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

• ChemBase ID: 130628
• Molecular Formular: C10H14O5S
• Molecular Mass: 246.28016
• Monoisotopic Mass: 246.05619455
• SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@@H](CO)O
• 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-/m1/s1
• InChIKey: DFQNMODTAFTGHS-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-[(4-methylbenzenesulfonyl)oxy]propane-1,2-diol
• IUPAC Traditional name: (2R)-3-[(4-methylbenzenesulfonyl)oxy]propane-1,2-diol
• Synonyms: (R)-Glycerol 1-(p-toluenesulfonate); (R)-3-(Tosyloxy)-1,2-propanediol; (R)-3-(p-Toluenesulfonyloxy)-1,2-propanediol; (R)-1,2,3-Propanetriol 4-methylbenzenesulfonate; (R)-1-Tosyloxyglycerol; (R)-1-Tosyloxy-2,3-propanediol; (R)-2,3-二羟基丙基对甲苯磺酸酯; (R)-3-甲苯磺酰氧基-1,2-丙二醇; sn-甘油基 1-(对甲苯磺酸酯); (R)-对甲苯磺酸-1-甘油酯

Database IDs

• CAS Number: 41274-09-3
• MDL Number: MFCD00270084
• PubChem SID: 162224906
• PubChem CID: 11413915

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: 54-59°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: 95% (TLC)

DETAILS

Toronto Research Chemicals - T685000

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

• Fuji, M., et al.: Chem. Pharm. Bull., 40, 2353 (1992)
• Meerpoel, L., et al.: J. Med. Chem., 48, 2184 (1992)