2-(6-broMopyridin-2-yl)propan-2-ol Chemical Properties

Boiling point:

273.2±25.0 °C(Predicted)

Density 

1.474±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

13.23±0.29(Predicted)

Appearance

Colorless to off-white Solid-liquid mixture

InChI

InChI=1S/C8H10BrNO/c1-8(2,11)6-4-3-5-7(9)10-6/h3-5,11H,1-2H3

InChIKey

OXSDDDKLMCHNHF-UHFFFAOYSA-N

SMILES

CC(C1=NC(Br)=CC=C1)(O)C

2-(6-broMopyridin-2-yl)propan-2-ol Usage And Synthesis

Application

2-(6-bromopyridine)-2-propanol can be used as an organic synthesis intermediate and a pharmaceutical intermediate, mainly in laboratory research and development processes and chemical and pharmaceutical production processes.

Synthesis

GENERAL STEPS: In a dry 250 mL round-bottomed flask equipped with a stir bar, septum and temperature probe, 1.6 M hexane solution of n-butyllithium (31.2 mL, 50 mmol) was added. The reaction system was cooled to -76 °C in a dry ice-acetone bath. Subsequently, THF (30 mL) was added to the reaction vial and a solution of 2,6-dibromopyridine (11.5 g, 50 mmol) in THF (60 mL) was added slowly dropwise by syringe, controlling the reaction temperature below -60 °C. Stirring of the dark yellow-brown solution was continued in a dry ice bath for 30 min, and then acetone (6 mL, 80 mmol) was added. The reaction mixture was stirred in a dry ice bath for 15 minutes and then slowly warmed to room temperature. After 1 hour of reaction, the reaction was quenched by careful addition of 5% aqueous ammonium chloride solution (50 mL). The reaction mixture was extracted with dichloromethane, the organic phases were combined and the solvent evaporated to give 2-(6-bromopyridin-2-yl)propan-2-ol (10.6 g, 98% yield) as an orange oil. The mass spectrum (MS) showed m/z: 216 and 218 (M+H)+.

References

[1] Patent: WO2009/131814, 2009, A2. Location in patent: Page/Page column 40
[2] Patent: US2013/178478, 2013, A1. Location in patent: Paragraph 0461; 0462
[3] Patent: WO2014/60371, 2014, A1. Location in patent: Page/Page column 76
[4] Chemical Communications, 2016, vol. 52, # 74, p. 11056 - 11059
[5] Patent: WO2004/814, 2003, A1. Location in patent: Page 50

2-(6-broMopyridin-2-yl)propan-2-ol(638218-78-7)Related Product Information

• 2-Bromopyridine
• 4-Bromotoluene
• 2-Bromoethanol
• Aspartame