(2R)-3-(benzyloxy)propane-1,2-diol

• ChemBase ID: 131351
• Molecular Formular: C10H14O3
• Molecular Mass: 182.21636
• Monoisotopic Mass: 182.09429431
• SMILES: c1ccc(cc1)COC[C@@H](CO)O
• Canonical SMILES: OC[C@H](COCc1ccccc1)O
• InChI: InChI=1S/C10H14O3/c11-6-10(12)8-13-7-9-4-2-1-3-5-9/h1-5,10-12H,6-8H2/t10-/m1/s1
• InChIKey: LWCIBYRXSHRIAP-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-(benzyloxy)propane-1,2-diol
• IUPAC Traditional name: (2R)-3-(benzyloxy)propane-1,2-diol
• Synonyms: (R)-(+)-3-Benzyloxy-1,2-propanediol; (R)-Glycerol 1-benzyl ether; 3-O-Benzyl-sn-glycerol; 3-Benzyl-sn-glycerol; (R)-甘油 1-苄醚; 3-苄基-sn-甘油; (R)-(+)-3-苄氧基-1,2-丙二醇; 3-O-苄基-sn-甘油

Database IDs

• CAS Number: 56552-80-8
• MDL Number: MFCD00067260
• Beilstein Number: 2048922
• PubChem SID: 24848323; 162225629; 24867485
• PubChem CID: 2724795

CALCULATED PROPERTIES

• Acid pKa: 13.640775
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.5285856
• LogD (pH = 7.4): 0.5285854
• Log P: 0.5285856
• Molar Refractivity: 49.8799 cm^3
• Polarizability: 19.622992 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 25-29 °C(lit.)
• Flash Point: 113 °C; 235.4 °F
• Optical Rotation: [α]20/D +5.5±1.0°, c = 20% in chloroform; [α]20/D +5.5°, c = 20 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~98%; ≥99.0% (sum of enantiomers, GC); 99%
• Grade: puriss.
• Linear Formula: C6H5CH2OCH2CH(OH)CH2OH
• Empirical Formula (Hill Notation): C10H14O3

DETAILS

Sigma Aldrich - 438960

Packaging
1 g in glass bottle
Application
Employed in the synthesis of a cyclopropyl chiron used in the preparation of 2,3-methanoamino acids.1 Chiral building block in the synthesis of petrosynes2 and biologically important phospholipid analogs.3,4

Sigma Aldrich - 13735

Other Notes
Important starting material for the synthesis of lipids, e.g. by diacylation or dialkylation 1; 1-mono-derivatization 2; Selective protection of primary OH 3