5331-33-9

Basic information

• Product Name: dimethyl (2Z)-2-chlorobut-2-enedioate
• Synonyms: 2-butenedioic acid, 2-chloro-, dimethyl ester, (2Z)-; Dimethyl (2Z)-2-chlorobut-2-enedioate; Dimethyl chlorobutenedioate
• CAS NO: 5331-33-9
• Molecular Formula: C₆H₇ClO₄
• Molecular Weight: 178.5704
• Mol File: 5331-33-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 224°C at 760 mmHg
• Flash Point: 91.5°C
• Density: 1.281g/cm³
• Vapor Pressure: 0.0934mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: dimethyl (2Z)-2-chlorobut-2-enedioate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (2Z)-2-chlorobut-2-enedioate(5331-33-9)
• EPA Substance Registry System: dimethyl (2Z)-2-chlorobut-2-enedioate(5331-33-9)

Safety Data

• Hazardous Substances Data: 5331-33-9(Hazardous Substances Data)

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 74427-60-4 1-(phenylsulphonylamino)acetyl chloride 
• 563-79-1 2,3-Dimethyl-2-butene 
• 76937-39-8 threo-dimethyl α-fluoro-α'-chlorosuccinate 
• 56218-62-3 2-(4-methylphenylsulfonamido)acetyl chloride 

Downstream Products

• 118657-84-4 r-1,t-3-bis(methoxycarbonyl)-1-chloro-t-2-methyl-c-2-phenylcyclopropane 
• 118657-84-4 1-chloro-r-1,t-3-bis(methoxycarbonyl)-c-2-methyl-t-2-phenylcyclopropane 
• 118657-85-5 trans-1,3-bis(methoxycarbonyl)-1-chloro-2,2-diphenylcyclopropane 
• 31419-01-9 dimethyl 3,3-diphenyl-3H-pyrazole-4,5-dicarboxylate 
• 118657-83-3 3-chloro-r-3,t-4-bis(methoxycarbonyl)-c-5-methyl-t-5-phenyl-1-pyrazoline 

Relevant articles and documents

A Simple Approach to the Synthesis of 1,4-Bis(arylsulfonyl) tetrahydropyrazine-2,5-diones

The addition of triphenylphosphine to dimethyl acetylenedicarboxylate in the presence of arylsulfonylglycyl chlorides leads to 1,4-bis-arylsulfonyl- tetrahydropyrazine-2,5-diones and dimethyl (E)-2-chloro-2-butenedioate.

APPLICATIONS OF THE ENE REACTION. SYNTHESIS AND PROPPERTIES OF SUBSTITUTED &α-METHYLENE-&γ-LACTONES

Substituted dimethyl 1,4-pentadiene-1,2-dicarboxylates ( 1 or 3 ) may be prepared by AlCl3-promoted or thermal ene reaction of olefins with dimethyl acetylenedicarboxylate.Lactonization of these adducts is catalyzed by acid.In the presence of 80 percent H2SO4 the predominant product ( ca. 80 percent ) is a (Z)-dihydro-3-carbomethoxymethylene-2(3H)-furanone ( 2 or 4 ).Cyclization with anhydrous HCl affords a mixture of products the composition of which depends on the starting material; major products include the corresponding (E)- and γ-lactone isomers ( 6 and 7 ).Detailed 1H and 13C nmr are reported for all compounds.The structures of the (E)-4,5,5-trimethyl-, (Z)-4,5,5-trimethyl-, and (Z)-4,4,5,5-tetramethyl furanone derivatives ( 6a, 2a, and, 2b,) have been established by X-ray crystallography.The properties of some of these lactones are discussed, as are possible methods of removal of the carbomethoxyl from 2.