Pentafluoromethylbenzene
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| Names | |
|---|---|
| Preferred IUPAC name
1,2,3,4,5-pentafluoro-6-methylbenzene | |
| Other names
2,3,4,5,6-Pentafluorotoluene, Pentafluorotoluene, PFT
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.011.121 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H3F5 | |
| Molar mass | 182.093 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 1.439 g/mL at 25 °C (lit.) |
| Melting point | −29.8 °C (−21.6 °F; 243.3 K) |
| Boiling point | 90–120 °C (194–248 °F; 363–393 K) |
| Poorly soluble | |
| Hazards | |
| GHS labelling: | |
 
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| Warning | |
| H226, H302+H312+H332, H315, H319, H335 | |
| Flash point | 34 °C (93 °F; 307 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pentafluoromethylbenzene is a synthetic organofluoride compound with the molecular formula C6F5CH3.[1][2]
Synthesis
[edit]The compound can be obtained by the Friedel–Crafts reaction of pentafluorobenzene with methyl chloride.[3]
Also, the compound can be prepared by reacting hexafluorobenzene with methyllithium.[4][5]
Physical properties
[edit]Pentafluoromethylbenzene is a colorless, volatile liquid with a distinctive sweet smell.[5] 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.[6]
Chemical properties
[edit]The presence of electron-withdrawing fluorine atoms on its aromatic ring significantly enhances the compound reactivity.[6]
Under the influence of light, pentafluoromethylbenzene reacts with bromine to form pentafluorobenzyl bromide.[7]
Uses
[edit]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.[6]
See also
[edit]References
[edit]- ^ Lide, David R. (29 June 2004). CRC Handbook of Chemistry and Physics, 85th Edition. CRC Press. pp. 6–120. ISBN 978-0-8493-0485-9. Retrieved 21 April 2025.
- ^ Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S. Z.; Hu, L. Q.; Sung, K. S.; Desmarteau, D. D.; Yagupolskii, L. M. (1994). "Benzene, pentafluoromethyl-". NIST. p. 3047. doi:10.1021/ja00086a038. Retrieved 21 April 2025.
- ^ "2,3,4,5,6-Pentafluorotoluene". Sigma Aldrich. Retrieved 21 April 2025.
- ^ Filler, R.; Kang, H. H. (1 January 1965). "Tetrafluorotyrosine: synthesis and properties". Chemical Communications (24): 626–627. doi:10.1039/C19650000626. ISSN 0009-241X. Retrieved 21 April 2025.
- ^ a b Knunyants, I. L.; Yakobson, G. G. (6 December 2012). Syntheses of Fluoroorganic Compounds. Springer Science & Business Media. p. 129. ISBN 978-3-642-70207-5. Retrieved 21 April 2025.
- ^ a b c "2,3,4,5,6-Pentafluorotoluene | CAS 771-56-2 | SCBT - Santa Cruz Biotechnology". scbt.com. Retrieved 21 April 2025.
- ^ Filler, Robert; Heffern, Edward W. (1 October 1967). "Bis(pentafluorophenyl)acetylene and 2,3,4,5,6-pentafluorodiphenylacetylene". The Journal of Organic Chemistry. 32 (10): 3249–3251. doi:10.1021/jo01285a089. ISSN 0022-3263. Retrieved 21 April 2025.