776-39-6

Basic information

• Product Name: Pentafluorophenetole
• Synonyms: Ethoxypentafluorobenzene;Pentafluorophenetole
• CAS NO: 776-39-6
• Molecular Formula: C₈H₅F₅O
• Molecular Weight: 212.116716
• Mol File: 776-39-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 152-153℃ (800 Torr)
• Appearance: /
• Density: 1.404±0.06 g/cm3(Predicted)
• Refractive Index: 1.4120 (589.3 nm 23℃)
• CAS DataBase Reference: Pentafluorophenetole(CAS DataBase Reference)
• NIST Chemistry Reference: Pentafluorophenetole(776-39-6)
• EPA Substance Registry System: Pentafluorophenetole(776-39-6)

Safety Data

• Hazardous Substances Data: 776-39-6(Hazardous Substances Data)

Usage

General Description

Pentafluorophenetole, also known as 1,2,3,4,5-pentafluoroanisole, is a chemical compound with the molecular formula C7H10F5O. It is a colorless liquid with a sweet, fruity odor, and is used as a solvent in organic synthesis and as a reagent in the research of organic chemistry. Pentafluorophenetole is known for its strong electron-withdrawing properties due to the presence of five fluorine atoms, and it is highly stable and inert under normal conditions. It is also used in the preparation of pharmaceuticals, agrochemicals, and electronic materials. Additionally, pentafluorophenetole has potential applications in the field of fluorous chemistry and as a precursor in the synthesis of other fluorinated compounds.

Upstream product

• 31665-24-4 1,3,4,5,5,6,6-heptafluoro-2-ethoxy-1,3-cyclohexadiene 
• 110-86-1 pyridine 
• 392-56-3 Hexafluorobenzene 
• 64-17-5 ethanol 
• 780-69-8 triethoxyphenylsilane 
• 377-70-8 perfluoro-1,3-cyclohexadiene 
• 141-52-6 sodium ethanolate 
• 816-65-9 N-(1-ethoxyvinyl)-N,N-dimethylamine 

Downstream Products

• 1617508-02-7 C₃₁H₂₀AuF₄NO 
• 96028-38-5 3-ethoxy-7-phenyl-8-tert-butyl-1,2,4,5,6-pentafluorobicyclo<4.2.0>octatriene 
• 96028-41-0 3-phenyl-4-methyl-7-ethoxy-1,2,5,6,8-pentafluoro<4.2.0>octatriene 

Relevant articles and documents

NHC Nickel Catalyzed Hiyama- and Negishi-Type Cross-Coupling of Aryl Fluorides and Investigations on the Stability of Nickel(II) Fluoroaryl Alkyl Complexes

The reactivity of [Ni(iPr2Im)4(μ-COD)] 1 (iPr2Im = 1,3-diisopropyl-imidazolin-2-ylidene, COD = 1,4-cyclooctadiene) in Hiyama- and Negishi-type cross-coupling reactions as well as the synthesis of several novel nickel fluoroaryl alkyl complexes is reported. Hiyama coupling of 1.1 equiv. perfluoroaromatics and 1 equiv. PhSi(OR)3 (R = Me, Et) with 5 mol-% of 1 as catalyst leads to the C–C coupling product ArF–Ph in good to fair yields. In presence of the additive NMe4F alkoxy transfer from PhSi(OR)3 to the perfluoroarene occurs to yield ArF–OR and PhSiF(OR)2. Negishi cross-coupling between C6F6 or C7F8 (1 equiv.), diorganozinc reagents [ZnR2] (R = Me, Et) (2.1 equiv.) and 5 mol-% 1 as the catalyst in toluene at 115 °C leads to ArF–R only in traces. However, NMR experiments revealed that nickel alkyl complexes are readily formed from the reaction of trans-[Ni(iPr2Im)2(F)(ArF)] with [ZnR2] (R = Me, Et). In course of these investigations, a series of novel nickel alkyl complexes trans-[Ni(iPr2Im)2(R)(ArF)] (R = Me, ArF = C6F5 2, C7F7 3, C12F9 4; R = Et, ArF = C6F5 5, C7F7 6, C12F9 7) have been synthesized in stoichiometric reactions starting from trans-[Ni(iPr2Im)2(F)(ArF)] (ArF = C6F5, C7F7, C12F9) and [ZnR2] (R = Me, Et) in thf at –78 °C. As these nickel alkyl complexes 2–7 are stable at room temperature in solution for several days with respect to reductive elimination, their thermal stability was investigated. Heating trans-[Ni(iPr2Im)2(Me)(C6F5)] 2 for 24 hours at 100 °C leads to 91 % unreacted complex 2 and only traces of reductive elimination product, i.e. C6F5Me, are formed. Furthermore, the nickel ethyl complex trans-[Ni(iPr2Im)2(Et)(C6F5)] 5 is also very stable, even with respect to β-hydride elimination. After heating this complex to 100 °C for 24 hours there is still 26 % unreacted 5 left.

Condensation of αβ-unsaturated amines with perfluoroarenes

Condensation of αβ-unsaturated amines (enamines, keten ON-acetals, ynamines) with perfluoroarenes (perfluorobenzene, perfluorotoluene, bromopentafluorobenzene, perfluoropyridine) leads to the formation of ketones, esters, and amines α-substituted by a perfluoroaryl group. In the case of enamines, C-arylation can be followed by intramolecular N-arylation, giving fluorinated tetrahydrocarbazoles which can then be dehydrogenated by chloranil to give fluorinated carbazoles.