2-Amino-3-bromo-5-chloropyridine Chemical Properties

Melting point:

82-83°C

Boiling point:

256.2±35.0 °C(Predicted)

Density 

1.834±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Crystalline Powder

pka

1.91±0.49(Predicted)

color 

White to light brown

InChI

InChI=1S/C5H4BrClN2/c6-4-1-3(7)2-9-5(4)8/h1-2H,(H2,8,9)

InChIKey

UWGGGYYCKDCTGN-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Cl)C=C1Br

CAS DataBase Reference

26163-03-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22-21/22

Safety Statements 

26-36/37/39-39-36/37

RIDADR 

UN2811

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29333990

2-Amino-3-bromo-5-chloropyridine Usage And Synthesis

Uses

2-Amino-3-bromo-5-chloropyridine has a wide range of applications, including the synthesis of resins, surfactants, plastics, rubber, leather, papermaking, dyes, pharmaceuticals, pesticides, photographic film, explosives, building materials, and in disinfection, fumigation, and preservation processes. Furthermore, 2-amino-3-bromo-5-chloropyridine can be used as a basic organic chemical raw material and a high-quality fuel, primarily in the fields of fine chemicals and plastics.

Chemical Properties

Cream powder

Synthesis Reference(s)

Tetrahedron, 51, p. 8649, 1995 DOI: 10.1016/0040-4020(95)00478-Q

Synthesis

General procedure for the synthesis of 2-amino-3-bromo-5-chloropyridine from 2-amino-5-chloropyridine: In a 50L round bottom three-necked flask, a mixed solvent of DMF and ethanol (1:1.8 by volume, total 18.7L) was added, a thermometer and a reflux condenser were installed, and a magnetic stirrer was started. Sequentially, 4986.6 g of 2-amino-5-chloropyridine and 17336.3 g of N-bromosuccinimide were added, the temperature was raised to 85 °C and the reaction was stirred for 3.5 hours. The progress of the reaction was monitored by GC and TLC and after confirming the completion of the reaction, the solvent was removed using a rotary evaporator. The crude product obtained was recrystallized with hexane to give the pure 2-amino-3-bromo-5-chloropyridine. After drying, the calculated yield was 70.4% and purity was 99.15%.

References

[1] Patent: US2014/315888, 2014, A1. Location in patent: Paragraph 0620-0622
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2949 - 2961
[3] Patent: US2009/156603, 2009, A1. Location in patent: Page/Page column 46
[4] Patent: EP1202994, 2004, B1. Location in patent: Page 18
[5] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 115 - 126

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