(2R)-2-phenyloxirane

• ChemBase ID: 4072
• Molecular Formular: C8H8O
• Molecular Mass: 120.14852
• Monoisotopic Mass: 120.05751488
• SMILES: C1O[C@@H]1c1ccccc1
• Canonical SMILES: O1C[C@H]1c1ccccc1
• InChI: InChI=1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2/t8-/m0/s1
• InChIKey: AWMVMTVKBNGEAK-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-phenyloxirane
• IUPAC Traditional name: R-styrene oxide
• Synonyms: R-Styrene Oxide; (R)-Styrene oxide; (R)-Phenyloxirane; (R)-(+)-Phenyloxirane; (R)-Phenylethylene oxide; (R)-(+)-Styrene oxide; (R)-2-Phenyloxirane; (R)-Phenyloxirane; 2-Phenyl-oxirane; (R)-(+)-(Epoxyethyl)benzene; (2R)-2-Phenyloxirane; (R)-Epoxystyrene; (R)-(+)-Styrene Oxide; (R)-氧化苯乙烯; (R)-苯基环氧乙烷; (R)-(+)-环氧乙基苯; (R)-环氧苯乙烷; (R)-(+)-氧化苯乙烯

Database IDs

• CAS Number: 20780-53-4
• MDL Number: MFCD00066210
• Beilstein Number: 1984
• PubChem SID: 24878440; 46507332; 160967506; 24887378
• PubChem CID: 114705

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7372646
• LogD (pH = 7.4): 1.7372646
• Log P: 1.7372646
• Molar Refractivity: 35.3263 cm^3
• Polarizability: 13.976154 Å^3
• Polar Surface Area: 12.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.72
• LOG S: -1.98
• Solubility (Water): 1.26e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Colorless Oil
• Boiling Point: 192-194 °C(lit.); 89-90 °C/23 mmHg(lit.)
• Flash Point: 176 °F; 80 °C
• Density: 1.051 g/mL at 20 °C(lit.); 1.051 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.534(lit.); n20/D 1.535
• Optical Rotation: [α]/D +33±2°, neat; [α]/D -24±2°, c = 1 in chloroform; [α]20/D +33°, neat

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• RTECS: CZ9625010
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-21-36
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• Explode Limits: ~22 %
• GHS Hazard statements: H312-H319-H350
• GHS Precautionary statements: P201-P280-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥98.0% (GC); ≥98.0% (sum of enantiomers, HPLC); 97%; 98%
• Grade: produced by BASF; purum
• Optical Purity: ee: 97% (GLC); enantiomeric excess: ≥98.0%
• Empirical Formula (Hill Notation): C8H8O

DETAILS

DrugBank - DB04499

Drug information: experimental

Sigma Aldrich - 540099

Application
Used to produce a homologated epoxide as part of a synthetic approach to (+)-allosedamine.1
Packaging
25 g in poly bottle
5 g in glass bottle
Legal Information
Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.

Sigma Aldrich - 726508

Packaging
25, 100 g in glass bottle
Legal Information
ChiPros is a registered trademark of BASF SE

Sigma Aldrich - 78880

Other Notes
This chiral building block reacts with various nucleophiles, e.g. carbanions and amines, to chiral α-substituted benzyl alcohols 1,2,3

Toronto Research Chemicals - S687800

Main metabolite of Styrene (S687790), catalyzed by epoxide hydrolase.

REFERENCES

• Harvilchuck, J., et al.: Toxicol. Lett., 183, 28 (2008)
• Harvilchuck, J., et al.: Toxicol., 264, 171 (2008)
• Woo, J., et al.: App. Microbiol., Biotechnol., 82, 873 (2008)