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540102

Sigma-Aldrich

(S)-(−)-Styrene oxide

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

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Synonym(s):
(S)-(−)-Phenyloxirane, (S)-Phenylethylene oxide
Empirical Formula (Hill Notation):
C8H8O
CAS Number:
20780-54-5
Molecular Weight:
120.15
Beilstein:
3587977
MDL number:
MFCD00064310
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.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Semi-aromatic polyesters by alternating ring-opening copolymerisation of styrene oxide and anhydrides
Nejad EH, et al.
Polym. Chem., 3(5), 1308-1313 (2012)
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)
Highly selective synthesis of CO2 copolymer from styrene oxide.
Wu GP, et al.
Macromolecules, 43(21), 9202-9204 (2010)
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
Gary P Carlson
Drug and chemical toxicology, 34(4), 440-444 (2011-07-14)
Styrene is known to be hepatotoxic and pneumotoxic in rodents, and these adverse effects are related to its metabolism. Mice deficient in the enzymes responsible for both the activation and detoxification of styrene are useful in examining this relationship more
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