4-Amino-3-bromopyridine Chemical Properties

Melting point:

61-69 °C

Boiling point:

275.8±20.0 °C(Predicted)

Density 

1.6065 (rough estimate)

refractive index 

1.5182 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

pK1: 7.04(+1) (20°C)

form 

Crystalline Powder

color 

White to off-white

BRN 

110183

InChI

InChI=1S/C5H5BrN2/c6-4-3-8-2-1-5(4)7/h1-3H,(H2,7,8)

InChIKey

DDQYSZWFFXOXER-UHFFFAOYSA-N

SMILES

C1=NC=CC(N)=C1Br

CAS DataBase Reference

13534-98-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

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

Safety Statements 

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

WGK Germany 

3

HazardClass 

IRRITANT, AIR SENSITIVE

HS Code 

29333990

MSDS

• Language:English Provider:3-Bromo-4-aminopyridine

4-Amino-3-bromopyridine Usage And Synthesis

Uses

4-Amino-3-bromopyridine is used as an intermediate in organic synthesis and pharmaceuticals.

Chemical Properties

yellow Cryst

Synthesis

General procedure for the synthesis of 4-amino-3-bromopyridine from 4-aminopyridine: To a mixture of 4-aminopyridine (20.0 g, 0.21 mol) and acetonitrile (300.0 mL) was added N-bromosuccinimide (NBS) (39.8 g, 0.22 mol) in batches at 0 °C, the reaction was to be carried out protected from light. Subsequently, the reaction mixture was stirred at room temperature for 24 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by fast column chromatography (silica gel as stationary phase and dichloromethane/methanol=20:1 as eluent) to afford the target compound 4-amino-3-bromopyridine (33.2 g, 91.4% yield) as a light yellow solid. Mass spectrum (ESI) m/z: 172.9 [M + H]+.

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 120, p. 37 - 50
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 15, p. 3216 - 3231
[3] Patent: US2003/22883, 2003, A1
[4] Journal of the American Chemical Society, 2012, vol. 134, # 31, p. 12928 - 12931

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