3-(Trifluoromethyl)cinnamic acid methyl ester

Base Information

• Chemical Name: 3-(Trifluoromethyl)cinnamic acid methyl ester
• CAS No.: 104201-66-3
• Molecular Formula: C₁₁H₉F₃O₂
• Molecular Weight: 230.186
• DSSTox Substance ID: DTXSID001210220
• Nikkaji Number: J1.321.483B,J2.564.585E
• Mol file: 104201-66-3.mol

Synonyms:3-(Trifluoromethyl)cinnamic acid methyl ester;104201-66-3;87087-35-2;Methyl 3-(3-(trifluoromethyl)phenyl)acrylate;(E)-Methyl 3-(3-(trifluoromethyl)phenyl)acrylate;methyl (E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoate;Methyl (E)-3-(3-(trifluoromethyl)phenyl)acrylate;methyl (2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoate;ghl.PD_Mitscher_leg0.718;SCHEMBL12677375;ZQAIZQSBGPNEEN-AATRIKPKSA-N;DTXSID001210220;MFCD08704704;2-Propenoic acid, 3-[3-(trifluoromethyl)phenyl]-, methyl ester, (E)-;AKOS017259730;AS-72403;CS-0037422;(E)-Methyl3-(3-(trifluoromethyl)phenyl)acrylate;EN300-1453742;A856416;(E)-Methyl 3-(3-(trifluoromethoxy)phenyl)acrylate;3-(Trifluoromethyl)benzeneacrylic acid methyl ester;Methyl (2E)-3-[3-(trifluoromethyl)phenyl]-2-propenoate;(2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid methyl ester

Chemical Property of 3-(Trifluoromethyl)cinnamic acid methyl ester

Chemical Property:

• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 230.05546401
• Heavy Atom Count: 16
• Complexity: 271

Purity/Quality:

98% ^*data from raw suppliers

(E)-Methyl3-(3-(trifluoromethyl)phenyl)acrylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC(=CC=C1)C(F)(F)F
• Isomeric SMILES: COC(=O)/C=C/C1=CC(=CC=C1)C(F)(F)F

Technology Process of 3-(Trifluoromethyl)cinnamic acid methyl ester

There total 16 articles about 3-(Trifluoromethyl)cinnamic acid methyl ester 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: 99.0%

m-trifluoromethylphenyl iodide (401-81-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → trans-methyl 3-(3-(trifluoromethyl)phenyl)acrylate (104201-66-3)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; toluene; at 100 ℃; for 20h;

DOI:10.1039/c0ob00523a

Reference yield: 96.0%

3-(trifluoromethyl)benzenediazonium tetrafluoroborate (454-87-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → trans-methyl 3-(3-(trifluoromethyl)phenyl)acrylate (104201-66-3)

Guidance literature:

With palladium diacetate; In methanol; at 25 ℃; for 12h;

DOI:10.1002/chem.200903050

Reference yield: 95.0%

methanol (67-56-1) + 3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4) → trans-methyl 3-(3-(trifluoromethyl)phenyl)acrylate (104201-66-3)

Guidance literature:

With thionyl chloride; at 0 ℃; for 6h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201410039

upstream raw materials:

3-(trifluoromethyl)cinnamic acid

dimethyl sulfate

3-bromo-1-trifluoromethylbenzene

acrylic acid methyl ester

Downstream raw materials:

(E)-3-(3-trifluoromethylphenyl)prop-2-en-1-ol

methyl 3-(3-(trifluoromethyl)phenyl)propanoate

Refernces

• 1、 Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.. "Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer". supporting information. p. 558 - 564. Retrieved 2020/12/07.
• 2、 Wang, Mei-Ling,Xu, Hui,Li, Han-Yuan,Ma, Biao,Wang, Zhen-Yu,Wang, Xing,Dai, Hui-Xiong. "Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination". supporting information. p. 2147 - 2152. Retrieved 2021/04/05.