Bromopentafluorobenzene

Bromopentafluorobenzene
Names
	Preferred IUPAC name Bromopenta(fluoro)benzene
	Other names Bromoperfluorobenzene
Identifiers
CAS Number	344-04-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1231233;
ChemSpider	21168727;
ECHA InfoCard	100.005.863
EC Number	206-449-0;
PubChem CID	9578;
UNII	S88219080S;
CompTox Dashboard (EPA)	DTXSID3047136 ;
	InChI InChI=1S/C6BrF5/c7-1-2(8)4(10)6(12)5(11)3(1)9 Key: XEKTVXADUPBFOA-UHFFFAOYSA-N;
	SMILES C1(=C(C(=C(C(=C1F)F)Br)F)F)F;
Properties
Chemical formula	C6BrF5
Molar mass	246.962 g·mol−1
Appearance	colorless liquid
Density	1.9503 g/cm3
Melting point	−31 °C (−24 °F; 242 K)
Boiling point	137 °C (279 °F; 410 K)
Solubility in water	low
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Bromopentafluorobenzene is an organofluorine compound with the formula C₆F₅Br. It is a colorless liquid that is used to prepare pentafluophenyl compounds. These syntheses typically proceed via the intermediacy of C₆F₅Li or the Grignard reagent.^[1] Illustrative is preparation of tris(pentafluorophenyl)borane:^[2]

3 C₆F₅MgBr + BCl₃ → (C₆F₅)₃B + 3 MgBrCl

Other derivatives include LiB(C₆F₅)₄,^[3] [CuC₆F₅]₄,^[1] and Ni(C₆F₅)₂(dioxane)₂.^[4]

References

^ ^a ^b Allan Cairncross; William A. Sheppard; Edward Wonchoba (1979). "Pentafluorophenylcopper Tetramer, A Reagent for Synthesis of Fluorinated Aromatic Compounds". Org. Synth. 59: 122. doi:10.15227/orgsyn.059.0122.
^ Piers, W. E.; Chivers, T. “Pentafluorophenylboranes: from Obscurity to Applications”, Chemical Society Reviews, 1997, 26, 345-354. doi:10.1039/cs9972600345
^ Tanaka, Katsunori; Fukase, Koichi (2007). "Lithium tetra(pentafluorophenyl)borate". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00752. ISBN 978-0471936237. S2CID 96944152.
^ Sanchez, G.; Momblona, F.; Sanchez, M.; Perez, J.; Lopez, G.; Casabo, J.; Molins, E.; Miravitlles, C. (1998). "Synthesis of Homo- and Heterobimetallic Complexes Containing the Ni(C6F5)2 Moiety. Crystal Structure of [(C₆F₅)₂Ni(μ-SPh)₂Pd(dppe)]". Eur. J. Inorg. Chem. 1998 (8): 1199–1204. doi:10.1002/(SICI)1099-0682(199808)1998:8<1199::AID-EJIC1199>3.0.CO;2-K.

[OS-1] Allan Cairncross; William A. Sheppard; Edward Wonchoba (1979). "Pentafluorophenylcopper Tetramer, A Reagent for Synthesis of Fluorinated Aromatic Compounds". Org. Synth. 59: 122. doi:10.15227/orgsyn.059.0122.

[2] Piers, W. E.; Chivers, T. “Pentafluorophenylboranes: from Obscurity to Applications”, Chemical Society Reviews, 1997, 26, 345-354. doi:10.1039/cs9972600345

[3] Tanaka, Katsunori; Fukase, Koichi (2007). "Lithium tetra(pentafluorophenyl)borate". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00752. ISBN 978-0471936237. S2CID 96944152.

[4] Sanchez, G.; Momblona, F.; Sanchez, M.; Perez, J.; Lopez, G.; Casabo, J.; Molins, E.; Miravitlles, C. (1998). "Synthesis of Homo- and Heterobimetallic Complexes Containing the Ni(C6F5)2 Moiety. Crystal Structure of [(C₆F₅)₂Ni(μ-SPh)₂Pd(dppe)]". Eur. J. Inorg. Chem. 1998 (8): 1199–1204. doi:10.1002/(SICI)1099-0682(199808)1998:8<1199::AID-EJIC1199>3.0.CO;2-K.

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