Ethyl 4,4,4-trifluoroacetoacetate

Base Information

• Chemical Name: Ethyl 4,4,4-trifluoroacetoacetate
• CAS No.: 372-31-6
• Molecular Formula: C6H7F3O3
• Molecular Weight: 184.115
• Hs Code.: 29183000
• European Community (EC) Number: 206-750-7
• NSC Number: 42739
• UNII: KM9XB46R5T
• DSSTox Substance ID: DTXSID5059905
• Nikkaji Number: J150.821K
• Wikidata: Q17321524
• ChEMBL ID: CHEMBL152164
• Mol file: 372-31-6.mol

Synonyms:ethyl 4,4,4-trifluoroacetoacetate;ethyl-4,4,4-trifluoroacetoacetate

Chemical Property of Ethyl 4,4,4-trifluoroacetoacetate

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: 8hPa at 20℃
• Melting Point: -39 °C
• Refractive Index: n20/D 1.375(lit.)
• Boiling Point: 129.5 °C at 760 mmHg
• PKA: 7.76±0.10(Predicted)
• Flash Point: 28.9 °C
• PSA: 43.37000
• Density: 1.273 g/cm³
• LogP: 1.07100
• Storage Temp.: Flammables area
• Solubility.: 10g/l
• Water Solubility.: 10 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 184.03472857
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

98% ^*data from raw suppliers

4,4,4-Trifluoro-3-oxobutanoic Acid Ethyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F, C, Xi
• Hazard Codes: Xn,F,C,Xi
• Statements: 10-22-52/53
• Safety Statements: 61-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CCOC(=O)CC(=O)C(F)(F)F
• Uses: Intermediate for agro chemicals and pharmaceuticals (mefloquine). Product Data Sheet Widely used in the synthetic process of medicine, pesticides and organic intermediate. Ethyl 4,4,4-trifluoroacetoacetate is used in the synthesis of fluorinated 2-thiouracil analogs as antithyroid agents.

Technology Process of Ethyl 4,4,4-trifluoroacetoacetate

There total 22 articles about Ethyl 4,4,4-trifluoroacetoacetate 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: 96.1%

1,1,1-trifluoro-2-propanone (421-50-1) + chloroformic acid ethyl ester (541-41-3) → ethyl 4,4,4-trifluoroacetoacetate (372-31-6)

Guidance literature:

With hydrogenchloride; In toluene; at 90 ℃; for 0.333333h; under 5250.53 Torr; Solvent; Temperature; Pressure;

Reference yield: 94.5%

formic acid (64-18-6) + sodium 4-ethoxy-1,1,1-trifluoro-4-oxobut-2-en-2-olate (22466-45-1) → sodium formate (141-53-7) + ethyl 4,4,4-trifluoroacetoacetate (372-31-6)

Guidance literature:

With formic acid ethyl ester; at 30 ℃; for 3h; Temperature;

Reference yield: 85.0%

ethyl trifluoroacetate, (383-63-1) + ethyl acetate (141-78-6) → ethyl 4,4,4-trifluoroacetoacetate (372-31-6)

Guidance literature:

With sodium hydride; In diethyl ether; paraffin; reflux, 2 h and r.t., 12 h;

DOI:10.1016/S0022-1139(00)82207-1

upstream raw materials:

ethyl 2-fluoroacetate

ethyl difluoroacetate

ethyl trifluoroacetate,

ethyl acetate

Downstream raw materials:

ethyl (Z)-4,4,4-trifluoro-3-oxo-2-(ureidomethylidene)butanoate

ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate

3-trifluoromethyl-1-phenyl-1H-pyrazol-5(4H)-one

2-methyl-4-(trifluoromethyl)-1H-pyrimidin-6-one

Refernces

• 1、 -. "Preparation method of sodium formate". Paragraph 0025-0044. . Retrieved 2021/06/26.
• 2、 Liu, Hao-Nan,Cao, Hao-Qiang,Cheung, Chi Wai,Ma, Jun-An. "Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis". supporting information. p. 1396 - 1401. Retrieved 2020/02/22.