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540102

Sigma-Aldrich

(S)-(−)-Styrene oxide

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.

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

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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Highly selective synthesis of CO2 copolymer from styrene oxide.
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Macromolecules, 43(21), 9202-9204 (2010)
Laurent Gaté et al.
Toxicology letters, 211(3), 211-219 (2012-04-18)
The cytogenetic alterations in leukocytes and the increased risk for leukemia, lymphoma, or all lymphohematopoietic cancer observed in workers occupationally exposed to styrene have been associated with its hepatic metabolisation into styrene-7,8-oxide, an epoxide which can induce DNA damages. However
G Cruzan et al.
Regulatory toxicology and pharmacology : RTP, 62(1), 214-220 (2011-11-02)
Styrene induces lung tumors in mice but not in rats. Although metabolism of styrene to 7,8-styrene oxide (SO) by CYP2E1 has been suggested as a mediator of styrene toxicity, lung toxicity is not attenuated in CYP2E1 knockout mice. However, styrene
Feng Yu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(50), 14234-14240 (2011-11-09)
In the presence of PhSiH(3) as the reductant, the combination of enantiomeric dipyridylphosphane ligands and Cu(OAc)(2)·H(2)O, which is an easy-to-handle and inexpensive copper salt, led to a remarkably practical and versatile chiral catalyst system. The stereoselective formation of a selection
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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