2-Bromo-3-hydroxypyridine Chemical Properties

Melting point:

185-188 °C(lit.)

Boiling point:

321.7±22.0 °C(Predicted)

Density 

1.5643 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

pka

4.32±0.10(Predicted)

form 

Crystalline Powder

color 

Light brown to gray

Water Solubility 

Soluble in alcohol. Insoluble in water.

BRN 

109829

InChI

InChI=1S/C5H4BrNO/c6-5-4(8)2-1-3-7-5/h1-3,8H

InChIKey

YKHQFTANTNMYPP-UHFFFAOYSA-N

SMILES

C1(Br)=NC=CC=C1O

CAS DataBase Reference

6602-32-0(CAS DataBase Reference)

NIST Chemistry Reference

3-Pyridinol, 2-bromo-(6602-32-0)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-24/25

WGK Germany 

3

RTECS 

UU7705000

F 

10

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:2-Bromo-3-hydroxypyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Bromo-3-hydroxypyridine Usage And Synthesis

Chemical Properties

LIGHT BROWN TO GREY CRYSTALLINE POWDER

Uses

2-Bromo-3-hydroxypyridine is used to produce 2-bromo-4,6-diiodo-3-pyridinol. It is also used in azo dyes and in the synthesis of pterocellin A by reacting with kojic acid and in synthesis of orelline.

Synthesis

The general procedure for the synthesis of 2-bromo-3-hydroxypyridine from 3-hydroxypyridine was as follows: (a) A hypobromite solution was prepared by slowly adding bromine (2.74 mL, 8.49 g, 5.31 mmol) to 10% sodium hydroxide solution (50 mL) at 5°C to 10°C. Subsequently, this hypobromite solution was added dropwise to 10% sodium hydroxide solution (50 mL) containing 3-hydroxypyridine (5.0 g, 52.6 mmol) over 20 minutes. The reaction mixture was continued to be stirred for 30 minutes. The pH of the reaction solution was adjusted to 6-7 with acetic acid. the mixture was cooled to 5°C and maintained for 1 h. The solid product was subsequently collected by filtration. The product was washed with water and dried under vacuum at 85°C to give 2-bromo-3-hydroxypyridine (6.22 g, 67% yield). References: 1) GJ Clark and L W Deedy, Australian J Chem, (1981), 34, 927.

References

[1] Patent: US5646286, 1997, A
[2] Patent: US5726315, 1998, A
[3] Chemistry - A European Journal, 2010, vol. 16, # 28, p. 8439 - 8445
[4] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932
[5] Helvetica Chimica Acta, 1988, vol. 71, p. 957 - 963

2-Bromo-3-hydroxypyridine(6602-32-0)Related Product Information

• 2-BROMO-3-METHOXYPYRIDINE
• 2-BROMO-3-(TETRAHYDRO-2-PYRANYLOXY)PYRIDINE
• 2-BROMO-3-METHOXYPYRIDINE-4-CARBOXALDEHYDE
• 2,6-DIBROMO-3-HYDROXYPYRIDINE
• 2-Bromo-3-ethoxypyridine
• 2-Bromo-3-hydroxy-6-methylpyridine
• 2-Bromo-3-methoxy-6-methylpyridine
• 2,4,6-TRIBROMO-3-PYRIDINOL
• 2-Bromo-3-hydroxypyridine
• 6-Bromo-5-methoxypicolinic acid
• Methyl 5-Bromo-2-hydroxypyridine-4-carboxylate, 5-Bromo-4-methoxycarbonyl-2(1H)-pyridinone
• 2-FLUORO-3-BROMO-5-HYDROXYPYRIDINE
• 2-Chloro-3-Bromo-5-Hydroxypyridine
• 2-Hydroxy-3-Amino-5-Bromopyridine
• 4-BROMO-3-HYDROXYPYRIDINE
• 3,5-DIBROMO-2-HYDROXYPYRIDINE
• METHYL 5-BROMO-2-HYDROXYPYRIDINE-3-CARBOXYLATE
• 3-BROMO-4-HYDROXYPYRIDINE 97%,3-BROMO-4-HYDROXYPYRIDINE