2-Pyridinamine, 5-bromo-4-chloro- Chemical Properties

Boiling point:

271.6±35.0 °C(Predicted)

Density 

1.834±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

3.61±0.24(Predicted)

form 

powder

color 

Faint beige

InChI

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

InChIKey

DDOFUMWLNSICHU-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

2-Pyridinamine, 5-bromo-4-chloro- Usage And Synthesis

Uses

2-Amino-4-chloro-5-bromopyridine can be used to synthesize 2,4-dichloro-5-bromopyridine. 2,4-Dichloro-5-bromopyridine is an important biopharmaceutical intermediate widely used in the synthesis of various drugs. Its small molecular weight and unique structure allow for the derivation of numerous downstream products, giving it a wide range of applications.

Synthesis

The general procedure for the synthesis of 2-amino-4-chloro-5-bromopyridine from 2-amino-4-chloropyridine was as follows: 4-chloropyridin-2-amine (8 g, 62.2 mmol) was dissolved in acetonitrile (600 mL) at room temperature, and N-bromosuccinimide (NBS, 11.08 g, 62.2 mmol) was added in batches under stirring. The reaction mixture was stirred continuously for 14 hours at room temperature. After completion of the reaction, the solvent was removed by concentration under reduced pressure. The residue was redissolved in a solvent mixture of ethyl acetate and water. The organic phase was extracted with ethyl acetate (3 x 50 mL) and the combined organic layers were washed sequentially with water (100 mL) and brine (100 mL) and dried over anhydrous sodium sulfate. Concentration of the organic phase under reduced pressure afforded 5-bromo-4-chloropyridin-2-amine as a yellow solid (13 g, 99% yield), which could be used for subsequent reactions without further purification. The product was confirmed by LC-MS (ESI), m/z 207.0 [(M + H)+, calculated value 206.9 for C5H5BrClN2]; LC/MS retention time (Method B): tR = 0.8 min; 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1H), 6.63 (s, 1H), 4.59 (s, 2H) .

References

[1] Patent: WO2015/38112, 2015, A1. Location in patent: Page/Page column 92; 93
[2] Patent: JP2015/528018, 2015, A. Location in patent: Paragraph 0207
[3] Patent: WO2018/68283, 2018, A1. Location in patent: Paragraph 00263
[4] Patent: WO2015/157360, 2015, A1. Location in patent: Page/Page column 39-40
[5] Patent: WO2014/63778, 2014, A1. Location in patent: Page/Page column 22; 23

2-Pyridinamine, 5-bromo-4-chloro-(942947-94-6)Related Product Information

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