3-Amino-2-bromopyridine Chemical Properties

Melting point:

76-80 °C

Boiling point:

292.5±20.0 °C(Predicted)

Density 

1.710±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

1.72±0.10(Predicted)

color 

Beige to dark brown

Water Solubility 

Slightly soluble in water.

BRN 

109830

InChIKey

HKDVVTLISGIPFE-UHFFFAOYSA-N

CAS DataBase Reference

39856-58-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

26-36/39-37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Amino-2-bromopyridine Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

Used in a palladium-catalyzed synthesis of indole systems containing fused medium- and large-ring heterocycles. pyrrole derivatives ahs been prepared using 3-Amino-2-bromopyridine. Used in P-C coupling reaction.

Synthesis

Preparation of Example S-1: 2-Bromo-3-nitropyridine (3 g, 15 mmol) was dissolved in a solvent mixture of tetrahydrofuran (15 mL) and water (5 mL), followed by the addition of iron powder (1 g, 18 mmol) and ammonium chloride (2 g, 37 mmol). The reaction mixture was stirred at 60°C to 70°C for 5 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the filtrate was washed with brine and extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1:4) to afford 2-bromo-3-aminopyridine (2.6 g, 15 mmol, quantitative yield).1H-NMR (DMSO-d6) δ (ppm): 5.47 (2H, brs), 7.07-7.09 (2H, m), 7.54 (1H, dd, J=). 2.0,3.6Hz).

References

[1] Patent: EP1782811, 2007, A1. Location in patent: Page/Page column 63
[2] Patent: EP1669348, 2006, A1. Location in patent: Page/Page column 71
[3] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84
[4] Journal of the Chemical Society, 1952, p. 2042,2044
[5] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328

3-Amino-2-bromopyridine(39856-58-1)Related Product Information

• 2-Bromo-3-nitropyridine
• AMINO-5-BROMOPYRIDINE,2-AMINO-5-BROMOPYRIDINE
• 2-Bromo-4-methylpyridine
• 2-Bromo-3-methylbenzaldehyde
• 2-Bromo-4-nitroimidazole
• 2-Bromo-4-fluoropyridine
• 2-Bromo-5,6-diphenylpyrazine
• 2-Bromo-3-trifluoromethylpyridine
• 2-Bromo-4-chloropyridine
• 2-Bromo-3-fluoropyridine
• 2-Bromopyridine-4-carboxylic acid
• BenzenaMine, 2-broMo-5-fluoro-4-nitro-
• 2-Bromo-3,5-dichloropyridine
• Pyridine, 2-bromo-3,5-dichloro-6-methyl-
• 5-Amino-2-bromo-3-methylpyridine
• 6-Bromopicolinic acid
• 2-Bromo-3-methyl-5-chloropyridine
• 2-Bromo-3-methyl-5-nitropyridine