Pentafluoromethylbenzene
{{Chembox
| Name = Pentafluoromethylbenzene
| ImageFile = Pentafluorotoluene.svg
| ImageSize = 120px
| ImageAlt =
| PIN = 1,2,3,4,5-pentafluoro-6-methylbenzene
| OtherNames = 2,3,4,5,6-Pentafluorotoluene, Pentafluorotoluene, PFT
| Section1 = {{Chembox Identifiers
| CASNo = 771-56-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YZ42CXN177
| DTXSID = DTXSID0061119
| PubChem = 24846631
| ChemSpiderID = 21168888
| EINECS = 212-233-7
| SMILES = FC=1C(F)=C(F)C(=C(F)C1F)C
| StdInChI= InChI=1S/C7H3F5/c1-2-3(8)5(10)7(12)6(11)4(2)9/h1H3
| StdInChIKey= SXPRVMIZFRCAGC-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=7|H=3|F=5
| Appearance = Colorless liquid
| Density = 1.439 g/mL at 25 °C (lit.)
| Solubility = Poorly soluble
| MeltingPtC = −29.8
| BoilingPtC = 90-120
| VaporPressure =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS02}} {{GHS07}}
| GHSSignalWord = WARNING
| HPhrases = {{H-phrases|226|302+312+332|315|319|335}}
| PPhrases =
| FlashPtC = 34
| AutoignitionPt =
}}
}}
Pentafluoromethylbenzene is a synthetic organofluoride compound with the molecular formula {{chem2|C6F5CH3}}.{{cite book |last1=Lide |first1=David R. |title=CRC Handbook of Chemistry and Physics, 85th Edition |date=29 June 2004 |publisher=CRC Press |isbn=978-0-8493-0485-9 |page=6-120 |url=https://www.google.ru/books/edition/CRC_Handbook_of_Chemistry_and_Physics_85/WDll8hA006AC?hl=en&gbpv=1&dq=2,3,4,5,6-Pentafluorotoluene&pg=RA59-SA6-PA120&printsec=frontcover |access-date=21 April 2025 |language=en}}{{cite web |title=Benzene, pentafluoromethyl- |url=https://webbook.nist.gov/cgi/inchi?ID=C771562&Mask=8 |publisher=NIST |access-date=21 April 2025}}
Synthesis
The compound can be obtained by the Friedel–Crafts reaction of pentafluorobenzene with methyl chloride.{{cite web |title=2,3,4,5,6-Pentafluorotoluene |url=https://www.sigmaaldrich.com/RU/en/product/aldrich/103977?srsltid=AfmBOop5B899W_qfxnLaUs3XTFk5cmBjors5pG9Xrx1X0hrguyZarAa9 |publisher=Sigma Aldrich |access-date=21 April 2025}}
Also, the compound can be prepared by reacting hexafluorobenzene with methyllithium.{{cite journal |last1=Filler |first1=R. |last2=Kang |first2=H. H. |title=Tetrafluorotyrosine: synthesis and properties |journal=Chemical Communications (London) |date=1 January 1965 |issue=24 |pages=626–627 |doi=10.1039/C19650000626 |url=https://pubs.rsc.org/en/content/articlelanding/1965/c1/c19650000626 |access-date=21 April 2025 |language=en |issn=0009-241X}}
Physical properties
Pentafluoromethylbenzene is a colorless, volatile liquid with a distinctive sweet smell.{{cite book |last1=Knunyants |first1=I. L. |last2=Yakobson |first2=G. G. |title=Syntheses of Fluoroorganic Compounds |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-3-642-70207-5 |page=129 |url=https://www.google.ru/books/edition/Syntheses_of_Fluoroorganic_Compounds/m6zxCAAAQBAJ?hl=en&gbpv=1&dq=2,3,4,5,6-Pentafluorotoluene&pg=PA129&printsec=frontcover |access-date=21 April 2025 |language=en}} It is known for its high reactivity, low toxicity, and limited solubility. Additionally, it has the ability to form complexes with metals such as iron and copper.{{cite web |title=2,3,4,5,6-Pentafluorotoluene {{!}} CAS 771-56-2 {{!}} SCBT - Santa Cruz Biotechnology |url=https://www.scbt.com/p/2-3-4-5-6-pentafluorotoluene-771-56-2?srsltid=AfmBOop-nbxVnipVO8IhxNOaCeSUN1gRddj288OpVfiAg4zA_pdRSHYT |publisher=scbt.com |access-date=21 April 2025 |language=en}}
Chemical properties
The presence of electron-withdrawing fluorine atoms on its aromatic ring significantly enhances the compound reactivity.
Under the influence of light, pentafluoromethylbenzene reacts with bromine to form pentafluorobenzyl bromide.{{cite journal |last1=Filler |first1=Robert |last2=Heffern |first2=Edward W. |title=Bis(pentafluorophenyl)acetylene and 2,3,4,5,6-pentafluorodiphenylacetylene |journal=The Journal of Organic Chemistry |date=1 October 1967 |volume=32 |issue=10 |pages=3249–3251 |doi=10.1021/jo01285a089 |url=https://pubs.acs.org/doi/abs/10.1021/jo01285a089 |access-date=21 April 2025 |issn=0022-3263}}
Uses
This halogenated aromatic hydrocarbon is widely utilized in organic synthesis and analytical chemistry due to its unique characteristics. In scientific studies, the compound is frequently employed to synthesize a variety of organic compounds, including amides, ketones, and carboxylic acids.