5230-78-4

Usage

Chemical Properties

colorless to light yellow liqui

InChI:InChI=1/C7H4F4/c1-3-6(10)4(8)2-5(9)7(3)11/h2H,1H3

Upstream product

• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 74-88-4 methyl iodide 
• 771-56-2 2,3,4,5,6-pentafluorotoluene 
• 917-54-4 methyllithium 
• 60903-82-4 4-chloro-2,3,5,6-tetrafluorotoluene 
• 107-05-1 3-chloroprop-1-ene 
• 87228-30-6 p-Chloro-o,o,m,m-tetrafluorotrichloromethylbenzene 
• 4232-72-8 2,3,5,6-Tetrafluor-4-methylphenylhydrazin 

Downstream Products

• 652-32-4 2,3,5,6-tetrafluoro-4-methylbenzoic acid 
• 703-87-7 1,4-dimethyl-2,3,5,6-tetrafluorobenzene 
• 1178578-06-7 2,3,5,6-tetrafluoro-4-methyl-3',4'-methylenedioxy-biphenyl 
• 1199939-51-9 1-methoxy-4-(2,3,5,6-tetrafluoro-4-methylphenyl)naphthalene 
• 652-18-6 2,3,5,6-tetrafluorobenzoic acid 
• 79538-03-7 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol 
• 1374747-93-9 1,2,4,5-tetrafluoro-3-methyl-6-(1-phenylhepta-1,2-dien-3-yl)benzene 
• 1374747-99-5 1,2,4,5-tetrafluoro-3-methyl-6-(1-phenylhepta-1,2-dien-1-yl)benzene 
• 1375272-40-4 4-(2,3,5,6-tetrafluoro-4-methylphenyl)pyrrolo[1,2-a]quinoline 
• 1358531-55-1 1-methyl-3-(2,3,5,6-tetrafluoro-4-methylphenyl)quinolin-4(1H)-one 
• 1350327-38-6 (E)-ethyl 3-(2,3,5,6-tetrafluoro-4-methylphenyl)acrylate 
• 1304685-30-0 N,N-dibenzyl-2,3,5,6-tetrafluoro-4-methylaniline 

Relevant academic research and scientific papers

Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4

Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH4. The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid E/Z isomerization.

Diazaphospholene-Catalyzed Hydrodefluorination of Polyfluoroarenes with Phenylsilane via Concerted Nucleophilic Aromatic Substitution

The metal-free catalytic C-F bond activation of polyfluoroarenes was achieved with diazaphospholene as the catalyst and phenylsilane as the terminal reductant. Density functional theory calculations suggested a concerted nucleophilic aromatic substitution mechanism.

NOVEL CRYSTALLINE FORM OF TEFLUTHRIN, PROCESS FOR ITS PREPARATION AND USE THEREOF

Provided are the crystalline form of tefluthrin of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare stable agrochemical formulation. Also provided is the use of various solvents towards the crystalline form preparation conditions.

Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate

A transition-metal-free catalytic hydrodefluorination (HDF) reaction of polyfluoroarenes is described. The reaction involves direct hydride transfer from a hydrosilicate as the key intermediate, which is generated from a hydrosilane and a fluoride salt. The eliminated fluoride regenerates the hydrosilicate to complete the catalytic cycle. Dispersion-corrected DFT calculations indicated that the HDF reaction proceeds through a concerted nucleophilic aromatic substitution (CSNAr) process.

Substitution of fluorine in M[C6F5BF3] with organolithium compounds: Distinctions between O- and N-nucleophiles

Borates M[C6F5BF3] (M = K, Li, Bu4N) react with organolithium compounds, RLi (R = Me, Bu, Ph), in 1,2-dimethoxyethane or diglyme to give M[4-RC6F4BF3] and M[2-RC6Fsub

Catalytic C-F bond hydrogenolysis of fluoroaromatics by [(η5-C5Me5)RhI(2,2′-bipyridine)]

A new class of efficient catalyst, the Rh(I) complex [(η5-C5Me5)RhI(bpy)] (1; bpy = 2,2′-bipyridine), for the C-F bond hydrogenolysis of fluoroaromatics (C6F5CF3, C6F6, C6F5H, and C6F5CH3) is presented. The best turnover number of 380 for C6F6 is afforded by using 0.1 mol % of 1, 0.8 MPa of H2, and 2 equiv of Et2NH in CH3CN at 25 °C. The successful isolation of the C-F bond cleavage product [(η5-C5Me5)RhIII(bpy)(C6F5)](F) as a plausible intermediate of the catalytic hydrogenolysis of C6F6 by 1 is also described.

Organozinc reagents from polyfluoroarenes: Preparation and reactions with allyl halides. Synthesis of allylpolyfluoroarenes

Organozinc compounds of the general formula ArFZnX (X = Cl, ArF) were synthesized by reactions of Zn with chloropolyfluoroarenes and of Zn/SnCl2 with polyfluoroarenes. Polyflorinated organozinc compounds reacted with allyl

Reductive transformations of organofluorine compounds: II. Hydrodechlorination of chloropolyfluoroarenes by the action of zinc

Polyfluoroarenes containing chlorine atoms in the aromatic ring and/or in the benzylic position undergo hydrodechlorination by the action of zinc in aqueous dimethylformamide. The use of Zn/Cu and addition of salts (NaCl, Na2SO4, NH4Cl) favor reductive dechlorination of the Carom - Cl bond. Polyfluorobenzotrichlorides react with excess zinc to give the corresponding CH3-substituted derivatives, otherwise CH2Cl- and CHCl2-containing compounds are formed. The reduction of C6F5CCl3 and C6F5CH2Cl with zinc in the presence of copper provides lower yields of the hydrodechlorination products and leads to formation of 1,2-bis(pentafluorophenyl)ethane.

REACTIONS OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA. REACTION OF POLYFLUORINATED DERIVATIVES OF BENZENE WITH SODIUM AMIDE

Under the influence of sodium amide in liquid ammonia at a temperature no higher than -33 deg C pentafluorobenzene, 1,2,4,5-tetrafluorobenzene, and 1,3-difluorobenzene undergo deprotonation with the formation of fluorinated phenyl anions, which are resistant to the elimination of a fluoride ion and can be detected by the formation of the products from interaction with electrophiles (with the initial compound in the first case and with methyl iodide in the other two cases). 1,3,5-Trifluorobenzene behaves similarly in reaction with one equivalent of sodium amide, but with two equivalents of sodium amide this compound and 1,2,3,5-tetrafluorob enzene undergo substitution of a fluorine atom by an amino group with the formation of 3,5-di- and 3,4,5-trifluoroanilines respectively.This is clearly due to the double deprotonation of these compounds with the formation of polyfluorinated m-phenylene dianions, which are then converted with the elimination of a fluoride ion into the corresponding dehydrophenyl anions.

REACTION OF AROMATIC COMPOUNDS WITH NUCLEOPHILIC REAGENTS IN LIQUID AMMONIA IV.* THE NUCLEOPHILIC AND PROTOPHILIC ACTIVITY OF METHOXIDE AND HYDROXIDE IONS IN REACTIONS WITH POLYFLUORINATED AROMATIC COMPOUNDS

In the reaction of polyfluorinated derivatives of benzene with potassium methoxide in liquid ammonia a fluorine atom is substituted by a methoxy group.With potassium hydroxide reactions involving removal of a proton from a ring carbon atom take place preferentially.The possibility of polyfluoroarylation and methylation catalyzed by potassium hydroxide in polyfluorinated aromatic compounds, based on capture of the polyflurinated aryl anion by the electrophile, was demonstrated.