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
• Article Data: 9

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

Description

2,3,5,6-Tetrafluoronitrobenzene is an organic compound with the molecular formula C6HF4NO2. It is characterized by the presence of four fluorine atoms and a nitro group (NO2) attached to a benzene ring. 2,3,5,6-TETRAFLUORONITROBENZENE is known for its unique chemical properties and potential applications in various industries.

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 
• 880-78-4 pentafluoronitrobenzen 
• 617-86-7 triethylsilane 
• 700-17-4 2,3,5,6-tetrafluoroaniline 

Downstream Products

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

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.

Copper-catalyzed hydrodefluorination of fluoroarenes by copper hydride intermediates

Breaking bad: Efficient copper-catalyzed C-F bond activation has been achieved by replacing fluorine with hydrogen. A copper hydride is proposed as the active intermediate, which proceeds through a nucleophilic attack on the fluorocarbon, as determined by experimental and theoretical results (see structure; C gray, H white, Cu light red, F light blue; distances in ?).

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

We report the first example of gold catalyzing C-F bond activation for perfluoroarenes in the presence of silanes. Tricoordinated gold(I) complexes supported by Xantphos-type ligands, such as Xantphos and tBuXantphos ligands, exhibit efficacy in the hydrodefluorination (HDF) of various types of perfluoroarenes. For [tBuXantphosAu(AuCl2)], the highest turnover number is up to 1000 in the HDF of pentafluoronitrobenzene with diphenylsilane. An examination of functional group tolerance shows the orthogonality of this gold(I) catalytic protocol to ketone, ester, carboxylate, alkynyl, alkenyl and amide groups, suggesting its potential application in chemoselective C-F activations. Mechanistic studies show that the equilibrium between tetracoordinated [L2Au]+ and [LAu]+ is important for the reactivity of gold catalysts, which is dependent on the sterically bulky group of Xantphos-type ligands. Furthermore, computational studies for the possible reaction pathways suggest that direct oxidative addition of C-F bonds by gold(I) cation might be the key step during these catalytic reactions. Copyright