7338-27-4

Usage

Uses

Used in Chemical Production:
ITACONIC ACID MONOMETHYL ESTER is used as a monomer for the synthesis of various copolymers, contributing to the creation of a diverse range of polymeric materials with unique properties.
Used in Adhesive and Resin Production:
ITACONIC ACID MONOMETHYL ESTER is used as a component in the production of resins and adhesives, enhancing their performance characteristics and providing specific adhesive or binding properties for various applications.
Used in Coatings and Inks Manufacturing:
ITACONIC ACID MONOMETHYL ESTER is used as a plasticizer in the manufacturing of coatings and inks, improving the flexibility, workability, and performance of these products.
Used in Flavoring and Fragrance Industry:
ITACONIC ACID MONOMETHYL ESTER is used as a building block for the production of flavoring agents and fragrances, adding to the complexity and variety of scents and tastes in various consumer products.
Used in Pharmaceutical Industry:
ITACONIC ACID MONOMETHYL ESTER is used as a pharmaceutical intermediate, playing a crucial role in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medicines.

InChI:InChI=1/C6H8O4/c1-4(6(8)9)3-5(7)10-2/h1,3H2,2H3,(H,8,9)

Upstream product

• 67-56-1 methanol 
• 97-65-4 2-methylenesuccinic acid 
• 2170-03-8 itaconic acid anhydride 

Downstream Products

• 91891-24-6 N-(3-hydroxyphenyl)-2-oxopyrrolidine-4-carboxylic acid 
• 23268-03-3 (R)-2-methyl-succinic acid 4-methyl ester 
• 111266-27-4 (2S)-4-methoxy-2-methyl-4-oxobutanoic acid 
• 193006-24-5 3-(3-cyanophenyl)-5-(carbomethoxymethyl)isoxazoline-5-carboxylic acid 
• 498-21-5 2-methylbutanedioic acid 
• 942924-66-5 3-((but-3-enyl)phenethylcarbamoyl)but-3-enoic acid methyl ester 
• 942924-67-6 3-[but-3-enyl-(3-phenylpropyl)carbamoyl]but-3-enoic acid methyl ester 
• 942924-68-7 3-[but-3-enyl-(4-phenylbutyl)carbamoyl]but-3-enoic acid methyl ester 
• 64190-48-3 (S)-3-methyl-4-butanolide 
• 173209-00-2 (3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 
• 138306-24-8 methyl (3S)-4-hydroxy-3-methylbutanoate 
• 620172-41-0 methyl (3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutanoate 
• 860426-07-9 methyl 3-(methyl(phenyl)carbamoyl)but-3-enoate 
• 24345-85-5 1-benzyl-4-methyl itaconate 

Relevant academic research and scientific papers

Preparation and thermal properties of poly[acrylonitrile-co-(β- methylhydrogen itaconate)] used as carbon fiber precursor

In order to replace terpolymer with bipolymer, a bifunctional comonomer β-methylhydrogen itaconate (MHI) containing carboxyl group and ester group was synthesized to prepare poly[acrylonitrile-co-(β-methylhydrogen itaconate)] [P(AN-co-MHI)] bipolymers used as carbon fiber precursor for improving the stabilization and spinnability at the same time. The P(AN-co-MHI) bipolymers with different monomer feed ratios were characterized by elemental analysis, Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), and differential scanning calorimetry (DSC). The results show that both the polymerization conversion and molecular mass of P(AN-co-MHI) reduce with the increasing MHI amounts in the feed due to the larger molecular volume of MHI than acrylonitrile (AN). The monomer reactivity ratios were calculated by Fineman-Ross and Kelen-Tuedos methods, the results show good agreement and MHI possesses higher reactivity than AN. Two parameters Es = A1, 629 cm-1 / A2, 244 cm 1 and SI = (I0 - I S) / I0 were defined to evaluate the extent of stabilization, and the activation energy (E a) of the cyclization was calculated by Kissinger method and Ozawa method. The FTIR, XRD, and DSC results show that P(AN-co-MHI) bipolymers exhibit significantly improved stabilization characteristics than PAN homopolymer, such as larger extent of stabilization, lower initiation temperature, and smaller E a of cyclization, which is attributed to the ionic initiation by MHI comonomer and it is beneficial to preparing high-performance carbon fiber.

