3,5-Bis(trifluoromethyl)cinnamic acid

Base Information

• Chemical Name: 3,5-Bis(trifluoromethyl)cinnamic acid
• CAS No.: 155814-20-3
• Molecular Formula: C₁₁H₆F₆O₂
• Molecular Weight: 284.158
• Hs Code.: 2916399090
• European Community (EC) Number: 623-253-4
• Wikidata: Q76145324
• ChEMBL ID: CHEMBL2409277
• Mol file: 155814-20-3.mol

Synonyms:155814-20-3;3,5-Bis(trifluoromethyl)cinnamic acid;trans-3,5-Bis(trifluoromethyl)cinnamic acid;3-(3,5-Bis(trifluoromethyl)phenyl)acrylic acid;(2E)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoic acid;(E)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoic acid;(E)-3-(3,5-bis(trifluoromethyl)phenyl)acrylic acid;SCHEMBL1711391;CHEMBL2409277;IZKCKOPHMWHBHR-OWOJBTEDSA-N;HMS1732B09;2-Propenoic acid, 3-[3,5-bis(trifluoromethyl)phenyl]-, (2E)-;3,5-bis(Trifluoromethyl)cinnamicacid;AKOS001082211;AKOS025310214;CS-W012244;PS-7203;503179-72-4;EN300-11141;D81954;EN300-364683;trans-3,5-Bis(trifluoromethyl)cinnamic acid, 98%;J-009229;Z57033996;2-Propenoic acid,3-[3,5-bis(trifluoromethyl)phenyl]-,(2E)-

Chemical Property of 3,5-Bis(trifluoromethyl)cinnamic acid

Chemical Property:

• Vapor Pressure: 0.00271mmHg at 25°C
• Melting Point: 166-169 °C
• Refractive Index: 1.47
• Boiling Point: 273.9 °C at 760 mmHg
• PKA: 4.07±0.10(Predicted)
• Flash Point: 119.5 °C
• PSA: 37.30000
• Density: 1.479 g/cm³
• LogP: 3.82200
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 284.02719840
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,5-Bis(trifluoromethyl)cinnamicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1C(F)(F)F)C(F)(F)F)C=CC(=O)O
• Isomeric SMILES: C1=C(C=C(C=C1C(F)(F)F)C(F)(F)F)/C=C/C(=O)O
• Uses: trans-3,5-Bis(trifluoromethyl)cinnamic acid (F-CIN) was employed as hydrophobic probe to investigate the interactions between hydrophobic guest molecules and polymers forming the micelle core.

Technology Process of 3,5-Bis(trifluoromethyl)cinnamic acid

There total 2 articles about 3,5-Bis(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: 93.0%

ethyl 3-(3,5-bis(trifluoromethyl)phenyl)acrylate (184969-49-1) → (Z)-3-[3,5-bis(trifluoromethyl)phenyl]acrylic acid (1340475-16-2,155814-20-3)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 20 ℃; for 4h;

DOI:10.1016/j.phytochem.2013.08.013

Reference yield:

malonic acid (141-82-2) + 3,5-Bis(trifluoromethyl)benzaldehyde (401-95-6) → 3,5-bis(trifluoromethyl) cinnamic acid (503179-72-4,155814-20-3)

Guidance literature:

With piperidine; pyridine; for 2h; Reflux;

DOI:10.1016/j.bmc.2009.04.010

Reference yield:

3,5-bis(trifluoromethyl) cinnamic acid (503179-72-4,155814-20-3) + cyclopentanone (120-92-3) → C16H14F6O3 + C16H14F6O3

Guidance literature:

With (3,5-bis(cyclopentyloxy)-2-iodophenyl)boronic acid; (R)-2,6-diisopropoxy-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepine; In dichloromethane; at 50 ℃; for 240h; enantioselective reaction; Molecular sieve;

DOI:10.1002/anie.202007639

upstream raw materials:

malonic acid

3,5-Bis(trifluoromethyl)benzaldehyde

ethyl 3-(3,5-bis(trifluoromethyl)phenyl)acrylate

Refernces

• 1、 Li, Fu-Nan,Kim, Nam-Jung,Paek, Seung-Mann,Kwon, Do-Yeon,Min, Kyung Hoon,Jeong, Yeon-Su,Kim, Sun-Young,Park, Young-Ho,Kim, Hee-Doo,Park, Hyeung-Geun,Suh, Young-Ger. "Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists". experimental part. p. 3557 - 3567. Retrieved 2009/09/27.