57718-07-7

Basic information

• Product Name: DIETHYL ITACONATE
• Synonyms: DIETHYL ITACONATE;ITACONIC ACID DIETHYL ESTER;4-Ethoxy-2-methylene-4-oxobutyric acid;Ethyl itaconate, min. 95 %;2-Methylenesuccinic acid 4-ethyl ester;3-Methylenesuccinic acid hydrogen 1-ethyl ester;3-Monoethyl 1-propene-2,3-dicarboxylate;Itaconic acid 4-ethyl ester
• CAS NO: 57718-07-7
• Molecular Formula: C₇H₁₀O₄
• Molecular Weight: 158.15
• Mol File: 57718-07-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 56 °C
• Boiling Point: 153 °C / 12mmHg
• Flash Point: 122.5 °C
• Appearance: /
• Density: 1.153 g/cm³
• Vapor Pressure: 0.000324mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: 0-10°C
• PKA: 3.88±0.11(Predicted)
• CAS DataBase Reference: DIETHYL ITACONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL ITACONATE(57718-07-7)
• EPA Substance Registry System: DIETHYL ITACONATE(57718-07-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 57718-07-7(Hazardous Substances Data)

Usage

General Description

DIETHYL ITACONATE is a colorless, liquid chemical compound with a fruity odor. It is primarily used as a monomer in the production of polymers and resins, particularly for the manufacture of acrylic and vinyl-based polymers. Diethyl itaconate exhibits excellent reactivity and compatibility with a wide range of other monomers, making it a valuable component in the synthesis of various specialty polymers. Additionally, it is used as a raw material in the production of adhesives, coatings, and other industrial applications. Its low volatility and high boiling point also make it a suitable candidate for use in personal care products, such as hair sprays and cosmetics. Overall, diethyl itaconate is a versatile and valuable chemical in the polymer industry due to its reactivity, compatibility, and wide range of applications.

InChI:InChI=1/C7H10O4/c1-3-11-6(8)4-5(2)7(9)10/h2-4H2,1H3,(H,9,10)

Upstream product

• 64-17-5 ethanol 
• 97-65-4 2-methylenesuccinic acid 
• 2170-03-8 itaconic acid anhydride 
• 53841-07-9 ethyl cyanoacetate 
• 7732-18-5 water 
• 64-19-7 acetic acid 

Downstream Products

• 2409-52-1 diethylitaconate 
• 1446318-45-1 ethyl 2-((6S)-6-(5-bromo-2-fluorophenyl)-1-(2,4-dimethoxybenzyl)-6-methyl-2-oxopiperidin-3-yl)acetate 
• 1446318-44-0 [(S)-6-(5-bromo-2-fluoro-phenyl)-1-(2,4-dimethoxy-benzyl)-6-methyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl]-acetic acid ethyl ester 
• 1446318-43-9 3-[[(S)-1-(5-bromo-2-fluoro-phenyl)-1-methyl-but-3-enyl]-(2,4-dimethoxy-benzyl)-carbamoyl]-but-3-enoic acid ethyl ester 
• 1383105-34-7 3-(2,4-dihydroxybenzyl)-1-butylpyrrolidine-2,5-dione 
• 22195-18-2 β-methylene butyrolactone 
• 558483-95-7 N-(2-bromo-5-methoxybenzyl)-2-methylene-N-(2,2,2-trifluoroethyl)-succinylamide-4-ethyl ester 

Relevant articles and documents

Matsuda-Heck arylation of itaconates: A versatile approach to heterocycles from a renewable resource

Itaconic acid esters and hemiesters undergo Pd-catalyzed coupling reactions with arene diazonium salts in high to excellent yields. The coupling products of ortho-nitro arene diazonium salts can be converted in one or two steps to benzazepine-2-ones.

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.

An efficient and regiospecific esterification of dioic acids using PTSA

Regiospecific mono alkyl esters of dioic acids have been obtained in excellent yield using PTSA as a catalyst. This method is mild and simpler than the previous methods.