Short Enantioselective Total Syntheses of Cheloviolenes A and B and Dendrillolide C via Convergent Fragment Coupling Using a Tertiary Carbon Radical

The development of a convergent fragment coupling strategy for the enantioselective total syntheses of a group of rearranged spongian diterpenoids that harbor the cis-2,8-dioxabicyclo[3.3.0]octan-3-one unit is described. The key bond disconnection relies on a late-stage fragment coupling between a tertiary carbon radical and an electron-deficient alkene to unite two ring systems and form two new stereocenters, one of which is quaternary, in a stereoselective and efficient manner. This strategy is applied toward scalable 14-15 step syntheses of three rearranged spongian diterpenoids, cheloviolenes A and B, and dendrillolide C.

A novel poly[acrylonitrile-co-(3-ammoniumcarboxylate-butenoic acid-methylester)]copolymer for carbon fiber precursor

A novel bifunctional comonomer 3-ammoniumcarboxylate-butenoic acid-methyl ester (ACBM) was synthesized for preparing poly[acrylonitrile-co-(3- ammoniumcarboxylate-butenoic acid-methyl ester)] [P(AN-co-ACBM)] copolymer as a carbon fiber precursor. Differential scanning calorimetry results show that the P(AN-co-ACBM) exhibits a significantly improved stabilization performance compared with polyacrylonitrile (PAN), such as lower cyclization temperature and smaller rate of heat release, which is mainly attributed to the initiation of ACBM through an ionic cyclization mechanism. Simultaneously, the rheological analysis shows that P(AN-co-ACBM) possesses better spinnability than PAN.

Poly(acrylonitrile-co-3-aminocarbonyl-3-butenoic acid methyl ester): A better precursor material for carbon fiber than acrylonitrile terpolymer

In order to improve the stabilization and spinnability of polyacrylonitrile, a bifunctional comonomer containing both ester and amide groups was synthesized to prepare poly(acrylonitrile-co-3-aminocarbonyl-3-butenoic acid methyl ester) [P(AN-co-ABM)] copolymers used as the carbon fiber precursor instead of poly(acrylonitrile-acrylamide-methyl acrylate) [P(AN-AM-MA)] terpolymer. The differential scanning calorimetry and thermogravimetry results show that the stabilization of P(AN-co-ABM) have been remarkably improved by ABM compared with P(AN-AM-MA) terpolymer, such as lower initiation temperature, broadened exothermic peak and smaller activation energy. Moreover, the spinnability of P(AN-co-ABM) is also improved by ABM due to the lubrication of ester groups in ABM. This study clearly shows that P(AN-co-ABM) copolymer is a better material for use as a carbon fiber precursor than P(AN-AM-MA) terpolymer.

A high molecular weight acrylonitrile copolymer prepared by mixed solvent polymerization: I. effect of monomer feed ratios on polymerization and stabilization

