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540099

Sigma-Aldrich

(R)-(+)-Styrene oxide

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

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C8H8O
Numero CAS:
20780-53-4
Peso molecolare:
120.15
Beilstein:
1984
Numero MDL:
MFCD00066210
Codice UNSPSC:
12352005
ID PubChem:
24878440
NACRES:
NA.22

Livello qualitativo

100

Saggio

97%

Attività ottica

[α]20/D +33°, neat

Purezza ottica

ee: 97% (GLC)

Limite di esplosione

~22 %

Indice di rifrazione

n20/D 1.534 (lit.)

P. eboll.

89-90 °C/23 mmHg (lit.)

Densità

1.051 g/mL at 25 °C (lit.)

Gruppo funzionale

ether
phenyl

Stringa SMILE

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
AWMVMTVKBNGEAK-QMMMGPOBSA-N

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Applicazioni

(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.

Note legali

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

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H312,H319,H350

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

176.0 °F - closed cup

Punto d’infiammabilità (°C)

80 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
MKCL7305
MKBR3101V
MKBL6813V
90198MJ
01101KJ

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Sigma-Aldrich

540048

(R)-(+)-Propylene oxide

1-Phenyl-1,2-ethanediol 97%

Sigma-Aldrich

P24055

1-Phenyl-1,2-ethanediol

1,3-Diaminopropane ≥99%

Sigma-Aldrich

D23602

1,3-Diaminopropane

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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