353-85-5

Usage

Uses

Used in Chemical Synthesis:
Trifluoroacetonitrile is used as a solvent for chemical synthesis, particularly in the preparation of various organic compounds. Its unique properties, including high reactivity and the presence of fluorine atoms, make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Biochemical Research:
In biochemical research, Trifluoroacetonitrile is employed as a reagent for the synthesis of biologically active compounds. Its ability to form stable complexes with biomolecules and its compatibility with various biochemical reactions contribute to its utility in the development of new drugs and the study of biological processes.
Used in Material Science:
Trifluoroacetonitrile is also utilized in material science for the synthesis of advanced materials with unique properties. Its high reactivity and the presence of fluorine atoms enable the creation of materials with enhanced stability, chemical resistance, and other desirable characteristics.
Safety Considerations:
While Trifluoroacetonitrile is not classified as extremely hazardous, it requires careful handling due to its high reactivity. It can cause irritation upon contact with eyes, skin, or if inhaled, necessitating the use of appropriate safety measures during its application in various industries.

InChI:InChI=1/C2HBr2FO2/c3-2(4,5)1(6)7/h(H,6,7)

Upstream product

• 545-06-2 trichloroacetonitrile 
• 75-05-8 acetonitrile 
• 354-32-5 trifluoracetyl chloride 
• 118949-58-9 sodium (difluoroamino)difluoromethyltetrazolate 
• 124044-31-1 sodium 5-(pentafluoroethyl)tetrazolate 
• 74-90-8 hydrogen cyanide 
• 2314-97-8 iodotrifluoromethane 
• 815-28-1 perfluoro(dimethylethylamine) 
• 677-66-7 N,N-Dichlor-1,1,2,2,2-pentafluorethanamin 
• 83357-91-9 Pentafluorethylamin-hydrochlorid 
• 74352-98-0 1,2,2,2-Tetrafluorethanimin 
• 75350-66-2 (1S,5S)-1,4,5,6,7-Pentakis-trifluoromethyl-2,3-diaza-bicyclo[3.2.0]hepta-3,6-diene 
• 684-16-2 Hexafluoroacetone 
• 506-77-4 cyanogen chloride 

Downstream Products

• 14618-45-2 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone 
• 318-54-7 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethan-1-one 
• 443-47-0 2,2,2-trifluoro-1-(7-methyl-1H-indol-3-yl)-ethanone 
• 584-41-8 1-(5-ethyl-2,4-dihydroxy-phenyl)-2,2,2-trifluoro-ethanone 
• 2924-26-7 2,2,2-trifluoro-1-(2-hydroxy-4,5-dimethoxy-phenyl)-ethanone 
• 387-24-6 2,2,2-trifluoro-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone 
• 1620-72-0 2-methyl-6-(trifluoromethyl)pyridine 
• 569-32-4 1-(2,6-dihydroxy-4-methoxy-3-methyl-phenyl)-2,2,2-trifluoro-ethanone 
• 577-54-8 1-(3-ethyl-2,4-dihydroxy-phenyl)-2,2,2-trifluoro-ethanone 
• 383-56-2 1,1,1-trifluoro-pentan-2-one 
• 677-71-4 hexafluoroacetone hydrate 
• 684-16-2 Hexafluoroacetone 
• 753-90-2 trifluoroethylamine 
• 421-53-4 2,2,2-trifluoro-1,1-ethanediol 

Relevant academic research and scientific papers

REACTION OF PERFLUOROTRIMETHYLAMINE WITH ANTIMONY PENTAFLUORIDE. SYNTHESIS AND X-RAY STRUCTURE OF A PERFLUORINATED HEXAHYDRO-TRIAZINEDIONE DERIVATIVE

Perfluorotrimethylamine and SbF5 at an elevated temperature slowly eliminate CF4 to form the cation (III). (III) is also obtained from the reaction of CF3NCF2 with SbF5 in nearly quantitative yield.The hexahydrotriazinedione (IV) has been obtained by hydrolysis of (III).The constitution and structure of (IV) are established by X-ray crystallography.

Arrhenius Parameters for the Reaction of Trifluoromethyl Radicals with Cyanogen Chloride

The reaction of CF3 radicals with ClCN has been studied over a wide temperature range, 268-693 K, using CF3 radicals generated by the photolysis of CH3I.Over the range 408-473 K, CF3COCF3 was also used as a CF3 radical source.The radicals react with ClCN by addition followed by decomposition of the adduct and by chlorine abstraction: .The Arrhenius plot for this reaction is strongly curved.Using data from the low- and high-temperature regions, the following expressions for the rate constants for addition reaction (1) and chlorine abstraction (3) relative to CF3 recombination have been obtained: .The combination of E1 with the difference E-1-E2, which can be estimated, gives an upper limit for ΔH03 from which an approximate value of ΔH0f(CN) of 393.4 kJ mol-1 or less has been obtained.

Reactions of aromatic methyl ketimines with halonitriles as a new route to pyrimidines with two polyhaloalkyl groups

N-Isopropyl-(1-phenylethylidene)amine reacts with trichloroacetonitrile to give 1-azabutadiene derivative, which undergoes a double addition reaction with a variety of halonitriles affording fluoro- and chloro-containing pyrimidines. Pyrimidines with two polyhaloalkyl groups were obtained by the reaction of methyl ketimines with an excess of trichloroacetonitrile, trifluoroacetonitrile and 2,2,3,3-tetrafluoropropionitrile.

