sodium 4-[(1R,2R)-2-(2,2-dichloroacetamido)-1,3-dihydroxypropyl]benzene-1-sulfonate

• ChemBase ID: 177990
• Molecular Formular: C11H12Cl2NNaO6S
• Molecular Mass: 380.17685
• Monoisotopic Mass: 378.96600775
• SMILES: c1([C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)ccc(cc1)S(=O)(=O)[O-].[Na+]
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)[O-])O)NC(=O)C(Cl)Cl.[Na+]
• InChI: InChI=1S/C11H13Cl2NO6S.Na/c12-10(13)11(17)14-8(5-15)9(16)6-1-3-7(4-2-6)21(18,19)20;/h1-4,8-10,15-16H,5H2,(H,14,17)(H,18,19,20);/q;+1/p-1/t8-,9-;/m1./s1
• InChIKey: QFWZEJZHFNJQOE-VTLYIQCISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 4-[(1R,2R)-2-(2,2-dichloroacetamido)-1,3-dihydroxypropyl]benzene-1-sulfonate
• IUPAC Traditional name: sodium 4-[(1R,2R)-2-(2,2-dichloroacetamido)-1,3-dihydroxypropyl]benzenesulfonate
• Synonyms: 4-[(1R,2R)-2-[(2,2-dichloroacetyl)amino]-1,3-dihydroxypropyl]benzenesulfonic Acid Sodium Salt; D-threo-p-[2-(2,2-Dichloroacetamido)-1,3-dihydroxypropyl]benzene-sulfonic Acid Sodium Salt; D-threo-1-(4-Sulfonylphenyl)-2-dichloroacetylamino-1,3-propanediol Sodium Salt

Database IDs

• CAS Number: 903508-30-5
• PubChem SID: 164233900
• PubChem CID: 71433990

CALCULATED PROPERTIES

• Acid pKa: -2.1167197
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.259196
• LogD (pH = 7.4): -2.4093997
• Log P: -1.8100836
• Molar Refractivity: 75.3768 cm^3
• Polarizability: 30.49708 Å^3
• Polar Surface Area: 126.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699095

Used in the synthesis of new optically active analogs of Chloramphenicol (C325030).

REFERENCES

• Shemyakin, M.M., et al.: J. Gen. Chem. U.S.S.R., 25, 1147 (1955)