771-56-2

Usage

Uses

1. Chemical Synthesis:
2,3,4,5,6-Pentafluorotoluene is used as an organic fluorinated building block for chemical synthesis. Its fluorinated nature allows for the creation of a variety of compounds with diverse applications in various industries.
2. Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,4,5,6-pentafluorotoluene is used as a pharmaceutical intermediate. Its unique chemical properties make it a valuable component in the development of new drugs and medications.
3. Material Science:
2,3,4,5,6-Pentafluorotoluene can also be utilized in the field of material science, where its fluorinated structure can contribute to the development of advanced materials with specific properties, such as enhanced chemical resistance or improved thermal stability.

InChI:InChI=1/C7H3F5/c1-2-3(8)5(10)7(12)6(11)4(2)9/h1H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 392-56-3 Hexafluorobenzene 
• 60-29-7 diethyl ether 
• 34557-54-5 methane 
• 917-54-4 methyllithium 
• 363-72-4 Pentafluorobenzene 
• 865-33-8 potassium methanolate 
• 973-17-1 bis(pentafluorophenyl)mercury(II) 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 108-88-3 toluene 
• 1765-40-8 (bromomethyl)pentafluorobenzene 
• 344-04-7 bromopentafluorobenzene 
• 74-88-4 methyl iodide 
• 1206-46-8 trimethyl(pentafluorophenyl)silane 

Downstream Products

• 3150-40-1 4-methoxy-2,3,5,6-tetrafluorotoluene 
• 1644-90-2 2,3,5,6-tetrafluoro-4-methylphenol 
• 652-30-2 pentafluorobenzylidene chloride 
• 10534-43-7 1-(difluoromethyl)nonafluorocyclohex-1-ene 
• 653-35-0 2,3,4,5,6-pentafluorobenzyl chloride 
• 1765-40-8 (bromomethyl)pentafluorobenzene 
• 55810-53-2 (Tetrafluor-p-tolyl)-malonsaeureethylester-nitril 
• 55810-42-9 4-Methyl-tetrafluorphenylmalonester 
• 86651-84-5 2,4-dimethyltetrafluorocyclohexa-2,5-dien-1-one 
• 86651-83-4 3,4-dimethyltetrafluorocyclohexa-2,5-dien-1-one 
• 86651-82-3 4,4-dimethyltetrafluorocyclohexa-2,5-dien-1-one 
• 80588-36-9 4-methylnonafluorodiphenylamine 
• 31673-21-9 1-methylheptafluoro-1,4-cyclohexadiene 
• 22006-43-5 2,3,4,5,6-pentafluorobenzyl fluoride 

Relevant academic research and scientific papers

Hydrodehalogenation of organohalides by Et3SiH catalysed by group 4 metal complexes and B(C6F5)3

Catalytic hydrodehalogenation (HDH) of aliphatic organohalides such as trifluorotoluenes by Et3SiH proceeds in the presence of readily available group 4 metal compounds: Cp′2MX2 (Cp′ = η5-C5H5 or η5-C5Me5; X = F, Cl, or Me; M = Ti, Zr, or Hf), CpTiCl3 and TiCl4 with a catalytic amount of B(C6F5)3. The use of metallocenes in combination with the borane activator leads to a better selectivity of the reaction, i.e., suppression of Friedel-Crafts alkylations of arenes.

ORGANOSILICON ON SOLID OXIDES, AND RELATED COMPLEXES, COMPOSITIONS, METHODS AND SYSTEMS

Organosilicon Lewis acids supported on activated oxides and metal oxo complexes grafted on the organosilicon Lewis acids as heterogeneous catalysts and the related compositions, methods and systems are described. These organosilicon Lewis acids and the grafted metal oxo complexes catalyze industrially important chemical reactions including, respectively, C—F bond activation and olefin metathesis reactions such as homocoupling and polymerizations.

Activation of C?F Bonds by Electrophilic Organosilicon Sites Supported on Sulfated Zirconia

The reaction of allyltriisopropylsilane with partially dehydroxylated sulfated zirconium oxide (SZO) forms surface organosilicon species. Solid-state NMR studies of the organosilicon functionalized SZO shows that electrophilic [TIPS][SZO] sites are present on the surface, in addition to less reactive TIPS-Ox and SiOx species. The electrophilic [TIPS][SZO] sites are strong Lewis acids from solid-state 31P NMR analysis of triethylphosphine oxide (O=PEt3) contacted materials. [TIPS][SZO] is active in hydrodefluorination reactions in the presence of Et3SiH.

