Iodotrimethylsilane, CAS No. 16029-98-4

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16029-98-4

Catalog No. EBD32187

CAS 16029-98-4

Name Iodotrimethylsilane

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Basic Information

Synonyms: Trimethylsilyliodide Trimethyliodosilane Iodotrimethylsilane TMIS Iodotrmethylsilane Trimethyliodosilanestabilizedwithcoppergranules TMSiodide

Molecular Formula: C3H9ISi

Molecular Weight: 200.09

MDL Number: MFCD00001028

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

Product Description:

Trimethyliodosilane is an organosilicon compound with the formula (CH3)3SiI. It is a colorless to pale yellow liquid that is highly reactive and moisture-sensitive, typically handled under inert atmosphere conditions. Its primary application is as a versatile reagent in organic synthesis. It is most notably used as a powerful and selective dealkylating agent, particularly for the cleavage of methyl ethers to yield the corresponding alcohols. This reaction is milder and more selective than traditional methods using boron tribromide or hydroiodic acid. It is also employed for the deprotection of silyl ethers and in the conversion of esters to iodides (via the TMSI-mediated reduction). Furthermore, it serves as an efficient source of iodide ion and as a silylating agent in various transformations. Due to its reactivity with water and air, generating corrosive hydrogen iodide, it requires careful storage and handling. Its utility as a specialized reagent for deprotection and functional group interconversion makes it a staple in synthetic chemistry laboratories, especially for the synthesis of complex molecules including pharmaceuticals and natural products.

Physical Properties

Melting Point: <0°C

Boiling Point: 106 °C(lit.)

Flash Point: -31 °C

Density: 1.406 g/mL at 25 °C(lit.)

Solubility: reacts

Refractivity: n20/D 1.471(lit.)

Storage: −20°C

Safety Information

Packing Level: II

Hazard Category: 8(3)

Transport Codes: 2924

Analytical Data

Appearance: Straw liquid