2-(2,2,2-Trifluoroethoxy)phenol Chemical Properties

Melting point:

49-50 ºC

Boiling point:

202 ºC

Density 

1.327

Flash point:

102 ºC

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.22±0.30(Predicted)

color 

Off-White to Pale Grey

Safety Information

HS Code 

2907290090

2-(2,2,2-Trifluoroethoxy)phenol Usage And Synthesis

Uses

2-(2,2,2-Trifluoroethoxy)phenol is a reactant used for the preparation of phenyl acetate compounds with short sedative and hypnotic effect.

Synthesis

GENERAL STEPS: A 1M solution of boron tribromide (30mL, 0.03mol) in dichloromethane was slowly added dropwise to a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (4.3g, 0.02mol) in anhydrous dichloromethane (50mL) at -20°C. The reaction was quenched by addition of excess saturated aqueous sodium bicarbonate (40mL). After the reaction mixture was naturally warmed to room temperature, the reaction was quenched by the addition of excess saturated aqueous sodium bicarbonate solution (40 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product obtained was sufficiently pure (98% yield) to be used directly in the subsequent reaction. The product was a yellow oil (3.8 g) and UPLC/MS analysis showed a purity of 99% with a retention time of tR = 5.37 min. molecular formula C8H7F3O2, molecular weight 192.14, single isotope mass 192.04, [M+H]- m/z 191.0. 1H-NMR (300 MHz, CDCl3) δ 4.36 (q, J = 8.4 Hz, 2H, O-CH2-CF3), 6.81-7.11 (m, 4H, Ar-H), 9.72 (br.s., 1H, OH).13C-NMR (75 MHz, CDCl3) δ 56.2, 68.1, 119.2, 121.5, 122.4, 123.7, 126.4, 127.3, 136.4.

References

[1] Molecules, 2018, vol. 23, # 9,
[2] Patent: US5387603, 1995, A
[3] Patent: WO2011/30356, 2011, A2. Location in patent: Page/Page column 23
[4] Patent: WO2011/101864, 2011, A1. Location in patent: Page/Page column 21-22
[5] Patent: US2012/165548, 2012, A1. Location in patent: Page/Page column 11