diazomethyl-trimethyl-silane, CAS No. 18107-18-1

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18107-18-1

Catalog No. EBD36745

CAS 18107-18-1

Name diazomethyl-trimethyl-silane

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Basic Information

Synonyms: TMSCHN2 diazomethyl-trimethyl-silane (trimethylsilyl)diazomethane tms-diazomethane (diazomethyl)trimethylsilane diazo(trimethylsilyl)methane trimethyl(diazomethyl)silane (trimethylsilyl)diazomethanesolution trimethylsilyl)diazomethanesolution2m (trimethylsilyl)diazomethane,2.0mind (trimethylsilyl)diazomethane,2minhexanes trimethylsilyldiazomethane2.0mindiethylester

Molecular Formula: C4H10N2Si

Molecular Weight: 114.22

MDL Number: MFCD00053946

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Other Basic Synthetic Reagents Synthetic Chemistry > Organometallic Reagents > Organosilicon Reagents

Product Description:

Trimethylsilyldiazomethane (TMS-diazomethane), CAS 18107-18-1, is a versatile and commercially important organosilicon reagent. It is a yellow liquid or gas, often supplied as a solution in hexane or diethyl ether for safe handling. Its chemical structure features a diazomethane group (-CHN₂) bonded to a trimethylsilyl (TMS) group, which significantly alters its properties compared to the highly toxic and explosive parent compound, diazomethane. The primary application of TMS-diazomethane is as a safe and efficient methylating agent, particularly for carboxylic acids to produce methyl esters in analytical chemistry and organic synthesis. It is also widely used for the preparation of homologated ketones via the Arndt-Eistert synthesis and for the methylation of phenols and enolizable ketones. Its reactivity as a carbene precursor makes it valuable for cyclopropanation reactions. The TMS group stabilizes the molecule, making it less hazardous and easier to handle than diazomethane, though it still requires careful use under inert atmosphere due to its toxicity and potential for exothermic decomposition. As a specialized reagent, it is a staple in synthetic and analytical laboratories. It is classified as an organic silicon reagent due to its core TMS-CHN₂ structure and is fundamentally a synthetic tool rather than a material or an API intermediate, placing it firmly within the domain of synthetic chemistry reagents.

Physical Properties

Boiling Point: 96 °C

Flash Point: -35 °C

Density: 0.773 g/mL at 25 °C

Refractivity: 1.4362

Storage: 2-8°C

Safety Information

Packing Level: I

Hazard Category: 6.1(3)

Transport Codes: 3383

Analytical Data

Appearance: clear yellow solution