65859-90-7

Basic information

• Product Name: Butanedioic acid, (phenylmethylene)-, dimethyl ester, (E)-
• CAS NO: 65859-90-7
• Molecular Formula: C13H14O4
• Molecular Weight: 234.252
• Mol File: 65859-90-7.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Butanedioic acid, (phenylmethylene)-, dimethyl ester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanedioic acid, (phenylmethylene)-, dimethyl ester, (E)-(65859-90-7)
• EPA Substance Registry System: Butanedioic acid, (phenylmethylene)-, dimethyl ester, (E)-(65859-90-7)

Safety Data

• Hazardous Substances Data: 65859-90-7(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 125702-14-9 (E)-3-(methoxycarbonyl)-4-phenylbut-3-enoic acid 
• 622-42-4 1-nitro-1-phenylmethane 
• 624-49-7 dimethylfumarate 
• 92466-70-1 bis(2,2,2-trifluoroethyl)phosphite 
• 100-52-7 benzaldehyde 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 108-86-1 bromobenzene 
• 617-52-7 Dimethyl itakonate 
• 591-50-4 iodobenzene 
• 106-65-0 Dimethyl succinate 
• 67-56-1 methanol 
• 100-39-0 benzyl bromide 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 35262-43-2 dimethyl 2-benzylsuccinate 
• 108988-23-4 1-phenyl-propane-1,2,3-tricarboxylic acid 
• 131188-70-0 (E)-2-phenylmethylidene-1,4-butanediol 
• 152815-94-6 methyl hydrogen (2E,3E)-2-benzylidene-3-(3,4,5-trimethoxybenzylidene)-succinate 
• 130272-52-5 dimethyl (R)-(+)-benzylsuccinate 
• 197979-65-0 2-[1-(3',5'-dimethoxyphenyl)-(E)-ethylidene]-3-[1-phenyl-(E)-methylidene]-succinic acid 1-methyl ester 
• 197979-53-6 2-[1-(3',5'-dimethoxyphenyl)-(Z)-ethylidene]-3-[1-phenyl-(E)-methylidene]-succinic acid 1-methyl ester 
• 5653-88-3 trans-phenylitaconic acid 
• 18654-24-5 dimethyl (3E)-2-benzyl-3-benzylidenesuccinate 
• 1129282-90-1 (+/-)-benzyl-((E)-benzylidene)-succinic acid 
• 71481-05-5 2,3-dibenzylbut-2-en-dioic anhydride 
• 197979-64-9 2-[1-(3',5'-dimethoxyphenyl)-ethylidene]-3-[1-phenyl-(E)-methylidene]-succinic acid 1-methyl ester 
• 197978-61-3 C₂₃H₂₄O₇ 
• 1094172-77-6 C₂₄H₂₆O₇ 

Relevant articles and documents

Phosphine-Catalyzed Cross-Coupling of Benzyl Halides and Fumarates

A phosphine-catalyzed olefinic cross-coupling between benzyl halides and fumarates is described, which affords trisubstituted alkenes in good yields and excellent E-selectivity under metal-free conditions. Mechanistic studies suggest a catalytic cycle involving phosphorus ylide formation, Michael addition, water-assisted hydrogen transfer, and phosphine elimination.

Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes

A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.

First Base-Free Catalytic Wittig Reaction

The first base-free catalytic Wittig reaction utilizing readily available Bu3P (5 mol %) as an organocatalyst is reported. The initial Michael addition of the phosphine to a suitable acceptor substituted alkene ultimately results in the formation of an ylide which is subsequently converted with an aldehyde. The presented 1H NMR studies actually reveal evidence for the Michael addition and proposed ylide formation. Under the optimized reaction conditions various maleates and fumarates were converted with aromatic, heteroaromatic, and aliphatic aldehydes to evaluate the scope and limitations of this unprecedented reaction. Notably, maleates and fumarates react in a stereoconvergent fashion. The corresponding products were obtained in up to 95% isolated yield and E/Z-selectivities up to 99:1.