(1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE Property

Boiling point:

201-207 °C(lit.)

Density 

1.006 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.518(lit.)

Flash point:

156 °F

optical activity

[α]20/D +110°, neat

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DA0177000

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.

(1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE Chemical Properties,Usage,Production

Synthesis

A solution of 0.05 M Na2HPO4 (10.0 mL) was added to a 25-mL solution of undiluted commercial household bleach (Clorox). The pH of the resulting buffered solution (0.55 M in NaOCl) was adjusted to pH 11.3 by addition of a few drops of 1 M NaOH solution. This solution was cooled to 0 °C and then added at once to a 0 °C solution of the manganese catalyst (260 mg, 0.4 mmol) and cis-o-methylstyrene (1.18 g, 10 mmol) in 10 mL of CH2Cl2. The two-phase mixture was stirred at room temperature, and the reaction progress was monitored by TLC. After 3 h, 100 mL of hexane was added to the mixture and the brown organic phase was separated, washed twice with 100 mL of H2O and once with 100 mL of saturated NaCl solution, and then dried (Na2SO4). After solvent removal, the residue was purifified by flflash chromatography on silica gel to afford the epoxide (0.912 g, 68%). The ee of the epoxide was determined to be 84% by 1 H NMR analysis in the presence of Eu(hfc)3.

Reference: Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296−2298.

Uses

Chiral building block. Tool for studying enzyme hydrolysis rates.