N-[(1R,2R)-1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]-2,2-dichloroacetamide hydrochloride

• ChemBase ID: 160405
• Molecular Formular: C11H15Cl3N2O3
• Molecular Mass: 329.6074
• Monoisotopic Mass: 328.01482539
• SMILES: c1c(ccc(c1)[C@@H](O)[C@H](NC(=O)C(Cl)Cl)CO)N.Cl
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)N)O)NC(=O)C(Cl)Cl.Cl
• InChI: InChI=1S/C11H14Cl2N2O3.ClH/c12-10(13)11(18)15-8(5-16)9(17)6-1-3-7(14)4-2-6;/h1-4,8-10,16-17H,5,14H2,(H,15,18);1H/t8-,9-;/m1./s1
• InChIKey: AUVANTYWDCEWMP-VTLYIQCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1R,2R)-1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]-2,2-dichloroacetamide hydrochloride
• IUPAC Traditional name: N-[(1R,2R)-1-(4-aminophenyl)-1,3-dihydroxypropan-2-yl]-2,2-dichloroacetamide hydrochloride
• Synonyms: cis-N-[2-(4-Aminophenyl)-2-hydroxy-1-(hydroxymethyl)ethyl]-2,2-dichloroacetamide Monohydrochloride; D-threo-1-(4-Aminophenyl)-2-dichloroacetylamino-1,3-propanediol Hydrochloride

Database IDs

• CAS Number: 57704-36-6
• PubChem SID: 162254540
• PubChem CID: 46780332

CALCULATED PROPERTIES

• Acid pKa: 8.234499
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.09718344
• LogD (pH = 7.4): 0.05750511
• Log P: 0.10979334
• Molar Refractivity: 70.5764 cm^3
• Polarizability: 26.93622 Å^3
• Polar Surface Area: 95.58 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Beige to Pale Yellow Solid
• Melting Point: >157°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A622670

An analogue of Chloramphenicol (C325030).

REFERENCES

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