2-phenyloxirane

• ChemBase ID: 107325
• Molecular Formular: C8H8O
• Molecular Mass: 120.14852
• Monoisotopic Mass: 120.05751488
• SMILES: C1OC1c1ccccc1
• Canonical SMILES: O1CC1c1ccccc1
• InChI: InChI=1S/C8H8O/c1-2-4-7(5-3-1)8-6-9-8/h1-5,8H,6H2
• InChIKey: AWMVMTVKBNGEAK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenyloxirane
• IUPAC Traditional name: styrene oxide; (+-)-styrene oxide
• Synonyms: PHENYLETHYLENE OXIDE; 2-phenyloxirane; Phenyloxirane; Epoxystyrene; Styryl oxide; Phenylethylene oxide; Styrene oxide; 1,2-Epoxyethylbenzene; Styrene oxide; (±)-Epoxystyrene; (±)-2-Phenyloxirane; (±)-Styrene oxide; 2-Phenyloxirane; (Epoxyethyl)benzene; 1,2-Epoxy-1-phenylethane; (±)-Phenylethylene Oxide; (±)-Phenyloxirane; (±)-Styrene Oxide; 1-Phenyl-1,2-epoxyethane; NSC 637; NSC 7582; Phenethylene Oxide; STO; Styrene 1',2'-Oxide; Styrene 7,8-Oxide; Styrene epoxide; α,β-Epoxystyrene; rac Styrene Oxide; 1,2-环氧乙基苯; 环氧苯乙烷; 苯基环氧乙烷; 氧化苯乙烯; (±)-氧化苯乙烯

Database IDs

• CAS Number: 96-09-3
• EC Number: 202-476-7
• MDL Number: MFCD00005121
• Beilstein Number: 108582
• PubChem SID: 24899628; 162093431; 24887149; 24902068
• PubChem CID: 7276
• KEGG ID: C02083
• Wikipedia Title: Styrene_oxide

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Apperance: Colorless to light yellow liquid
• Melting Point: -37 °C(lit.); -37°C; -37°C
• Boiling Point: 193-196°C; 194 °C(lit.); 194°C
• Flash Point: 176 °F; 74°C(165°F); 80 °C
• Auto Ignition Point: 928 °F
• Density: 1.052 g/mL; 1.053; 1.054 g/mL at 25 °C(lit.)
• Refractive Index: 1.5350; n20/D 1.535(lit.); n20/D 1.536
• Vapor Pressure: <1 mmHg ( 20 °C)
• Vapor Density: 4.14 (vs air)

Safety Information

• RTECS: CZ9625000
• European Hazard Symbols: Toxic (T)
• UN Number: 2810; UN2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 45-21-36; R:21-36-45; R20 R22 R34 R36 R37 R38
• Safety Statements: 53-45; S:45-53
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• Explode Limits: ~22 %
• GHS Hazard statements: H302-H311-H319-H350; H350-H302-H312-H319-H227
• GHS Precautionary statements: P201-P280-P305 + P351 + P338-P308 + P313; P210-P280-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 3

Product Information

• Purity: ≥97%; ≥97.0% (GC); 97%; 98+%
• Grade: purum
• Empirical Formula (Hill Notation): C8H8O

DETAILS

MP Biomedicals - 05203338

MP Biomedicals Rare Chemical collection

Sigma Aldrich - S5006

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - W513504

Packaging
1 kg in glass bottle
1 sample in glass bottle
5, 10 kg in poly drum

Toronto Research Chemicals - S687795

A major (toxic) metabolite of Styrene (S687790), catalyzed by epoxide hydrolase.

REFERENCES

• Shen, S. et al.: Drug Metab. Disp., 38, 1934 (2010)
• Carlson, G.P. et al.: J. Toxicol. Env. Health, 73, 1689 (2010)
• Aryl substituted epoxides undergo rearrangement in the presence of NaBH₄ in benzene to give arylacetaldehydes: Gazz. Chim. Ital., 121, 579 (1991).
• In the presence of Pd(OAc)₂ and Bu₃P, a tandem isomerization-aldol condensation occurs: J. Org. Chem., 61, 7565 (1996):
  
• In the presence of excess of a second aldehyde, crossed aldol reactions occur in moderate yield.