17950-94-6

Basic information

• Product Name: DIPHENYLSILANE-D2
• Synonyms: DIPHENYLSILANE-D2;DIPHENYLSILANE-D2, 97 ATOM % D;diphenylsilicon
• CAS NO: 17950-94-6
• Molecular Formula: C₁₂H₁₂Si
• Molecular Weight: 186.32
• EINECS: 212-271-4
• Product Categories: Alphabetical Listings;D;Stable Isotopes
• Mol File: 17950-94-6.mol

Chemical Properties

• Boiling Point: 95-97 °C13 mm Hg(lit.)
• Flash Point: 209 °F
• Appearance: /
• Density: 1.004 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.184mmHg at 25°C
• Refractive Index: n20/D 1.579(lit.)
• CAS DataBase Reference: DIPHENYLSILANE-D2(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYLSILANE-D2(17950-94-6)
• EPA Substance Registry System: DIPHENYLSILANE-D2(17950-94-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 17950-94-6(Hazardous Substances Data)

Usage

Uses

Used in Inorganic Chemistry:
DIPHENYLSILANE-D2 is used as a ligand for the formation of inorganic gold (Au) complexes. These complexes serve as catalysts in the --functionalization of organosilane compounds. The use of DIPHENYLSILANE-D2 in this application is due to its ability to form stable complexes with gold, which in turn enhances the catalytic activity and selectivity in the functionalization process.

InChI:InChI=1/C12H12Si/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H,13H2/i13D2

Upstream product

• 80-10-4 diphenylsilyl dichloride 
• 775-12-2 diphenylsilane 
• 126971-98-0 diphenyl(silane-d₁) 

Downstream Products

• 138924-41-1 C₁₆H₁₇⁽²⁾HOSi 
• 1101847-75-9 (C₅(CH₃)5)RuH(Si⁽²⁾H(C₆H₅)2)(C⁽²⁾HHN(CH₃)C₉H₆P(CH(CH₃)2)2) 
• 51276-65-4 diphenyl(1-phenylethoxy)silane 

Relevant articles and documents

An H-Substituted Rhodium Silylene

Divergent reactivity of organometallic rhodium(I) complexes, which led to the isolation of neutral rhodium silylenes, is described. Addition of PhRSiH2 (R=H, Ph) to the rhodium cyclooctene complex (iPrNNN)Rh(COE) (1-COE; iPr/su

Synthesis of Stereodefined Trisubstituted Alkenyl Silanes Enabled by Borane Catalysis and Nickel Catalysis

Regioselective and stereoselective synthesis of trisubstituted alkenyl silanes via hydrosilylation is challenging. Herein, we report the first β-anti-selective addition of silanes to thioalkynes with B(C6F5)3as the catalyst. The reaction shows broad substrate scope. The products were proven to be useful intermediates to other trisubstituted alkenyl silanes by Ni-catalyzed stereoretentive cross-coupling reactions of the C-S bond. A mechanism study suggests that nucleophilic attack of thioalkyne to an activated silylium intermediate might be the rate-determining step.

Cu-Catalyzed Regioselective C-H Alkylation of Benzimidazoles with Aromatic Alkenes

Herein we report a novel Cu-catalyzed regioselective C2-H alkylation of benzimidazoles with aromatic alkenes. The reaction features exclusive regioselectivity and broad substrate scope in the intermolecular alkylation of benzimidazoles with terminal and i

Enantioselective Copper-Catalyzed Alkylation of Quinoline N-Oxides with Vinylarenes

An asymmetric copper-catalyzed alkylation of quinoline N-oxides with chiral Cu–alkyl species, generated by migratory insertion of a vinylarene into a chiral Cu?H complex, is reported. A variety of quinoline N-oxides and vinylarenes underwent this Cu-catalyzed enantioselective alkylation reaction, affording the corresponding chiral alkylated N-heteroarenes in high yield with high-to-excellent enantioselectivity. This enantioselective protocol represents the first general and practical approach to access a wide range of chiral alkylated quinolines.

A Ni0(η2-(Si-H))(η2-H2) Complex That Mediates Facile H Atom Exchange between Two σ-Ligands

σ-adduct complexes of low-valent, late first-row metal complexes are highly unusual, and this is particularly true of d10 systems. We have discovered a nickel/phosphine/silyl system that undergoes reaction with H2 in solution to gene

Selective Silylative Reduction of Pyridines Leading to Structurally Diverse Azacyclic Compounds with the Formation of sp3 C-Si Bonds

Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp3 C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylation as an initial step depending on the substituent position, followed by selective hydrosilylation of enamine double bonds eventually affording β-silylated azacyclic compounds.

Iron-catalysed chemo-, regio-, and stereoselective hydrosilylation of alkenes and alkynes using a bench-stable iron(II) pre-catalyst

The chemo-, regio-, and stereoselective iron-catalysed hydrosilylation of alkenes and alkynes with excellent functional group tolerance is reported (34 examples, 41-96% yield). The catalyst and reagents are commercially available and easy to handle, with the active iron catalyst being generated in situ, thus providing a simple and practical methodology for iron-catalysed hydrosilylation. The silane products can be oxidised to the anti-Markovnikov product of olefin hydration, and the one-pot iron-catalysed hydrosilylation-oxidation of olefins to give silane(di)ols directly is also reported. The iron pre-catalyst was used at loadings as low as 0.07 mol%, and displayed catalyst turnover frequencies (TOF) approaching 60,000 molh-1. Initial mechanistic studies indicate an iron(I) active catalyst.

Large-scale preparation and labelling reactions of deuterated silanes

A catalytic synthesis of deuterated silanes SiEt3D, SiMe 2PhD and SiPh2D2 is reported that allows their facile generation in a 3-4g scale, utilizing D2 (0.5bar) as the hydrogen isotope source and low

Catalytic deuteration of silanes mediated by N-heterocyclic carbene-Ir(iii) complexes

The catalytic activity of a series of coordinatively unsaturated NHC-M(iii) (M = Rh, Ir; NHC = N-heterocyclic carbene) complexes was tested in the deuteration of secondary and tertiary silanes. Among these, [IrCl(I tBu′)2] provides t

Hydrosilylation with biscarbene Rh(I) complexes: Experimental evidence for a silylene-based mechanism

A detailed study investigating the mechanism of the hydrosilylation of 4-F-acetophenone by N-heterocyclic biscarbene rhodium(I) complexes was performed, delivering substantial experimental evidence for a recently proposed catalytic cycle and explaining the observed side-product formation. Labeling experiments, silylene trapping reactions, and specific catalytic reactions were employed to substantiate each step of the catalytic cycle and explain the differences observed for different types of chiral catalysts. It is further shown that hydrosilylation and dehydrocoupling reactions with dihydrosilanes are mechanistically related.