Lewis acidity of organofluorophosphonium salts: Hydrodefluorination by a saturated acceptor

Prototypical Lewis acids, such as boranes, derive their reactivity from electronic unsaturation. Here, we report the Lewis acidity and catalytic application of electronically saturated phosphorus-centered electrophilic acceptors. Organofluorophosphonium salts of the formula [(C6F 5)3-xPhxPF][B(C6F5) 4] (x = 0 or 1; Ph, phenyl) are shown to form adducts with neutral Lewis bases and to react rapidly with fluoroalkanes to produce difluorophosphoranes. In the presence of hydrosilane, the cation [(C 6F5)3PF]+ is shown to catalyze the hydrodefluorination of fluoroalkanes, affording alkanes and fluorosilane. The mechanism demonstrates the impressive fluoride ion affinity of this highly electron-deficient phosphonium center.

Ti-catalyzed homolytic opening of ozonides: A sustainable C-C bond-forming reaction

The unprecedented homolytic opening of ozonides promoted and catalyzed by titanocene(III) is reported. This novel reaction proceeds at room temperature under neutral, mild conditions compatible with many functional groups and provides carbon radicals suitable to form C-C bonds via both homocoupling and cross-coupling processes. The procedure has been advantageously exploited for the straightforward synthesis of the natural product brittonin A.

Exhaustive chlorination of [B12H12]2- without chlorine gas and the use of [B12Cl12]2- as a supporting anion in catalytic hydrodefluorination of aliphatic C-F bonds

The fully chlorinated closo-dodecaborate salt Cs2[B 12Cl12] was prepared in high yield from Cs 2[B12H12] and SO2Cl2 in acetonitrile at refluxing temperature. [Ph3C]2[B 12Cl12] was obtained by simple metathesis reactions. Catalytic hydrodefluorination of benzotrifluoride sp3 C-F bonds was accomplished using [Ph3C]2[B12Cl12] as a precatalyst and Et3SiH as a stoichiometric reagent. Full consumption of the sp3 C-F bonds in p-FC6H 4CF3 and C6F5CF3 with a turnover number up to 2000 was achieved.

C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids

Previously, alkylgold(III) fluorides have been proposed as catalytic intermediates that undergo C-C coupling with reagents such as arylboronic acids in Au(I)/Au(III) cross-coupling reactions. Here is reported the first experimental evidence for this elementary mechanistic step. Complexes of the type (NHC)AuMe (NHC = N-heterocyclic carbene) were oxidized with XeF2 to yield cis-(NHC)AuMeF2 products, which were found to be in equilibrium with their fluoride-dissociated, dimeric [(NHC)AuMe(μ-F)] 2[F]2 forms. In one case, a monomeric cis-(NHC)AuMeF 2 complex was favored exclusively in solution, and it was found to react with a variety of ArB(OH)2 reagents to yield Ar-CH3 products.

Hydrodefluorination and other hydrodehalogenation of aliphatic carbon-halogen bonds using silylium catalysis

Trialkylsilylium cation equivalents partnered with halogenated carborane anions (such as Et3Si[HCB11H5Cl6]) function as efficient and long-lived catalysts for hydrodehalogenation of C-F, C-Cl, and C-Br bonds with trialkylsilanes as stoichiometric reagents. Only C(sp3)-halogen bonds undergo this reaction. The range of C-F bond-containing substrates that participate in this reaction is quite broad and includes simple alkyl fluorides, benzotrifluorides, and compounds with perfluoroalkyl groups attached to an aliphatic chain. However, CF4 has proven immune to this reaction. Hydrodechlorination was carried out with a series of alkyl chlorides and benzotrichlorides, and hydrodebromination was studied only with primary alkyl bromide substrates. Competitive experiments established a pronounced kinetic preference of the catalytic system for activation of a carbon-halogen bond of a lighter halide in primary alkyl halides. On the contrary, hydrodechlorination of C6F 5CCl3 proceeded much faster than hydrodefluorination of C6F5CF3 in one-pot experiments. A solid-state structure of Et3Si[HCB11H5Cl6] was determined by X-ray diffraction methods.

Room-temperature catalytic hydrodefluorination of C(sp3)-F bonds

Room-temperature catalytic hydrodefluorination of the strong C(sp3)-F bonds in benzotrifluorides and fluoropentane is catalyzed by Et3Si[B(C6F5)4] and uses Et3SiH as the source of H. Ar-CF

Flash vacuum pyrolysis over magnesium. Part 1 - Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides

Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E, E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.