A bifunctional comonomer β-methylhydrogen itaconate (MHI) was employed to prepare high molecular weight poly[acrylonitrile-co-(β-methylhydrogen itaconate)] [P(AN-co-MHI)] copolymers by radical polymerization in a mixed solvent of dimethyl sulfoxide/deionized water = 60/40 (wt/wt), which was used as a carbon fiber precursor instead of acrylonitrile terpolymers for improving the stabilization and spinnability simultaneously. The structure and stabilization of P(AN-co-MHI) copolymers with different monomer feed ratios were characterized by elemental analysis (EA), Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD) and differential scanning calorimetry (DSC). The results show that both the polymerization conversion and molecular weight reduce with the increase of MHI content in the feed due to the larger molecular volume of MHI. The monomer reactivity ratios were calculated by Fineman-Ross and Kelen-Tüds methods and the reactivity of MHI is higher than that of AN. Two parameters Es = A1618 cm-1/A2244 cm-1 and SI = (I0 - Is)/I0 were defined to evaluate the extent of stabilization and the activation energy (Ea) of the cyclization. The FTIR, XRD and DSC results show that P(AN-co-MHI) copolymers exhibit significantly improved stabilization characteristics than the PAN homopolymer and poly(acrlonitrile-methyl acrylate-acrylic acid) terpolymer, such as a larger extent of stabilization, lower initiation temperature and smaller Ea of cyclization, which is attributed to the ionic initiation of the MHI comonomer and is beneficial for preparing high performance carbon fiber.

Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals

Spiroimides exhibit a wide range of biological activities, such as anticonvulsant, antiarrhythmic, and antihyperglycemic activities. Herein, a novel synthetic application of renewable chemicals, itaconic acid and formamides, is described. Proper exploitation of the reactivity of itaconic acid and formamide allows for the development of an efficient synthetic approach for the production of several new biobased spiroimides, spiro[dihydroquinolin-2-one-succinimides] and spiro[indolin-2-one-glutarimides], in excellent overall yields (up to 98%).

A Br?nsted acidic, ionic liquid containing, heteropolyacid functionalized polysiloxane network as a highly selective catalyst for the esterification of dicarboxylic acids

A Br?nsted acidic, ionic liquid containing, heteropolyanion functionalized polysiloxane network was formed by self-condensation of dodecatungstophosphoric acid and a zwitterionic organosilane precursor containing both imidazolinium and sulfonate groups. The resulting hybrid material POS-HPA-IL was investigated as a catalyst for the selective esterification of dicarboxylic acids.

Synthesis and Bioactivity of Polymer-Based Synthetic Mimics of Antimicrobial Peptides (SMAMPs) Made from Asymmetrically Disubstituted Itaconates

A series of asymmetrically disubstituted diitaconate monomers is presented. Starting from itaconic anhydride, functional groups could be placed selectively at the two nonequivalent carbonyl groups. By using 2D NMR spectroscopy, it was shown that the first functionalization step occurred at the carbonyl group in the β position to the double bond. These monomers were copolymerized with N,N-dimethylacrylamide (DMAA) to yield polymer-based synthetic mimics of antimicrobial peptides (SMAMPs). They were obtained by free radical polymerization, a metal-free process, and still maintained facial amphiphilicity at the repeat unit level. This eliminates the need for laborious metal removal and is advantageous from a regulatory and product safety perspective. The poly(diitaconate-co-DMAA) copolymers obtained were statistical to alternating, and the monomer feed ratio roughly matched that of the repeat unit content of the copolymers. Investigations of varied R group hydrophobicity, repeat unit ratio, and molecular mass on antimicrobial activity against Escherichia coli and on compatibility with human keratinocytes showed that the polymers with the longest R groups and lowest DMAA content were the most antimicrobial and hemolytic. This is in agreement with the biological activity of previously reported SMAMPs. Thus, the design concept of facial amphiphilicity has successfully been transferred, but the selectivity of these polymers for bacteria over mammalian cells still needs to be optimized.

Rh(III)-catalyzed halogenation of vinylic C-H bonds: Rapid and general access to Z-halo acrylamides

Herein, the regio- and stereoselective iodination, along with some examples for the bromination, of readily available acrylamides to access a variety of differently substituted Z-haloacrylic acid derivatives is reported. The reaction proceeds under mild conditions via a Rh(III)-catalyzed C-H-activation/ halogenation mechanism and represents a rare example of a direct halogenation of electron-poor acrylic acid derivatives.

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.