1351520-69-8

Basic information

• Product Name: 1-phenyl-4-(phenylsilyl)butane
• Synonyms: 1-phenyl-4-(phenylsilyl)butane
• CAS NO: 1351520-69-8
• Molecular Weight: 240.42
• Mol File: 1351520-69-8.mol

Chemical Properties

• CAS DataBase Reference: 1-phenyl-4-(phenylsilyl)butane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-4-(phenylsilyl)butane(1351520-69-8)
• EPA Substance Registry System: 1-phenyl-4-(phenylsilyl)butane(1351520-69-8)

Safety Data

• Hazardous Substances Data: 1351520-69-8(Hazardous Substances Data)

Upstream product

• 768-56-9 4-Phenylbut-1-ene 
• 694-53-1 phenylsilane 
• 16520-62-0 4-Phenyl-1-butyne 
• 775-12-2 diphenylsilane 
• 1075-74-7 5-phenylpent-1-ene 
• 4206-75-1 phenylchlorosilane 

Relevant articles and documents

Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C-H borylation using counterion activated earth-abundant metal catalysis

The widespread adoption of earth-abundant metal catalysis lags behind that of the second- and third-row transition metals due to the often challenging practical requirements needed to generate the active low oxidation-state catalysts. Here we report the development of a single endogenous activation protocol across five reaction classes using both iron- and cobalt pre-catalysts. This simple catalytic manifold uses commercially available, bench-stable iron- or cobalt tetrafluoroborate salts to perform regiodivergent alkene and alkyne hydrosilylation, 1,3-diene hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C-H borylation. The activation protocol proceeds by fluoride dissociation from the counterion, in situ formation of a hydridic activator and generation of a low oxidation-state catalyst.

Cobalt-Catalyzed Asymmetric Synthesis of gem-Bis(silyl)alkanes by Double Hydrosilylation of Aliphatic Terminal Alkynes

Chiral organosilanes are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. Compared with single-silyl compounds, bis(silyl) ones are understudied because of the lack of the efficient synthetic protocols. The development of efficient synthetic approaches to access bis(silyl) compounds is highly desirable for studying their basic properties and potential utilities. Here, a cobalt-catalyzed sequential double hydrosilylation of aliphatic alkynes was developed to synthesize highly enantioenriched gem-bis(silyl)alkanes. This protocol used simple aliphatic alkynes and silanes to construct valuable chiral gem-bis(silyl)alkanes. The control experiments, isotopic labeling experiments, kinetic studies, and density functional theory calculations were conducted to elucidate the reaction mechanism. The synthetic versatility of gem-bis(silyl)alkanes was demonstrated by the synthesis of chiral organosilanols, α-hydroxysilanes through selective C–Si bond transformation and hydrosilylation of alkynes to construct chiral silanes containing adjacent C-stereocenter and Si-stereocenter. Chiral organosilanes are important synthetic intermediates for chiral catalysts, functional materials, and silasubstitution in medicinal chemistry. Because of the absence of highly efficient catalytic synthetic methods, enantiopure polysilyl-substituted compounds are rare and their applications are not well explored. Our methodology enables double hydrosilylation of aliphatic alkynes for the construction of unique chiral gem-bis(silyl)alkanes via cobalt catalysis with excellent chemo-, regio-, and enantioselectivity. We anticipate that this strategy will be a useful tool for synthesis of diverse chiral organosilanes. Furthermore, we also expect the unique gem-bis(silyl)alkanes will be employed not only in stereoselective organic synthesis but also in chiral catalyst and functional materials. A cobalt-catalyzed sequential highly enantioselective double hydrosilylation of aliphatic alkynes for the precise synthesis of chiral gem-bis(silyl)alkanes was achieved. This protocol used relatively simple and available starting materials to construct more valuable products with excellent chemo-, regio- and enantioselectivities. Synthetic versatility of gem-bis(silyl)alkanes was demonstrated by the synthesis of chiral organosilanols and α-hydroxysilanes and hydrosilylation of alkynes to construct chiral silanes. The control experiments, isotopic labeling experiments, kinetic studies, and density functional theory calculations were conducted to elucidate the reaction mechanism.

