195529

Iodotrimethylsilane

97%

• Synonym(s): TMIS, Trimethyliodosilane
• Linear Formula: (CH₃)₃SiI
• CAS Number: 16029-98-4
• Molecular Weight: 200.09
• Beilstein: 1731136
• EC Number: 240-171-0
• MDL number: MFCD00001028
• UNSPSC Code: 12352103
• PubChem Substance ID: 24851696
• NACRES: NA.22

Properties

• Assay: 97%
• form: liquid
• contains: copper as stabilizer
• refractive index: n20/D 1.471 (lit.)
• bp: 106 °C (lit.)
• density: 1.406 g/mL at 25 °C (lit.)
• storage temp.: −20°C
• SMILES string: C[Si](C)(C)I
• InChI: 1S/C3H9ISi/c1-5(2,3)4/h1-3H3
• InChI key: CSRZQMIRAZTJOY-UHFFFAOYSA-N

Description

General description

Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.

Iodotrimethylsilane is a hard-soft reagent that reacts readily with organic compounds containing oxygen (a hard base) forming a strong siliconoxygen bond.

Application

Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.

For the introduction of the TMS group, e.g., TMS enol ethers. Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.

Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.

Safety Information

• Pictograms: GHS02,GHS05
• Signal Word: Danger
• Hazard Statements: H225,H314
• Precautionary Statements: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
• Supplementary Hazards: EUH014
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): -23.8 °F - closed cup
• Flash Point(C): -31 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves