542-91-6

Basic information

• Product Name: DIETHYLSILANE
• Synonyms: (C2H5)2SiH2;diethyl-silan;Silane, diethyl-;DIETHYLSILANE;Diethylsilanealso high purity;Diethylsilane,98+%;Diethylsilane,97%;Diethylsilane,highpuritymin99%
• CAS NO: 542-91-6
• Molecular Formula: C₄H₁₂Si
• Molecular Weight: 88.22
• EINECS: 208-834-9
• Product Categories: Pharmaceutical Intermediates;Reduction;Si (Classes of Silicon Compounds);Si-H Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Organometallic Reagents;Organosilicon;Others
• Mol File: 542-91-6.mol

Chemical Properties

• Melting Point: -132°C
• Boiling Point: 56 °C(lit.)
• Flash Point: −20 °F
• Appearance: /liquid
• Density: 0.681 g/mL at 25 °C(lit.)
• Vapor Pressure: 279mmHg at 25°C
• Refractive Index: n20/D 1.391(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Miscible with terahydrofuran, diethyl ether, 1,4-dioxane and ben
• Sensitive: Air Sensitive
• Merck: 14,3128
• BRN: 1730902
• CAS DataBase Reference: DIETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLSILANE(542-91-6)
• EPA Substance Registry System: DIETHYLSILANE(542-91-6)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-23-24/25
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 542-91-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Diethylsilane is used as a precursor for the synthesis of (3-allylsulfanyl-propyl)-diethyl-silane, employing (Ph3P)3RhCl as a reagent. This application highlights its role in creating complex organic compounds.
Used in Microelectronics:
In the microelectronics industry, Diethylsilane is used in the chemical vapor deposition of SiO2, which is crucial for the fabrication of semiconductor devices and integrated circuits.
Used in Catalytic Reduction:
Diethylsilane serves as a reductant in the catalytic reduction of secondary amides to imines and secondary amines using iridium catalysts like [Ir(COE)2Cl]2. This system demonstrates high efficiency and functional group tolerance, making it valuable in organic synthesis.
Used in the Preparation of Diborane and Haloboranes:
Diethylsilane is also utilized in the 'in-situ' preparation of diborane and haloboranes, which are essential reagents in various chemical reactions, particularly in organic synthesis and polymer chemistry.

Sources

Levy, R. A., J. M. Grow, and G. S. Chakravarthy. "Low-pressure chemical vapor deposition of silicon dioxide using diethylsilane." Cheminform 24.28(1993):851-854. https://www.alfa.com/en/catalog/L16468/ https://www.sigmaaldrich.com/catalog/product/aldrich/423815?lang=en®ion=US https://pubs.acs.org/doi/full/10.1021/ja304547s#citing Nimmagadda, Rama D., and C. Mcrae. Cheminform 37.35(2006):3505-3508.

InChI:InChI=1/C4H10Si/c1-3-5-4-2/h3-4H2,1-2H3

Upstream product

• 617-86-7 triethylsilane 
• 1719-53-5 diethyldichlorosilane 
• 7446-70-0 aluminium trichloride 
• 16853-85-3 lithium aluminium tetrahydride 
• 925-90-6 ethylmagnesium bromide 
• 4109-96-0 Dichlorosilane 
• 766-08-5 methylphenylsilane 
• 811-49-4 ethyllithium 
• 7440-21-3 monosilane 
• 7646-69-7 sodium hydride 
• 5577-67-3 trimethyl(tert-butylamino)silane 
• 280757-21-3 [3H₃]ethylsilylium ion 
• 74-85-1 ethene 
• 123-91-1 1,4-dioxane 

