Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate

Base Information

• Chemical Name: Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate
• CAS No.: 680-15-9
• Molecular Formula: C3H3F3O4S
• Molecular Weight: 192.116
• Hs Code.: 29159000
• Mol file: 680-15-9.mol

Synonyms:Aceticacid, difluoro(fluorosulfonyl)-, methyl ester (6CI,7CI,8CI,9CI);(Fluorosulfonyl)difluoroacetic acid methyl ester;2,2-Difluoro-2-fluorosulfonylacetic acid methyl ester;Difluoro(fluorosulfonyl)acetic acid methyl ester;Methyl(fluorosulfonyl)difluoroacetate;Methyl 2-fluorosulfonyldifluoroacetate;Methyl difluoro(fluorosulfonyl)acetate;Methyl fluorosulphonyldifluoroacetate;

Chemical Property of Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 1170mmHg at 25°C
• Refractive Index: n20/D 1.351(lit.)
• Boiling Point: 150 °C at 760 mmHg
• Flash Point: 44.5 °C
• PSA: 68.82000
• Density: 1.614 g/cm³
• LogP: 1.13230
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

98%, ^*data from raw suppliers

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 10-34
• Safety Statements: 26-36/37/39-45-16

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) serves as a key reagent in the copper(I) iodide-mediated trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles, facilitated by tetrabutylammonium iodide (TBAI) as a promoter. This method enables the efficient synthesis of 1-aryl-4-trifluoromethyl-1,2,3-triazoles, compounds of interest due to the pharmacological and agrochemical relevance of the trifluoromethyl group and the 1,2,3-triazole scaffold. The reaction conditions, optimized through solvent, copper source, and additive screening, highlight MDFA's utility in generating trifluoromethylated heterocycles with functional group compatibility and scalability.

Technology Process of Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate

There total 13 articles about Methyl 2,2-Difluoro-2-(fluorosulfonyl)acetate 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: 99.0%

methanol (67-56-1) + 2-fluorosulfonyl-2,2-difluoroacetyl chloride (1648-30-2) → hydrogenchloride (7647-01-0,15364-23-5) + 2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9)

Guidance literature:

In neat (no solvent);

Reference yield: 95.0%

methanol (67-56-1) + tetrafluoroethane-β-sultone (697-18-7) → 2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9)

Guidance literature:

at 0-5°C;

Reference yield: 92.0%

methanol (67-56-1) + 5,5,6,6-tetrafluoro-2,2,4,4-tetroxo-1,3-dioxa-2,4-dithiane (1858-59-9) → 2,2-difluoro-2-(fluorosulfonyl)acetate (680-15-9)

Guidance literature:

at -20°C for 1 h, warming to room temp.;

upstream raw materials:

methanol

tetrafluoroethane-β-sultone

sodium methylate

4-heptafluoropropoxytrifluoro-1,2-oxathietane 2,2-dioxide

Downstream raw materials:

difluoro-phenylsulfamoyl-acetic acid anilide

p-nitrobenzotrifluoride

p-nitrophenyl trifluoromethyl sulfide

methyl iodide

Refernces

Methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA)/copper (I) iodide mediated and tetrabutylammonium iodide promoted trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles

10.1016/j.jfluchem.2020.109516

The research focuses on the development of a general methodology for the trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles using methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA) and copper (I) iodide, promoted by tetrabutylammonium iodide (TBAI). The study explores the synthesis of 1-aryl-4-trifluoromethyl-1,2,3-triazoles, which are important due to the unique properties of the 1,2,3-triazole ring and the significance of the trifluoromethyl group in pharmaceuticals and agrochemicals. The experiments involved the optimization of reaction conditions, including the evaluation of different solvents, copper sources, and additives, with a particular emphasis on the role of TBAI in enhancing conversion rates. The analyses used to monitor the progress and outcomes of the reactions included liquid chromatography-mass spectrometry (LCMS), high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS). These techniques were crucial for characterizing the intermediates and final products, as well as for optimizing the reaction conditions to achieve the desired trifluoromethylated heterocycles with broad functional group tolerance and on a multi-gram scale.