59832-45-0

Basic information

• Product Name: Propanedioic acid, [(4-methylphenyl)methylene]-, dimethyl ester
• CAS NO: 59832-45-0
• Molecular Formula: C13H14O4
• Molecular Weight: 234.252
• Mol File: 59832-45-0.mol

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, [(4-methylphenyl)methylene]-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, [(4-methylphenyl)methylene]-, dimethyl ester(59832-45-0)
• EPA Substance Registry System: Propanedioic acid, [(4-methylphenyl)methylene]-, dimethyl ester(59832-45-0)

Safety Data

• Hazardous Substances Data: 59832-45-0(Hazardous Substances Data)

Upstream product

• 6773-29-1 dimethyl diazomalonate 
• 104-87-0 4-methyl-benzaldehyde 
• 108-24-7 acetic anhydride 
• 108-59-8 malonic acid dimethyl ester 
• 14062-78-3 N,N-dimethyl-4-toluamide 
• 106098-05-9 (Z)-tert-butyl methyl(α-bromo-p-methylbenzylidene)-malonate 

Downstream Products

• 1116152-90-9 (R)-dimethyl 2-[1-p-tolyl-2-(furan-2-yl)-2-oxoethyl]malonate 
• 1195497-54-1 dimethyl 2-((4,4,5,5-tetramethyl-1,3-dioxalan-2-yl)(4-tolyl)methyl)malonate 
• 1202403-57-3 dimethyl 2-(2-{5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxysulfonyl}-2-phenyl-1-p-tolylethyl)malonate 
• 103883-90-5 dimethyl β-bromo-(p-methylbenzylidene)malonate 
• 103883-89-2 dimethyl β-chloro-(p-methylbenzylidene)malonate 
• 380356-22-9 2-{(S)-1-[(3aR,8aR)-2,2-dimethyl-6-oxo-4,4,8,8-tetraphenylperhydro-6λ⁵-phosphepino[4,5-d][1,3]dioxol-6-yl]-1-(4-methylphenyl)methyl}malonic acid dimethyl ester 
• 135923-64-7 2-dimethoxycarbonyl-3-(4-methylphenyl)cyclopropane-1,1-dicarboxylate de diethyle 
• 103883-93-8 2-Bromo-2-(bromo-p-tolyl-methyl)-malonic acid dimethyl ester 
• 103883-92-7 2-Chloro-2-(chloro-p-tolyl-methyl)-malonic acid dimethyl ester 
• 49769-82-6 dimethyl 2-(4'-methylbenzyl)malonate 
• 3901-07-3 3-(4-methoxy-phenyl)acrylic acid methyl ester 
• 19310-29-3 3-(4-methoxyphenyl)acrylic acid methyl ester 
• 50363-84-3 (Z)-methyl 3-(4-methylphenyl)propenoate 
• 20754-20-5 3-p-tolyl-acrylic acid methyl ester 

Relevant articles and documents

A novel sublimable organic salt: Synthesis, characterization, thermal behavior, and catalytic activity for the synthesis of arylidene, heteroarylidene, and alkylidene malonates

A novel sublimable organic salt was synthesized, and its chemical structure was characterized by FTIR, 1D NMR, 2D NMR, and elemental analysis. In addition, the thermal phase transitions and thermal stability of new organic salt were investigated. The DSC and TGA results showed that the organic salt could convert into constituent molecules at dec. ~ 200?°C) under atmospheric pressure without forming the liquid phase. Then, it was recondensed to regenerate the initial organic salt in the cool part of the vial. Therefore, it can be a promising organic salt towards the regeneration of spent catalyst from synthesis processes when the reaction mixture contains poorly volatile components and includes its use in gas-phase procedures. Also, the catalytic efficiency of new organic salt was investigated in the Knoevenagel condensation reaction. A variety of substituted arylidene and alkylidene malonates were isolated in 78–95% yield within six hours.? Under the optimized reaction conditions, the current catalytic procedure exhibited superiority compared to the mixed piperazine/acetic acid, piperidine/acetic acid, and piperidinium acetate. There were no significant changes in the new organic salt chemical structure and catalytic activity even after the 5th run. This work revealed the importance of the existence of simultaneous hydrogen bond acceptor/donor groups in our environmentally friendly catalyst to promote the Knoevenagel condensation reaction without the use of metal-containing catalysts.

