
- 18107-18-1
- ~%
- In-stock
  
  50735-34-7
References
- AFFINIUM PHARMACEUTICALS, INC. Patent: WO2007/67416 A2, 2007 ; Location in patent: Page/Page column 111 ; WO 2007/067416 A2

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 65.21
LogP 1.2129
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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Methyl 2-amino-5-bromonicotinate

CAS No. 50735-34-7

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