14624-11-4

Basic information

• Product Name: 5,6-Dichloro-2-cyclohexene-1,4-dione
• CAS NO: 14624-11-4
• Molecular Weight: 179.003
• Mol File: 14624-11-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5,6-Dichloro-2-cyclohexene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dichloro-2-cyclohexene-1,4-dione(14624-11-4)
• EPA Substance Registry System: 5,6-Dichloro-2-cyclohexene-1,4-dione(14624-11-4)

Safety Data

• Hazardous Substances Data: 14624-11-4(Hazardous Substances Data)

Upstream product

• 106-51-4 p-benzoquinone 
• 67-66-3 chloroform 
• 7782-50-5 chlorine 

Downstream Products

• 1073-95-6 5,6-Dichloro-2-cyclohexene-1,4-dione 
• 57982-12-4 2,3-dichlorohydroquinone diacetate 
• 608-44-6 2,3-dichlorohydroquinone 
• 57166-01-5 Methyl-6-chlorhomogentisat 
• 824-69-1 2,5-dichloro-1,4-hydroquinone 

Relevant articles and documents

Benzoquinones and Related Compounds. Part 4. Thermolysis of the Diels-Alder Adduct of 2-Acetyl-5,6-dichloro-1,4-benzoquinone and Cyclopentadiene: Evidence for a Partial Retro-diene Reaction

Addition of chlorine to (2-methyl-1,3-dioxolan-2-yl)-1,4-benzoquinone occurs at the unsubstituted double bond.Subsequent enolisation and cleavage of the acetal affords 2-acetyl-5,6-dichlorohydroquinone in 50percent overall yield.Oxidation of this gives the corresponding 1,4-benzoquinone which with cyclopentadiene yields, predominantly, the 1 : 1 Diels-Alder adduct (6) by endo-addition to the 2,3-double bond.Thermolysis of this adduct in benzene results in disproportionation to cyclopentadiene and the spiro-acetal (13); thermolysis in acetic acid also yields (13), but the major product is the dihydrobenzofuran (14), an isomer of the Diels-Alder adduct.Mechanisms for the formation of these products are discussed.