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Triethylsilane

Triethylsilane is an organosilicon compound with the molecular formula C₆H₁₆Si and the structural formula (CH₃CH₂)₃SiH, featuring a central silicon atom bonded to three ethyl groups and one hydrogen atom.^[1] This colorless, volatile liquid has a boiling point of 107–108 °C, a melting point of -157 °C, and a density of 0.728 g/mL at 25 °C, making it highly flammable with a flash point of -3 °C.^[2] It is commonly used as a mild reducing agent in organic synthesis due to its reactive Si–H bond, which facilitates hydrosilylation and transfer hydrogenation reactions.^[3] Triethylsilane finds extensive application in the chemoselective reduction of functional groups such as carbonyls, imines, and sulfoxides, often in the presence of Lewis acids like BF₃·OEt₂ or transition metal catalysts.^[3] For instance, it enables the conversion of aldehydes and ketones to silyl enol ethers or the deoxygenation of sulfoxides to sulfides under mild conditions.^[4] Additionally, it serves as a silylating agent for protecting alcohols as triethylsilyl ethers, which are stable under basic conditions but removable under acidic ones, aiding in multi-step syntheses of pharmaceuticals and natural products.^[3] Its role extends to radical-mediated reductions and deprotection strategies, highlighting its versatility in modern organic chemistry.^[5] The compound is typically synthesized by the reduction of chlorotriethylsilane ((CH₃CH₂)₃SiCl) with lithium aluminum hydride (LiAlH₄) in ether solvents, replacing the chlorine with hydrogen to yield the hydrosilane.^[6] Industrially, it is produced on a large scale for use in silicone polymer precursors and as an intermediate in silane chemistry, though it requires careful handling due to its flammability and potential to form explosive mixtures with air.^[7] Safety precautions include storage under inert atmospheres and avoidance of ignition sources.^[8]

Structure and Properties

Molecular Structure

Triethylsilane has the chemical formula (C₂H₅)₃SiH, equivalently expressed as C₆H₁₆Si, and a molecular weight of 116.28 g/mol. The molecule consists of a central silicon atom covalently bonded to three ethyl (–CH₂CH₃) groups and one terminal hydrogen atom, forming a trialkylsilane structure. The Si–C bond lengths are approximately 1.88 Å, while the Si–H bond length measures about 1.48 Å.^[9] The arrangement around the silicon center adopts a tetrahedral geometry, with bond angles approaching the ideal value of 109.5° for sp³ hybridization.^[9] The Si–H bond is polar, with partial positive charge on silicon (Siδ+) and partial negative charge on hydrogen (Hδ–), arising from silicon's lower electronegativity (1.90) relative to hydrogen (2.20). This reversed polarity compared to C–H bonds (where carbon is δ–) facilitates the molecule's role in reactions involving hydride donation. The overall molecular dipole moment is 0.50 D, reflecting the asymmetric distribution of electron density due to the single Si–H bond amid the nonpolar ethyl substituents.^[9] Triethylsilane exists as a monomeric species in the gas phase, consistent with the behavior of simple organosilanes lacking intermolecular association. No X-ray crystal structure data for the neutral molecule is reported, as it is a low-melting liquid (-157 °C).^[9]

Physical Properties

Triethylsilane appears as a colorless liquid with low viscosity at room temperature.^[10] Its melting point is -157 °C, indicating it remains liquid under typical laboratory conditions.^[11] The compound has a boiling point of 107–108 °C at 760 mmHg and a density of 0.728 g/mL at 25 °C.^[2] Its vapor pressure exceeds 1 hPa at 20 °C, contributing to its volatility.^[11] The refractive index is 1.412 (n_D^{20}).^[2] Triethylsilane is insoluble in water but miscible with organic solvents such as ethanol, ether, and acetone.^[12] The flash point is approximately -3 °C (closed cup), reflecting its high flammability, which is further detailed in safety considerations.^[11]

Property	Value	Conditions
Appearance	Colorless, low-viscosity liquid	Room temperature
Boiling point	107–108 °C	760 mmHg
Melting point	-157 °C	-
Density	0.728 g/mL	25 °C
Vapor pressure	>1 hPa	20 °C
Refractive index	1.412	20 °C (n_D)
Flash point	-3 °C	Closed cup
Solubility in water	Insoluble	-

