2-{2,3-dichloro-4-[2-(hydroxymethyl)butanoyl]phenoxy}acetic acid

• ChemBase ID: 166256
• Molecular Formular: C13H14Cl2O5
• Molecular Mass: 321.15326
• Monoisotopic Mass: 320.02182891
• SMILES: c1c(c(c(c(c1)C(=O)C(CC)CO)Cl)Cl)OCC(=O)O
• Canonical SMILES: CCC(C(=O)c1ccc(c(c1Cl)Cl)OCC(=O)O)CO
• InChI: InChI=1S/C13H14Cl2O5/c1-2-7(5-16)13(19)8-3-4-9(12(15)11(8)14)20-6-10(17)18/h3-4,7,16H,2,5-6H2,1H3,(H,17,18)
• InChIKey: JZUOOKOWCATTNI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2,3-dichloro-4-[2-(hydroxymethyl)butanoyl]phenoxy}acetic acid
• IUPAC Traditional name: 2,3-dichloro-4-[2-(hydroxymethyl)butanoyl]phenoxyacetic acid
• Synonyms: 2-[2,3-Dichloro-4-[2-(hydroxymethyl)-1-oxobutyl]phenoxy]acetic Acid; Ethacrynic Acid Impurity B; 2-Desmethylene-2-chloromethyl Ethacrynic Acid

Database IDs

• CAS Number: 95772-54-6
• PubChem SID: 162260389
• PubChem CID: 15593754

CALCULATED PROPERTIES

• Acid pKa: 2.7872677
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.18531856
• LogD (pH = 7.4): -1.0284145
• Log P: 2.4666142
• Molar Refractivity: 74.1953 cm^3
• Polarizability: 29.086609 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291660

2-Desmethylene-2-chloromethyl Ethacrynic Acid is an impurity of Ethacrynic Acid (E676000).

REFERENCES

• Yarwood, R.J. et al.: J. Pharmac. Sci., 74, 220 (1985)
• Yarwood, R.H. et al.: J. Pharmac. Biomed. Anal., 5, 369 (1985)