Solid-phase synthesis of arylidene and alkylidene malonates, as versatile intermediates, catalyzed using mesoporous poly-melamine–formaldehyde as a nitrogen-rich porous organic polymer (POP)

An efficient solid/slurry-state synthesis of arylidene and alkylidene malonates as versatile intermediates is developed in the presence of mesoporous poly-melamine–formaldehyde. The condensation reaction was conducted through a ball milling process as a non-conventional procedure and a greener methodology at room temperature under solvent-free conditions. The mesoporous heterogeneous catalyst could be recovered and reused ten times, and the results showed a negligible loss of catalytic activity. Various aryl- and heteroarylidene malonates, as well as dimethyl (cyclohexylidene)malonate, were isolated in good to high yields under optimal conditions. The use of hazardous reagents and solvents were minimized in the current method, and separation of catalyst and products, as well as the recovery and reusing of catalyst, were performed by cost-effective procedures. This work revealed that the synergistic effect of numerous Lewis base sites together with acceptor-donner hydrogen bonding functional groups in porous organic polymer (POP), and its high porosity plays a vital role to promote the carbon–carbon coupling reaction in the solid phase synthesis.

Reductive Knoevenagel Condensation with the Zn-AcOH System

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Asymmetric catalytic [4+3] cycloaddition ofortho-quinone methides with oxiranes

Catalytic enantioselective [4+3] cycloaddition reaction betweeno-quinone methides and oxiranes was achieved by using a chiralN,N′-dioxide/TbIIIcomplex as the catalyst, affording medium-sized hydrodioxepine derivatives in high yields (up to 99%)

Synthesis of Substituted β-Styrylmalonates by Sequential Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates and (2-Arylethylidene)malonates

A method has been developed for the synthesis of substituted β-styrylmalonates by conversion of 2-arylcyclopropane-1,1-dicarboxylates (ACDCs) in the presence of gallium trichloride into the corresponding- 1,2-zwitterionic intermediates or (2-arylethyl-idene)malonates, followed by treatment with pyridine at room temperature leading to an isomerization of the emerging double bond. This method allows one to expand these reactions to include ACDCs with acceptor substituents at the aromatic ring.

Amides as surrogates of aldehydes for C-C bond formation: amide-based direct Knoevenagel-type condensation reaction and related reactions

Aldehydes are perhaps the most versatile compounds that enable many C-C bond forming reactions, which are not amenable for other subclasses of carbonyl compounds. We report the first use of amides as surrogates of aldehydes for C-C bond formation, namely,

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.

Nucleophilic Ring Opening of Donor-Acceptor Cyclopropanes Catalyzed by a Br?nsted Acid in Hexafluoroisopropanol

A general, Br?nsted acid catalyzed method for the room temperature, nucleophilic ring opening of donor-acceptor cyclopropanes in fluorinated alcohol solvent, HFIP, is described. Salient features of this method include an expanded cyclopropane scope, including those bearing single keto-acceptor groups and those bearing electron-deficient aryl groups. Notably, the catalytic system proved amenable to a wide range of nucleophiles including arenes, indoles, azides, diketones, and alcohols.

Intermolecular Reductive Couplings of Arylidene Malonates via Lewis Acid/Photoredox Cooperative Catalysis

A cooperative Lewis acid/photocatalytic reduction of arylidene malonates yields a versatile radical anion species. This intermediate preferentially undergoes intermolecular radical-radical coupling reactions, and not the conjugate addition-dimerization reactivity typically observed in the single-electron reduction of conjugate acceptors. Reported here is the development of this open-shell species in intermolecular radical-radical cross couplings, radical dimerizations, and transfer hydrogenations. This reactivity underscores the enabling modularity of cooperative catalysis and demonstrates the utility of stabilized enoate-derived radical anions in intermolecular bond forming reactions.

Scandium(III) Trifluoromethanesulfonate Catalyzed Selective Reactions of Donor–Acceptor Cyclopropanes with 1,1-Diphenylethanols: An Approach to Polysubstituted Olefins

An unexpected synthetic approach to polysubstituted olefins through the scandium(III) trifluoromethanesulfonate catalyzed ring-opening reaction of donor–acceptor cyclopropanes with 1,1-diphenylethanols was developed. The reactions, which are experimentally easy to handle, feature tolerance of various functional groups and mild reaction conditions. On the basis of experimental evidence, a plausible mechanism was also proposed.