382-90-1

Usage

Uses

Used in Polymer Production:
Methyl 2-(trifluoromethyl)acrylate is used as a monomer for the production of polymers and copolymers, leveraging its high reactivity to undergo polymerization and copolymerization reactions with other monomers. This process results in the formation of various polymers with unique properties, enhancing the material's versatility and applicability in different industries.
Used in Pharmaceutical and Agrochemical Synthesis:
In the pharmaceutical and agrochemical industries, Methyl 2-(trifluoromethyl)acrylate serves as an important building block. Its role in the synthesis of these compounds underscores its utility in creating new and innovative products that can address various medical and agricultural needs.
Used in Organic Synthesis:
As an intermediate in organic synthesis, Methyl 2-(trifluoromethyl)acrylate is instrumental in the development of a wide range of organic compounds. Its unique structure and reactivity contribute to the creation of novel chemical entities with potential applications in various fields.

InChI:InChI=1/C4H4F4O2/c1-10-3(9)2(5)4(6,7)8/h2H,1H3

Upstream product

• 428-18-2 α-acetoxy-β,β,β-trifluoro-isobutyric acid methyl ester 
• 186581-53-3 diazomethane 
• 381-98-6 trifluoromethyacrylic acid 
• 67-56-1 methanol 
• 661-54-1 3,3,3-trifluoroprop-1-yne 
• 201230-82-2 carbon monoxide 
• 475636-84-1 hexafluoroisobutylene fluorosulfate 
• 77-78-1 dimethyl sulfate 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 

Downstream Products

• 874218-15-2 (R/S)-1-benzyl-3-trifluoromethyl-pyrrolidine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Fluorosulfates of hexafluoroisobutylene and its higher homologs

Hexafluoroisobutylene and its higher homologs are easily reacted with SO3 to give fluorosulfates of the formula CH2═C(R)CF2OSO2F, wherein R is a linear, branched or cyclic fluoroalkyl group comprised of 1 to 10 carbon atoms and may contain ether oxygen. These compounds react under mild conditions with many nucleophiles to give CH2═C(R)CF2X, where X is derived from the nucleophile. This reaction provides a route to many substituted hexafluoroisobutylenes, which copolymerize easily with other fluoro- and hydrocarbon monomers such as vinylidene fluoride and ethylene.

Alkoxycarbonylation of 3,3,3-Trifluoropropyne: An Intriguing Reaction to Prepare Trifluoromethyl-Substituted Unsaturated Acid Derivatives

The addition of CO and methanol to 3,3,3-trifluoropropyne is catalysed by Pd(OAc)2 in the presence of (6-methylpyrid-2-yl)diphenylphosphine and CH3SO3H. The main products of the reaction are the methyl esters of 2-(trifluoromethyl)propenoic acid 1 and of 3-(trifluoromethyl)propenoic acid 2 (4,4,4-trifluorobut-2-enoic acid). The regioselectivity of the reaction can be controlled to a great extent by a suitable choice of the composition of the catalytic system and the reaction conditions. Thus, 1 can be obtained in 93% yield by using P(CO) = 20 atm and high ligand/Pd and acid/Pd ratios. On the other hand, selectivity up to 85% in 2 can be achieved using P(CO) = 80 atm and a low ligand/Pd ratio together with a high acid/Pd ratio. The reaction mechanism is also discussed.

Studies on the preparation of 2-(trifluoromethyl)acrylic acid and its esters from 3,3,3-trifluoropropene via hydrocarbonylation reactions

The synthesis of methyl α-(trifluoromethyl)acrylate (MTFMA) has been carried out in three steps starting from commercially available 3,3,3,-trifluoropropene; this route involving the cobalt-catalyzed carbonylation of 2-bromo-3,3,3-trifluoropropene (2-Br-TFP) under very mild reaction conditions, gave only about 30% yield of the desired methyl ester. 2-(Trifluoromethyl)propanal, available in 90% yield by rhodium catalyzed hydroformylation of 3,3,3-trifluoropropene, proved to be an interesting starting product for the preparation of MTFMA: while the synthetic route involving the α-halogenation of 2-(trifluoromethyl)propanoic acid (TFMPA) failed to give any results, the reaction scheme based on the α-selenenylation of the above aldehyde followed by H2O2-oxidation afforded 68% yield of 2-(trifluoromethyl)acrylic acid (TFMAA).

FACILE SYNTHESES OF FLUORINE-CONTAINING α,β-UNSATURATED ACIDS AND ESTERS FROM 2-TRIFLUOROMETHYLACRYLIC ACID

Various types of fluorine-containing α,β-unsaturated acids and their esters were synthesized from 2-trifluoromethylacrylic acid as a sole starting material.