1797-75-7

Usage

Uses

Used in Polymer and Resin Production:
Diallyl malonate is used as a monomer for the production of polymers and resins, where it acts as a crosslinking agent. This enhances the durability and strength of the resulting materials.
Used in Pharmaceutical Production:
Diallyl malonate serves as a chemical intermediate in the production of pharmaceuticals, contributing to the synthesis of various medicinal compounds.
Used in Perfume and Fragrance Synthesis:
In the fragrance industry, diallyl malonate is utilized in the synthesis of perfumes and fragrances, adding unique scents to various products.
Used in Food Product Flavoring (with limitations):
Although diallyl malonate can be used as a flavoring agent in food products, its application is limited due to its potentially toxic properties. It is essential to ensure that the compound is used within safe limits to avoid health risks.

InChI:InChI=1/C9H12O4/c1-3-5-12-8(10)7-9(11)13-6-4-2/h3-4H,1-2,5-7H2

Upstream product

• 504-64-3 carbon suboxide 
• 107-18-6 allyl alcohol 
• 108-59-8 malonic acid dimethyl ester 
• 205114-96-1 2-Bromo-malonic acid allyl ester methyl ester 
• 141-82-2 malonic acid 
• 1663-67-8 malonoyl dichloride 
• 868-26-8 dimethyl 2-bromomalonate 
• 141-95-7 sodium malonate 
• 107-05-1 3-chloroprop-1-ene 
• 16854-72-1 Dithiomalonsaeure-S,S'-diphenylester 
• 106-95-6 allyl bromide 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 52505-39-2 diallyl 2-benzylidenemalonate 
• 1168-85-0 Di-(3-cyclohexylpropyl)-malonat 
• 1027542-25-1 (S)-2-Allyloxycarbonyl-3-((S)-3-tert-butoxycarbonylamino-4,4-dimethyl-2-oxo-pentyl)-succinic acid 1-allyl ester 4-benzyl ester 
• 249588-49-6 2-[2-(tert-butyl-dimethyl-silanyloxy)-3-tritylsulfanyl-propyl]-malonic acid diallyl ester 
• 1078631-95-4 C₂₁H₂₄O₆ 
• 1078632-14-0 C₂₀H₂₂O₆ 
• 1078631-88-5 C₂₀H₂₂O₆ 
• 934737-76-5 diallyl 2-(4-methoxycarbonylbenzyl)malonate 
• 934738-13-3 diallyl 2-(4-cyanobenzyl)malonate 
• 1175184-76-5 C₁₄H₁₀O₆ 
• 339283-33-9 allyl 2-oxo-2H-chromene-3-carboxylate 
• 934738-39-3 diallyl 2-[2-(4-methoxycarbonylphenyl)ethyl]malonate 

Relevant academic research and scientific papers

Ball-Milling-Enabled Reactivity of Manganese Metal**

Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.

A stereocontrolled total synthesis of (±)-saframycin A

A thirteen-step total synthesis of (±)-saframycin A from a tricyclic lactam intermediate is described. The key step of this total synthesis is the stereocontrolled construction of a pentacyclic saframycin framework via a modified Pictet-Spengler type cyclization generating a bis-carboxylic acid ester derivative, followed by decarboxylation. The cytotoxicity profiles are also presented.

Synthesis and structure of allylated derivatives of fullerenes C60 and C70

New chromatographically pure monoand hexamethanofullerenes C60 and C70 containing active allylic groups were synthesized by Bingel—Hirsch reaction. These compounds are promising for the studies of biological activity, as well as for obtaining on their basis new fullerenecontaining materials. The purity and composition of the synthesized compounds were confirmed by MALDI-TOF mass spectrometry and HPLC, their structure was established by 1H and 13C NMR spectroscopy and X-ray diffraction.

A highly-ordered 3D covalent fullerene framework

A highly-ordered 3D covalent fullerene framework is presented with a structure based on octahedrally functionalized fullerene building blocks in which every fullerene is separated from the next by six functional groups and whose mesoporosity is controlled by cooperative self-assembly with a liquid-crystalline block copolymer. The new fullerene-framework material was obtained in the form of supported films by spin coating the synthesis solution directly on glass or silicon substrates, followed by a heat treatment. The fullerene building blocks coassemble with a liquid-crystalline block copolymer to produce a highly ordered covalent fullerene framework with orthorhombic Fmmm symmetry, accessible 7.5 nm pores, and high surface area, as revealed by gas adsorption, NMR spectroscopy, small-angle X-ray scattering (SAXS), and TEM. We also note that the 3D covalent fullerene framework exhibits a dielectric constant significantly lower than that of the nonporous precursor material. Self-assembling C60: A highly ordered 3D fullerene framework is prepared with a structure based on octahedrally functionalized fullerene building blocks. The C60 building blocks coassemble with a liquid-crystalline block copolymer to produce a covalent fullerene framework with orthorhombic Fmmm symmetry and 7.5 nm pores.

Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols

A FeCl3-catalyzed multicomponent reaction was developed for the facile synthesis of coumarin-3-carboxylic ester derivatives in a highly atom-economic and environmentally friendly way. Using simple and cheaply available salicylaldehydes, Meldrum's acid and alcohols as the starting materials, the method needs no extra additives and features wide substrate scope, good functional group tolerance and mild reaction conditions.

Titanium isopropoxide promoted tandem self-cross and ring-closing metathesis approach for the synthesis of macrotetralides

A new approach is demonstrated for the synthesis of macrotetralides through an olefin metathesis reaction using Grubbs' second-generation catalyst with titanium isopropoxide as a cocatalyst. This study demonstrates a tandem self-cross and ring-closing metathesis approach to form macrocyclic ring systems with excellent (E) selectivity. The reaction was optimized with regard to functional group, catalyst, solvent, Lewis acid, concentration, and temperature. A new approach is demonstrated for the synthesis of macrotetralides through tandem self-cross and ring-closing metathesis reactions using Grubbs' second-generation catalyst and titanium isopropoxide. Copyright

Titanium Isopropoxide Promoted Tandem Self-Cross and Ring-Closing Metathesis Approach for the Synthesis of Macrotetralides

A new approach is demonstrated for the synthesis of macrotetralides through an olefin metathesis reaction using Grubbs' second-generation catalyst with titanium isopropoxide as a cocatalyst. This study demonstrates a tandem self-cross and ring-closing metathesis approach to form macrocyclic ring systems with excellent (E) selectivity. The reaction was optimized with regard to functional group, catalyst, solvent, Lewis acid, concentration, and temperature. A new approach is demonstrated for the synthesis of macrotetralides through tandem self-cross and ring-closing metathesis reactions using Grubbs' second-generation catalyst and titanium isopropoxide.

Formation of nanostructured fullerene interlayer through accelerated self-assembly and cross-linking of trichlorosilane moieties leading to enhanced efficiency of photovoltaic cells

A new cross-linkable fullerene material, bis(2-(trichlorosilyl)propyl)- malonate C60 (TSMC), functionalized with two trichlorosilane groups, was easily synthesized by Pt-catalyzed olefin hydrosilylation. By making use of facile hydrolysis of the trichlorosilyl moieties, TSMC can be spontaneously self-assembled and cross-linked on the TiOx surface by a simple spin-coating processing without the aid of photoirradiation or post-thermal treatments. The rapid formation of self-assembled and cross-linked TSMC (SA-C-TSMC) effectively passivates the residual hydroxyl groups on the TiO x surface. More significantly, the solvent-resistant TSMC network features a nanostructured surface to provide extra charge-generating interfacial area and straight electron transport pathways. The device (ITO/TiO x/SA-C-TSMC/P3HT:PC61BM (1:1, w/w)/PEDOT:PSS/Ag) with this C60 interlayer exhibited an efficiency of 3.9% which greatly outperformed the device without this layer. Furthermore, the strategy can also be effectively applied to the device (ITO/TiOx/PDITTDTBT:PC 71BM(1:4, w/w)/MoOx/Ag) incorporating a conjugated polymer, poly(diindenothiophene-alt-dithienylbenzothiadizole) copolymer (PDITTDTBT). This device delivered a high efficiency of 5.8% which represents a 35% enhancement over the device without SA-C-TSMC. This new generation of trichlorosilane-based fullerene offers an easy and accelerated processing technique to produce efficient and cost-effective inverted solar cells.

Thiol-ene clickable carbon-chain polymers based on diallyl cyclopropane-1,1-dicarboxylate

A novel type of clickable polymers with a very high local density of allyl side groups was developed. These polymers were obtained by the anionic ring-opening (co)polymerization of diallyl cyclopropane- 1,1-dicarboxylate using as an initiating system a protic precursor whose acidebase reaction with the t-BuP4 phosphazene base generated the initiator in situ. The obtained polymers display geminated allyl groups on every third carbon alongside the macromolecular backbone. Homopolymers as well as block and statistical copolymers have been synthesized, with controlled molecular weights and narrow molecular weight distributions. The coupling of mercaptans with the allyl C]C double bonds has been investigated both thermally and photochemically, with the influence of the type of initiation on the efficiency of the polymer modification being discussed in comparison with other clickable systems. Further functionalization by several thiols was performed, leading to a range of functional poly(cyclopropane-1,1-dicarboxylate)s.

Catalytic asymmetric conjugate allylation of coumarins

A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. A dual activation strategy was employed by using N,N′-dioxide-Yb(OTf) 3 to activate coumarins and using (CuOTf)2?C 7H8 to activate tetraallyltin via transmetalation, respectively. Good yields and enantioselectivities were obtained under mild conditions.