6439-57-2

Basic information

• Product Name: ITACONIC ACID MONO-N-BUTYL ESTER
• Synonyms: ITACONIC ACID MONO-N-BUTYL ESTER;BETA-BUTYL ITACONATE;4-BUTYL METHYLENESUCCINATE;MONO-N-BUTYL ITACONATE;MONO-BUTYL ITACONATE;ITACONIC ACID MONO-N-BUTYL ESTER 90+%;ITACONIC ACID MONOBUTYL ESTER;2-Methylenesuccinic acid 4-butyl ester
• CAS NO: 6439-57-2
• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.21
• Product Categories: monomer
• Mol File: 6439-57-2.mol

Chemical Properties

• Melting Point: 35°C
• Boiling Point: 322.6 °C at 760 mmHg
• Flash Point: 125.7 °C
• Appearance: /
• Density: 1.094 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.461
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.84±0.11(Predicted)
• CAS DataBase Reference: ITACONIC ACID MONO-N-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ITACONIC ACID MONO-N-BUTYL ESTER(6439-57-2)
• EPA Substance Registry System: ITACONIC ACID MONO-N-BUTYL ESTER(6439-57-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 6439-57-2(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Coating Industry:
ITACONIC ACID MONO-N-BUTYL ESTER is used as a plasticizer to improve the flexibility and durability of polymers and coatings. Its incorporation enhances the performance characteristics of these materials, making them more suitable for various applications.
Used in Specialty Chemicals and Pharmaceutical Industry:
ITACONIC ACID MONO-N-BUTYL ESTER serves as a precursor in the synthesis of various specialty chemicals and pharmaceutical intermediates. Its unique chemical structure allows for the development of new compounds with specific properties and applications in these industries.

InChI:InChI=1/C9H14O4/c1-3-4-5-13-9(12)7(2)6-8(10)11/h2-6H2,1H3,(H,10,11)

Upstream product

• 2170-03-8 itaconic acid anhydride 
• 71-36-3 butan-1-ol 
• 97-65-4 2-methylenesuccinic acid 

Downstream Products

• 1174270-44-0 butyl 2-(2-oxo-5,6-diphenyl-2H-pyran-3-yl)acetate 

Relevant articles and documents

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.

Highly chemoselective esterification for the synthesis of monobutyl itaconate catalyzed by hierarchical porous zeolites

Monobutyl itaconate (MBI) are commercially prepared by using freshly distilled acetyl chloride as catalysts, which, however, always results in complicated purification processes due to the usage of water-carrying agents. Here, we report the highly selecti

Renewable biobased polymeric materials: Facile synthesis of itaconic anhydride-based copolymers with poly(l -lactic acid) grafts

This paper reports a new synthesis of biobased polymers by using itaconic anhydride (IAn) and lactic acid (LA) as renewable starting materials. Poly(lactic acid) (PLA)-graft copolymers were synthesized via two approaches. First, the macromonomer approach utilized IAn for Sn-catalyzed synthesis of PLA-containing macromonomers (IAn-PLA Macro). The macromonomer was radically copolymerized with n-butyl methacrylate (BMA), n-butyl acrylate (BA), methyl methacrylate (MMA), and ethyl methacrylate (EMA) to give efficiently graft copolymers (PLA-Graft copolymer (I)) with molecular weight Mn up to 1.61 × 105 having biomass content higher than 34 wt %. Second, the copolymer approach employed first IAn as comonomer for radical copolymerization with BMA, giving rise to IAn-BMA copolymer with Mn higher than 5.76 ×104. Then, Sn-catalyzed grafting of PLA onto IAn moiety of the copolymer produced PLA-Graft copolymer (II) with Mn higher than 5.88 × 104, showing biomass content ≥29 wt %. In addition, radical homopolymerization of IAn was examined to give polyIAn. By using these two approaches employing IAn as a starting reactive material, PLA-graft copolymers were obtained as biomass-plastics. Properties of PLA-Graft copolymers (I) were also examined, which revealed possible applications for coatings and plastics. Furthermore, the IAn-containing graft copolymers will be a convenient starting biomass polymer having reactive IAn moiety in the main chain for further grafting or various functional group-introducing reactions.