F-Ethylamine and F-Ethylimine

The new compounds F-ethylamine, C2F5NH2, and F-ethylimine, CF3CF=NH, are readily prepared by the reaction of N,N-dichloro-F-ethylamine with trimethylsilane at -45 or -25 deg C, respectively.Both compounds are subject to dehydrofluorination.Thus, CF3CF=NH may be obtained by the loss of a single HF molecule from CF3CF2NH2 at -25 deg C.CF3CF2NH2 will react with SF4 to form CF3CF2N=SF2.Similarly, CF3CF=NH forms CF3CF=NCl with ClF in the presence of CsF.

A Convenient Preparation of Trifluoroacetonitrile: Application to the Synthesis of a Novel Pyrimidinone Building Block

The generation of trifluoroacetonitrile (1) under mild conditions and controlled rates from easily accessible starting materials is described. Dehydration of trifluoroacetamide (2) with trifluoroacetic anhydride in pyridine generates trifluoroacetonitrile at ambient temperatures. As the trifluoroacetonitrile is formed, it distills out of the pyridine reaction mixture and is bubbled into a primary reaction vessel. The rate at which the gas is formed is controlled by the rate of addition of the reactants. The practicality of this method is exemplified via the synthesis of multigram quantities of a novel pyrimidinone building block 3.

Synthesis and characterization of perfluorinated nitriles and the corresponding sodium 5-perfluoroalkyltetrazolate salts

The high-yield syntheses of trifluoroacetonitrile (1a), pentafluoropropionitrile (1b) and heptafluorobutyronitrile (1c) under mild reaction conditions using readily available starting materials (trifluoroacetamide, pentafluoropropionamide, heptafluorobutanamide) are described. Furthermore, the reactions of the perfluoroalkyl nitriles with sodium azide in acetonitrile forming sodium 5-trifluoromethyltetrazolate (2a), sodium 5-pentafluoroethyltetrazolate (2b) and sodium 5-heptafluoropropyltetrazolate (2c) were undertaken. The 5-perfluoroalkyltetrazolate salts were characterized using vibrational (Raman and infrared) and multinuclear (13C, 14/15N, 19F) NMR spectroscopy, differential scanning calorimetry, mass spectrometry and elemental analysis. Additionally, the single crystal X-ray structure of the monohydrate of 2a was determined. Crystal data: 2a·H2O: monoclinic, C2/m, a = 18.8588(6) A?, b = 7.1857(2) A?, c = 9.3731(3) A?, β = 102.938(3)°, V = 1237.94(7) A?3, Z = 8, Dcalc = 1.911 g cm-3.

KINETICS OF THE HYDROGEN ABSTRACTION FROM HYDROGEN CYANIDE BY TRIFLUOROMETHYL RADICALS.

The reaction of CF//3 radicals with HCN in the gas phase has been studied in the temperature range 573-673 K using CF//3 radicals generated by thermal decomposition of CF//3I. Arrhenius parameters. Rate parameters are compared with those for reactions of CF//3 with polar and non-polar substrates.

2,2,2-Trifluoroacetaldehyde O-(Aryl)oxime: A Precursor of Trifluoroacetonitrile

The preparation of 2,2,2-trifluoroacetaldehyde O-(aryl)oxime, a previously inaccessible precursor of trifluoroacetonitrile, via reaction of hydroxylamine and trifluoroacetaldehyde hydrate is reported. This precursor released CF3CN in quantitative yield under mildly basic conditions. The precursor was successfully used in the synthesis of trifluoromethylated oxadiazoles. The facile, cost-effective, scalable, and recyclable procedure makes these trifluoroacetonitrile precursors generally applicable.

Preparation method of trifluoroacetamidine

The invention discloses a preparation method of trifluoroacetamidine, and belongs to the technical field of organic synthesis. Trifluoroacetamide is used as a raw material, gas-state trifluoroacetonitrile is collected through reflux and water diversion under the action of a catalyst, then trifluoroacetonitrile is introduced into DBU/liquid ammonia for a reaction, a polymerization inhibitor is added, distillation is performed, and trifluoroacetamidine is obtained. The method is coherent in reaction steps, simple and convenient to operate and high in yield; three wastes are reduced, the catalyst can be repeatedly utilized for more than 10 times in the dehydration process, the content of the obtained product is more than 99%, and the method has a potential industrial amplification prospect.

Process for fluorinating inorganic or organic compounds by direct fluorination

The invention relates to the use of a fluorinated gas, wherein the elemental fluorine (F2) is present at a high concentration, the present invention relates to a process for producing fluorinated compounds by direct fluorination using a fluorination gas in which elemental fluorine (F2) is present at a high concentration, such as a concentration of elemental fluorine (F2), in particular equal to much higher than 15 vol% or even 20 vol% (i.e., at least 15 vol% or even 20 vol%), and to a process for producing fluorinated compounds by direct fluorination using a fluorination gas. The process of the present invention relates to the manufacture of fluorinated compounds other than fluorinated benzene by direct fluorination, in particular to the preparation of fluorinated organic compounds, end products and intermediates for use in agricultural, pharmaceutical, electronic, catalyst, solvent and other functional chemical applications. The fluorination process of the invention can be carried outin batches or in a continuous manner. If the process of the invention is carried out in batches, a column (tower) reactor may be used. If the process of the invention is continuous, a microreactor may be used.