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Merck
CN

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

Key Documents

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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.)

functional group

ether
phenyl

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.

Disclaimer

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW2155
MKCW4333
MKCT1679
MKCS3664
MKCQ0433

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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)
Wen-Jing Chen et al.
Journal of biotechnology, 162(2-3), 183-190 (2012-09-22)
A comparative study was made of Mung bean epoxide hydrolases-catalyzed asymmetric hydrolysis of styrene oxide to (R)-1-phenyl-1,2-ethanediol in an n-hexane/buffer biphasic system containing various hydrophilic ionic liquids (ILs). Compared to the n-hexane/buffer biphasic system alone, addition of a small amount
Michel Oelschlägel et al.
Applied and environmental microbiology, 78(12), 4330-4337 (2012-04-17)
Styrene oxide isomerase (SOI) is involved in peripheral styrene catabolism of bacteria and converts styrene oxide to phenylacetaldehyde. Here, we report on the identification, enrichment, and biochemical characterization of a novel representative from the actinobacterium Rhodococcus opacus 1CP. The enzyme
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