4-AMINO-3-BROMO-2-CHLOROPYRIDINE Chemical Properties

Melting point:

150-151°

Boiling point:

329.0±37.0 °C(Predicted)

Density 

1.834±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

2.73±0.42(Predicted)

form 

solid

Appearance

White to off-white Solid

Sensitive 

Air Sensitive

InChI

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

InChIKey

KTWAUKYSQFZIET-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

T

Risk Statements 

25-37/38-41

Safety Statements 

26-39-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

4-AMINO-3-BROMO-2-CHLOROPYRIDINE Usage And Synthesis

Uses

4-Amino-3-bromo-2-chloropyridine is an organic compound, which is often used as a synthetic intermediate for certain drugs, including peptide drugs, hormone drugs, anti-tumor drugs, etc. It is also used in the synthesis of dyes.

Synthesis

General procedure for the synthesis of 3-bromo-2-chloropyridin-4-amine from 2-chloro-4-aminopyridine: N-bromosuccinimide (NBS, 2.77 g, 15.56 mmol) was added batchwise to a stirred solution of 2-chloropyridin-4-amine (17A, 2 g, 15.56 mmol) in acetic acid (20 mL) at 0 °C and under nitrogen protection. The reaction mixture was then stirred at room temperature for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and azeotropic distillation with ethanol was performed to further remove the residual solvent. The crude product was purified by silica gel column chromatography (using a 40 g RediSep column with a gradient elution using a petroleum ether solution of 10-20% ethyl acetate as eluent) to afford the target compound, 3-bromo-2-chloropyridin-4-amine (15B, 2 g, 9.64 mmol, 62.0% yield), as a white solid.LCMS analysis: m/z = 209.0 [M + H]+; retention time 0.84 min; condition B.

References

[1] Patent: WO2016/133838, 2016, A1. Location in patent: Paragraph 0315
[2] Patent: US2016/16951, 2016, A1. Location in patent: Paragraph 0878; 0879
[3] Patent: WO2008/8539, 2008, A2. Location in patent: Page/Page column 133
[4] Patent: US2014/336182, 2014, A1. Location in patent: Paragraph 0306-0307
[5] Patent: WO2008/124083, 2008, A2. Location in patent: Page/Page column 47

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