Chemical Properties

The Si-H bond in triethylsilane exhibits a hydridic nature due to the polarity of the bond, with silicon bearing a partial positive charge, rendering it susceptible to electrophilic attack and enabling its role as a hydride donor in reactions with electron-deficient centers.^[12] The bond dissociation energy of this Si-H linkage is approximately 90 kcal/mol, which contributes to its moderate reactivity compared to more labile hydrides.^[13] Triethylsilane demonstrates good stability under ambient conditions, remaining air-stable and non-pyrophoric, though it is highly flammable and can form explosive vapor-air mixtures.^[8] At elevated temperatures, it undergoes thermal decomposition, yielding silicon oxides, carbon oxides, and potentially lower silanes or hydrocarbons as byproducts.^[14] The Si-H proton in triethylsilane is weakly acidic, allowing deprotonation by strong bases such as n-butyllithium to generate triethylsilyl anions, which are useful intermediates in organosilicon chemistry. Triethylsilane shows sensitivity to oxidation, slowly reacting with atmospheric oxygen over time to form siloxanes through insertion of oxygen into the Si-H bond, particularly under prolonged exposure or in the presence of catalysts.^[9] Characteristic spectroscopic features of triethylsilane include a strong infrared absorption band for the Si-H stretch at approximately 2100 cm⁻¹, a ¹H NMR signal for the Si-H proton at δ ≈ 3.6 ppm (often appearing as a septet due to coupling with adjacent protons), and a ²⁹Si NMR resonance at δ ≈ -5 ppm, reflecting the tetrahedral silicon environment with three ethyl substituents.^[15]^[16]^[17] In comparison to polymethylhydrosiloxane (PMHS), triethylsilane serves as a milder reducing agent owing to the greater steric hindrance imposed by its ethyl groups, which limits access to the Si-H bond in congested substrates, whereas PMHS's smaller methyl substituents enable broader reactivity.^[18]

Synthesis

Discovery and Early Preparation

Triethylsilane (Et₃SiH) was first isolated in 1872 by German chemist Albert Ladenburg during his investigations into organosilicon compounds. Ladenburg achieved this through the reduction of tetraethyl orthosilicate (Si(OEt)₄) using sodium metal and diethylzinc (ZnEt₂), a method that produced triethylsilane among other byproducts in a complex reaction mixture. This synthesis marked an early milestone in the field, as Ladenburg's work built on prior attempts to create silicon analogs to carbon-based organics, such as the 1863 preparation of tetraethylsilane by Friedel and Crafts. The reaction conditions were rudimentary by modern standards, involving heating the reagents to facilitate reduction, which resulted in a gaseous product that Ladenburg purified via fractional distillation under reduced pressure. The isolated triethylsilane was noted for its boiling point of 107 °C and density of approximately 0.73 g/mL. Ladenburg detailed these observations in his key publication, "Ueber die Reductionsproducte des Kieselsäureäthers und deren Derivate," appearing in Justus Liebigs Annalen der Chemie (volume 164, pages 300–319).^[19] This discovery occurred amid broader 19th-century debates on the potential of silicon to mimic carbon in forming stable organometallic structures, a contentious idea given silicon's tendency toward higher coordination and reactivity compared to carbon. Ladenburg's successful isolation of triethylsilane provided empirical evidence for the stability of Si–C bonds in alkylsilanes, challenging skepticism and inspiring subsequent researchers like Pape and Kipping to explore silane derivatives.^[20] By demonstrating practical synthesis routes for such compounds, Ladenburg's contributions laid foundational groundwork that influenced the evolution of organosilicon chemistry into the industrial production of silicones in the 20th century.^[20]

Modern Synthetic Methods

The primary modern synthetic method for triethylsilane involves the reduction of chlorotriethylsilane with lithium aluminum hydride in diethyl ether under anhydrous conditions.^[21]^[22] This reaction replaces the chlorine with hydrogen to yield the hydrosilane, typically requiring careful addition of the silane to a suspension of the hydride at low temperature (0–10°C) followed by reflux and workup with water or acid to hydrolyze aluminum species.^[21] Anhydrous conditions are essential to avoid hydrolysis of the reagents or product, which can lead to siloxane formation.^[22] Typical yields for this method exceed 90%, making it efficient for laboratory-scale production from grams to kilograms.^[21] Industrially, hydride reductions like this are preferred despite the cost of LiAlH₄, as they provide reliable access to high-purity triethylsilane compared to earlier routes.^[21] An alternative route utilizes sodium trimethoxyborohydride (Na[BH(OMe)₃]) prepared in situ from sodium hydride and trimethyl borate, which is then reacted with chlorotriethylsilane under nitrogen atmosphere.^[21] The mixture is stirred at low temperature (-50°C to 10°C) for 1–5 hours, followed by warming to room temperature and filtration to remove sodium chloride byproduct; acidification may be employed in the workup to decompose excess borohydride species.^[21] This method offers a milder alternative to LiAlH₄, avoiding aluminum byproducts, though it requires precise control of the borohydride preparation.^[21] Purification of triethylsilane from either route is achieved by distillation under reduced pressure, which effectively separates the product from residual chlorosilane or siloxane impurities.^[22] This step ensures high purity (>99%) suitable for synthetic applications, with the process scalable to multikilogram batches in laboratory settings.^[23]

