1058-08-8

Basic information

• Product Name: Triphenyl(pentafluorophenyl)stannane
• Synonyms: (Pentafluorophenyl)triphenylstannane;Triphenyl(pentafluorophenyl)stannane
• CAS NO: 1058-08-8
• Molecular Formula: C₂₄H₁₅F₅Sn
• Molecular Weight: 517.0779
• Mol File: 1058-08-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 468.3°Cat760mmHg
• Flash Point: 237°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.7E-08mmHg at 25°C
• CAS DataBase Reference: Triphenyl(pentafluorophenyl)stannane(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenyl(pentafluorophenyl)stannane(1058-08-8)
• EPA Substance Registry System: Triphenyl(pentafluorophenyl)stannane(1058-08-8)

Safety Data

• Hazardous Substances Data: 1058-08-8(Hazardous Substances Data)

Usage

General Description

Triphenyl(pentafluorophenyl)stannane is an organotin compound with the molecular formula C18H11F5Sn. It is a white crystalline solid that is insoluble in water. This chemical is often used as a reagent in organic synthesis and as a catalyst in various reactions, particularly in the formation of carbon-carbon bonds. It can also be used as a starting material for the synthesis of other organotin compounds. Additionally, its pentafluorophenyl group provides increased reactivity and stability compared to other tin compounds. However, it is important to note that organotin compounds can be toxic and should be handled with care in a controlled laboratory environment.

InChI:InChI=1/C6F5.3C6H5.Sn/c7-2-1-3(8)5(10)6(11)4(2)9;3*1-2-4-6-5-3-1;/h;3*1-5H;/rC24H15F5Sn/c25-19-20(26)22(28)24(23(29)21(19)27)30(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

Upstream product

• 363-72-4 Pentafluorobenzene 
• 88068-44-4 methylytterbium 
• 639-58-7 triphenyltin chloride 
• 26138-28-3 phenylytterbium iodide 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel⁽⁰⁾ 
• 1158383-88-0 MeNC₅H₄NiPr 
• 2117-48-8 triphenyl-vinyl stannane 
• 4167-90-2 lithium triphenylstannide 
• 894-09-7 iodotriphenylstannane 
• 96868-89-2 (C₆H₅)3SnC₆H₄-p-CH₂CHCH₂ 
• 96469-14-6 (C₆H₅)3SnC₆H₄-p-cyclo-C₆H₁₁ 
• 15807-57-5 (C₆H₅)3SnC₆H₄-o-CH₃ 
• 15807-28-0 triphenyl(p-tolyl)tin 
• 88020-63-7 pentafluorophenylytterbium bromide 

Relevant articles and documents

THIENYL AND PERFLUOROPHENYL DERIVATIVES OF DIVALENT LANTHANIDES

The reflection of oxidative addition of α-iodothiophene and bromopentafluorobenzene to zero-valent lanthanides has been carried out.The formation of organolanthanide derivatives RLnX (R0α-C4H3S, C6F5) has been confirmed by isolation of the corresponding R

A mechanistic investigation of carbon-hydrogen bond stannylation: Synthesis and characterization of nickel catalysts

The complex (iPr3P)Ni(η2-Bu 3SnCHCH2)2 (1a) was characterized by NMR spectroscopy and was identified as the active species for catalytic C-H bond stannylation of partially fluorinated aromatics, for example in the reaction between pentafluorobenzene and Bu3SnCHCH2, which generates C6F5SnBu3 and ethylene. The crystalline complex (iPr3P)Ni(η2-Ph 3SnCHCH2)2 (1b) provides a more easily handled analogue, and is also capable of catalytic stannylation with added Ph 3SnCHCH2 and C6F5H. Mechanistic studies on 1b show that the catalytically active species remains mononuclear. The rate of catalytic stannylation is proportional to [C6F 5H] and inversely proportional to [Ph3SnCHCH2]. This is consistent with a mechanism where reversible Ph3SnCHCH 2 dissociation provides (iPr3P) Ni(η2-Ph3SnCHCH2), followed by a rate-determining reaction with C6F5H to generate the stannylation products. Kinetic competition reactions between the fluorinated aromatics pentafluorobenzene, 1,2,4,5-tetrafluorobenzene, 1,2,3,5- tetrafluorobenzene, 1,2,4-trifluorobenzene, 1,3,5-trifluorobenzene and 1,3-difluorobenzene all suggest significant Ni-aryl bond formation in the rate-determining step under catalytic conditions. Labelling studies are consistent with an insertion of the hydrogen of the arene into the vinyl group, followed by β-elimination or β-abstraction of the SnPh3 moiety.