57547-55-4

Basic information

• Product Name: 3-chloro-4-methylfuran-2,5-dione
• Synonyms: 2-Chloro-3-methylmaleic anhydride; 3-Chloro-4-methyl-2,5-furandione
• CAS NO: 57547-55-4
• Molecular Formula: C₅H₃ClO₃
• Molecular Weight: 146.5285
• Mol File: 57547-55-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 202.6°C at 760 mmHg
• Flash Point: 93.8°C
• Density: 1.49g/cm³
• Vapor Pressure: 0.289mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: 3-chloro-4-methylfuran-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-4-methylfuran-2,5-dione(57547-55-4)
• EPA Substance Registry System: 3-chloro-4-methylfuran-2,5-dione(57547-55-4)

Safety Data

• Hazardous Substances Data: 57547-55-4(Hazardous Substances Data)

Upstream product

• 498-23-7 citraconic acid 
• 498-24-8 Mesaconic acid 
• 499-12-7 1 propene 1,2,3 tricarboxylic acid 
• 97-65-4 2-methylenesuccinic acid 
• 77-92-9 citric acid 
• 616-02-4 citraconic acid anhydride 
• 1384256-40-9 (Z)-3-(trichloroacetyl)-2-ethylidene-1,3-thiazinane 

Relevant articles and documents

CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N,S- acetals: A new way to prepare disubstituted maleic anhydrides

The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N,X(X=O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N,O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N,NR-acetalspenta-atomic cyclic ketene-N,S-acetalshexa-atomic cyclic ketene-N,S-acetals. Invariably the catalytic cycle begins with the formation of a carbamoyl methyl radical. This leads to a cascade of reactions, including a radical polar crossover step, which ends with the formation of the maleimide nucleus, or precursors of this. Products from the RC of the hexa-atomic cyclic ketene-N,S-acetals, were efficiently transformed into disubstituted maleic anhydrides.