880-78-4

Basic information

• Product Name: PENTAFLUORONITROBENZENE
• Synonyms: pentaflurophenylacetic acid;Pentafluoronitrobenzene,98%;Pentafluoronitrobenzene 98%;1-Nitropentafluorobenzene;2,3,4,5,6-Pentafluoro-1-nitrobenzene;PENTAFLUORONITROBENZ;1-Nitro-2,3,4,5,6-pentafluorobenzene, Perfluoronitrobenzene;2,3,4,5,6-PENTAFLUORONITROBENZENE
• CAS NO: 880-78-4
• Molecular Formula: C₆F₅NO₂
• Molecular Weight: 213.06
• EINECS: 212-915-4
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 880-78-4.mol

Chemical Properties

• Melting Point: -22.65°C
• Boiling Point: 158-161 °C(lit.)
• Flash Point: 195 °F
• Appearance: Clear colorless to light yellow liquid
• Density: 1.656 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.24mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: PENTAFLUORONITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUORONITROBENZENE(880-78-4)
• EPA Substance Registry System: PENTAFLUORONITROBENZENE(880-78-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 880-78-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Pentafluoronitrobenzene is used as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its unique structure allows for selective reactions and functional group transformations, making it a valuable building block in organic chemistry.
Used in the Preparation of Photoaffinity Reagents:
Pentafluoronitrobenzene has been utilized in the preparation of p-azidotetrafluoroaniline, a novel photoaffinity reagent. This reagent is employed in the study of biomolecular interactions, particularly in the fields of biochemistry and molecular biology, to investigate the binding sites and mechanisms of action of various biomolecules.
Used in Electron Attachment Studies:
The electron attachment to pentafluoronitrobenzene has been studied in the energy range of 0-16 eV using a crossed electron-molecular beam experiment with mass spectrometric detection of the anions. This research provides valuable insights into the electron attachment processes and the formation of anions, which can be useful in understanding the fundamental aspects of electron-molecule interactions.
Used in Electrochemical Reduction:
The electroreduction of pentafluoronitrobenzene in dimethylformamide solution results in the formation of the dimer, octafluoro-4,4′-dinitro-biphenyl. This process highlights the potential applications of pentafluoronitrobenzene in electrochemistry and the synthesis of novel compounds with potential applications in various industries.

InChI:InChI=1/C6F5NO2/c7-1-2(8)4(10)6(12(13)14)5(11)3(1)9

Upstream product

• 363-72-4 Pentafluorobenzene 
• 1423-13-8 pentafluoronitrosobenzene 
• 853-75-8 N-pentafluorophenyl-pentafluorophenylaldimine 
• 143896-70-2 N-(2,3,4,5,6-pentafluorophenyl)-1-phenylmethanimine 
• 771-60-8 2,3,4,5,6-pentafluoroaniline 
• 407-25-0 trifluoroacetic anhydride 
• 7697-37-2 nitric acid 
• 126-33-0 sulfolane 
• 5272-26-4 trifluoro(pentafluorophenyl)silane 
• 5580-79-0 2,3,4,5-tetrafluoro-1-nitrobenzene 

Downstream Products

• 17480-16-9 Perfluoroisopropylbenzene 
• 20017-50-9 1-Nitroperfluor-(4-isopropylbenzol) 
• 20017-51-0 1-Nitroperfluor-(2,4-diisopropylbenzol) 
• 122134-93-4 4-nitro-2,3,5,6-tetrafluoro-4'-hydroxydiphenylamine 
• 113423-72-6 ethyl 2-cyano-2-(2,3,5,6-tetrafluoro-4-nitrophenyl)butyrate 
• 969-25-5 4-aminononafluorobiphenyl 
• 2106-01-6 4,5,6-trifluoro-2-nitro-1,3-phenylenediamine 
• 2106-00-5 2,4,5-trifluoro-6-nitro-1,3-phenylenediamine 
• 6157-98-8 2,3,4,5-tetrafluoro-6-nitroaniline 
• 776-16-9 2,3,5,6-tetrafluoro-4-nitroaniline 
• 220030-82-0 2-(2,3,5,6-tetrafluoro-4-nitrophenyl)hydrazinecarboxylate, ethyl ester 
• 1887-74-7 N-methyl-3,4,5,6-tetrafluoro-2-nitroaniline 
• 2415-25-0 N-methyl-2,3,5,6-tetrafluoro-4-nitroaniline 
• 197903-69-8 3'-O-(4-methoxytetrahydropyran-4-yl)-5'-O-(2,3,5,6-tetrafluoro-4-nitrophenyl)-2'-deoxyuridine 

Relevant articles and documents

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

The generation and use of the highly potent oxidising agent HOF·MeCN in a controlled single continuous flow process is described. Oxidations of amines and azides to corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Oxidation in flow: The oxidation of amines and azides to the corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Copyright

PROCESS FOR MAKING AND USING HOF.RCN

The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.

Fluorination of tetrafluorobenzenes C6HF4R with XeF2

Replacement of hydrogen by fluorine and addition of fluorine atoms to the aromatic ring were found in the reaction of XeF2 with 1-R-2,3,4,5-tetrafluorobenzene (R = H, F, Br, NO2) or 1-R-2,3,4,6-tetrafluorobenzene (R = H, CF3) in HF or CH2Cl2-BF3·OEt2. Only fluorine addition took place in the case of 1-R-2,3,5,6-tetrafluorobenzenes (R = H, Br, CF3) or 1-Br-2,3,4,6-tetrafluorobenzene. The role of cation radicals as reactive intermediates is discusseed.

Preparation, NMR spectra and reactivity of pentafluorophenyltetrafluorosilicates M+-

Pentafluorophenyltetrafluorosilicates M+ - were obtained from pentafluorophenyltrifluorosilane C6F5SiF3 and ionic fluorides MF (M=K, Cs, Me4N) in anhydrous MeCN or diglyme.The reactivity of M+ - toward electrophiles was studied.Keywords: Pentafluorophenyl; Fluorosilicate anion; Desilylation

Nitration of Strongly Deactivated Aromatics with Superacidic Mixed Nitric-Triflatoboric Acid (HNO3/2CF3SO3H-B(O3SCF3)3)

The nitration of various deactivated arenes (including methanesulfonyl-, nitro-, and polyhalobenzenes) was carried out in good yield with mixed nitric-triflatoboric superacid.For example pentafluorobenzene gave pentafluoronitrobenzene in 99percent yield, nitrobenzene to m-dinitrobenzene in 92percent selectivity with 85percent overall yield, and methyl phenyl sulfone gave only the m-nitro isomer in 78percent isolated yield.Thus the new nitrating system gives high regioselectivity and yields under generally mild reaction conditions.The reagent system is compatible with many functional groups of arenes.

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.