Applications in Synthesis

Reduction Reactions

Triethylsilane acts as a versatile mild reducing agent in organic synthesis, particularly for deoxygenation and deprotection reactions involving heteroatom-containing functional groups, often promoted by acidic catalysts. Its Si-H bond provides hydridic character, enabling selective hydride transfer under conditions that avoid interference with other sensitive moieties.^[24] The primary mechanism for these reductions involves ionic hydride delivery, where a Lewis acid such as BF₃·OEt₂ or a Brønsted acid like trifluoroacetic acid (TFA) activates the substrate by protonation, generating an electrophilic intermediate (e.g., oxocarbenium ion or carbocation) that accepts the hydride from triethylsilane, forming a silyl ether or silane adduct. This process typically proceeds via a six-membered transition state for hydride transfer, as elucidated in computational studies of the reaction geometry. In certain systems, such as those with strong bases like potassium tert-butoxide, proton-coupled electron transfer can contribute, generating radical or anionic intermediates for hydride donation.^[25]^[25]^[26] In carbonyl reductions, triethylsilane with TFA selectively converts aldehydes and ketones to alkanes by deoxygenation, proceeding through an initial silyl ether intermediate that undergoes further reduction. For instance, aryl aldehydes are transformed to the corresponding methylarenes in yields often exceeding 80%, offering a clean method for carbonyl removal without affecting aromatic rings. The reaction is represented as:

\text{RCHO} + \text{Et}_3\text{SiH} \xrightarrow{\text{TFA}} \text{RCH}_3 + \text{Et}_3\text{SiOTFA}

This approach is particularly useful for aryl substrates, where selectivity for methylene formation is high.^[24]^[24] Deoxygenation extends to alcohols and ethers under acidic conditions, removing the oxygen atom to yield hydrocarbons. Tertiary and secondary benzylic alcohols, for example, are reduced to alkanes using triethylsilane and a solid acid catalyst like tin(IV)-exchanged montmorillonite, via an S_N1-type pathway involving stable carbocation intermediates, with yields up to quantitative for tertiary cases. Ethers follow a similar activation, protonation leading to cleavage and hydride trapping.^[27]^[27] Triethylsilane excels in deprotection reactions, selectively cleaving acetals, oximes, and benzyl groups while preserving other functionalities. Benzylidene acetals in carbohydrates are regioselectively reduced to benzyl ethers using triethylsilane and BF₃·OEt₂, opening the acetal at the less hindered position without disrupting glycosidic bonds. Oximes are reduced to amines in TFA, providing a mild alternative to metal hydrides. Benzyl protecting groups on phosphates or alcohols are removed chemoselectively, even in the presence of redox-sensitive moieties like quinones.^[28]^[29] Notable examples include the radical-initiated reduction of aromatic azides to amines, catalyzed by thiols like tert-dodecanethiol, proceeding via a chain mechanism to deliver near-quantitative yields without tin reagents. In carbohydrate chemistry, triethylsilane enables stereoselective reductions, such as in the formation of β-C-arylglucosides from ketals, where the reagent's hydride delivery favors axial attack for high diastereoselectivity. These applications highlight triethylsilane's advantages: mild reaction conditions (often room temperature), compatibility with acid-labile groups like alkenes and sulfides, and high functional group tolerance due to the non-nucleophilic nature of the silane.^[5]^[5]^[30]

