66684-57-9

Basic information

• Product Name: 1,2,5-trifluoro-3-nitrobenzene
• Synonyms: 1,2,5-trifluoro-3-nitrobenzene;1,2,5-trifluoro-3-nitrobenzene/1,2,5-trifluoro-3-nitrobenzene
• CAS NO: 66684-57-9
• Molecular Formula: C₆H₂F₃NO₂
• Molecular Weight: 177.0807896
• EINECS: 266-446-5
• Mol File: 66684-57-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: -20 °C (approx)
• Boiling Point: 214.2°Cat760mmHg
• Flash Point: 83.4°C
• Appearance: /
• Density: 1.554g/cm³
• Vapor Pressure: 0.23mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1,2,5-trifluoro-3-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,5-trifluoro-3-nitrobenzene(66684-57-9)
• EPA Substance Registry System: 1,2,5-trifluoro-3-nitrobenzene(66684-57-9)

Safety Data

• Hazardous Substances Data: 66684-57-9(Hazardous Substances Data)

Usage

General Description

1,2,5-trifluoro-3-nitrobenzene is a chemical compound with the molecular formula C6H3F3NO2. It is a colorless liquid with a strong, pungent odor. This chemical is primarily used as an intermediate in the production of pharmaceuticals, agrochemicals, and dyes. It is also used as a solvent in various industrial processes. 1,2,5-trifluoro-3-nitrobenzene is classified as a hazardous substance and should be handled with caution due to its potential health and environmental risks. It is important to follow proper safety protocols when working with this chemical to minimize the risk of exposure.

InChI:InChI=1/C6H2F3NO2/c7-3-1-4(8)6(9)5(2-3)10(11)12/h1-2H

Upstream product

• 367-23-7 1,2,4-trifluorobenzene 
• 366-50-7 N-(2,4,5-trifluorophenyl)acetamide 
• 617-86-7 triethylsilane 
• 5580-79-0 2,3,4,5-tetrafluoro-1-nitrobenzene 
• 880-78-4 pentafluoronitrobenzen 
• 361-39-7 3,4,6-trifluoro-2-nitro-aniline 

Downstream Products

• 363-80-4 2,3,5-trifluoro aniline 

Relevant articles and documents

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 ?).

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.