4-[bromo(chloro)methyl]-3-chloro-5-hydroxy-2,5-dihydrofuran-2-one

• ChemBase ID: 162806
• Molecular Formular: C5H3BrCl2O3
• Molecular Mass: 261.88552
• Monoisotopic Mass: 259.86426132
• SMILES: C1(=C(C(OC1=O)O)C(Br)Cl)Cl
• Canonical SMILES: ClC(C1=C(Cl)C(=O)OC1O)Br
• InChI: InChI=1S/C5H3BrCl2O3/c6-3(8)1-2(7)5(10)11-4(1)9/h3-4,9H
• InChIKey: VJOQLLUPRMECKH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[bromo(chloro)methyl]-3-chloro-5-hydroxy-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 4-[bromo(chloro)methyl]-3-chloro-5-hydroxy-5H-furan-2-one
• Synonyms: 3-Chloro-4-(bromochloromethyl)-5-hydroxy-2(5H)-furanone; BMX 1; 4-(Bromochloromethyl)-3-chloro-5-hydroxy-2(5H)-furanone (Mixture of Diastereomers)

Database IDs

• CAS Number: 132059-51-9
• PubChem SID: 162256941
• PubChem CID: 154414

CALCULATED PROPERTIES

• Acid pKa: 11.4912815
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.1238906
• LogD (pH = 7.4): 1.123856
• Log P: 1.1238911
• Molar Refractivity: 44.047 cm^3
• Polarizability: 17.432695 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Oil

Safety Information

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

DETAILS

Toronto Research Chemicals - B682395

A brominated analog of the highly mutagenic drinking water micropollutant MX (C365665). Carcinogenic.

REFERENCES

• Hakulinen, P., et al.: Toxicol. Lett., 151, 439 (2004)
• Richardson, S., et al.: Mutat. Res., 636, 178 (2004)
• Kim, J., et al.: Environ. Toxicol., 23, 319 (2004)