4-(Trifluoromethyl)cinnamic acid

Base Information

• Chemical Name: 4-(Trifluoromethyl)cinnamic acid
• CAS No.: 16642-92-5
• Molecular Formula: C₁₀H₇F₃O₂
• Molecular Weight: 216.16
• Hs Code.: 29163990
• European Community (EC) Number: 218-169-6
• UNII: YH27VC974F
• DSSTox Substance ID: DTXSID501224492
• Nikkaji Number: J150.107K,J298.678G
• Wikidata: Q27128549
• Metabolomics Workbench ID: 61238
• ChEMBL ID: CHEMBL1927249
• Mol file: 16642-92-5.mol

Synonyms:2-Propenoicacid, 3-[4-(trifluoromethyl)phenyl]-, (E)-;Cinnamic acid, p-(trifluoromethyl)-,(E)- (8CI);(E)-3-(4-(Trifluoromethyl)phenyl)acrylic acid;(E)-3-(4-Trifluoromethylphenyl)-2-propenoic acid;(E)-4-Trifluoromethylcinnamicacid;(E)-p-(Trifluoromethyl)cinnamic acid;4-Trifluoromethyl-trans-cinnamicacid;trans-3-(4-Trifluoromethylphenyl)acrylic acid;trans-4-Trifluoromethylcinnamic acid;2-Propenoicacid, 3-[4-(trifluoromethyl)phenyl]-, (2E)-;

Chemical Property of 4-(Trifluoromethyl)cinnamic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 231-233 °C(lit.)
• Boiling Point: 279.2 °C at 760 mmHg
• PKA: 4.21±0.10(Predicted)
• Flash Point: 122.6 °C
• PSA: 37.30000
• Density: 1.363 g/cm³
• LogP: 2.80320
• Storage Temp.: Sealed in dry,Room Temperature
• 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: 250

Purity/Quality:

≥99% ^*data from raw suppliers

4-(Trifluoromethyl)cinnamic Acid >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC(=O)O)C(F)(F)F
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C(=O)O)C(F)(F)F
• Uses: trans-4-(Trifluoromethyl)cinnamic acid has been employed as internal standard for the determination of A77 1726 (2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide) in plasma by HPLC.

Technology Process of 4-(Trifluoromethyl)cinnamic acid

There total 28 articles about 4-(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: 100.0%

4-Trifluoromethylbenzaldehyde (455-19-6) + malonic acid (141-82-2) → 4-(trifluoromethyl)cinnamic acid (16642-92-5,87212-84-8,2062-26-2)

Guidance literature:

With pyridine; aniline; In toluene; for 18h; Reflux;

DOI:10.1016/j.bmc.2017.05.011

Reference yield: 99.0%

ethyl (E)-4-trifluoromethylcinnamate (101466-85-7,128408-03-7) → 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2,87212-84-8,16642-92-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 24h;

DOI:10.1016/j.bmc.2021.116299

Reference yield: 99.0%

(2E)-3-(4-trifluoromethylphenyl)prop-2-enal (95123-61-8) → 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2,87212-84-8,16642-92-5)

Guidance literature:

With C₄H₁₁FeMo₆NO₂₄^(3-)*3C₁₆H₃₆N⁽¹⁺⁾; water; oxygen; sodium carbonate; at 50 ℃; for 8h; under 760.051 Torr; Green chemistry;

DOI:10.1002/anie.201612225

upstream raw materials:

4-Trifluoromethylbenzaldehyde

malonic acid

carbon dioxide

5,5-dimethyl-2-[2-(4-trifluoromethylphenyl)ethen-1-yl]-1,3,2-dioxaborinane

Downstream raw materials:

ethyl 4-trifluoromethylcinnamate

methyl (2E)-3-(4-(trifluoromethyl)phenyl)prop-2-enoate

3-(4-trifluoromethylphenyl)propionic acid

methyl 4-trifluoromethylcinnamate

Refernces

• 1、 Zhang, Peng,Min, Zhihui,Gao, Yang,Bian, Jiang,Lin, Xin,He, Jie,Ye, Deyong,Li, Yilin,Peng, Chao,Cheng, Yunfeng,Chu, Yong. "Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia". . p. 7341 - 7358. Retrieved 2021/06/28.
• 2、 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.