(2R)-2-(phenoxymethyl)oxirane

• ChemBase ID: 142036
• Molecular Formular: C9H10O2
• Molecular Mass: 150.1745
• Monoisotopic Mass: 150.06807956
• SMILES: c1ccc(cc1)OC[C@H]1CO1
• Canonical SMILES: O1C[C@@H]1COc1ccccc1
• InChI: InChI=1S/C9H10O2/c1-2-4-8(5-3-1)10-6-9-7-11-9/h1-5,9H,6-7H2/t9-/m0/s1
• InChIKey: FQYUMYWMJTYZTK-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(phenoxymethyl)oxirane
• IUPAC Traditional name: (2R)-2-(phenoxymethyl)oxirane
• Synonyms: (R)-Phenoxymethyloxirane; (R)-α-(2-Oxiranyl)anisole; (R)-Glycidyl phenyl ether; (R)-2-Oxiranylanisole; (R)-α-(2-环氧乙基)苯甲醚; (R)-缩水甘油基苯基醚; (R)-2-苯氧甲基环氧乙烷

Database IDs

• CAS Number: 71031-02-2
• MDL Number: MFCD06659025
• PubChem SID: 162236267; 24857711
• PubChem CID: 1534344

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6568412
• LogD (pH = 7.4): 1.6568412
• Log P: 1.6568412
• Molar Refractivity: 41.2659 cm^3
• Polarizability: 16.490126 Å^3
• Polar Surface Area: 21.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 159.8 °F; 71 °C

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-20/21-37/38-41-43-52/53-68
• Safety Statements: 53-26-36/37/39-45-61
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H312-H315-H317-H318-H332-H335-H350
• GHS Precautionary statements: P201-P261-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

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC)
• Empirical Formula (Hill Notation): C9H10O2

DETAILS

Sigma Aldrich - 29438

Packaging
1 g in glass bottle
Application
Reactant involved in the synthesis of:
• Neuroprotective small molecules1
• Piperidinol analogs for studies of anti-tuberculosis activity2
• 2-Substituted 3,4-dihydro-2H-1,4-benzoxazines via cyclization of hydroxyl sulfonamides3
• Bicyclic azetidines via ring opening, esterification, chlorination and intramolecular alkylation4
• Bromoalkanes via ring opening and addition across C-O bonds5Involved in biological studies as a substrate for Bacillus-produced enantioselective eposide hydrolase6