5-Bromo-4-chloro-3-nitropyridin-2-amine

Name: 5-Bromo-4-chloro-3-nitropyridin-2-amine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 942947-95-7
Cat. No. CS-0019371
Purity≥95%
MDL No.MFCD11110693

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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+
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5-Bromo-4-chloro-3-nitropyridin-2-amine|CS-0019371

Structure of 942947-95-7

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General Information

CAS No. 942947-95-7
Cat. No. CS-0019371
Purity ≥95%
MDL No. MFCD11110693
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₃BrClN₃O₂
Molecular Weight 252.45
Synonym(s) 2-Amino-5-bromo-4-chloro-3-nitropyridine; 5-Bromo-4-chloro-3-nitropyridin-2-amine; 5-Bromo-4-chloro-3-nitro-pyridin-2-ylamine
SMILES NC1=NC=C(Br)C(Cl)=C1[N+]([O-])=O

Description

5-Bromo-4-chloro-3-nitropyridin-2-amine features a densely functionalized pyridine core with bromo, chloro, and nitro groups positioned for orthogonal reactivity. This electron-deficient heterocycle enables selective cross-coupling and nucleophilic substitution under standard conditions, serving as a key intermediate in the synthesis of advanced pharmaceuticals and agrochemicals.

Application

5-Bromo-4-chloro-3-nitropyridin-2-amine serves as a versatile building block in heterocyclic synthesis, enabling sequential functionalization via cross-coupling and nucleophilic substitution. The nitro group facilitates reduction to an amine for further derivatization, while the bromo and chloro substituents support palladium-catalyzed coupling reactions. Its bench-stable nature and orthogonal reactivity profile make it well-suited for modular assembly of complex pyridine-based scaffolds in medicinal chemistry and agrochemical research.

Synthesis

Route1
- In-stock
  
  6980-08-1
- ~86%
- In-stock
  
  942947-95-7
References
- CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon Patent: WO2013/190320 A1, 2013 ; Location in patent: Paragraph 00119 ;
Route2
- In-stock
  
  942947-94-6
- ~%
- In-stock
  
  942947-95-7
References
- US2009/247507 A1, ; Page/Page column 8 ;
Route3
- In-stock
  
  19798-80-2
- ~%
- In-stock
  
  942947-95-7
References
- Journal of Medicinal Chemistry, , vol. 55, # 20 p. 8721 - 8734,14 Journal of Medicinal Chemistry, , vol. 55, # 20 p. 8721 - 8734

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 82.05
LogP 1.9879
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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5-Bromo-4-chloro-3-nitropyridin-2-amine

CAS No. 942947-95-7

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