Nickel-Catalyzed Hydrosilylation of Terminal Alkenes with Primary Silanes via Electrophilic Silicon-Hydrogen Bond Activation

We report a simple and effective nickel-based catalytic system, NiCl2·6H2O/tBuOK, for the electrophilically activated hydrosilylation of terminal alkenes with primary silanes. This protocol provides excellent performance under mild reaction conditions: ex

Solution Synthesis of N,N-Dimethylformamide-Stabilized Iron-Oxide Nanoparticles as an Efficient and Recyclable Catalyst for Alkene Hydrosilylation

Highly activated, monodispersed N,N-dimethylformamide (DMF)-stabilized iron-oxide nanoparticles (Fe2O3 NPs) were synthesized by using iron(III) acetylacetonate as a precursor under open-air conditions. The resulting Fe2Os

Manganese-Catalyzed Hydrofunctionalization of Alkenes

The manganese-catalyzed hydrosilylation and hydroboration of alkenes has been developed using a single manganese(II) precatalyst and reaction protocol. Both reactions proceed with excellent control of regioselectivity and in high yields across a variety of sterically and electronically differentiated substrates (25 examples). Alkoxide activation, using NaOtBu, was key to precatalyst activation and reactivity. Catalysis was achieved across various functional groups and on gram-scale for both the developed methodologies with catalysts loadings as low as 0.5 mol %.

Synthesis of divalent ytterbium terphenylamide and catalytic application for regioselective hydrosilylation of alkenes

The dimeric heteroleptic ytterbium amido complex [(2,6-(3,5-Me2C6H3)2C6H3NH)Yb(N(SiMe3)2)]2 (1) has been prepared and characterized. This divalent terphenyl

Cobalt-Catalyzed Regiodivergent Hydrosilylation of Vinylarenes and Aliphatic Alkenes: Ligand- and Silane-Dependent Regioselectivities

We report a regiodivergent hydrosilylation of alkenes catalyzed by catalysts generated in situ from bench-stable Co(acac)2 and phosphine- or nitrogen-based ligands. A wide range of vinylarenes and aliphatic alkenes reacted to afford either branched (45 examples) or linear (37 examples) organosilanes in high isolated yields (average: 84%) and high regioselectivities (from 91:9 to >99:1). This transformation tolerates a variety of functional groups including ether, silyloxy, thioether, epoxide, halogen, amine, ester, boronic ester, acetal, cyano, and ketone moieties. Mechanistic studies suggested that the hydrosilylation of alkenes catalyzed by the cobalt/bisphosphine system follows the Chalk-Harrod mechanism (with a Co-H intermediate), and the hydrosilylation of alkenes catalyzed by the cobalt/pyridine-2,6-diimine system follows the modified Chalk-Harrod mechanism (with a Co-Si intermediate). Systematic studies with sterically varied silanes revealed that the steric properties of silanes play a pivotal role in controlling the regioselectivity of vinylarene hydrosilylation and the chemoselectivity of the reactions of aliphatic alkenes and silanes catalyzed by the cobalt/pyridine-2,6-diimine system.

Control of Selectivity through Synergy between Catalysts, Silanes, and Reaction Conditions in Cobalt-Catalyzed Hydrosilylation of Dienes and Terminal Alkenes

Readily accessible (i-PrPDI)CoCl2 [i-PrPDI = 2,6-bis(2,6-diisopropylphenyliminoethyl)pyridine] reacts with 2 equiv of NaEt3BH at -78 °C in toluene to generate a catalyst that effects highly selective anti-Markov

Activation of Ene-Diamido Samarium Methoxide with Hydrosilane for Selectively Catalytic Hydrosilylation of Alkenes and Polymerization of Styrene: An Experimental and Theoretical Mechanistic Study

Samarium methoxide incorporating the ene-diamido ligand L(DME)Sm(μ-OMe)2Sm(DME)L (1; L = [DipNC(Me)C(Me)NDip]2-, Dip = 2,6-iPr2C6H3, and DME = 1,2-dimethoxyethane) has been prepared and structurally c

METHOD OF PRODUCING ORGANIC SILANE COMPOUND AND CATALYST COMPOSITION FOR ORGANIC SILANE COMPOUND SYNTHESIS

PROBLEM TO BE SOLVED: To provide a production method which makes it possible to produce an organic silane compound efficiently and inexpensively by improving a catalyst for use in hydrosilylation reaction of alkene and alkyne. SOLUTION: This invention provides a method of producing an organic silane compound, including reaction between alkene and/or alkyne and hydrosilane in the presence of a catalyst, wherein an iron-containing nanoparticle with a solvent coordinated on the surface is used as a catalyst so that an organic silane compound can be produced efficiently and inexpensively. COPYRIGHT: (C)2015,JPO&INPIT