(6-BROMO-PYRIDIN-3-YL)-METHANOL Chemical Properties

Melting point:

48-51℃

Boiling point:

314.3±27.0 °C(Predicted)

Density 

1.668±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

13.29±0.10(Predicted)

color 

White to Light yellow to Light orange

InChIKey

QPPDKOIDAYZUHN-UHFFFAOYSA-N

CAS DataBase Reference

122306-01-8

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933399990

(6-BROMO-PYRIDIN-3-YL)-METHANOL Usage And Synthesis

Uses

2-Bromo-5-pyridinemethanol is used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 2-bromo-5-(hydroxymethyl)pyridine from 2-bromo-5-formylpyridine: Sodium borohydride (4.88 g, 0.026 mol) was added batchwise to a solution of 6-bromonicotinaldehyde (20.0 g, 0.11 mol) in methanol (108 mL) at 20-30 °C. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, the reaction mixture was diluted with saturated aqueous ammonium chloride solution. The mixture was concentrated to remove methanol and the resulting aqueous solution was extracted with ethyl acetate. The organic phase was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated to afford 2-bromo-5-(hydroxymethyl)pyridine (18.61 g, 92% yield) as a light yellow solid.1H-NMR (300 MHz, CDCl3) δ (ppm): 8.36 (d, J = 2.7Hz, 1H), 7.60 (dd, J = 8.1, 2.7Hz, 1H). 2.7 Hz, 1H), 7.49 (d, J = 8.1 Hz, 1H), 4.72 (s, 2H), 1.95 (s, 1H).

References

[1] Patent: WO2013/44360, 2013, A1. Location in patent: Paragraph 000299-000300
[2] Patent: WO2006/114213, 2006, A1. Location in patent: Page/Page column 29-30
[3] Patent: WO2012/177603, 2012, A2. Location in patent: Page/Page column 105-108
[4] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 250 - 262
[5] Dalton Transactions, 2012, vol. 41, # 3, p. 1074 - 1081

(6-BROMO-PYRIDIN-3-YL)-METHANOL(122306-01-8)Related Product Information

• Ethyl 6-bromopicolinate
• 6-Bromonicotinic acid
• 5,6-DIBROMOPYRIDINE-3-CARBOXYLIC ACID
• (6-BROMO-PYRIDIN-3-YL)-METHANOL
• t-butyl 6-bromo-3-pyridinecarboxylate
• ETHYL 6-BROMOPYRIDINE-3-CARBOXYLATE
• Methyl 6-bromonicotinate
• (6-BROMO-PYRIDIN-2-YL)-METHANOL,(6-Bromo-pyridin-2-yl)-methanol >97%
• (2-BROMO-PYRIDIN-4-YL)-METHANOL
• 5-Bromo-2-hydroxymethylpyridine
• (2-AMINO-5-BROMO-PYRIDIN-3-YL)-METHANOL
• (5-BROMO-PYRIDIN-3-YL)-METHANOL
• (2-BROMO-PYRIDIN-3-YL)-METHANOL
• 2-BROMO-3-METHYLPYRIDINE-5-CARBOXYLIC ACID
• 6-BROMO-5-FLUOROPYRIDINE-3-CARBOXYLIC ACID
• ethyl 6-bromonicotinimidate
• (6-BROMO-PYRIDIN-2-YL)-PHENYL-METHANOL