(2S)-1,1,2-triphenylethane-1,2-diol

• ChemBase ID: 150580
• Molecular Formular: C20H18O2
• Molecular Mass: 290.35572
• Monoisotopic Mass: 290.13067982
• SMILES: c1ccc(cc1)[C@@H](C(c1ccccc1)(c1ccccc1)O)O
• Canonical SMILES: O[C@H](C(c1ccccc1)(c1ccccc1)O)c1ccccc1
• InChI: InChI=1S/C20H18O2/c21-19(16-10-4-1-5-11-16)20(22,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19,21-22H/t19-/m0/s1
• InChIKey: GWVWUZJOQHWMFB-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1,1,2-triphenylethane-1,2-diol
• IUPAC Traditional name: (2S)-1,1,2-triphenylethane-1,2-diol
• Synonyms: (S)-(-)-1,1,2-Triphenyl-1,2-ethanediol; (R)-(+)-1,1,2-Triphenyl-1,2-ethanediol; (S)-(-)-1,1,2-Triphenylethane-1,2-diol; (S)-(-)-1,1,2-三苯基-1,2-乙二醇; (R)-(+)-1,1,2-三苯基-1,2-乙二醇

Database IDs

• CAS Number: 108998-83-0; 95061-46-4
• MDL Number: MFCD00075492
• Beilstein Number: 3208921; 3208922
• PubChem SID: 162244741; 24862750
• PubChem CID: 7000031

CALCULATED PROPERTIES

• Acid pKa: 12.321055
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.8693235
• LogD (pH = 7.4): 3.8693182
• Log P: 3.8693235
• Molar Refractivity: 87.8224 cm^3
• Polarizability: 34.471737 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 125-127 °C(lit.); 125-127°C; 126-128 °C
• Optical Rotation: [α]20/D +222±5°, c = 1% in ethanol; [α]20/D -214°, c = 1 in ethanol; -214 (c=1 in ethanol)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); 98%; 99%
• Grade: purum
• Linear Formula: C6H5CH(OH)C(C6H5)2OH
• Empirical Formula (Hill Notation): C20H18O2

DETAILS

Sigma Aldrich - 367435

Packaging
5 g in glass bottle

Sigma Aldrich - 92923

Other Notes
The 2-O-acetate is used for diastereoselective aldol condensations1,2; The silylated 2-O-propionate undergoes diastereoselective aldol condensations3,4