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

Melting point:

215-219 °C

Boiling point:

347.3±37.0 °C(Predicted)

Density 

1.9128 (rough estimate)

refractive index 

1.6200 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

0.06±0.49(Predicted)

form 

Powder

color 

Beige to orange-brown

InChI

InChI=1S/C5H4BrN3O2/c6-4-1-3(9(10)11)2-8-5(4)7/h1-2H,(H2,7,8)

InChIKey

OFXNHXMPRZDIDM-UHFFFAOYSA-N

SMILES

C1(N)=NC=C([N+]([O-])=O)C=C1Br

CAS DataBase Reference

15862-31-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ACROS

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

Chemical Properties

Beige to orange-brown powder

Uses

2-Amino-3-bromo-5-nitropyridine is a useful intermediate for organic synthesis.

Synthesis

Step a: Bromine (38 g, 0.24 mol) was slowly added dropwise to a solution of 2-amino-5-nitropyridine (30 g, 0.22 mol) in acetic acid (200 mL) at 10 °C. After the dropwise addition was completed, the reaction mixture was warmed to 20 °C and stirring was continued for 30 min. Upon completion of the reaction, the solid product was collected by filtration and dissolved in ethyl acetate (200 mL). The pH of the mixture was adjusted to 8-9 with saturated aqueous sodium bicarbonate. the organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL x 3). The organic layers were combined, washed sequentially with water and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 2-amino-3-bromo-5-nitropyridine (14.8 g, 32% yield). The product was characterized by 1H-NMR (CDCl3,400MHz): δ 8.94 (d, J=2.4Hz, 1H), 8.50 (d, J=2.4Hz, 1H), 5.67 (brs, 2H).

References

[1] Patent: US2009/253736, 2009, A1. Location in patent: Page/Page column 25
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3853 - 3860
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 494
[4] Chem. Zentralbl., 1923, vol. 94, # III, p. 1021
[5] Zhurnal Obshchei Khimii, 1940, vol. 10, p. 1827,1836

2-Amino-3-bromo-5-nitropyridine(15862-31-4)Related Product Information

• 2-Amino-3-nitropyridine
• 2-Amino-5-nitropyridine
• 5-Amino-2-methylpyridine
• Glycine
• 4-Aminopyridine
• 6-Aminocaproic acid
• 4-Dimethylaminopyridine
• 2-Bromo-5-nitropyridine
• 3-Aminopyridine
• 2-Chloro-5-chloromethylpyridine
• ALTRENOGEST
• Tris(hydroxymethyl)aminomethane
• Bromine
• 3-BROMO-2-HYDRAZINO-5-NITROPYRIDINE
• 4-AMINO-3-BROMO-5-NITROPYRIDINE
• 3-AMINO-5-BROMO-2-NITROPYRIDINE
• 2-AMINO-5-BROMO-3-NITROPYRIDINE
• 2-Amino-3-bromo-6-methyl-5-nitropyridine