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Merck
CN

78880

(R)-Phenyloxirane

purum, ≥98.0% (sum of enantiomers, HPLC)

Synonym(s):

(R)-Phenylethylene oxide, (R)-Styrene oxide

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About This Item

Empirical Formula (Hill Notation):
C8H8O
CAS Number:
20780-53-4
Molecular Weight:
120.15
PubChem Substance ID:
24887378
UNSPSC Code:
12352000
MDL number:
MFCD00066210
Beilstein/REAXYS Number:
1984

Key Documents

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grade

purum

assay

≥98.0% (sum of enantiomers, HPLC)

optical activity

[α]/D −24±2°, c = 1 in chloroform, [α]/D +33±2°, neat

refractive index

n20/D 1.535

bp

192-194 °C (lit.)

density

1.051 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

C1O[C@@H]1c2ccccc2

Other Notes

This chiral building block reacts with various nucleophiles, e.g. carbanions and amines, to chiral α-substituted benzyl alcohols

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Carc. 1B - Eye Irrit. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

176.0 °F - closed cup

flash_point_c

80 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Mohammad Movassaghi et al.
Journal of the American Chemical Society, 124(11), 2456-2457 (2002-03-14)
A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate
S. Calet et al.
Journal of the American Chemical Society, 111, 931-931 (1989)
O. De Lucchi et al.
Tetrahedron Letters, 28, 107-107 (1987)
Gary P Carlson
Journal of toxicology and environmental health. Part A, 73(24), 1689-1699 (2010-11-09)
Styrene, which is widely used in manufacturing, is both acutely and chronically toxic to mice. Styrene is metabolized by cytochromes P-450 to the toxic metabolite styrene oxide, which is detoxified via hydrolysis with microsomal epoxide hydrolase (mEH) playing a major
Jung-Hee Woo et al.
Biotechnology letters, 35(4), 599-606 (2012-12-18)
A novel epoxide hydrolase (EHase) from polycyclic aromatic hydrocarbon (PAH)-degrading bacteria was identified and characterized. EHase activity was identified in four strains of PAH-degrading bacteria isolated from commercial gasoline and oil-contaminated sediment based on their growth on styrene oxide and
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