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540099

Sigma-Aldrich

(R)-(+)-Styrene oxide

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

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/REAXYS Number:
1984
MDL number:
MFCD00066210
UNSPSC Code:
12352005
PubChem Substance ID:
24878440
NACRES:
NA.22

assay

97%

optical activity

[α]20/D +33°, neat

optical purity

ee: 97% (GLC)

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.)

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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Application

(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.

Legal Information

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

176.0 °F - closed cup

flash_point_c

80 °C - closed cup

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Enantioselective synthesis induced by chiral epoxides in conjunction with asymmetric autocatalysis
Kawasaki T, et al.
Tetrahedron Asymmetry, 15(23), 3699-3701 (2004)
Aluminumdodecatungstophosphate (AlPW12O40) as a reusable Lewis acid catalyst: Facile regioselective ring opening of epoxides with alcohols, acetic acid and thiols
Firouzabadi H, et al.
J. Mol. Catal. A: Chem., 250(1-2), 237-242 (2006)
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
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