(2Z)-2,3-dichloro-4-oxobut-2-enoic acid

• ChemBase ID: 174852
• Molecular Formular: C4H2Cl2O3
• Molecular Mass: 168.96288
• Monoisotopic Mass: 167.93809928
• SMILES: C(=C(\Cl)/C=O)(\Cl)/C(=O)O
• Canonical SMILES: O=C/C(=C(\C(=O)O)/Cl)/Cl
• InChI: InChI=1S/C4H2Cl2O3/c5-2(1-7)3(6)4(8)9/h1H,(H,8,9)/b3-2-
• InChIKey: LUMLZKVIXLWTCI-IHWYPQMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-2,3-dichloro-4-oxobut-2-enoic acid
• IUPAC Traditional name: mucochloric acid
• Synonyms: (Z)-2,3-Dichloro-4-oxo-2-butenoic Acid; Dichloromalealdehydic Acid; 2,3-Dichloromaleic Aldehyde Acid; α,β-Dichloro-β-formylacrylic Acid; Mucochloric Acid

Database IDs

• CAS Number: 87-56-9
• PubChem SID: 164230762
• PubChem CID: 2771871

CALCULATED PROPERTIES

• Acid pKa: 1.4658866
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -2.8329144
• LogD (pH = 7.4): -2.9493868
• Log P: 0.578374
• Molar Refractivity: 33.2642 cm^3
• Polarizability: 12.513528 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 125-127°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M790800

Mucochloric Acid is an intermediate product of the herbicide Burex that can cause poisioning and skin damage upon exposure. Mucochloric Acid is also a chlorine disinfection byproduct in drinking water with mutagenic activity.

REFERENCES

• Kolesar, D. et al.: Bratsilav. Lek. Listy, 64, 132 (1978)
• Romancik, V.E.: Ces.-Slov. Hyd., 21, 319 (1978)
• Jansson, K. et al.: Environ. Mol. Mutagen., 25, 284 (1978)