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

Melting point:

194-195°

Boiling point:

294.4±40.0 °C(Predicted)

Density 

1.80±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

0.72±0.49(Predicted)

color 

Beige

InChI

InChI=1S/C6H4BrN3/c7-5-1-4(2-8)3-10-6(5)9/h1,3H,(H2,9,10)

InChIKey

CKUQTHSGTPGGFK-UHFFFAOYSA-N

SMILES

C1=NC(N)=C(Br)C=C1C#N

Safety Information

TSCA 

N

HazardClass 

IRRITANT

HS Code 

2933599590

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

Synthesis

The general procedure for the synthesis of 6-amino-5-bromonicotinonitrile from 2-amino-5-cyanopyridine is as follows: Step 1: To a solution of 6-aminonicotinonitrile (102 mg, 0.86 mmol) in acetic acid (2 mL) was added a solution of bromine in acetic acid (0.86 mmol). The mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by rapid chromatography on silica gel (eluent: hexane/ethyl acetate, 3:1, v/v) to afford the title compound 6-amino-5-bromonicotinonitrile (110 mg, 65% yield). The product characterization data are as follows: 1H-NMR (DMSO, 300 MHz): δ 8.26 (d, 1H, J = 2.0 Hz), 8.10 (d, 1H, J = 2.0 Hz), 7.24 (bs, 2H). MS (APCI Neg): m/z 196, 198.

References

[1] Patent: WO2005/90337, 2005, A1. Location in patent: Page/Page column 42-43
[2] Patent: WO2008/60907, 2008, A2. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 9, p. 2073 - 2078
[4] Patent: US2015/266872, 2015, A1. Location in patent: Paragraph 0783; 0784
[5] Patent: EP3372601, 2018, A1. Location in patent: Paragraph 0743; 0744

2-Amino-3-bromo-5-cyanopyridine(477871-32-2)Related Product Information

• 2-Amino-3-bromo-5-methylpyridine
• 5-Bromonicotinonitrile
• 2-Amino-3-bromo-5-cyanopyridine