18834-17-8

Basic information

• Product Name: bis-benzhydryloxy-phenyl-silane
• Synonyms: bis-benzhydryloxy-phenyl-silane
• CAS NO: 18834-17-8
• Molecular Weight: 472.659
• Mol File: 18834-17-8.mol

Chemical Properties

• CAS DataBase Reference: bis-benzhydryloxy-phenyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: bis-benzhydryloxy-phenyl-silane(18834-17-8)
• EPA Substance Registry System: bis-benzhydryloxy-phenyl-silane(18834-17-8)

Safety Data

• Hazardous Substances Data: 18834-17-8(Hazardous Substances Data)

Upstream product

• 119-61-9 benzophenone 
• 694-53-1 phenylsilane 

Downstream Products

• 91-01-0 1,1-Diphenylmethanol 

Relevant articles and documents

Ring-Shaped Phosphinoamido-Magnesium-Hydride Complexes: Syntheses, Structures, Reactivity, and Catalysis

A series of magnesium(II) complexes bearing the sterically demanding phosphinoamide ligand, L?=Ph2PNDip?, Dip=2,6-diisopropylphenyl, including heteroleptic magnesium alkyl and hydride complexes are described. The ligand ge

Hydrosilylation of Aldehydes and Ketones Catalyzed by a 2-Iminopyrrolyl Alkyl-Manganese(II) Complex

A well-defined and very active single-component manganese(II) catalyst system for the hydrosilylation of aldehydes and ketones is presented. First, the reaction of 5-(2,4,6-iPr3C6H2)-2-[N-(2,6-iPr2C6H3)formimino]pyrrolyl potassium (KL) and [MnCl2(Py)2] afforded the binuclear 2-iminopyrrolyl manganese(II) pyridine chloride complex [Mn2{κ2N,N′-5-(2,4,6-iPr3C6H2)-NC4H2-2-C(H)═N(2,6-iPr2C6H3)}2(Py)2(μ-Cl)2] 1. Subsequently, the alkylation reaction of complex 1 with LiCH2SiMe3 afforded the respective (trimethylsilyl)methyl-Mn(II) complex [Mn{κ2N,N′-5-(2,4,6-iPr3C6H2)-NC4H2-2-C(H)═N(2,6-iPr2C6H3)}(Py)CH2SiMe3] 2 in a good yield. Complexes 1 and 2 were characterized by elemental analysis, 1H NMR spectroscopy, Evans' method, FTIR spectroscopy, and single-crystal X-ray diffraction. While the crystal structure of complex 1 has been identified as a binuclear entity, in which the Mn(II) centers present pentacoordinate coordination spheres, that of complex 2 corresponds to a monomer with a distorted tetrahedral coordination geometry. Complex 2 proved to be a very active precatalyst for the atom-economic hydrosilylation of several aldehydes and ketones under very mild conditions, with a maximum turnover frequency of 95 min-1, via a silyl-Mn(II) mechanistic route, as asserted by a combination of experimental and theoretical efforts, the respective silanes were cleanly converted to the respective alcoholic products in high yields.

Electrophilic Organobismuth Dication Catalyzes Carbonyl Hydrosilylation

Bismuth compounds are gaining importance as potential alternatives to transition-metal complexes and electron deficient lighter p-block compounds in homogeneous catalysis. Computational analysis on the two-coordinate [(Me2NC6H4)Bi]2+ possessing three electrophilic sites is experimentally evidenced by the isolation of [{Me2NC6H4}Bi{OP(NMe2)3}3][B(3,5-C6H3Cl2)4]2. These observations led us to generate dicationic organobismuth catalyst, [(Me2NC6H4)Bi(L)3]2+ (L=aldehyde/ketone), evidenced by NMR spectroscopy in solution and by single-crystal X-ray diffraction in the solid state. It efficiently catalyzes hydrosilylation of aldehydes and ketones resulting in silyl ethers as the only products in high yields. Our investigations support a carbonyl activation mechanism at the bismuth center followed by Si?H addition.

