(2S)-oxiran-2-ylmethanol

• ChemBase ID: 147260
• Molecular Formular: C3H6O2
• Molecular Mass: 74.07854
• Monoisotopic Mass: 74.03677943
• SMILES: C1[C@@H](O1)CO
• Canonical SMILES: OC[C@H]1CO1
• InChI: InChI=1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2/t3-/m0/s1
• InChIKey: CTKINSOISVBQLD-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-oxiran-2-ylmethanol; [(2S)-oxiran-2-yl]methanol
• IUPAC Traditional name: S-glycidol
• Synonyms: (S)-(-)-2,3-Epoxy-1-propanol; (S)-(-)-Oxirane-2-methanol; (S)-(-)-Glycidol; (S)-Glycidol; (2S)-oxiran-2-ylmethanol; (S)-Oxiran-2-ylmethanol; (S)-Oxiranemethanol; (S)-(-)-2,3-环氧-1-丙醇; (S)-(-)-环氧乙烷-2-甲醇; (S)-(-)-缩水甘油

Database IDs

• CAS Number: 60456-23-7
• MDL Number: MFCD00074874
• Beilstein Number: 79783
• PubChem SID: 24871051; 24873033; 162241450
• PubChem CID: 6973630

CALCULATED PROPERTIES

• Acid pKa: 14.602878
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.67731047
• LogD (pH = 7.4): -0.67731047
• Log P: -0.67731047
• Molar Refractivity: 17.006 cm^3
• Polarizability: 6.8989635 Å^3
• Polar Surface Area: 32.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 66-67 °C/19 mmHg(lit.)
• Flash Point: 150.8 °F; 66 °C
• Density: 1.116 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.432; n20/D 1.433(lit.)
• Optical Rotation: [α]20/D -15°, neat; [α]20/D -16±2°, neat
• Hydrophobicity(logP): -0.96

Safety Information

• RTECS: RR0508100
• European Hazard Symbols: Toxic (T)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 45-60-21/22-23-37/38-41-68
• Safety Statements: 53-26-36/37/39-45
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H315-H318-H331-H335-H350-H360
• GHS Precautionary statements: P201-P261-P280-P305 + P351 + P338-P311
• 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC); 95%; 95+%; 97%
• Grade: purum
• Optical Purity: ee: 98% (GLC); enantiomeric ratio: ≥99.0:1.0 (GC)
• Empirical Formula (Hill Notation): C3H6O2

DETAILS

Sigma Aldrich - 474789

Application
Employed in the synthesis of chiral (E)-allylic alcohol side-chains for introduction into prostacyclin and prostaglandin frameworks by cross-metathesis.1
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 50029

Other Notes
Chiral building block for lipids and phospholipids1