3-Fluorophenethyl alcohol

3-Fluorophenethyl alcohol Property

Boiling point:

90 °C/3 mmHg (lit.)

Density 

1.125 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.509(lit.)

Flash point:

225 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

pka

14.76±0.10(Predicted)

color 

Clear colorless

Safety

Hazard Codes 

C,Xn

Risk Statements 

36/37/38-21/22-34

Safety Statements 

26-36/37/39-45-27

RIDADR 

2810

WGK Germany 

3

HS Code 

29062990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

3-Fluorophenethyl alcohol Chemical Properties,Usage,Production

Chemical Properties

clear colorless liquid

General Description

3-Fluorophenethyl alcohol is a fluorinated β-phenethyl alcohol. Regioselective synthesis of 3-fluorophenethyl alcohol via regioselective hydroboration has been reported.

Synthesis

The general procedure for the synthesis of 3-fluorophenylethanol from 3-fluorophenylacetic acid was as follows: to a stirred solution of 3-fluorophenylacetic acid (5.0 g, 32.0 mmol) in ether (100 ml) was slowly added dropwise an ether solution of lithium aluminum hydroxide (32.4 ml, 1 M, 32.4 mmol) at -10 °C. The reaction mixture was gradually warmed to 25°C and stirred continuously for 1 hour. Subsequently, the reaction mixture was cooled again to -10°C and the reaction was quenched by sequential addition of methanol (20 ml) and 4M sodium hydroxide solution (20 ml). The resulting slurry was filtered and the filtrate was concentrated by evaporation under vacuum. The crude product was purified by silica gel column chromatography using CH2Cl2/MeOH/NH3 (80:8:1) as eluent to give 3-fluorophenylethanol (3.80 g, 84% yield) finally. The product was confirmed by NMR hydrogen spectrum (250 MHz, CDCl3): δ 2.87 (3H, t, J = 6.5 Hz, CH2), 3.87 (3H, t, J = 6.5 Hz, CH2), 6.89-7.02 (3H, m, Ar-H), 7.23-7.33 (1H, m, Ar-H).

References

[1] Journal of Organic Chemistry, 2005, vol. 70, # 14, p. 5528 - 5535
[2] Tetrahedron Asymmetry, 2001, vol. 12, # 4, p. 585 - 596
[3] Patent: US5889008, 1999, A
[4] Helvetica Chimica Acta, 1973, vol. 56, p. 2460 - 2479
[5] Journal of the American Chemical Society, 1978, vol. 100, p. 228 - 246