Hydridosilylamido complexes of Ta and Mo isolobal with Berry's zirconocenes: Syntheses, β-Si-H agostic interactions, catalytic hydrosilylation, and insight into mechanism

The syntheses of novel Group 5 and Group 6 hydrosilylamido complexes of the type R(ArN)M{N(tBu)SiMe2-H}X (M = Ta, R = Cp; M = Mo, R = ArN; X = Cl, H, OBn, Me) are described. The various substituents in the X position seem to play the

Hydrosilylation of Aldehydes and Ketones Catalyzed by a Terminal Zinc Hydride Complex, [κ3-Tptm]ZnH

Tris(2-pyridylthio)methyl zinc hydride, [κ3-Tptm]ZnH, is an effective catalyst for multiple insertions of carbonyl groups into the Si-H bonds of PhxSiH4-x (x = 1, 2). Specifically, [κ3-Tptm]ZnH catalyzes the insertion of a variety of aldehydes and ketones into the Si-H bonds of PhSiH3 and Ph2SiH2 to afford PhSi[OCH(R)R′]3 and Ph2Si[OCH(R)R′]2, respectively. The mechanism for hydrosilylation is proposed to involve insertion of the carbonyl group into the Zn-H bond to afford an alkoxy species, followed by metathesis with the silane to release the alkoxysilane and regenerate the zinc hydride catalyst. Multiple insertion of prochiral ketones results in the formation of diastereomeric mixtures of alkoxysilanes that can be identified by NMR spectroscopy.

A Pentacoordinate Mn(II) Precatalyst That Exhibits Notable Aldehyde and Ketone Hydrosilylation Turnover Frequencies

Heating (THF)2MnCl2 in the presence of the pyridine-substituted bis(imino)pyridine ligand, PyEtPDI, allowed preparation of the respective dihalide complex, (PyEtPDI)MnCl2. Reduction of this precursor using excess Na/Hg resulted in deprotonation of the chelate methyl groups to yield the bis(enamide)tris(pyridine)-supported product, (κ5-N,N,N,N,N-PyEtPDEA)Mn. This complex was characterized by single-crystal X-ray diffraction and found to possess an intermediate-spin (S = 3/2) Mn(II) center by the Evans method and electron paramagnetic resonance spectroscopy. Furthermore, (κ5-N,N,N,N,N-PyEtPDEA)Mn was determined to be an effective precatalyst for the hydrosilylation of aldehydes and ketones, exhibiting turnover frequencies of up to 2475 min-1 when employed under solvent-free conditions. This optimization allowed for isolation of the respective alcohols and, in two cases, the partially reacted silyl ethers, PhSiH(OR)2 [R = Cy and CH(Me)(nBu)]. The aldehyde hydrosilylation activity observed for (κ5-N,N,N,N,N-PyEtPDEA)Mn renders it one of the most efficient first-row transition metal catalysts for this transformation reported to date.

A highly active manganese precatalyst for the hydrosilylation of ketones and esters

The reduction of (Ph2 PPrPDI)MnCl2 allowed the preparation of the formally zerovalent complex, (Ph2 PPrPDI)Mn, which features a pentadentate bis(imino)pyridine chelate. This complex is a highly active precatalyst for the hydrosilylation of ketones, exhibiting TOFs of up to 76,800 h-1 in the absence of solvent. Loadings as low as 0.01 mol % were employed, and (Ph2 PPrPDI)Mn was found to mediate the atom-efficient utilization of Si-H bonds to form quaternary silane products. (Ph2PPrPDI)Mn was also shown to catalyze the dihydrosilylation of esters following cleavage of the substrate acyl C-O bond. Electronic structure investigation of (Ph 2PPrPDI)Mn revealed that this complex possesses an unpaired electron on the metal center, rendering it likely that catalysis takes place following electron transfer to the incoming carbonyl substituent.

A remarkably active iron catecholate catalyst immobilized in a porous organic Polymer

A single-site, iron catecholate-containing porous organic polymer was prepared and utilized as a stable and remarkably active catalyst for the hydrosilylation of ketones and aldehydes. In some instances, catalyst loadings of 0.043-2.1 mol % [Fe] were sufficient for complete hydrosilylation of aldehydes and ketones within 15 min at room temperature. The catalyst can be recycled at least three times without a drop in catalytic activity. This system is an example of an immobilized homogeneous catalyst with no homogeneous analogue.

Reduction of ketones with hydrocarbon-soluble calcium hydride: Stoichiometric reactions and catalytic hydrosilylation

Reactions of the dimeric calcium hydride complex [(DIPP-nacnac) CaH·thf]2 {1; DIPP-nacnac = CH[(CMe)(2,6-iPr2C 6H3N)]2} with the α-hydrogen containing ketones acetophenone, acetone, dibenzylketone and