6257-03-0

Basic information

• Product Name: 2,3,5,6-TETRAFLUORONITROBENZENE
• Synonyms: 1,2,4,5-Tetrafluoro-3-nitro-benzene;2,3,5,6-TETRAFLUORONITROBENZENE
• CAS NO: 6257-03-0
• Molecular Formula: C₆HF₄NO₂
• Molecular Weight: 195.07
• Mol File: 6257-03-0.mol

Chemical Properties

• Boiling Point: 223.6 °C at 760 mmHg
• Flash Point: 89 °C
• Appearance: /
• Density: 1.651 g/cm³
• Vapor Pressure: 0.142mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,3,5,6-TETRAFLUORONITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-TETRAFLUORONITROBENZENE(6257-03-0)
• EPA Substance Registry System: 2,3,5,6-TETRAFLUORONITROBENZENE(6257-03-0)

Safety Data

• Hazardous Substances Data: 6257-03-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3,5,6-Tetrafluoronitrobenzene is used as an intermediate in the synthesis of various organic compounds, particularly those with fluorinated structures. Its presence of fluorine atoms and a nitro group makes it a valuable building block for creating a wide range of products, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,5,6-tetrafluoronitrobenzene is used as a key intermediate for the development of new drugs with improved properties. The fluorine atoms in the compound can enhance the drug's bioavailability, metabolic stability, and overall efficacy. Additionally, the nitro group can be further functionalized to create various drug candidates with specific therapeutic applications.
Used in Agrochemical Industry:
2,3,5,6-Tetrafluoronitrobenzene is also utilized in the agrochemical industry for the synthesis of novel pesticides and insecticides. The fluorinated and nitro-containing structures can provide enhanced performance, selectivity, and environmental compatibility compared to traditional agrochemicals.
Used in Material Science:
In the field of material science, 2,3,5,6-tetrafluoronitrobenzene can be employed in the development of advanced materials with unique properties. The fluorine atoms can impart high chemical and thermal stability, while the nitro group can contribute to the material's mechanical strength and electrical properties.

InChI:InChI=1/C6HF4NO2/c7-2-1-3(8)5(10)6(4(2)9)11(12)13/h1H

Upstream product

• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 2010-64-2 2,3,5,6-tetrafluoronitrosobenzene 
• 28442-22-0 1,2,4,5-tetrafluoro-3,6-dinitrobenzene 
• 700-17-4 2,3,5,6-tetrafluoroaniline 
• 880-78-4 pentafluoronitrobenzen 
• 617-86-7 triethylsilane 

Downstream Products

• 123271-00-1 2,4,5-trifluoro-6-nitrophenol 
• 17823-37-9 1-bromo-2,3,5,6-tetrafluoro-4-nitrobenzene 
• 1244032-02-7 3,4,6-trifluoro-N,N-dimethyl-2-nitroaniline 
• 1244031-97-7 2,4,5-trifluoro-6-nitrobiphenyl 
• 1244032-04-9 2,5-difluoro-N₁,N₁,N₄,N₄-tetramethyl-3-nitrobenzene-1,4-diamine 

Relevant articles and documents

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.

Hydrodefluorination of Fluoroarenes Using Hydrogen Transfer Catalysts with a Bifunctional Iridium/NH Moiety

The hydrodefluorination of fluoroarenes with transfer hydrogenation catalysts using 2-propanol or potassium formate is described. With the aid of metal/NH cooperation, the C-N chelating Ir complexes derived from benzylic amines can efficiently promote the reduction involving the C-F bond cleavage under ambient conditions even in the absence of hydrosilanes or H2 gas, leading to the partially fluorinated products in good yields and with high selectivity.

Copper-catalyzed hydrodefluorination of fluoroarenes by copper hydride intermediates

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Catalytic C-F bond activation of perfluoroarenes by tricoordinated gold(I) complexes

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Sequential continuous flow processes for the oxidation of amines and azides by using HOF·MeCN

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π-π Interaction assisted hydrodefluorination of perfluoroarenes by gold hydride: A case of synergistic effect on C-F bond activation

