Pentafluorobenzene

Base Information

• Chemical Name: Pentafluorobenzene
• CAS No.: 363-72-4
• Molecular Formula: C6HF5
• Molecular Weight: 168.066
• Hs Code.: 29036990
• European Community (EC) Number: 206-658-7,690-865-6
• NSC Number: 88293
• UNII: IH36LU53XS
• DSSTox Substance ID: DTXSID8059893
• Nikkaji Number: J40J
• Wikipedia: Pentafluorobenzene
• Wikidata: Q1265485
• Mol file: 363-72-4.mol

Synonyms:PENTAFLUOROBENZENE;363-72-4;1,2,3,4,5-Pentafluorobenzene;Benzene, pentafluoro-;C6HF5;EINECS 206-658-7;NSC 88293;Benzene, 1,2,3,4,5-pentafluoro-;UNII-IH36LU53XS;IH36LU53XS;2,3,4,5,6-pentafluorobenzene;1,2,3,4,5-pentafluoro-benzene;NSC-88293;NSC88293;Pentafluorobenzene, 98%;C6F5H;SCHEMBL41646;1,3,4,5-Pentafluorobenzene;DTXSID8059893;WACNXHCZHTVBJM-UHFFFAOYSA-;AMY3639;C6-H-F5;MFCD00000286;AKOS000120026;Pentafluorobenzene, analytical standard;LS-30937;A6291;CS-0157880;FT-0632043;P0923;EN300-20344;Q1265485;F5B

Chemical Property of Pentafluorobenzene

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 77.3mmHg at 25°C
• Melting Point: -48 °C(lit.)
• Refractive Index: n20/D 1.391(lit.)
• Boiling Point: 85.5 °C at 760 mmHg
• Flash Point: 13.9 °C
• PSA: 0.00000
• Density: 1.521 g/cm³
• LogP: 2.38210
• Storage Temp.: 2-8°C
• Solubility.: 0.4g/l
• Water Solubility.: Insoluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 167.99984084
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

Pentafluorobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi, T
• Hazard Codes: F,Xn,Xi,T
• Statements: 11-22-36/38-36/37/38-41-37/38-39/23/24/25-23/24/25
• Safety Statements: 26-37/39-16-39-45-36/37-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=C(C(=C(C(=C1F)F)F)F)F
• General Description: Pentafluorobenzene is a fluorinated aromatic compound that serves as a key intermediate in nucleophilic substitution reactions, particularly in the formation of perfluorinated indane derivatives through intramolecular cyclization. Its reactivity is exemplified in reactions with perfluoroolefins, where it can generate perfluorinated carbanions that further cyclize or form arylolefins, demonstrating its versatility in synthesizing complex fluorinated structures.

Technology Process of Pentafluorobenzene

There total 410 articles about Pentafluorobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + potassium perfluorophenyltrifluoroborate → K (dimethoxy)difluoroborate + Pentafluorobenzene (363-72-4) + potassium methoxytrifluoroborate (15696-17-0)

Guidance literature:

With water; at 90 - 95 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Time; Sealed tube;

DOI:10.1016/j.jfluchem.2014.09.016

Reference yield: 99.0%

Pentafluorobenzoic acid (602-94-8) → Pentafluorobenzene (363-72-4)

Guidance literature:

With triethylamine; In toluene; at 100 - 110 ℃; for 24h; Solvent; Temperature;

Reference yield: 91.0%

Hexafluorobenzene (392-56-3) → Pentafluorobenzene (363-72-4)

Guidance literature:

With gold on titanium oxide; potassium carbonate; In isopropyl alcohol; for 2h; Reagent/catalyst; Sonication; Inert atmosphere; Irradiation;

upstream raw materials:

bromopentafluorobenzene

1H-heptafluorocyclohexa-1,3-diene

piperidine

trimethyl(pentafluorophenyl)silane

Downstream raw materials:

1,2,3,5-tetrafluorobenzene

bromopentafluorobenzene

2,3,5,6-tetrafluoroanisole

1,2,3,4,5-pentafluoro-6-iodobenzene

Refernces

FORMATION OF PERFLUORO-1,1,3-TRIMETHYLINDANE IN THE REACTION OF TRIMETHYLSILYLPENTAFLUOROBENZENE WITH PERFLUORO-4-METHYL-2-PENTENE

10.1007/BF00953645

The study investigates the intramolecular cyclization of pentafluorobenzene derivatives, focusing on the reaction of trimethylsilylpentafluorobenzene (I) with perfluoro-4-methyl-2-pentene (II) in the presence of cesium fluoride (CsF). This reaction unexpectedly yields approximately equal amounts of perfluoro-1,1,3-trimethylindane (IV) and perfluoro-4-methyl-2-phenyl-2-pentene (III). The authors propose a mechanism where the initial step involves nucleophilic pentafluorophenylation of olefin (II) by a complex of arylsilane (I) and CsF, leading to a perfluorinated carbanion (V). This carbanion can either lose a fluoride ion to form perfluorinated arylolefin (III) or undergo further reactions to form fluorinated indane (IV). The study also includes experimental details on the synthesis and characterization of these compounds, highlighting the unique formation of perfluoroindane derivatives through intramolecular nucleophilic cyclization.