Ethyl 4,4,4-trifluorobut-2-ynoate

Base Information

• Chemical Name: Ethyl 4,4,4-trifluorobut-2-ynoate
• CAS No.: 79424-03-6
• Molecular Formula: C6H5F3O2
• Molecular Weight: 166.1
• Hs Code.: 29161900
• European Community (EC) Number: 635-987-2
• DSSTox Substance ID: DTXSID70394009
• Nikkaji Number: J496.196J
• Wikidata: Q72511051
• ChEMBL ID: CHEMBL4778344
• Mol file: 79424-03-6.mol

Synonyms:Ethyl 4,4,4-trifluorobut-2-ynoate;79424-03-6;Ethyl 4,4,4-trifluoro-2-butynoate;4,4,4-Trifluoro-but-2-ynoic acid ethyl ester;MFCD00192167;ethyl 4,4,4-trifluoro-2-butynate;C6H5F3O2;Ethyl4,4,4-trifluoro-2-butynoate;4,4,4-trifluoro-2-butynoic acid ethyl ester;SCHEMBL126709;ethyl trifluoromethylpropiolate;CHEMBL4778344;DTXSID70394009;Ethyl4,4,4-trifluorobut-2-ynoate;AMY26513;BBL102405;STL556207;Trifluoro-2-butynoic acid ethyl ester;AKOS005063659;AB04643;CS-W016066;ETHYL 4,4,4-TRIFLUOROBUTYNOATE;AS-41313;PD168607;SY063070;Ethyl 4,4,4-trifluoro-2-butynoate, 97%;FT-0677871;EN300-136551;A839682

Chemical Property of Ethyl 4,4,4-trifluorobut-2-ynoate

Chemical Property:

• Vapor Pressure: 18.2mmHg at 25°C
• Refractive Index: n20/D 1.350(lit.)
• Boiling Point: 116.5 °C at 760 mmHg
• Flash Point: 24.6 °C
• PSA: 26.30000
• Density: 1.27 g/cm³
• LogP: 1.11520
• Storage Temp.: Keep Cold
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water (partly).
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 166.02416388
• Heavy Atom Count: 11
• Complexity: 205

Purity/Quality:

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

Ethyl 4,4,4-trifluoro-2-butynoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): XiF
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C#CC(F)(F)F
• Uses: Ethyl 4,4,4-trifluoro-2-butynoate is the suitable reagent used to investigate the regioselectivity of the insertion reaction with cyclometalated iridium and rhodium complexes. It may be used in the preparation of ethyl (Z)-3-iodo-4,4,4-trifluoro-2-butenoate.

Technology Process of Ethyl 4,4,4-trifluorobut-2-ynoate

There total 3 articles about Ethyl 4,4,4-trifluorobut-2-ynoate 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: 88.0%

4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid ethyl ester (83961-56-2) → ethyl 4,4,4-trifluoro-2-butynate (79424-03-6)

Guidance literature:

at 150 - 220 ℃;

DOI:10.1055/s-2002-32977

Reference yield: 39.0%

3,3,3-trifluoroprop-1-yne (661-54-1) + chloroformic acid ethyl ester (541-41-3) → ethyl 4,4,4-trifluoro-2-butynate (79424-03-6)

Guidance literature:

With n-butyllithium; water; In dibutyl ether; 1) -78 deg C, 1h, 2) r.t., 4h;

DOI:10.1016/S0022-1139(00)80446-7

Reference yield:

(3,3,3-trifluoroprop-1-yn-1-yl)lithium (14856-86-1) + chloroformic acid ethyl ester (541-41-3) → ethyl 4,4,4-trifluoro-2-butynate (79424-03-6)

Guidance literature:

With water; In dibutyl ether; Yield given; 1) -60 deg C, 1h, 2) r.t., 4h;

DOI:10.1016/S0022-1139(00)80446-7

upstream raw materials:

3,3,3-trifluoroprop-1-yne

chloroformic acid ethyl ester

(3,3,3-trifluoroprop-1-yn-1-yl)lithium

4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid ethyl ester

Downstream raw materials:

3-Hydroxy-5-(trifluoromethyl)pyrazole

ethyl 1-(4-methoxybenzyl)-5-(trifluoromethyl)-1H-1,2,3-triazole-4-carboxylate

ethyl 1-(4-methoxybenzyl)-4-(trifluoromethyl)-1H-1,2,3-triazole-5-carboxylate

[PdCl(C(CO2Et)=C(CF3)C6H4CH2NMe2-κC,N)(3,4-dimethyl-1-phenylphosphole)]

Refernces

• 1、 Henry, Lucas,Schneider, Christoph,Mützel, Benedict,Simpson, Peter V.,Nagel, Christoph,Fucke, Katharina,Schatzschneider, Ulrich. "Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide". supporting information. p. 15692 - 15695. Retrieved 2015/02/19.
• 2、 Gold, Brian,Shevchenko, Nikolay E.,Bonus, Natalie,Dudley, Gregory B.,Alabugin, Igor V.. "Selective transition state stabilization via hyperconjugative and conjugative assistance: Stereoelectronic concept for copper-free click chemistry". experimental part. p. 75 - 89. Retrieved 2012/03/10.