879-05-0

Basic information

• Product Name: PENTAFLUOROPHENYLMAGNESIUM BROMIDE
• Synonyms: PENTAFLUOROPHENYLMAGNESIUM BROMIDE;pentafluorophenylmagnesium bromide sol.;Pentafluorophenylmagnesium bromide solution;PENTAFLUOROPHENYLMAGNESIUM BROMIDE, 0.5M SOLUTION IN DIETHYL ETHER;PENTAFLUOROPHENYLMAGNESIUM BROMIDE SOL., ~0.5 M IN DIETHYL ET;PENTAFLUOROPHENYLMAGNESIUM BROMIDE SOL. TECH ABOUT 0.5 M IN DIETHYL ET;sol.techabout0.5mindiethylet;Magnesium, bromo(pentafluorophenyl)-
• CAS NO: 879-05-0
• Molecular Formula: Br*C₆F₅*Mg
• Molecular Weight: 271.27
• Product Categories: Aryl;Grignard Reagents;Organometallic Reagents
• Mol File: 879-05-0.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 34.6 °C
• Flash Point: −35 °F
• Appearance: /
• Density: 0.861 g/mL at 25 °C
• BRN: 3611565
• CAS DataBase Reference: PENTAFLUOROPHENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PENTAFLUOROPHENYLMAGNESIUM BROMIDE(879-05-0)
• EPA Substance Registry System: PENTAFLUOROPHENYLMAGNESIUM BROMIDE(879-05-0)

Safety Data

• Hazard Codes: F+,C
• Statements: 12-14-19-22-34-66-67
• Safety Statements: 26-36/37/39-43-45-16
• RIDADR: UN 2924 3/PG 1
• WGK Germany: 1
• F: 1-3-10
• Hazardous Substances Data: 879-05-0(Hazardous Substances Data)

Usage

Uses

Employed in the synthesis of novel arsonic and arsinic acids as ligands for potential transition-metal ion extractants, and in the synthesis of polyfluoroaryl alkyl sulfides.

Upstream product

• 344-04-7 bromopentafluorobenzene 
• 142-96-1 dibutyl ether 
• 925-90-6 ethylmagnesium bromide 
• 110-71-4 1,2-dimethoxyethane 
• 74-88-4 methyl iodide 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 111-43-3 Dipropyl ether 
• 927-77-5 n-propylmagnesium bromide 
• 74-96-4 ethyl bromide 
• 392-56-3 Hexafluorobenzene 
• 7439-95-4 magnesium 
• 106-93-4 ethylene dibromide 
• 13888-77-2 (pentafluorophenyl)dimethylsilane 
• 920-39-8 isopropylmagnesium bromide 

Downstream Products

• 2914-03-6 N-triphenyl-B-tris(pentafluorophenyl)borazine 
• 3008-31-9 4-pentafluorophenyl perfluoro biphenyl 
• 3008-32-0 4,4`-bis(pentafluorophenyl) perfluoro biphenyl 
• 89243-60-7 Bis(pentafluorphenyl)(pentamethyl-2,4-cyclopentadien-1-yl)phosphan 
• 138852-88-7 1,1-dimethyl-1-pentafluorophenyl-N,N-diphenyl-silanamine 
• 7531-41-1 2,2,2-trichloro-1-(perfluorophenyl)ethanol 
• 60575-47-5 Dimethyl-pentafluorophenyl-arsane 
• 1736-60-3 1-allyl-2,3,4,5,6-pentafluorobenzene 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 1016971-15-5 2-(pentafluorophenylhydroxymethyl)furan 
• 2720-03-8 bis(pentafluorophenyl)boron chloride 
• 74452-69-0 [N(C₄H₉)4]⁽¹⁺⁾*[PdBr(C₆F₅)2(P(C₆H₅)3)]^(1-)=[N(C₄H₉)4][PdBr(C₆F₅)2(P(C₆H₅)3)] 
• 74436-10-5 (NBu4)2{palladium(μ-Br)bis(pentafluorophenyl)}2 

Relevant articles and documents

PHOTO LEWIS ACID GENERATOR

Provided is a compound capable of generating a Lewis acid in response to light unlike conventional photo acid generators. The compound comprises an anionic moiety having a central boron atom and a particular cationic moiety (for example, a cation having a HOMO-LUMO gap of 5.3 eV or less). The cationic moiety may, for example, have a skeleton selected from an N-substituted pyridinium skeleton, an N-substituted bipyridinium skeleton, an N-substituted quinolinium skeleton, and a pyrylium skeleton.

Preparation of heptafluoronaphthyllithiums and -magnesiums: An unexpected difference in the reactivity of isomers C10F7H and C10F7Br towards organolithium and organomagnesium compounds

Significant differences in the reactivity of isomeric heptafluoronaphthalenes and bromoheptafluoronaphthalenes towards organolithium and organomagnesium compounds were found. Metalation of polyfluorinated naphthalenes 2-C10F7X (X = H, Br) occurs easily under the action of bases (BuLi, t-BuLi, LDA) as well as EtMgBr (X = Br) in ether. This fact was proven by 19F NMR spectroscopy and by trapping of 2-C10F7M (M = Li, MgBr, Mg(2-C10F7)) with electrophile ClSiMe3. The interaction of 1-C10F7Br with BuLi or EtMgBr proceeds in a similar way. In contrast to 2-C10F7H, isomeric 1-C10F7H is the less acidic substrate and undergoes only the nucleophilic alkyldefluorination when combined with BuLi or t-BuLi.

Bi- and tridentate silicon-based acceptor molecules

Triethynylphenylsilane (1), trivinylphenylsilane (2), diethynyldiphenylsilane (3) and diphenyldivinylsilane (4) were reacted with chlorodimethylsilane yielding the corresponding hydrosilylation products. To increase their Lewis acidity, the Si-Cl functions were directly transferred into Si-C6F5 units by salt elimination reactions leading to the (semi-) flexible molecules 5-8 bearing two or three Lewis-acidic sidearms. With the aim of providing host-guest complexes, the air-stable and readily soluble compounds 5-8 were converted with N- and O-Lewis bases of different size and geometry. In all cases, NMR spectroscopic investigations reveal no formation of Lewis acid-base complexes. X-ray diffraction experiments of host compounds 5-7 show intermolecular aryl perfluoroaryl interactions of dispersion nature in the solid state. By hydrosilylation of 1 with trichlorosilane the more Lewisacidic all-trans-tris[(trichlorosilyl)vinyl]phenylsilane (9) was obtained. Its Lewis acidity was further increased by fluorination to yield all-trans-tris[(trifluorosilyl)vinyl] phenylsilane (10); the conversion with nitrogen containing Lewis bases ends up in the formation of insoluble precipitates.