2925-22-6

Basic information

• Product Name: DIFLUOROACETYL FLUORIDE
• Synonyms: DIFLUOROACETYL FLUORIDE
• CAS NO: 2925-22-6
• Molecular Formula: C₂HF₃O
• Molecular Weight: 98.02
• Mol File: 2925-22-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: °C
• Appearance: /
• CAS DataBase Reference: DIFLUOROACETYL FLUORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIFLUOROACETYL FLUORIDE(2925-22-6)
• EPA Substance Registry System: DIFLUOROACETYL FLUORIDE(2925-22-6)

Safety Data

• Hazard Codes: C,T
• Statements: 20-34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: 3308
• Hazardous Substances Data: 2925-22-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4007, 1984 DOI: 10.1021/jo00195a025

Upstream product

• 401-67-2 2,2-difluoroacetic anhydride 
• 79-53-8 chloropentafluoroacetone 
• 359-11-5 1,1,2-trifluoroethylene 
• 512-51-6 Ethyl 1,1,2,2-tetrafluoroethyl ether 
• 425-88-7 1,1,2,2-tetrafluoro-1-methoxyethane 
• 79-36-7 dichloroacethyl chloride 
• 116-14-3 polytetrafluoroethylene 
• 141-78-6 ethyl acetate 
• 115611-57-9 (1,1,2,2-Tetrafluoro-ethoxymethyl)-benzene 
• 72844-39-4 Difluoro-acetic acid 2-chloro-1,1-difluoro-ethyl ester 
• 920-64-9 1-chloro-1,1,3,3-tetrafluoroacetone 
• 79-38-9 Chlorotrifluoroethylene 
• 152239-89-9 C₃HClF₆O 
• 75-38-7 Vinylidene fluoride 

Downstream Products

• 176969-34-9 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid 
• 359-13-7 difluoroethanol 
• 1300698-74-1 2,2-difluoroethyl 2,2-difluoroacetate 
• 26132-51-4 4-fluoro-α,α-difluorotoluene 
• 55805-10-2 4-cyano-1-difluoromethylbenzene 
• 455-31-2 difluoromethylbenzene 
• 381-73-7 Difluoroacetic acid 
• 934738-22-4 1-(difluoromethyl)-4-(trifluoromethoxy)benzene 
• 1214379-64-2 C₇H₄F₄ 
• 2251-82-3 1-(difluoromethyl)-4-(trifluoromethyl)benzene 
• 444915-76-8 methyl 4-(difluoromethyl)benzoate 
• 64747-71-3 ethyl p-(difluoromethyl) benzoate 
• 64747-73-5 4-[(difluoromethyl)phenyl](phenyl)methanone 
• 176969-33-8 (E/Z)-ethyl 2-(ethoxymethylene)-4,4-difluoro-3-oxobutanoate 

Relevant articles and documents

Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis

This Article describes the development of a decarbonylative Pd-catalyzed aryl-fluoroalkyl bond-forming reaction that couples fluoroalkylcarboxylic acid-derived electrophiles [RFC(O)X] with aryl organometallics (Ar-M′). This reaction was optimized by interrogating the individual steps of the catalytic cycle (oxidative addition, carbonyl de-insertion, transmetalation, and reductive elimination) to identify a compatible pair of coupling partners and an appropriate Pd catalyst. These stoichiometric organometallic studies revealed several critical elements for reaction design. First, uncatalyzed background reactions between RFC(O)X and Ar-M′ can be avoided by using M′ = boronate ester. Second, carbonyl de-insertion and Ar-RF reductive elimination are the two slowest steps of the catalytic cycle when RF = CF3. Both steps are dramatically accelerated upon changing to RF = CHF2. Computational studies reveal that a favorable F2C-H - -X interaction contributes to accelerating carbonyl de-insertion in this system. Finally, transmetalation is slow with X = difluoroacetate but fast with X = F. Ultimately, these studies enabled the development of an (SPhos)Pd-catalyzed decarbonylative difluoromethylation of aryl neopentylglycol boronate esters with difluoroacetyl fluoride.

Synthetic method of difluoroacetyl fluoride

The invention relates to a synthesis method of difluoroacetyl fluoride, which comprises the following steps: 1. reacting trichloroethylene with oxygen under the catalytic action of trialkyl boron shown in the formula I to generate dichloroacetyl chloride, and 2. reacting dichloroacetyl chloride with inorganic fluoride shown in the formula II under the action of a catalyst to generate difluoroacetyl fluoride. According to the synthetic method of difluoroacetyl fluoride, the raw materials are simple and easy to obtain, high-temperature reaction is not needed, and the yield is high.

Preparation method of 2,2-difluoroacetyl fluoride and derivative thereof

The invention belongs to the field of fluorine chemical industry and particularly relates to a preparation method of 2,2-difluoroacetyl fluoride and a derivative thereof. The preparation method takes 1,1,2,2-tetrafluoroethyl ethyl ether as a raw material, and the raw material reacts under the action of a catalyst to prepare the product. The catalyst is prepared by adopting a method comprising the following steps: taking rare-earth metal oxide as a raw material and activating at high temperature; and introducing CHF2Cl and reacting. The preparation method takes the 1,1,2,2-tetrafluoroethyl ethyl ether as the raw material, and the 1,1,2,2-tetrafluoroethyl ethyl ether has oxidization reaction under the action of the catalyst at 140 DEG C to 160 DEG C to generate acyl fluoride; and the preparation method has simple and safe production steps and short reaction time.