(3-bromopyridin-2-yl)methanol Chemical Properties

Boiling point:

260.9±25.0 °C(Predicted)

Density 

1.668±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

12.75±0.10(Predicted)

Appearance

Off-white to brown Solid

InChI

InChI=1S/C6H6BrNO/c7-5-2-1-3-8-6(5)4-9/h1-3,9H,4H2

InChIKey

FTTLCYCJDYIEFO-UHFFFAOYSA-N

SMILES

C1(CO)=NC=CC=C1Br

Safety Information

RIDADR 

UN2811

HS Code 

2933399990

(3-bromopyridin-2-yl)methanol Usage And Synthesis

Chemical Properties

(3-bromopyridin-2-yl)methanol is a solid,it is stable under recommended temperatures and pressures.It can react with strong oxidizing agents.

Uses

(3-bromopyridin-2-yl)methanol is commonly used as an intermediate in organic and pharmaceutical synthesis.

Uses

(3-bromopyridin-2-yl)methanol is commonly used as an intermediate in organic and pharmaceutical synthesis.

Hazard

(3-bromopyridin-2-yl)methanol is toxicity if swallowed. Skin contact with it may result in inflammation characterized by itching, scaling, reddening, blistering, pain or dryness. Eye contact may result in redness, pain or severe eye damage.

Synthesis

General procedure for the synthesis of 3-bromo-2-hydroxymethylpyridine from 3-bromopyridine-2-carboxaldehyde: Preparation of (3-bromopyridin-2-yl)methanol (B5.2) (0363): 3-bromopyridine-2-carboxaldehyde (B5.1) (1 g, 5.4 mmol) was dissolved in a mixture of solvents of MeOH (20 mL) and THF (10 mL) and cooled to 0 °C. NaBH4 (0.82 g, 21.6 mmol) was added in batches under stirring. The reaction mixture was gradually warmed to room temperature and stirred continuously for 4 hours. Upon completion of the reaction, the mixture was concentrated to remove most of the solvent and subsequently diluted with deionized water (40 mL). Extraction was carried out with dichloromethane (DCM, 40 mL x 3) and the organic layers were combined and washed with saturated brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to afford the target product 3-bromo-2-hydroxymethylpyridine (1 g, 99% yield) as a white solid.LC-MS detection: [M + H]+ = 190.0.

References

[1] Patent: US2016/176882, 2016, A1. Location in patent: Paragraph 0361; 0363
[2] Patent: WO2017/221100, 2017, A1. Location in patent: Paragraph 00171
[3] Patent: WO2017/221092, 2017, A1. Location in patent: Paragraph 00169

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