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540102

Sigma-Aldrich

(S)-(−)-Styrene oxide

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98%, optical purity ee: 98% (GC)

Synonym(s):

(S)-(−)-Phenyloxirane, (S)-Phenylethylene oxide

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About This Item

Empirical Formula (Hill Notation):
C8H8O
CAS Number:
20780-54-5
Molecular Weight:
120.15
Beilstein:
3587977
MDL number:
MFCD00064310
UNSPSC Code:
12352005
PubChem Substance ID:
24878441
NACRES:
NA.22

Quality Level

100

Assay

98%

optical activity

[α]20/D −33°, neat

optical purity

ee: 98% (GC)

refractive index

n20/D 1.535 (lit.)

bp

192-194 °C (lit.)

density

1.051 g/mL at 25 °C (lit.)

SMILES string

C1O[C@H]1c2ccccc2

InChI

1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2/t8-/m1/s1

InChI key

AWMVMTVKBNGEAK-MRVPVSSYSA-N

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General description

Styrene oxide is an oxirane derivative, which is used as a monomer for the synthesis of polyesters with relatively high Tg values via ring-opening copolymerization. It can also be used as a useful intermediate in the preparation of levamisole, a nematocide and anticancer agent.

Application

(S)-(-)-Styrene oxide can undergo copolymerization with CO2 to form the corresponding polycarbonate in the presence of a cobalt-based catalyst system.

Caution

Product should be sampled and packaged in a glove bag under nitrogen.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Chronic 2 - Carc. 1B - Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Enantioselective hydrolysis of styrene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200
Liu Z, et al.
Tetrahedron Asymmetry, 17(1), 47-52 (2006)
Semi-aromatic polyesters by alternating ring-opening copolymerisation of styrene oxide and anhydrides
Nejad EH, et al.
Polym. Chem., 3(5), 1308-1313 (2012)
Highly selective synthesis of CO2 copolymer from styrene oxide.
Wu GP, et al.
Macromolecules, 43(21), 9202-9204 (2010)
Rainer Gross et al.
Biotechnology and bioengineering, 110(2), 424-436 (2012-08-14)
This study evaluates the technical feasibility of biofilm-based biotransformations at an industrial scale by theoretically designing a process employing membrane fiber modules as being used in the chemical industry and compares the respective process parameters to classical stirred-tank studies. To
David M Hodgson et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(35), 9731-9737 (2011-07-19)
Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled Rh(II) -catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an
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