beta-Trifluoromethylcrotonic acid

Base Information

• Chemical Name: beta-Trifluoromethylcrotonic acid
• CAS No.: 93404-33-2
• Molecular Formula: C₅H₅F₃O₂
• Molecular Weight: 154.089
• Hs Code.: 2916199590
• European Community (EC) Number: 627-003-5
• Wikidata: Q76310724
• Mol file: 93404-33-2.mol

Synonyms:beta-Trifluoromethylcrotonic acid;93404-33-2;(Z)-4,4,4-trifluoro-3-methylbut-2-enoic acid;3-trifluoromethylcrotonic acid;Cis-3-(trifluoromethyl)crotonic acid;3-(TRIFLUOROMETHYL)CROTONICACID;MFCD00014374;starbld0000244;(2Z)-4,4,4-trifluoro-3-methylbut-2-enoic acid;3-trifluoromethyl crotonic acid;SCHEMBL3454104;AKOS006228071;AS-47379;CS-0357519;4,4,4-Trifluoro-3-methyl-2-butenoic acid, 97%;J-800344;2-Butenoic acid,4,4,4-trifluoro-3-methyl-,(2Z)-

Chemical Property of beta-Trifluoromethylcrotonic acid

Chemical Property:

• Vapor Pressure: 0.0507mmHg at 25°C
• Melting Point: 28-30 °C(lit.)
• Refractive Index: 1.3838
• Boiling Point: 158-163 °C(lit.)
• Flash Point: 175 °F
• PSA: 37.30000
• Density: 1.318 g/mL at 25 °C(lit.)
• LogP: 1.57960
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 154.02416388
• Heavy Atom Count: 10
• Complexity: 168

Purity/Quality:

98%min ^*data from raw suppliers

beta-Trifluoromethylcrotonic acid 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of beta-Trifluoromethylcrotonic acid

There total 6 articles about beta-Trifluoromethylcrotonic 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: 61.0%

β-trifluoromethylcrotonic acid methyl ester (671-82-9) → 3-methyl-4,4,4-trifluoro-2-butenoic acid (69056-67-3,93404-33-2)

Guidance literature:

With potassium tert-butylate; water; In diethyl ether; for 12h; Ambient temperature;

Reference yield:

(E)-3-trifluoromethyl-2-butenoic acid ethyl ester (691-77-0) → (2E)-4,4,4-Trifluoro-3-methylbut-2-enoic acid (400-28-2,93404-33-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 7h; Yield given; Ambient temperature;

DOI:10.1021/jo00108a022

Reference yield:

2,3-dihydroxy-3-methyl-4,4,4-trifluorobutanoic acid (119620-23-4) → 3-trifluoromethyl-2-butenoic acid (93404-33-2) + (2E)-4,4,4-Trifluoro-3-methylbut-2-enoic acid (400-28-2,93404-33-2)

Guidance literature:

With sulfuric acid; In water; at 200 ℃; for 16h; Overall yield = 8.78 g; Optical yield = 86.667 percent de;

DOI:10.1016/j.tet.2020.131758

upstream raw materials:

4,4,4-trifluoro-3-hydroxy-3-methyl-butanoic acid

4-methyl-4-trifluoromethyl-oxetan-2-one

β-trifluoromethylcrotonic acid methyl ester

2,3-dihydroxy-3-methyl-4,4,4-trifluorobutanoic acid

Refernces

• 1、 Agou, Tomohiro,Kawasaki-Takasuka, Tomoko,Kubota, Toshio,Taketsugi, Masahito,Yamazaki, Takashi. "Construction of CF3-containing quaternary chiral centers via Michael addition reactions". . p. 1815 - 1822. Retrieved 2021/08/13.
• 2、 Nemoto,Satoh,Fukumoto,Kabuto. "A rapid access to both enantiomers of 1,2,3,4-tetranor B-trienic 18,18,18-trifluorosteroids. The first enantiocontrolled total synthesis of 18,18,18-trifluorosteroids". . p. 594 - 600. Retrieved 2007/10/02.