3-Bromo-2-hydroxypyridine Chemical Properties

Melting point:

179-183 °C

Boiling point:

336.6±42.0 °C(Predicted)

Density 

1.776±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

10.53±0.10(Predicted)

form 

Crystalline Powder

color 

White to off-white

Water Solubility 

Slightly soluble in water.

BRN 

109846

InChI

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

InChIKey

YDUGVOUXNSWQSW-UHFFFAOYSA-N

SMILES

C1(=O)NC=CC=C1Br

CAS DataBase Reference

13466-43-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

26-36-39

WGK Germany 

3

HS Code 

29337900

MSDS

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3-Bromo-2-hydroxypyridine Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

3-Bromo-2-hydroxypyridine is used in the synthesis of pyrazolopyridines as γ-secratase modulators.

Uses

3-Bromo-2-hydroxypyridine is sued as an active ingredient pharmaceuticals, in medicine.

Synthesis

The general procedure for the synthesis of 3-bromo-2-hydroxypyridine from 2-amino-3-bromopyridine was as follows: sodium nitrite (24.2 g, 0.35 mol, 4.84 eq.) was dissolved in water (175 mL) at 0 °C and slowly added dropwise to a solution containing 2-amino-3-bromopyridine (12.5 g, 72.4 mmol) and sulfuric acid (35 mL, 0.66 mol , 9.10 eq.) in a solution of water (175 mL). The reaction mixture was stirred at 0 °C for 1 hour. Subsequently, the reaction mixture was neutralized with sodium hydroxide solution to pH=7. The neutralized solution was extracted with chloroform (3 x 200 mL), the organic phases were combined and washed with brine (200 mL), dried over magnesium sulfate, filtered and concentrated in vacuum to afford the milky white solid product 3-bromo-2-hydroxypyridine (11.3 g, 90% yield). The product was characterized as follows: melting point 183 °C; IR (pure) νmax 3339, 3105, 2991, 2942, 1776, 1650, 1610, 1464 cm-1; 1H NMR (500 MHz, CDCl3) δ 7.87 (dd, J = 7.3, 1.9 Hz, 1H), 7.49 (dd, J = 6.4, 1.9 Hz, 1H), 6.24 (dd, J = 7.3, 6.4 Hz, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ 161.9, 143.9, 134.4, 115.7, 107.7 ppm; HRMS (ESI) m/z [M + Na]+ Calculated value: 195.9369, measured value: 195.9373 (deviation +2.07 ppm).

References

[1] Organic Letters, 2016, vol. 18, # 13, p. 3106 - 3109
[2] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588

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