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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:
Molecular Weight:
120.15
Beilstein:
3587977
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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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