692-92-2

Basic information

• Product Name: (1E,3Z)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester
• Synonyms: (1E,3Z)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester;(2E,4Z)-2,4-Hexadienedioic acid dimethyl ester
• CAS NO: 692-92-2
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 0
• Mol File: 692-92-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1E,3Z)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1E,3Z)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester(692-92-2)
• EPA Substance Registry System: (1E,3Z)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester(692-92-2)

Safety Data

• Hazardous Substances Data: 692-92-2(Hazardous Substances Data)

Upstream product

• 6214-23-9 methyl (2Z)-3-iodoprop-2-enoate 
• 42599-23-5 ((E)-2-iodovinyl)cyclohexane 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 74-86-2 acetylene 

Downstream Products

• 628-94-4 adipamide 
• 111-69-3 hexanedinitrile 
• 629-11-8 1,6-hexanediol 
• 124-09-4 1,6-Hexanediamine 
• 2432-74-8 1-amino-5-cyanopentane 
• 105-60-2 caprolactam 
• 1257982-60-7 dimethyl 2-phenyl-cyclohexane-1,4-dicarboxylate 
• 145179-57-3 dibutyl hexa-2,4-dienedioate 
• 1257982-53-8 trimethyl cyclohex-5-ene-1,2,4-tricarboxylate 
• 2459-10-1 benzene-1,2,4-tricarboxylic acid trimethyl ester 
• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 142178-80-1 dimethyl 4-(dimethylphenylsilyl)-(2E)-hexenedioate 
• 142178-81-2 (Z)-4-(Dimethyl-phenyl-silanyl)-hex-2-enedioic acid dimethyl ester 

Relevant articles and documents

A stereoselective palladium-mediated reductive coupling of electron-deficient terminal iodoalkenes

Iodoacrylate esters undergo palladium-catalysed reductive homocoupling to derive dienyl diester derivatives. This reductive coupling can be extended to ester-substituted terminal iododienes to derive tetraene diesters. In all cases, the reactions show relatively high levels of stereocontrol, which shows an inversion of stereochemistry about one iodoalkene unit. This process, and the suggestion that the reaction releases diiodine, is consistent with a syn-1,2-addition of an iodopalladium(II)-alkene species across another iodoalkene unit (carbometallation step), followed by reductive syn-elimination of iodopalladium iodide to derive palladium(II) iodide. It appears that under the reaction conditions employed, palladium(II) iodide may equilibrate to palladium(O) and diiodine, which can be observed or trapped out from the reaction mixture.