Hydrosilylation and Silylation

Triethylsilane serves as a key reagent in hydrosilylation reactions, facilitating the anti-Markovnikov addition of its Si-H bond across carbon-carbon unsaturated bonds in alkenes and alkynes. This process typically involves terminal olefins reacting with triethylsilane under catalysis by transition metal complexes, yielding β-alkylsilanes such as \ce{RCH=CH2 + Et3SiH -> RCH2CH2SiEt3}. Speier's catalyst, hexachloroplatinic acid (\ce{H2PtCl6}), is commonly employed for hydrosilylation of terminal alkenes like styrene, promoting high yields under mild conditions, often in the presence of an alcohol solvent to enhance solubility and activity. Rhodium complexes, such as \ce{RhCl(PPh3)3}, offer alternative catalysis, particularly for achieving regioselectivity influenced by electronic factors in the substrate, where electron-withdrawing groups on the alkene favor anti-Markovnikov orientation. In silylation reactions, triethylsilane reacts with alcohols to form triethylsilyl ethers (\ce{ROH + Et3SiH -> ROSiEt3}), serving as protecting groups in organic synthesis. This dehydrogenative process is catalyzed by Lewis acids like tris(pentafluorophenyl)borane (\ce{B(C6F5)3}) or metal-free systems such as 4-amino-TEMPO, proceeding at room temperature with release of dihydrogen and providing mild conditions compatible with sensitive functional groups. The resulting triethylsilyl (TES) ethers exhibit stability toward basic conditions but are readily cleaved by fluoride sources like tetrabutylammonium fluoride (TBAF), enabling selective deprotection in multi-step sequences. These reactions find applications in the synthesis of functionalized alkylsilanes, which are valuable precursors for materials and pharmaceuticals, as the hydrosilylation product retains the C-Si bond for further elaboration. TES protection is particularly useful in complex assemblies, such as peptide synthesis, where temporary masking of hydroxyl groups on serine or threonine residues prevents side reactions during coupling steps, as demonstrated in solid-phase glycosylated peptide constructions. However, triethylsilane shows reduced efficiency for hydrosilylation of internal alkenes compared to polymeric alternatives like polymethylhydrosiloxane (PMHS), which provide multiple Si-H units and better solubility for challenging substrates. Recent advances include asymmetric hydrosilylation variants using chiral rhodium or palladium catalysts to produce enantioenriched silanes from prochiral alkenes, enabling the synthesis of optically active alkylsilanes for chiral ligand development.

Other Uses

Triethylsilane serves as a precursor for the synthesis of triethylsilyl cyanide (Et₃SiCN), a reagent employed in the cyanosilylation of aldehydes and ketones to form protected cyanohydrins. The preparation involves the reaction of triethylsilane with acetonitrile in the presence of a catalytic amount of methylcyclopentadienyl iron dicarbonyl (Cp(CO)₂FeMe), proceeding under mild conditions to afford Et₃SiCN in good yields.^[31] This silyl cyanide derivative facilitates the addition of the cyano group across the carbonyl, enabling subsequent transformations in organic synthesis while protecting the hydroxyl functionality.^[31] In polymer chemistry, triethylsilane participates in the cationic ring-opening polymerization of cyclic siloxanes, where it acts via hydride transfer to form trisilyloxonium ions, influencing the polymerization mechanism and enabling the production of siloxane oligomers.00452-2) Additionally, it supports reductive polycondensation processes, such as the conversion of isophthaldehyde to polyethers in the presence of triphenylmethyl perchlorate, demonstrating its utility in constructing polymer backbones through silane-mediated reductions.^[12] Triethylsilane functions as a chain transfer agent in free-radical polymerizations, such as that of styrene, where its Si-H bond interacts with growing polymer radicals to control molecular weight distribution; the chain transfer constant for triethylsilane in this system has been determined to be low, indicating moderate efficiency compared to other silanes like triphenylsilane.^[32] In radical chemistry, it enables the chain reduction of alkyl halides to alkanes through a thiol-catalyzed radical mechanism, achieving near-quantitative yields for primary, secondary, and tertiary substrates (e.g., conversion of ethyl 4-bromobutanoate to ethyl butanoate without affecting the ester group), serving as a non-toxic alternative to organotin hydrides. The distinct Si-H proton signal of triethylsilane, appearing as a septet around 3.6 ppm in ¹H NMR spectra due to coupling with the ethyl methylene protons, facilitates its identification and quantification in reaction mixtures, though it is not routinely employed as a primary internal standard.^[16] Emerging applications include its role as a cocatalyst activator in olefin metathesis systems based on molybdenum halides supported on silica gel, where triethylsilane enhances catalyst activity for the metathesis of hexene-1 at ambient to moderate temperatures (27–50°C), forming active centers comparable in effectiveness to other organosilicon activators like 1,1,3,3-tetramethyl-1,3-disilacyclobutane.^[33] Furthermore, triethylsilane participates in reductive etherification of carbonyl compounds, reacting with alkoxytrimethylsilanes in the presence of 5 mol% iron(III) chloride in nitromethane to produce alkyl ethers in good to excellent yields (>90% for most aldehydes), accommodating sterically hindered and electron-deficient substrates under mild conditions.^[34] Triethylsilane is commercially available from major chemical suppliers, including Sigma-Aldrich, where it is offered in high purity (≥99%) for laboratory use in 25 mL to 500 g quantities, supporting its accessibility for synthetic and research applications.^[2]

