Triethylsilane
[CAS# 617-86-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Silane
• Name: Triethylsilane
• Synonyms: Triethylsilyl hydride
• Molecular Formula: C₆H₁₆Si
• Molecular Weight: 116.28
• CAS Registry Number: 617-86-7
• EC Number: 210-535-3
• SMILES: CC[SiH](CC)CC

Properties

• Solubility: 0.3809 mg/L (25 °C water)
• Density: 0.728
• Melting point: 12.38 °C
• Boiling Point: 107.5±0.0 °C (760 mmHg), Calc.^*, -51.57 °C, 107-108 °C
• Flash Point: -3.9±0.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS09 Danger
• Risk Statements: H226-H315-H319-H335-H400-H410-H412
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P273-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovery and Applications

Triethylsilane, a chemical compound with the formula (C2H5)3SiH, was discovered as part of the broader exploration of organosilicon chemistry in the mid-20th century. Organosilicon compounds, characterized by silicon-carbon bonds, have been studied for their unique properties and applications. Triethylsilane was synthesized through reactions involving silicon and ethyl groups, leading to the creation of a compound where three ethyl groups are bonded to a silicon atom, with one remaining hydrogen atom.

Triethylsilane is widely used in organic synthesis and industrial processes due to its reducing properties and ability to act as a hydrogen source. One of its primary applications is in the reduction of organic compounds. Triethylsilane can effectively reduce a variety of functional groups, including carbonyls, alkenes, and alkynes, making it an essential reagent in synthetic chemistry. Its ability to transfer hydride ions under mild conditions allows chemists to achieve reductions that are often challenging with other reagents.

In pharmaceutical chemistry, triethylsilane is employed in the synthesis of complex molecules and active pharmaceutical ingredients (APIs). Its selective reducing power is particularly valuable in multi-step syntheses, where the preservation of sensitive functional groups is crucial. This selectivity ensures that only specific bonds are reduced, facilitating the creation of desired chemical structures with high precision.

Another significant application of triethylsilane is in the field of materials science. It is used in the production of silicon-based polymers and resins, which are integral to the manufacture of coatings, adhesives, and sealants. These materials benefit from the stability and durability imparted by the organosilicon compounds.

Furthermore, triethylsilane is utilized in the semiconductor industry. It serves as a precursor in the chemical vapor deposition (CVD) processes for creating silicon-based thin films and coatings. These thin films are essential for the fabrication of various electronic components, including transistors and integrated circuits.

References

2021. A New Protocol for Catalytic Reduction of Alkyl Chlorides Using an Iridium/Bis(benzimidazol-2′-yl)pyridine Catalyst and Triethylsilane. Synthesis, 53(20).
DOI: 10.1055/a-1527-4526

2002. Facile Cleavage of Triethylsilyl (TES) Ethers Using o-Iodoxybenzoic Acid (IBX) without Affecting tert-Butyldimethylsilyl (TBS) Ethers. Organic Letters, 4(11).
DOI: 10.1021/ol025946n

2000. Reductive Ring Opening of o-Nitrobenzylidene Acetals of Monosaccharides: Synthesis and Photolysis of Some Photolabile Sugars. Organic Letters, 2(25).
DOI: 10.1021/ol0068952