2-amino-5-bromopyridin-3-ol Chemical Properties

Melting point:

204-207℃

Boiling point:

368.7±42.0 °C(Predicted)

Density 

1.898

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

11.48±0.10(Predicted)

form 

Solid

color 

Off-white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H5BrN2O/c6-3-1-4(9)5(7)8-2-3/h1-2,9H,(H2,7,8)

InChIKey

YQADLKDQAXAIKW-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)C=C1O

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

HS Code 

2933399990

2-amino-5-bromopyridin-3-ol Usage And Synthesis

Uses

2-Amino-5-bromo-3-hydroxypyridine is used as an organic chemical synthesis intermediate.

Synthesis

General procedure for the synthesis of 3-hydroxy-2-amino-5-bromopyridine from 6-bromo-3H-oxazolo[4,5-b]pyridin-2-one: 6-bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in 2N NaOH solution (250 mL, 500 mmol). The mixture was refluxed and reacted overnight until a clarified solution was formed. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently neutralized with acid to a pH of about 7. During this process, the release of large amounts of CO2 gas as well as the formation of a precipitate was observed. The precipitate was collected by filtration, washed with water and dried under high vacuum to give the final 2-amino-5-bromopyridin-3-ol as an off-white solid (17.8 g, 98% yield).

References

[1] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 33-34
[2] Patent: WO2006/21886, 2006, A1. Location in patent: Page/Page column 64; 65
[3] Heterocycles, 2001, vol. 55, # 7, p. 1329 - 1345
[4] Heterocycles, 1995, vol. 41, # 12, p. 2799 - 2810
[5] Tetrahedron Letters, 2014, vol. 55, # 9, p. 1528 - 1531

2-amino-5-bromopyridin-3-ol(39903-01-0)Related Product Information

• 2-Amino-5-bromo-4-methylpyridine
• 2-Amino-5-bromo-3-nitropyridine
• 7-BROMO-1H-PYRIDO[2,3-B][1,4]OXAZIN-2(3H)-ONE
• 6-BROMO-3H-OXAZOLO[4,5-B]PYRIDIN-2-ONE
• 5-Bromo-2-methoxy-4-methyl-3-nitropyridine
• 5-Bromo-3-nitro-2-pyridinol
• 2-amino-5-bromopyridin-3-ol
• 5-BROMO-2-METHOXY-3-NITRO-PYRIDINE
• 3-Hydroxypyridine
• 2-Hydroxy-3-Amino-5-Bromopyridine
• 5-BROMO-2-HYDROXY-3-NITRO-4-PICOLINE
• 7-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
• (5-BROMO-2-METHOXY-PYRIDIN-3-YL)METHYLAMINE
• 5-BROMO-3-METHOXY-2-NITROPYRIDINE
• 2-AMINO-5-BROMO-4-CHLORO-3-HYDROXYPYRIDINE
• 3-AMINO-5-BROMO-6-METHYLPYRIDIN-2-OL
• 5-BROMO-2-PROPOXY-PYRIDIN-3-YLAMINE
• 5-BROMO-2-HYDROXY-3-NITRO-6-PICOLINE