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540099

Sigma-Aldrich

(R)-(+)-Styrene oxide

97%, optical purity ee: 97% (GLC)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C8H8O
Número CAS:
Peso molecular:
120.15
Beilstein:
1984
Número MDL:
Código UNSPSC:
12352005
ID de substância PubChem:
NACRES:
NA.22

Ensaio

97%

atividade óptica

[α]20/D +33°, neat

pureza óptica

ee: 97% (GLC)

Lim. expl.

~22 %

índice de refração

n20/D 1.534 (lit.)

p.e.

89-90 °C/23 mmHg (lit.)

densidade

1.051 g/mL at 25 °C (lit.)

grupo funcional

ether
phenyl

cadeia de caracteres SMILES

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

chave InChI

AWMVMTVKBNGEAK-QMMMGPOBSA-N

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Aplicação

(R)-(+)-Styrene oxide can be used:
  • As a chiral initiator in the synthesis of 5-pyrimidyl alkanol from its corresponding aldehyde using diisopropylzinc.
  • As a substrate in the stereoselective intermolecular O-alkylation of phenols with epoxides via Friedel–Crafts-type reaction.
  • As a substrate in the ring-opening reactions of epoxides with alcohols, carboxylic acids, and thiols using the AlPW12O40 catalyst.

Used to produce a homologated epoxide as part of a synthetic approach to (+)-allosedamine.

Informações legais

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Pictogramas

Health hazardExclamation mark

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

Acute Tox. 4 Dermal - Carc. 1B - Eye Irrit. 2

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

176.0 °F - closed cup

Ponto de fulgor (°C)

80 °C - closed cup

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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A new regio-and stereoselective intermolecular Friedel-Crafts alkylation of phenolic substrates with aryl epoxides
Bertolini F, et al.
Tetrahedron Letters, 47(1), 61-64 (2006)
Kang, B.; Chang, S.
Tetrahedron, 60, 7353-7353 (2004)
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
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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