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540099 Sigma-Aldrich

(R)-(+)-Styrene oxide

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

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

  • CAS Number 20780-53-4

  • Empirical Formula (Hill Notation) C8H8O

  • Molecular Weight 120.15

  •  Beilstein/REAXYS Number 1984

  •  MDL number MFCD00066210

  •  PubChem Substance ID 24878440

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Epoxides, Organic Building Blocks More...
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

Description

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.

Packaging

25 g in poly bottle

5 g in glass bottle

Legal Information

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
NA 1993 / PGIII
WGK Germany 
WGK 3
RTECS 
CZ9625010
Flash Point(F) 
176.0 °F - closed cup
Flash Point(C) 
80 °C - closed cup
Protocols & Articles

Articles

HKR Epoxides

One of the most effective and recent methods for obtaining several classes of chiral building blocks is Jacobsen’s hydrolytic kinetic resolution technique (HKR). The method provides general access to...
Aldrich ChemFiles 2005, 5.4, 17.
Keywords: Anti-inflammatory agents, Asymmetric synthesis, Building blocks, Chemfiles, Deprotonations, Ligands, Methods

Peer-Reviewed Papers
15

References

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