Butenoic acid, 4,4,4-trifluoro-, ethyl ester

Base Information

• Chemical Name: Butenoic acid, 4,4,4-trifluoro-, ethyl ester
• CAS No.: 406-10-0
• Molecular Formula: C₆H₇F₃O₂
• Molecular Weight: 168.116
• European Community (EC) Number: 609-851-8
• DSSTox Substance ID: DTXSID601246386
• Mol file: 406-10-0.mol

Synonyms:2-BUTENOIC ACID, 4,4,4-TRIFLUORO-, ETHYL ESTER;Butenoic acid, 4,4,4-trifluoro-, ethyl ester;ethyl4,4,4-trifluorocrotonate;4,4,4-TRIFLUORO-2-BUTENOIC ACID ETHYL ESTER;ethyl 3-trifluoromethylacrylate;ethyl beta-trifluoromethylacrylate;DTXSID601246386;AB01000;3-trifluoromethylacrylic acid ethyl ester;FT-0616976;FT-0695006

Chemical Property of Butenoic acid, 4,4,4-trifluoro-, ethyl ester

Chemical Property:

• Refractive Index: n20/D 1.3601(lit.)
• Boiling Point: 114.5oC at 760mmHg
• Flash Point: 25.6oC
• PSA: 26.30000
• Density: 1.191g/cm3
• LogP: 1.66800
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 168.03981395
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

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

Ethyl 4,4,4-trifluorocrotonate 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): symbol X ref. Details
• Hazard Codes: symbol X ref. Details

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CC(F)(F)F
• Uses: Ethyl 4,4,4-trifluorocrotonate was used in the synthesis of (2S,3S)-3-methyl- and (2S,3S)-3-trifluoromethylpyroglutamic acid. It undergoes diastereoselective Michael addition reaction with ethyl crotonate.

Technology Process of Butenoic acid, 4,4,4-trifluoro-, ethyl ester

There total 10 articles about Butenoic acid, 4,4,4-trifluoro-, ethyl 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: 95.0%

ethyl 4,4,4-trifluoro-2-butynate (79424-03-6) → ethyl 4,4,4-trifluorobut-2-enoate (25597-16-4,91600-34-9,406-10-0)

Guidance literature:

With [1,4-bis(diphenylphosphino)butane](1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; hydrogen; for 0.00138889h; under 1500.15 Torr;

DOI:10.1016/j.jmr.2011.06.011

Reference yield: 90.0%

ethyl 3-hydroxy-4,4,4-trifluorobutyrate (372-30-5) → ethyl 4,4,4-trifluorobut-2-enoate (25597-16-4,91600-34-9,406-10-0)

Guidance literature:

With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/j.jfluchem.2005.04.001

Reference yield: 80.0%

ethyl 4,4,4-trifluoro-2-butynate (79424-03-6) → ethyl (Z)-β-trifluoromethylacrylate (91600-34-9,406-10-0,25597-16-4)

Guidance literature:

With quinoline; Pd-BaSO₄; hydrogen; In methanol; for 0.666667h; under 2052 - 2789.2 Torr;

DOI:10.1039/P19900001281

upstream raw materials:

ethyl 3-hydroxy-4,4,4-trifluorobutyrate

ethyl 3-oxo-4,4,4-trifluorobutanoate enol

ethyl 4,4,4-trifluoro-2-butynate

2,2,2-Trifluoroacetaldehyde

Downstream raw materials:

4,4,4-trifluoro-3-(nitromethyl)butyric acid ethyl ester

(E,Z)-4,4,4-trifluoro-2-buten-1-ol

ethyl 4,4,4-trifluorobutanoate

Refernces

• 1、 Chung, Tim S.,Xue, Yang,Carranza, Alberto,Garcia-Garibay, Miguel A.. "Stereospecific photochemistry of Δ2-1,2,3-triazolines in solution and in the solid state: Scope and mechanistic studies". . p. 1458 - 1463. Retrieved 2017/09/23.
• 2、 Chung, Tim S.,Lopez, Steven A.,Houk,Garcia-Garibay, Miguel A.. "Stereospecific Synthesis of Substituted Aziridines by a Crystal-to-Crystal Photodenitrogenation of δ2-1,2,3-Triazolines". supporting information. p. 4568 - 4571. Retrieved 2015/09/28.