371-71-1

Basic information

• Product Name: (trifluoromethyl)carbonimidic difluoride
• Synonyms: (Trifluoromethyl)carbonimidic difluoride; carbonimidic difluoride, N-(trifluoromethyl)-
• CAS NO: 371-71-1
• Molecular Formula: C₂F₅N
• Molecular Weight: 133.0201
• Mol File: 371-71-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: -33.7 °C
• Density: 1.49g/cm³
• Vapor Pressure: 10800mmHg at 25°C
• Refractive Index: 1.262
• PKA: -6.19±0.50(Predicted)
• CAS DataBase Reference: (trifluoromethyl)carbonimidic difluoride(CAS DataBase Reference)
• NIST Chemistry Reference: (trifluoromethyl)carbonimidic difluoride(371-71-1)
• EPA Substance Registry System: (trifluoromethyl)carbonimidic difluoride(371-71-1)

Safety Data

• Hazardous Substances Data: 371-71-1(Hazardous Substances Data)

Usage

General Description

(trifluoromethyl)carbonimidic difluoride, also known as TFAF, is a chemical compound with the molecular formula CF3NFD. It is a colorless gas at room temperature and is commonly used in the chemical industry as a reagent for the synthesis of organic compounds. TFAF is highly reactive and can act as a strong fluorinating agent, and is often used to introduce trifluoromethyl groups into organic molecules. It is known for its high selectivity and efficiency in various chemical reactions, making it a valuable tool for organic chemists. TFAF is also used in the pharmaceutical industry for the development of new drugs and is a key building block in the synthesis of many important compounds. However, it is important to handle TFAF with caution as it is toxic and can cause severe irritation if inhaled or in contact with skin.

Upstream product

• 675-14-9 trifluoro-[1,3,5]triazine 
• 5764-87-4 N-Jod-bis(trifluormethyl)-amin 
• 1165952-91-9 cyclohexa-1,3-diene 
• 75995-67-4 trifluoro-1,2,4-triazine 
• 375-50-8 1,1,2,2,3,3,4,4-octafluoro-1,4-diiodobutane 
• 36525-64-1 perfluoro-NN'-dimethylethane-1,2-bis(amino-oxyl) diradical 
• 7276-63-3 bis{bis(trifluoromethyl)amino} mercury 
• 74-88-4 methyl iodide 
• 7719-12-2 phosphorus trichloride 
• 75-77-4 chloro-trimethyl-silane 
• 10544-50-0 sulfur 
• 105454-00-0 trithiazyl trichloride 
• 515-85-5 perfluoro(2-methyl-1,2-oxazetidine) 
• 432-00-8 bis(trifluoromethyl)carbamoyl fluoride 

Downstream Products

• 130138-79-3 1',1'-Dimethyl-2'-propynyl-N-trifluoromethylcarbamate 
• 76-16-4 Hexafluoroethane 
• 432-03-1 perfluorotrimethylamine 
• 50679-32-8 2-Phenylsulfanyl-N-trifluoromethyl-acetamide 
• 50679-26-0 2-CH₃S-C₆H₄-C(O)NHCF₃ 
• 50679-42-0 Benzoesaeure-N-trifluormethylamid 
• 50679-24-8 4-CH₃-C₆H₄ 
• 115-10-6 Dimethyl ether 
• 616-38-6 carbonic acid dimethyl ester 
• 50679-23-7 Cyclohexanecarboxylic acid trifluoromethyl-amide 
• 50679-39-5 1-cyclohexenyl-CONHCF₃ 
• 50679-30-6 4-CH₃-C₆H₄-C(O)NHCF₃ 
• 50679-28-2 2,4-Cl₂-C₆H₃-C(O)NHCF₃ 
• 50679-29-3 2,3,6-Cl₃-C₆H₂-C(O)NHCF₃-C(O)NHCF₃ 

Relevant articles and documents

The reaction of perfluoro-2,5-diazahexane 2,5-dioxyl with aromatic compounds and perfluoroiodoalkanes

Treatment of perfluoro-2,5-diazahexane 2,5-dioxyl (1) with the fluoroarenes C6F5X (X = F or Br at c. 20 deg C; X = CF3 at 50 deg C) and pentafluoropyridine (50 deg C) gives 2:1 copolymers in high yield, but pentachloropyridine is unreactive at 50 deg C.Copolymers are also formed between 1 and the arenes C6F5I, C6F5H and C6H6 which did not analyse correctly for 2:1 copolymers; in the latter case, hydrogen abstraction is taking place as shown by the presence of N-OH and C=O groups in the polymer.Hexafluorobenzene is not incorporated in the polymer formed by treatment of 1 with a mixture of vinylidene fluoride and hexafluorobenzene.Photochemical reaction of trifluoroiodomethane with 1 affords the bishydroxylamine CF3ON(CF3)CF2CF2N(CF3)OCF3 in quantitative yield, while the di-iodides I(CF2)nI (n = 2 and 4) give copolymers of 1 and the units (CF2)n (n = 2 and 4), which contain (CF2)nI end-groups.

The reaction of perfluoro-2,5-diazahexane 2,5-dioxyl with alkenes

The liquid-phase reaction at room temperature of the title dioxyl (1) with an excess of the alkenes CH2=CHR (R = H, F, COCl), CF2=CHF, CHCl=CCl2 and cis-CHCl=CHCl gives 1:1 copolymers 3 in high yield, although with the alkenes CH2=CH2, CH2=CHF and CF2=CHF cyclic 1:1 adducts 2 are also formed in low yield.The reactions with the alkenes CH2=CMe2, CH2=CHEt, CH2=CHCO2H, and cis-HO2CCH=CHCO2H produce copolymers which are not 1:1 copolymers.The 1:1 copolymer 3f from acryloyl chloride is hydrolysed readily by water to the acrylic acid/dioxyl 1 1:1 copolymer 3j.Gas-phase reaction at room temperature of 1 with an excess of the alkenes CH2=CHR (R=Cl, Br, COCl, COF), CH2=CXCH3 (X = Cl, Br), CHCl=CCl2, cis- and trans-CHCl=CHCl, CH2=CCl2, CF2=CCl2, CF2=CFCl and CF2=CFBr affords cyclic 1:1 adducts 2 (11.5-78percent) and copolymers 3 (18.5-76.5percent): hydrolysis of the acryloyl fluoride 1:1 adduct 2j gives the acrylic acid 1:1 adduct 2s in high yield.

Cycloaddition and Oxygen-Transfer Reactions of 2-(Trifluoromethyl)-3,3-difluorooxaziridine

The oxaziridine CF3-cyclo-NCF2O (1) cycloadds to various 1,1-difluoroolefins under mild conditions, forming perhalo-1,3-oxazolidines, and dialkyl ketones, forming the corresponding 1,3,4-dioxazolidines.Reaction of 1 with trimethylsilyl cyanide results in the formation of (CH3)3SiN=C=NCF3 and COF2, but 1 is unreactive with other alkyl nitriles and isocyanides.With 2,5-dimethylfuran and 2,3-dimethylbutene, 1 reacts rapidly and under mild conditions ( ca. - 50 deg C) to yield CF3N=CF2 and organic products derived from the transfer of a single oxygen atom.