Ethyl 4,4,4-trifluorocrotonate

Base Information

• Chemical Name: Ethyl 4,4,4-trifluorocrotonate
• CAS No.: 25597-16-4
• Molecular Formula: C6H7 F3 O2
• Molecular Weight: 168.116
• Hs Code.: 29161900
• European Community (EC) Number: 607-752-4,609-851-8
• NSC Number: 374114
• DSSTox Substance ID: DTXSID701282600
• Nikkaji Number: J654.921G,J992.153B
• Wikidata: Q76305577
• Mol file: 25597-16-4.mol

Synonyms:Ethyl 4,4,4-trifluorocrotonate;25597-16-4;406-10-0;ethyl 4,4,4-trifluorobut-2-enoate;ethyl (E)-4,4,4-trifluorobut-2-enoate;ethyl (2E)-4,4,4-trifluorobut-2-enoate;(E)-ETHYL 4,4,4-TRIFLUOROBUT-2-ENOATE;4,4,4-Trifluorocrotonic Acid Ethyl Ester;2-Butenoic acid, 4,4,4-trifluoro-, ethyl ester, (2E)-;Ethyl (2E)-4,4,4-trifluoro-2-butenoate;ETHYL TRANS-4,4,4-TRIFLUOROCROTONATE;2-BUTENOIC ACID,4,4,4-TRIFLUORO-,ETHYL ESTER,(2E)-;Butenoic acid, 4,4,4-trifluoro-, ethyl ester;NSC374114;ethyl trifluorocrotonate;4,4,4-TRIFLUORO-2-BUTENOIC ACID ETHYL ESTER;SCHEMBL195983;SCHEMBL195984;Ethyl-4,4,4-triflurocrotonate;ethyl-4,4,4-trifluorocrotonate;ethyl4,4,4-trifluoro-crotonate;ZKRJCMKLCDWROR-ONEGZZNKSA-;ethyl 4, 4,4-trifluorocrotonate;ethyl 4,4,4-trifluoro-crotonate;DTXSID701282600;CS-B1754;MFCD00009903;ethyl (E)-4,4,4-trifluorocrotonate;AKOS005063525;trans-Ethyl 4,4,4-trifluorocrotonate;ethyl 4,4,4-trifluoro-(E)-butenoate;NSC-374114;Ethyl 4,4,4-trifluorocrotonate, 98%;AS-30104;Ethyl 4,4,4-trifluoro-trans-2-butenoate;AM20090309;E0772;EN300-51154;Ethyl (2E)-4,4,4-trifluoro-2-butenoate #;4,4,4-trifluoro-but-2-enoic acid ethyl ester;EN300-305520;J-016064;J-521320;F8881-7852;InChI=1/C6H7F3O2/c1-2-11-5(10)3-4-6(7,8)9/h3-4H,2H2,1H3/b4-3+

Chemical Property of Ethyl 4,4,4-trifluorocrotonate

Chemical Property:

• Appearance/Colour: Colorless and clear liquid
• Vapor Pressure: 19.9mmHg at 25°C
• Refractive Index: n20/D 1.3601(lit.)
• Boiling Point: 114.5 °C at 760 mmHg
• Flash Point: 25.6 °C
• PSA: 26.30000
• Density: 1.191 g/cm³
• LogP: 1.66800
• Storage Temp.: Flammables area
• 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:

99% ^*data from raw suppliers

Ethyltrans-4,4,4-Trifluorocrotonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; F
• Hazard Codes: Xi,F
• Statements: 10-36/37-36/37/38
• Safety Statements: 16-26-27-28-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Ethyl 4,4,4-trifluorocrotonate

There total 22 articles about Ethyl 4,4,4-trifluorocrotonate 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%

ethyl 3-hydroxy-4,4,4-trifluorobutyrate (372-30-5) → ethyl 4,4,4-trifluorocrotonate (25597-16-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; Ambient temperature;

DOI:10.1021/jo00182a022

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: 93.0%

Togni's reagent II (887144-94-7) + (E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) → ethyl 4,4,4-trifluorocrotonate (25597-16-4)

Guidance literature:

In N,N-dimethyl-formamide; at 120 ℃; for 24h; stereoselective reaction; Sealed tube;

DOI:10.1002/adsc.201500631

upstream raw materials:

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

ethanol

4,4,4-trifluorobut-2-enoic acid

2,2,2-Trifluoroacetaldehyde

Downstream raw materials:

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

ethyl 4,4,4-trifluorobutanoate

4,4,4-trifluorobutanol

Ethyl 3-(trifluoromethyl)-5-oxo-5-phenylvalerate

Refernces

• 1、 Ishikawa, Nobuo,Koh, Moon Gyu,Kitazume, Tomoya,Choi, Sam Kwon. "PREPARATION OF TRIFLUOROMETHYLATED ALLYLIC ALCOHOLS FROM TRIFLUOROACETALDEHYDE AND ORGANOMETALLIC COMPOUNDS". . p. 419 - 430. Retrieved 1984.
• 2、 Hamans, Bob C.,Heerschap, Arend,Andreychenko, Anna,Wijmenga, Sybren S.,Tessari, Marco. "NMR at earth's magnetic field using para-hydrogen induced polarization". . p. 224 - 228,5. Retrieved 2011.
• 3、 -. "PROCESS FOR PREPARATION OF 4,4,4- TRIFLUOROBUT-2-EN-1-OL AND INTERMEDIATE THEREOF". Page/Page column 11. . Retrieved 2020/07/31.
• 4、 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.