Safety and Environmental Impact

Health and Fire Hazards

Triethylsilane is a highly flammable liquid with a flash point of -3 °C, capable of forming explosive vapor-air mixtures at concentrations between its lower and upper explosion limits.^[7] Its autoignition temperature is approximately 245 °C, posing significant fire and explosion risks during handling or storage near ignition sources.^[7] Combustion of triethylsilane produces irritating fumes, including hydrogen gas, formaldehyde, carbon monoxide, organic acid vapors, and silicon dioxide.^[8] Exposure to triethylsilane can cause irritation to the skin, eyes, and respiratory tract, with symptoms including redness, pain, and coughing upon contact or inhalation.^[7] Inhalation of high vapor concentrations may lead to headache, dizziness, tiredness, nausea, and vomiting.^[7] The compound exhibits low acute mammalian toxicity, with an oral LD50 in rats exceeding 2000 mg/kg, indicating it is not highly lethal in single exposures.^[35] Triethylsilane is very toxic to aquatic life, classified under GHS as Aquatic Acute Category 1 and Aquatic Chronic Category 1, with LC50 values for fish typically below 1 mg/L, leading to long-lasting adverse effects in aquatic environments.^[36] No specific occupational exposure limits have been established by OSHA, and it is recommended to handle the substance in a well-ventilated fume hood to minimize risks.^[37] Under the Globally Harmonized System (GHS), triethylsilane is classified as a Flammable Liquid Category 2 (H225: Highly flammable liquid and vapor), Skin Irritation Category 2 (H315: Causes skin irritation), and Serious Eye Damage/Eye Irritation Category 2 (H319: Causes serious eye irritation).^[8] Its volatility contributes to the fire risk, as vapors can travel to ignition sources and flash back.^[7]

Handling and Disposal

Triethylsilane should be stored in a cool, dry, well-ventilated area, preferably under an inert atmosphere to maintain purity and prevent reactions with moisture or air contaminants, using compatible containers such as glass or Teflon-lined vessels, and kept away from oxidizers, water, alkalis, and ignition sources.^[8]^[38] During handling, operations must be conducted in a glove box, fume hood, or other well-ventilated enclosure to minimize exposure to vapors; personnel should wear appropriate personal protective equipment, including chemical-resistant gloves (e.g., neoprene or nitrile rubber), safety goggles, flame-retardant clothing, and a respirator with organic vapor cartridges if vapors are present, while grounding all equipment and using non-sparking tools to prevent static discharge or ignition.^[8]^[38]^[39] In the event of a spill, evacuate the area, ensure adequate ventilation, and use non-sparking tools to contain the spill; absorb the liquid with an inert material such as vermiculite or sand, collect for proper disposal, and clean the affected area thoroughly, preventing entry into drains or waterways.^[8]^[38]^[39] For disposal, triethylsilane and its waste should be incinerated at an approved facility equipped for flammable materials or chemically treated with an oxidizing agent under controlled conditions, in compliance with local, national, and international regulations, including classification as a hazardous waste under RCRA (D001 ignitable) in the United States.^[8]^[38] Triethylsilane is registered under the European Union's REACH regulation and listed on the United States Toxic Substances Control Act (TSCA) inventory, requiring adherence to these frameworks for import, use, and waste management.^[40]^[8] In fire emergencies involving triethylsilane, utilize dry chemical, carbon dioxide, or alcohol-resistant foam extinguishers, avoiding water due to the compound's inherent flammability and potential for violent reactions; emergency responders should employ self-contained breathing apparatus and full protective gear.^[8]^[38]

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Silane, triethyl-. Formula: C6H16Si; Molecular weight: 116.2767. IUPAC Standard InChI: InChI=1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3 Copy. InChI version 1.06.Missing: stretch | Show results with:stretch
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### Abstract
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Melting point. : -157 °C. Freezing point. : No data available. Boiling point. : 107 – 108 °C. Flash point. : -3 °C. Auto-ignition temperature. : 250 °C.
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