Synergistic effect is prevalent in natural metalloenzymes in activating small molecules, and the success has inspired the development of artificial catalysts capable of unprecedented organic transformations. In this work, we found that the attractive π-π interaction between organic additives (as electron-donors) and the perfluorinated arenes (as electron acceptors) is effective in gold hydride catalyzed activation of C-F bonds, specifically hydrodefluorination (HDF) of perfluoroarenes catalyzed by the Sadighi's gold hydrides [(NHC)AuH] (NHC = N-heterocyclic carbene). Although a weak interaction between [(NHC)AuH] and perfluoroarenes was observed from 1H NMR and UV-vis spectroscopies, low reactivity of [(NHC)AuH] toward HDF was found. In contrast, in the presence of p-N,N-dimethylaminopyridine (DMAP), the HDF of perfluoroarenes with silanes can be efficiently catalyzed by [(NHC)AuH], resulting in mainly the para-hydrodefluorinated products with up to 90% yield and 9 turnovers. The yield of the reaction increases with the more electron-withdrawing groups and degree of fluorination on the arenes, and the HDF reaction also tolerates different function groups (such as formyl, alkynyl, ketone, ester, and carboxylate groups), without reduction or hydrogenation of these function groups. To reveal the role of DMAP in the reactions, the possible π-π interaction between DMAP and perfluoroarenes was suggested by UV-vis spectral titrations, 1H NMR spectroscopic studies, and DFT calculations. Moreover, 1H and 19F-NMR studies show that this π-π interaction promotes hydrogen transfer from [(NHC)AuH] to pyridyl N atom, resulting in C-F bond cleavage. The interpretation of π-π interaction assisted C-F activation is supported by the reduced activation barriers in the presence of DMAP (31.6 kcal/mol) than that in the absence of DMAP (40.8 kcal/mol) for this reaction. An analysis of the charge distribution and transition state geometries indicate that this HDF process is controlled by the π-π interaction between DMAP and perfluoroarenes, accompanied with the changes of partial atomic charges.

ANION-RADICALS OF AROMATIC COMPOUNDS. XXIII. SUBSTITUTION OF A NITRO GROUP BY A HYDROGEN ATOM DURING ELECTROLYTIC REDUCTION OF 1,2,4,5-TETRAFLUORO-3,6-DINITROBENZENE AND 1,4-DINITROBENZENE

The electrochemical reduction of 1,2,4,5-tetrafluoro-3,6-dinitrobenzene in DMFA in the presence of various proton donors (water, phenol, ammonium and triethylammonium ions) results in 1,2,4,5-tetrafluoro-3-nitrobenzene.The formation of nitrobenzene from 1

ACTION OF ELECTROPHILIC AGENTS ON POLYFLUORINATED AROMATIC COMPOUNDS. XIX. FACTORS WHICH DETERMINE THE RATIO OF THE PRODUCTS FROM SUBSTITUTION OF HYDROGEN AND IPSO-ADDITION IN THE REACTION OF PARTIALLY FLUORINATED DERIVATIVES OF BENZENE WITH NITRATION REAGENTS

It was shown that the previously discovered tendency, in the reaction of 1-H-heptafluoronaphthalene with nitration reagents, for the contribution from the reaction involving addition of NO2+ at the unsubstituted position (in relation to ipso addition) to increase in the transition from a solution of nitric acid in hydrogen fluoride to the nitronium fluoroborate-sulfolane system also applies to 1,2,4,5-tetrafluorobenzene and pentafluorobenzene.The addition of antimony pentafluoride to the solution of nitric acid in hydrogen fluoride also reduces the contribution from ipso-addition.This is consistent with the formation of pentafluorophenol during an attempt at the generation of the hydroxybenzenonium ion by the protonation of 4-nitropentafluorocyclohexa-2,5-dien-1-one in the HSO3-SbF5-SO2 and HF-SbF5-SO2ClF systems.

AROMATIC FLUORDERIVATIVES. XCV. THE INVESTIGATION OF THE BEHAVIOUR OF THE POLYFLUOROAROMATIC COMPOUNDS CONTAINING GROUP VA ELEMENTS IN ACID MEDIA

The formation of the stable phosphonium ions from polyfluoroaromatic phosphines of C6F5PX2 type in HSO3F-SbF5 (1:1) at -70 to -10 deg C has been shown, as well as the transformation of the investigated phosphines in HSO3F at 20 deg C into the pentavalent phosphorus derivatives.The same processes take place also for the trivalent arsenic and antimony derivatives.The possible routes of the latter reaction together with the determining factors have been discussed.The unusual formation of the protonated form of difluoroanhydride of pentafluouobenzenephosphonic acid from C6F5P(OCH3)2 and C6F5P(CN)2 in HSO3F has been found.The generation of nitrenium cations from the polyfluorinated nitrosobenzenes in the strong acids at -60 deg C has been proved.At 20 deg C in the same media these cations undergo oxidation leading to the corresponding nitrobenzenes.The influence of the acidity of media on the reactions of nitrosobenzenes has been investigated.