3-(Trifluoromethyl)cinnamic acid

Base Information

• Chemical Name: 3-(Trifluoromethyl)cinnamic acid
• CAS No.: 67801-07-4
• Molecular Formula: C₁₀H₇F₃O₂
• Molecular Weight: 216.16
• European Community (EC) Number: 267-126-8,212-301-6
• UNII: P9LJ9ON37W
• DSSTox Substance ID: DTXSID8061135,DTXSID90886895
• Nikkaji Number: J534.255D,J103A
• Wikidata: Q27128532
• Metabolomics Workbench ID: 61237
• ChEMBL ID: CHEMBL2387748
• Mol file: 67801-07-4.mol

Synonyms:3-(Trifluoromethyl)cinnamic acid;779-89-5;67801-07-4;(E)-m-(Trifluoromethyl)cinnamic acid;3-(3-(Trifluoromethyl)phenyl)acrylic acid;m-(trifluoromethyl)cinnamic acid;3-Trifluoromethylcinnamic acid;(E)-3-(Trifluoromethyl)cinnamic acid;(E)-3-(3-(Trifluoromethyl)phenyl)acrylic acid;(E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoic acid;(2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoic acid;CHEBI:60704;2-Propenoic acid, 3-[3-(trifluoromethyl)phenyl]-, (2E)-;UNII-P9LJ9ON37W;trans-3-(trifluoromethyl)cinnamic acid;P9LJ9ON37W;3-(Trifluoromethyl)cinnamic acid, predominantly trans;3-[3-(trifluoromethyl)phenyl]acrylic acid;CHEMBL2387748;C10H7F3O2;(E)-3-trifluoromethylcinnamic acid;meta-(trifluoromethyl)cinnamic acid;trans-3-trifluoromethylcinnamic acid;2-Propenoic acid, 3-(3-(trifluoromethyl)phenyl)-;EINECS 212-301-6;EINECS 267-126-8;3-[3-(TRIFLUOROMETHYL)PHENYL]-2-PROPENOIC ACID;2-Propenoic acid, 3-(3-(trifluoromethyl)phenyl)-, (2E)-;m-(Trifluoromethyl)cinnamic acid, (trans)-;3-(3-(Trifluoromethyl)phenyl)-2-propenoic acid;(~{E})-3-[3-(trifluoromethyl)phenyl]prop-2-enoic acid;2-Propenoic acid, 3-[3-(trifluoromethyl)phenyl]-, (E)-;3-[3-(trifluoromethyl)phenyl]prop-2-enoic acid;MFCD00004393;MTF-CNA;2-Propenoic acid, 3-[3-(trifluoromethyl)phenyl]-;3-trifluoromethyl cinnamic acid;3-(3-Trifluoromethylphenyl)acrylic acid;3-(3-trifluoromethyl-phenyl)-acrylic acid;CINACALCET (M8);SCHEMBL80207;DTXSID8061135;KSBWHDDGWSYETA-SNAWJCMRSA-;DTXSID90886895;3-(trifluoromethyl)-cinnamic acid;BCP22719;CS-M1820;AC7564;BDBM50527799;CK2546;trans-3-trifluoromethyl-cinnamic acid;3-(Trifluoromethyl)benzeneacrylic acid;AKOS000119367;AC-9777;CS-T-45320;PS-6824;trans-3-(trifluoromethyl)-cinnamic acid;AM20060151;E-3-(3-trifluoromethylphenyl)propenoic acid;T1547;EN300-20461;(E)-3-(3-(Trifluoromethyl)phenyl)acrylicacid;(E)-3-(3-trifluoromethyl-phenyl)-acrylic acid;A21722;EN300-395998;W-104291;Q27128532;(2E)-3-[3-(Trifluoromethyl)phenyl]-2-propenoic acid #;Z2942851046;3-(Trifluoromethyl)cinnamic acid, predominantly trans, 98%;3-[3-(Trifluoromethyl)phenyl]prop-2-enoic acid;Trans-3-(trifluoromethyl)cinnamic acid;LRW

Chemical Property of 3-(Trifluoromethyl)cinnamic acid

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 135-136 °C
• Boiling Point: 289.6°C at 760 mmHg
• PKA: 4.25±0.10(Predicted)
• Flash Point: 129°C
• PSA: 37.30000
• Density: 1.363g/cm³
• LogP: 2.80320
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 216.03981395
• Heavy Atom Count: 15
• Complexity: 258

Purity/Quality:

99%, ^*data from raw suppliers

(E)-3-(3-(Trifluoromethyl)phenyl)acrylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC(=C1)C(F)(F)F)C=CC(=O)O
• Isomeric SMILES: C1=CC(=CC(=C1)C(F)(F)F)/C=C/C(=O)O
• Uses: (E)-3-(3-(Trifluoromethyl)phenyl)acrylic Acid is a reagent used in the preparation of new tacrine-cinnamic acid hybrids as cholinerase inhibitors against Alzheimer’s diseases.

Technology Process of 3-(Trifluoromethyl)cinnamic acid

There total 17 articles about 3-(Trifluoromethyl)cinnamic acid 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: 96.0%

m-trifluoromethylphenyl iodide (401-81-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4)

Guidance literature:

With triethylamine; di-(3-methylphenyl)phosphinopolystyrene palladium catalyst; In acetonitrile; at 80 ℃; for 20h;

DOI:10.1002/adsc.200600503

Reference yield: 95.0%

m-trifluoromethylphenyl iodide (401-81-0) + acrylic acid (79-10-7) → 3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4)

Guidance literature:

With tributyl-amine; at 110 ℃; for 3h;

DOI:10.1016/j.reactfunctpolym.2021.104843

Reference yield: 90.0%

malonic acid (141-82-2) + 3-Trifluoromethylbenzaldehyde (454-89-7) → 3-(trifluoromethyl)cinnamic acid (779-89-5,67801-07-4)

Guidance literature:

malonic acid; 3-Trifluoromethylbenzaldehyde; With piperidine; pyridine; at 20 - 120 ℃; for 4.25h; Inert atmosphere;

With hydrogenchloride; In water; pH=2;

DOI:10.3762/bjoc.8.158

upstream raw materials:

piperidine

3-Trifluoromethylbenzaldehyde

malonic acid

acetic anhydride

Downstream raw materials:

1-{(2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl}-5,6-dihydropyridin-2(1H)-one

Refernces

• 1、 Xu, Hehuan,Liu, Jiayu,Nie, Feiyun,Zhao, Xiaowei,Jiang, Zhiyong. "Metal-Free Hydropyridylation of Thioester-Activated Alkenes via Electroreductive Radical Coupling". . p. 16204 - 16212. Retrieved 2021/10/25.
• 2、 Xiao, Jian,Zhang, Haonan,Ejike, Anyaegbu Chima,Wang, Lu,Tao, Minli,Zhang, Wenqin. "Phenanthroline functionalized polyacrylonitrile fiber with Pd(0) nanoparticles as a highly active catalyst for the Heck reaction". . . Retrieved 2021/03/03.