Methyl 2-methoxytetrafluoropropionate

Base Information

• Chemical Name: Methyl 2-methoxytetrafluoropropionate
• CAS No.: 10186-63-7
• Molecular Formula: C5H6 F4 O3
• Molecular Weight: 190.094
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID20379548
• Nikkaji Number: J1.638.480A
• Mol file: 10186-63-7.mol

Synonyms:Methyl 2-methoxytetrafluoropropionate;10186-63-7;methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate;Methyl tetrafluoro-2-(methoxy)propionate;methyl 2-methoxytetrafluoropropanoate;Propanoic acid, 2,3,3,3-tetrafluoro-2-methoxy-, methyl ester;CH3OCF(CF3)COOMe;CF3CF(OCH3)COOCH3;SCHEMBL5960637;DTXSID20379548;MFCD00155951;AKOS001270594;AKOS017343590;FT-0676774;Z104484390;2,3,3,3-Tetrafluoro-2-methoxypropanoic acid methyl ester

Chemical Property of Methyl 2-methoxytetrafluoropropionate

Chemical Property:

• Vapor Pressure: 2.24mmHg at 25°C
• Refractive Index: 1.332
• Boiling Point: 161.7°Cat760mmHg
• Flash Point: 50.8°C
• PSA: 35.53000
• Density: 1.331g/cm³
• LogP: 1.03390
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 190.02530670
• Heavy Atom Count: 12
• Complexity: 178

Purity/Quality:

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

Methyl2-Methoxytetrafluoropropionate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C(F)(F)F)(OC)F
• General Description: Methyl 2-methoxytetrafluoropropionate is a stable and synthetically versatile reagent that acts as an effective equivalent of methyl trifluoropyruvate in Claisen condensations. It is readily synthesized from hexafluoropropene epoxide and methanol and serves as a key intermediate in the preparation of trifluoromethylated heterocycles, such as 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones. The compound’s utility lies in its ability to facilitate efficient transformations under mild conditions, making it a valuable tool in the synthesis of biologically and chemically significant trifluoromethyl-containing molecules.

Technology Process of Methyl 2-methoxytetrafluoropropionate

There total 14 articles about Methyl 2-methoxytetrafluoropropionate 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%

methanol (67-56-1) + Hexafluoropropene oxide (428-59-1,25038-02-2) → 2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7)

Guidance literature:

With sodium carbonate; at 20 ℃;

Reference yield: 94.0%

methanol (67-56-1) + α-methoxytetrafluoropropionyl fluoride (85036-47-1) → 2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7)

Guidance literature:

at 10 ℃;

DOI:10.1007/BF00961240

Reference yield: 87.0%

Hexafluoropropene oxide (428-59-1,25038-02-2) → 2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7)

Guidance literature:

In methanol; water;

upstream raw materials:

methanol

Hexafluoropropene oxide

α-methoxytetrafluoropropionyl fluoride

2,3-epoxyperfluoropentane

Downstream raw materials:

methyl 3,3,3-trifluoropyruvate

2.3.3.3-Tetrafluor-2-methoxy-propionsaeureamid

α,α-Bis(3,5-dimethyl-4-hydroxyphenyl)trifluoropropionic acid methyl ester

Methyl fluorosulfonate

Refernces

Methyl 2-methoxytetrafluoropropionate as a synthetic equivalent of methyl trifluoropyruvate in the Claisen condensation. The first synthesis of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones

10.1016/j.tetlet.2009.06.067

The research focuses on the development of a novel synthetic method for the preparation of 2-(trifluoroacetyl)chromones and 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones. The study utilizes methyl 2-methoxytetrafluoropropionate as a key reagent, which is easily prepared from hexafluoropropene epoxide and methanol. This compound serves as a stable and effective equivalent of methyl trifluoropyruvate in the Claisen condensation with various acetophenones, yielding intermediates that are subsequently deprotected using sulfuric acid to obtain the desired products. The synthesized compounds exhibit unique physical and biological properties due to the presence of the trifluoromethyl group, making them valuable precursors for the construction of more complex trifluoromethylated heterocycles. The research highlights the practicality and efficiency of this approach, demonstrating its potential for further synthetic applications in the field of organic chemistry.