Methyl 2-(trifluoromethyl)acrylate

Base Information

• Chemical Name: Methyl 2-(trifluoromethyl)acrylate
• CAS No.: 382-90-1
• Molecular Formula: C5H5F3O2
• Molecular Weight: 154.089
• Hs Code.: 29161900
• European Community (EC) Number: 671-829-9
• DSSTox Substance ID: DTXSID10382061
• Nikkaji Number: J429.864K
• Wikidata: Q72491953
• Mol file: 382-90-1.mol

Synonyms:Methyl-2(trifluoromethyl)acrylate;Acrylicacid, 2-(trifluoromethyl)-, methyl ester (8CI);Methyl2-(trifluoromethyl)acrylate;Methyl a-(trifluoromethyl)acrylate;

Chemical Property of Methyl 2-(trifluoromethyl)acrylate

Chemical Property:

• Vapor Pressure: 97.4mmHg at 25°C
• Melting Point: 48-52oC
• Refractive Index: 1.3528
• Boiling Point: 114.9 °C at 760 mmHg
• Flash Point: 24.8 °C
• PSA: 26.30000
• Density: 1.224 g/cm³
• LogP: 1.27790
• Storage Temp.: Keep Cold
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 154.02416388
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2-(trifluoromethyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F,Xn
• Statements: 10-36/37/38-20
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=C)C(F)(F)F

Technology Process of Methyl 2-(trifluoromethyl)acrylate

There total 6 articles about Methyl 2-(trifluoromethyl)acrylate 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: 82.0%

methanol (67-56-1) + 3,3,3-trifluoroprop-1-yne (661-54-1) + carbon monoxide (201230-82-2) → methyl α-trifluoromethylacrylate (382-90-1) + β,β,β-trifluoro-β'-methoxy-isobutyric acid methyl ester (359-88-6) + methyl (E)-3-(trifluoromethyl)propenoate (189287-30-7) + methyl (Z)-3-trifluoromethylpropenoate

Guidance literature:

With methanesulfonic acid; Pd(OAc)2*(6-methylpyrid-2-yl)diphenylphosphine; In 1-methyl-pyrrolidin-2-one; dichloromethane; at 80 ℃; for 48h; under 15201 Torr; Further Variations:; Temperatures; Pressures; Solvents; ratio Pd:ligand:acid; Product distribution;

DOI:10.1002/1615-4169(200207)344:5<543::AID-ADSC543>3.0.CO;2-U

Reference yield: 76.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + trifluoromethyacrylic acid (381-98-6) → methyl α-trifluoromethylacrylate (382-90-1)

Guidance literature:

DOI:10.1016/S0040-4039(00)84746-2

Reference yield: 70.0%

trifluoromethyacrylic acid (381-98-6) + dimethyl sulfate (77-78-1) → methyl α-trifluoromethylacrylate (382-90-1)

Guidance literature:

With potassium carbonate; In acetone; for 5h; Heating;

DOI:10.1016/S0022-1139(96)03571-3

upstream raw materials:

α-acetoxy-β,β,β-trifluoro-isobutyric acid methyl ester

diazomethane

trifluoromethyacrylic acid

methanol

Downstream raw materials:

methyl 2-(2-benzyloxyethyl)-3,3-difluoroacrylate

(R/S)-1-benzyl-3-trifluoromethyl-pyrrolidine-3-carboxylic acid methyl ester

Refernces

• 1、 Scrivanti,Beghetto,Matteoli. "Alkoxycarbonylation of 3,3,3-Trifluoropropyne: An Intriguing Reaction to Prepare Trifluoromethyl-Substituted Unsaturated Acid Derivatives". . p. 543 - 547. Retrieved 2007/10/03.
• 2、 Fuchikami, Takamasa,Shibata, Yoshiko,Suzuki, Yasuyuki. "FACILE SYNTHESES OF FLUORINE-CONTAINING α,β-UNSATURATED ACIDS AND ESTERS FROM 2-TRIFLUOROMETHYLACRYLIC ACID". . p. 3173 - 3176. Retrieved 2007/10/02.