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726834

Sigma-Aldrich

(S)-Phenyloxirane

ChiPros®, produced by BASF, 98%

Synonym(s):

(S)-Phenylethylene oxide, (S)-Styrene 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:
329764269

grade

produced by BASF

Assay

≥97.5% (GC)
98%

form

liquid

optical purity

enantiomeric excess: ≥97.5%

bp

192-194 °C (lit.)

density

1.051 g/mL at 20 °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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Legal Information

ChiPros is a registered trademark of BASF SE

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)

174.2 °F

Flash Point(C)

79 °C

Regulatory Information

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Michael Kotik et al.
Journal of biotechnology, 156(1), 1-10 (2011-08-23)
We performed a laboratory evolution study with the epoxide hydrolase from Aspergillus niger M200. This enzyme exhibits no enantioconvergence with the substrates styrene oxide or para-chlorostyrene oxide, i.e. racemic vicinal diols are produced from the racemic substrates. After saturation mutagenesis
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
Daniel Kuhn et al.
Journal of industrial microbiology & biotechnology, 39(8), 1125-1133 (2012-04-25)
Selection of the ideal microbe is crucial for whole-cell biotransformations, especially if the target reaction intensively interacts with host cell functions. Asymmetric styrene epoxidation is an example of a reaction which is strongly dependent on the host cell owing to
Alessandra Lattanzi et al.
Chirality, 22 Suppl 1, E130-E135 (2010-11-03)
Density Functional Theory (DFT) calculations of optical rotation (OR) and vibrational circular dichroism (VCD) have been used to assign the absolute configuration (AC) of a recently prepared (3-phenyloxirane-2,2-diyl)bis(phenylmethanone), 3, by asymmetric epoxidation of the corresponding 2-arylidene-1,3-diketone. The experimental OR at
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