ethyl 3,3-difluoroacrylate

Base Information

• Chemical Name: ethyl 3,3-difluoroacrylate
• CAS No.: 407-35-2
• Molecular Formula: C5H6F2O2
• Molecular Weight: 136.098
• Mol file: 407-35-2.mol

Synonyms:ethyl 3,3-difluoroacrylate

Chemical Property of ethyl 3,3-difluoroacrylate

Chemical Property:

• Boiling Point: 97 - 98 °C
• PSA: 26.30000
• LogP: 1.32990

Purity/Quality:

99.3% ^*data from raw suppliers

ethyl3,3-difluoroprop-2-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Ethyl 3,3-difluoroacrylate is a reactive fluorinated acrylate derivative that serves as a valuable intermediate for introducing fluorine atoms into organic molecules. It exhibits higher reactivity compared to methyl acrylate, particularly in Diels-Alder reactions, as demonstrated by its cycloaddition with furan to form difluorocyclohexadienol derivatives. ethyl 3,3-difluoroacrylate can be synthesized efficiently from ethyl vinyl ether and dibromodifluoromethane, highlighting its utility in the preparation of fluorinated organic frameworks.

Technology Process of ethyl 3,3-difluoroacrylate

There total 4 articles about ethyl 3,3-difluoroacrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

ethyl 3-bromo-3,3-difluoropropanoate (105836-29-1) → ethyl β,β-difluoroacrylate (407-35-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00378a028

Reference yield:

ethyl 3,3,3-trifluoropropanoate (352-23-8) → ethyl β,β-difluoroacrylate (407-35-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; titanium tetrachloride; triethylamine; In chloroform; at 0 - 25 ℃; for 1h;

Reference yield:

C8H15F3O2Si → ethyl β,β-difluoroacrylate (407-35-2)

Guidance literature:

With titanium tetrachloride; In chloroform-d1; dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/acs.joc.5b00853

upstream raw materials:

ethyl 3-bromo-3,3-difluoropropanoate

Diethyl 3-bromo-3,3-difluoropropanal diethyl acetal

ethyl 3,3,3-trifluoropropanoate

Downstream raw materials:

ethyl 2-bromo-3,3,3-trifluoropropanoate

Refernces

Facile Synthesis of Ethyl 3,3-Difluoroacrylate from Dibromodifluoromethane and Diels-Alder Cycloaddition with Furan

10.1021/jo00378a028

The research focuses on the synthesis of ethyl 3,3-difluoroacrylate (6) and its subsequent Diels-Alder reaction with furan to produce difluorocyclohexadienol derivatives. The purpose of this study was to develop an efficient method for synthesizing ethyl 3,3-difluoroacrylate, a compound of interest for its potential to introduce fluorine atoms into organic molecules, and to explore its reactivity in the Diels-Alder reaction. The researchers successfully developed a synthesis route with an overall yield of 36%, starting from ethyl vinyl ether and dibromodifluoromethane. Key chemicals used in the process include ethyl vinyl ether, dibromodifluoromethane, ethanol, Caro's acid, m-chloroperoxybenzoic acid, and triethylamine. The study concluded that ethyl 3,3-difluoroacrylate is more reactive than methyl acrylate and that the Diels-Alder reaction with furan, although accompanied by decomposition, yielded a mixture of epimers, demonstrating the potential of this approach for synthesizing complex molecules with fluorine substitution.

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