(2-Trifluoromethyl-pyridin-3-yl)-methanol

(2-Trifluoromethyl-pyridin-3-yl)-methanol Property

Boiling point:

209℃

Density 

1.362

Flash point:

80℃

storage temp. 

Sealed in dry,Room Temperature

pka

13.08±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(2-Trifluoromethyl-pyridin-3-yl)-methanol Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of (2-trifluoromethyl-pyridin-3-yl)-methanol from ethyl 2-trifluoromethylnicotinate: sodium borohydride (0.35 g, 9.1 mmol) was suspended in anhydrous tetrahydrofuran (20 mL). Anhydrous tetrahydrofuran solution (20 mL) of ethyl 2-trifluoromethylnicotinate (1.00 g, 0.46 mmol) was added dropwise to the stirred suspension under ice bath cooling. The reaction mixture was stirred at 4°C for 16 hours. Upon completion of the reaction, methanol (5 mL) was added to quench the residual sodium borohydride, followed by the addition of 15% aqueous sodium hydroxide solution (25 mL). The resulting mixture was continued to be stirred at 25 °C for 30 min, followed by removal of tetrahydrofuran and methanol by rotary evaporation. The remaining aqueous phase was extracted with ethyl acetate (3 x 25 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to afford the target product (2-trifluoromethyl-pyridin-3-yl)-methanol as a yellow oil (0.61 g, 75% yield), which could be used in subsequent reactions without further purification. The product was characterized by 1H-NMR (CDCl3): δ 8.64 (d, J = 4.5 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.57 (dd, J = 8.0, 4.5 Hz, 1H), 4.98 (s, 2H), 1.99 (s, 1H). Mass spectrum (ESI+): m/z (M + H)+ = 178.

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5352 - 5359
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 12, p. 2146 - 2163
[3] Synthesis, 2005, # 16, p. 2751 - 2757
[4] Patent: WO2015/187934, 2015, A1. Location in patent: Paragraph 0228