165606-93-9

Basic information

• Product Name: 3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione
• Synonyms: 2,5-pyrrolidinedione, 3,3-dichloro-4-(dichloromethylene)-; 3,3-Dichloro-4-(dichloromethylene)pyrrolidine-2,5-dione
• CAS NO: 165606-93-9
• Molecular Formula: C₅HCl₄NO₂
• Molecular Weight: 248.8789
• Mol File: 165606-93-9.mol

Chemical Properties

• Density: 1.84g/cm³
• Refractive Index: 1.595
• CAS DataBase Reference: 3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione(165606-93-9)
• EPA Substance Registry System: 3,3-dichloro-4-(dichloromethylidene)pyrrolidine-2,5-dione(165606-93-9)

Safety Data

• Hazardous Substances Data: 165606-93-9(Hazardous Substances Data)

Upstream product

• 170660-65-8 3-methyl-3,4,4-trichloro-2,5-pyrrolidinedione 
• 1072-87-3 citraconimide 
• 69636-50-6 3-chloro-4-methyl-1H-pyrrole-2,5-dione 

Relevant articles and documents

Halogenated 2,5-pyrrolidinediones: Synthesis, bacterial mutagenicity in Ames tester strain TA-100 and semi-empirical molecular orbital calculations

The chloroimide 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione, a tetrachloroitaconimide, is the principal mutagen produced by chlorination of simulated poultry chiller water. It is the second most potent mutagenic disinfection by-product of chlorination ever reported. Six of seven new synthetic analogs of this compound are direct-acting mutagens in Ames tester strain TA-100. Computed energies of the lowest unoccupied molecular orbital (ELUMO) and of the radical anion stability (ΔHf/rad - ΔHf) from MNDO-PM3 for the chloroimides show a quantitative correlation with the Ames TA-100 bacterial mutagenicity values. The molar mutagenicities of these direct acting mutagenic imides having an exocyclic double bond fit the same linear correlation (lnMm vs. ELUMO; lnMm vs. ΔHf/rad - ΔHf) as the chlorinated 2(5H)-furanones, including the potent mutagen MX, 3-chloro-4-(dichloro-methyl)-5-hydroxy-2(5H)-furanone, a by-product of water chlorination and paper bleaching with chlorine. Mutagenicity data for related haloimides having endocyclic double bonds are also given. For the same number of chlorine atoms, the imides with endocyclic double bonds have significantly higher Ames mutagenicity compared to their structural analogs with exocyclic double bonds, but do not follow the same ELUMO or ΔHf/rad - ΔHf correlation as the exocyclic chloroimides and the chlorinated 2(5H)-furanones.

Potent Bacterial Mutagens Produced by Chlorination of Simulated Poultry Chiller Water

Hypochlorite treatment of a simulated food-processing mixture produces 3,4-dichloromaleimide and 3,3-dichloro-4-(dichloromethylene)-2,5-pyrrolidinedione (C5HCl4NO2). The tetrachloro compound and two analogs, which can be synthesized from citraconic anhydride and itaconic anhydride, are direct-acting Ames mutagens in Salmonella typhimurium TA100 tester strain. These novel five-carbon cyclic imides are structurally similar to 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), the principal mutagenic compound present in paper pulp bleaching liquors. Molecular structure analysis of the mutagens was based on X-ray crystallography, 13C NMR, and mass spectrometry of synthetic chlorinated imides with identical mass spectra and gas chromatographic retention indices. The tetrachloroimide accounts for much of the mutagenicity of the dichloromethane-extractable pH 2 fraction from chlorination of a simulated food-processing system consisting of chicken frankfurters. In the Ames TA100 tester strain it has a molecular mutagenicity of 1450 revertants/ nmol without microsomal activation, making it the second most potent mutagen reported from a chlorination process.