(1R)-1-phenylethane-1,2-diol

• ChemBase ID: 86875
• Molecular Formular: C8H10O2
• Molecular Mass: 138.1638
• Monoisotopic Mass: 138.06807956
• SMILES: OC[C@@H](c1ccccc1)O
• Canonical SMILES: OC[C@@H](c1ccccc1)O
• InChI: InChI=1S/C8H10O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8-10H,6H2/t8-/m0/s1
• InChIKey: PWMWNFMRSKOCEY-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-phenylethane-1,2-diol
• IUPAC Traditional name: (1R)-1-phenylethane-1,2-diol
• Synonyms: S-(+)-1-Phenyl-1,2-ethanediol; (R)-(-)-Styrene glycol; (R)-(-)-Phenyl-1,2-ethanediol; (-)-Styrene glycol; (R)-(-)-Phenylethylene glycol; (R)-(-)-1-Phenyl-1,2-ethanediol; (R)-(-)-1-Phenyl-1,2-ethanediol; (-)-1-Phenylethane-1,2-diol; (-)-1-Phenylethylene Glycol; (-)-Phenyl Glycol; (-)-Phenyl-1,2-ethanediol; (1R)-1-Phenyl-1,2-ethanediol; (R)-(-)-1-Phenylethane-1,2-diol; (R)-1-Phenyl-1,2-ethanediol; (R)-2-Phenyl-1,2-ethanediol; (R)-(-)-1-Phenyl-1,2-ethanediol; (R)-Styrene Glycol; (R)-(-)-苯基-1,2-乙二醇; (-)-苯乙二醇; (R)-(-)-苯基乙二醇; (R)-(-)-1-苯基-1,2-乙二醇

Database IDs

• CAS Number: 16355-00-3
• MDL Number: MFCD00064262; MFCD00066256
• Beilstein Number: 2355547
• PubChem SID: 162073991; 24858238
• PubChem CID: 2724621

CALCULATED PROPERTIES

• Acid pKa: 13.6545925
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.5755611
• LogD (pH = 7.4): 0.57556087
• Log P: 0.5755611
• Molar Refractivity: 38.8364 cm^3
• Polarizability: 15.2415085 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 64-67 °C(lit.); 67-69°C
• Boiling Point: 272-274 °C(lit.); 272-274°C
• Optical Rotation: [α]/D -69±4°, c = 1 in chloroform; [α]20/D -69°, c = 1 in chloroform; -39 (c=3 in ethanol)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC); 97%; 99%
• Grade: purum
• Linear Formula: HOCH2CH(C6H5)OH

DETAILS

Sigma Aldrich - 302163

Packaging
1 g in glass bottle
Application
Intermediate for the synthesis of chiral phosphine catalysts for asymmetric hydrogenations.1,2

Sigma Aldrich - 77847

Other Notes
Chiral building block used in various syntheses1,2,3,4

Toronto Research Chemicals - S687815

Intermediate for the synthesis of enantiopure substituted 1,4-Dioxanes. Extremely valuable and versatile alcohol used as a chiral building block in organic synthesis.

REFERENCES

• Bagnoli, L., et al.: Chem. Eur. J., 17, 993 (2011)