Methyl Trifluoropyruvate

Base Information

• Chemical Name: Methyl Trifluoropyruvate
• CAS No.: 13089-11-7
• Molecular Formula: C4H3F3O3
• Molecular Weight: 156.061
• Hs Code.: 29183000
• European Community (EC) Number: 629-146-9
• DSSTox Substance ID: DTXSID30370581
• Nikkaji Number: J772.797F
• Wikidata: Q72492165
• Mol file: 13089-11-7.mol

Synonyms:Methyl Trifluoropyruvate;13089-11-7;methyl 3,3,3-trifluoro-2-oxopropanoate;Methyl 3,3,3-trifluoropyruvate;Trifluoropyruvic Acid Methyl Ester;METHYL 2-OXO-3,3,3-TRIFLUOROPROPANOATE;Propanoic acid, 3,3,3-trifluoro-2-oxo-, methyl ester;SCHEMBL486217;methyl-3,3,3-trifluoropyruvate;AMY3627;DTXSID30370581;FD2023;MFCD00114936;AKOS005063372;CS-W002382;methyl3,3,3-trifluoro-2-oxopropanoate;Methyl 3,3,3-trifluoropyruvate, 97%;AS-48914;FT-0613981;T1785;EN300-42930;3,3,3-trifluoro-2-oxo-propionic acid methyl ester;J-005895;J-522701

Chemical Property of Methyl Trifluoropyruvate

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Melting Point: 84-86 °C
• Refractive Index: n20/D 1.332(lit.)
• Boiling Point: 58.5 °C at 760 mmHg
• Flash Point: 80 °F
• PSA: 43.37000
• Density: 1.398 g/cm³
• LogP: 0.29080
• Storage Temp.: Flammables area
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 156.00342844
• Heavy Atom Count: 10
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

Methyl Trifluoropyruvate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F,Xi
• Hazard Codes: C,F,Xi
• Statements: 10
• Safety Statements: 45-36/37/39-26-16-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(=O)C(F)(F)F
• General Description: Methyl trifluoropyruvate is a versatile reagent used in cyclocondensation reactions with N-substituted ureas to form trifluoromethyl-substituted imidazolidine-2,4-diones, which are valuable intermediates for modifying biologically active compounds. Additionally, it serves as a synthetic equivalent in Claisen condensations, enabling the preparation of trifluoromethylated heterocycles such as 2-(trifluoroacetyl)chromones and furan-3(2H)-ones, which exhibit unique properties for further applications in drug development and organic synthesis.

Technology Process of Methyl Trifluoropyruvate

There total 8 articles about Methyl Trifluoropyruvate 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: 94.5%

2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7) → methyl 3,3,3-trifluoropyruvate (13089-11-7) + methyl 3,3,3-trifluoro-2-hydroxy-2-methoxypropanoate (19607-21-7)

Guidance literature:

With sulfuric acid; silica gel; at 125 ℃; for 0.5h;

DOI:10.1016/S0022-1139(02)00007-6

Reference yield: 12.0%

2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7) → trifluoroacetic acid-methyl ester (431-47-0) + methyl 3,3,3-trifluoropyruvate (13089-11-7) + methyl 3,3,3-trifluoro-2,2-dihydroxypropanoate (19390-75-1)

Guidance literature:

With sulfuric acid; silica gel; at 140 ℃;

DOI:10.1016/S0022-1139(02)00007-6

Reference yield:

2-fluoro-2-methoxy trifluoropropanoic acid methyl ester (10186-63-7) → Methyl fluoride (593-53-3) + methyl 3,3,3-trifluoropyruvate (13089-11-7)

Guidance literature:

With Fe₂(SO₄)3/Al₂O₃; at 180 ℃; for 7h;

DOI:10.1016/j.jfluchem.2008.01.001

upstream raw materials:

2-fluoro-2-methoxy trifluoropropanoic acid methyl ester

methanol

Hexafluoropropene oxide

Sodium; 2,3,3,3-tetrafluoro-2-methoxy-propionate

Downstream raw materials:

methyl ester of 2-hydroxy-2-trifluoromethyl-4-pentenoic acid

dimethyl bis(trifluoromethyl)tartarate, meso form

dimethyl bis(trifluoromethyl)tartarate, racemate

α-hydroxy-α-trifluoromethyl-2,5-dihydroxyphenylacetic acid methyl ester

Refernces

Methyl Trifluoropyruvate in Cyclocondensation Reactions with N-Substituted Ureas

10.1134/S1070363219010286

The study primarily investigates the cyclocondensation reactions of methyl trifluoropyruvate with N-substituted ureas, resulting in the formation of 3-substituted 5-hydroxy- or 5-methoxy-5-trifluoromethylimidazolidine-2,4-diones. These compounds serve as potential precursors for the modification of biologically active substances, such as phenothiazine. The chemicals used in the study include methyl trifluoropyruvate, various N-substituted ureas, triethylamine as a catalyst, and copper-catalyzed alkyne azide 1,3-dipolar cycloaddition reagents. The purpose of these chemicals is to synthesize and modify heterocycles with trifluoromethyl groups, which can be further used to modify drugs and create new biologically active compounds.

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.