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726508

Sigma-Aldrich

(R)-(+)-Styrene oxide

ChiPros®, produced by BASF, ≥98%

Synonym(s):

(R)-(+)-Phenyloxirane, (R)-Phenylethylene oxide

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About This Item

Empirical Formula (Hill Notation):
C8H8O
CAS Number:
20780-53-4
Molecular Weight:
120.15
Beilstein:
1984
MDL number:
MFCD00066210
UNSPSC Code:
12352005
PubChem Substance ID:
329764241
NACRES:
NA.22

grade

produced by BASF

Quality Level

100

Assay

≥98%
≥98.0% (GC)

form

liquid

optical purity

enantiomeric excess: ≥98.0%

expl. lim.

~22 %

refractive index

n20/D 1.534 (lit.)

bp

89-90 °C/23 mmHg (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-/m0/s1

InChI key

AWMVMTVKBNGEAK-QMMMGPOBSA-N

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Legal Information

ChiPros is a registered trademark of BASF SE

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H312,H319,H350

Hazard Classifications

Acute Tox. 4 Dermal - Carc. 1B - Eye 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)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
BCBL3764V
BCBJ3638V
BCBC5260V
BCBC5260

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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
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
Shuangjun Lin et al.
Organic letters, 12(17), 3816-3819 (2010-08-14)
Neocarzinostatin (1) biosynthesis is proposed to involve a vicinal diol intermediate. It is reported that NcsF2, one of two epoxide hydrolases encoded by the NCS gene cluster, catalyzes regiospecific addition of H(2)O to C-2 of both (R)- and (S)-styrene oxides
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
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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ChiPros® Chiral Epoxides

There are several alternative routes towards chiral aryl-substituted epoxides, among them Jacobsen’s asymmetric epoxidation1 or his hydrolytic kinetic resolution2 method, Sharpless’s asymmetric epoxidation3 using catalytic titan(IV)- isopropylate/diethyl tartrate complexes and tert-butylhydroperoxide

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