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Merck
CN

540099

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

Key Documents

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Product Name

(R)-(+)-Styrene oxide, 97%, optical purity ee: 97% (GLC)

InChI

1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2/t8-/m0/s1

SMILES string

C1O[C@@H]1c2ccccc2

InChI key

AWMVMTVKBNGEAK-QMMMGPOBSA-N

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.)

functional group

ether
phenyl

Quality Level

100

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCL7305
MKBR3101V
MKBL6813V
90198MJ
01101KJ

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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)
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)
Enantioselective synthesis induced by chiral epoxides in conjunction with asymmetric autocatalysis
Kawasaki T, et al.
Tetrahedron Asymmetry, 15(23), 3699-3701 (2004)
Gary P Carlson
Drug and chemical toxicology, 34(4), 440-444 (2011-07-14)
Styrene is known to be hepatotoxic and pneumotoxic in rodents, and these adverse effects are related to its metabolism. Mice deficient in the enzymes responsible for both the activation and detoxification of styrene are useful in examining this relationship more
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