(2S)-3-[(4-methylbenzenesulfonyl)oxy]propane-1,2-diol

• ChemBase ID: 178784
• Molecular Formular: C10H14O5S
• Molecular Mass: 246.28016
• Monoisotopic Mass: 246.05619455
• SMILES: c1c(ccc(c1)C)S(=O)(=O)OC[C@@H](O)CO
• Canonical SMILES: OC[C@@H](COS(=O)(=O)c1ccc(cc1)C)O
• InChI: InChI=1S/C10H14O5S/c1-8-2-4-10(5-3-8)16(13,14)15-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3/t9-/m0/s1
• InChIKey: DFQNMODTAFTGHS-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-[(4-methylbenzenesulfonyl)oxy]propane-1,2-diol
• IUPAC Traditional name: (2S)-3-[(4-methylbenzenesulfonyl)oxy]propane-1,2-diol
• Synonyms: (S)-3-(Tosyloxy)-1,2-propanediol; (S)-3-(p-Toluenesulfonyloxy)-1,2-propanediol; (S)-1,2,3-Propanetriol 4-methylbenzenesulfonate; (S)-1-Tosyloxyglycerol; (S)-1-Tosyloxy-2,3-propanediol

Database IDs

• CAS Number: 50765-70-3
• PubChem SID: 164234694
• PubChem CID: 11043038

CALCULATED PROPERTIES

• Acid pKa: 13.580837
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7250977
• LogD (pH = 7.4): 0.7250974
• Log P: 0.7250977
• Molar Refractivity: 58.4588 cm^3
• Polarizability: 23.770042 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-58°C

DETAILS

Toronto Research Chemicals - T685500

A chiral synthon for general asymmetric synthesis. An intermediate for the synthesis of chiral aryloxypropanolamines, which make up the majority of known potent beta-adrenergic blockers.

REFERENCES

• Kurimura, M., et al.: Chem. Pharm. Bull., 39, 2590 (1991)
• Meerpoel, L., et al.: J. Med. Chem., 48, 2184 (1991)