Downstream Products

• 39579-27-6 Benzhydryloxy-diethyl-silane 
• 32135-11-8 Diethyl-p-tolyloxy-silane 
• 32135-12-9 Diethyl-bis-p-tolyloxy-silane 
• 32135-15-2 Diethyl-m-tolyloxy-silane 
• 32135-13-0 Diethyl-o-tolyloxy-silane 
• 41842-52-8 Bis-(o-methylphenylthio)-diaethylsilan 
• 49543-88-6 Benzyl-diethylsilanyl-methyl-amine 
• 32135-09-4 bis(benzyloxy)diethylsilane 
• 64031-47-6 2-Diethylsilanyloxy-1-phenyl-propan-1-one 
• 32135-10-7 Bis-cyclohexyloxy-diethyl-silane 
• 1609-19-4 diethylchlorosilane 
• 1000-05-1 1,1,3,3,5,5,7,7-octamethyltetrasiloxane 
• 995-83-5 1,1,3,3,5,5,7,7,9,9-decamethylpentasiloxane 
• 995-82-4 1,1,3,3,5,5,7,7,9,9,11,11-dodecamethylhexasiloxane 

Relevant articles and documents

Towards Naked Zinc(II) in the Condensed Phase: A Highly Lewis Acidic ZnII Dication Stabilized by Weakly Coordinating Carborate Anions

The employment of the hexyl-substituted anion [HexCB11Cl11]? allowed the synthesis of a ZnII species, Zn[HexCB11Cl11]2, 3, in which the Zn2+ cation is only weakly coordinated to two carborate counterions and that is soluble in low polarity organic solvents such as bromobenzene. DOSY NMR studies show the facile displacement of at least one of the counterions, and this near nakedness of the cation results in high catalytic activity in the hydrosilylation of 1-hexene and 1-methyl-1cyclohexene. Fluoride ion affinity (FIA) calculations reveal a solution Lewis acidity of 3 (FIA=262.1 kJ mol?1) that is higher than that of the landmark Lewis acid B(C6F5)3 (FIA=220.5 kJ mol?1). This high Lewis acidity leads to a high activity in catalytic CO2 and Ph2CO reduction by Et3SiH and hydrogenation of 1,1-diphenylethylene using 1,4-cyclohexadiene as the hydrogen source. Compound 3 was characterized by multinuclear NMR spectroscopy, mass spectrometry, single crystal X-ray diffraction, and DFT studies.

Synthesis of the first persilylated ammonium ion, [(Me3Si) 3NSi(H)Me2]+, by silylium-catalyzed methyl/hydrogen exchange reactions

This work describes the unexpected synthesis and characterization of the first persilylated ammonium ion, [(Me3Si)3NSi(H)Me 2]+, in the reaction of (Me3Si)3N with [Me3Si-H-SiMe3][B(C6F5) 4]. NMR and Raman studies revealed a transition-metal-free silylium ion catalyzed substituent redistribution process when [Me3Si-H- SiMe3]+ was used as the silylating reagent. These observations were affirmed in the reaction with [Et3Si-H-SiEt 3][B(C6F5)4]. A Lewis acid catalyzed scrambling process always occurs if an excess of silanes is present in the formation of silylium cations while employing the standard Bartlett-Schneider- Condon type reaction. Additionally, the thermodynamics of this process was accessed by DFT computations at the pbe1pbe/aug-cc-pVDZ level, indicating alkyl substituent exchange equilibria at the silane and preference of the formation of [(Me3Si)3NSi(H)Me2]+ over [(Me 3Si)4N]+.

Gas-phase ion-molecular reactions of free ethylsilylium ions with ethylene

Gas-phase reaction of ethylsilylium ions with ethylene was studied by the radiochemical method. The reaction occurs via excited adduct C4H11Si+ which structurally is a complex of ethylsilylium cation with ethylene. The lifetime of this complex is long enough for the isotope exchange between tritium atoms of the cation and a proton of ethylene, as well as the isomerization of ethylsilylium cation to dimethylsilylium to occur. Decomposition of the complex results in predominant formation of labeled ethylene.

Ion-molecule reactions of monosubstituted ethylsilylium ions with trimethyl(tert-butylamino)silane in the gas phase

Reaction of nuclear-chemically generated ethylsilylium ions with trimethyl(rert-butylamino)silane in the gas phase was studied. In the course of reaction the ethylsilylium ion completely isomerizes into the dimethylsilylium ion. Experiments show that the pathway involving proton transfer practically is not realized, in contrast to the reactions of carbenium ions with amines.