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195529 Sigma-Aldrich

Iodotrimethylsilane

97%

Synonym: TMIS, Trimethyliodosilane

  • CAS Number 16029-98-4

  • Linear Formula (CH3)3SiI

  • Molecular Weight 200.09

  •  Beilstein/REAXYS Number 1731136

  •  EC Number 240-171-0

  •  MDL number MFCD00001028

  •  PubChem Substance ID 24851696

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents More...
assay   97%
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.

Packaging

5, 25, 100 g in ampule

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 & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
Reacts violently with water.
RIDADR 
UN 2924 8(3) / PGII
WGK Germany 
3
Flash Point(F) 
-23.8 °F
Flash Point(C) 
-31 °C

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
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What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
What is known of the mechanism of reactions involving product 195529, Iodotrimethylsilane?
The mechanism for cleavage of esters is described in PNAS, 75(1), 4-6 (1978).The authors go on to explain that the data do not support a previously published mechanism via a carbenium iodide.The paper also discusses the cleavage of ethers using iodotrimethylsilane. It appears that this is not as efficient as cleavage of esters, and a couple of mechanisms (pages 5 and 6) are proposed.Olah also described the cleavage of the phosphate esters in peptides that contain phosphate esters, using iodotrimethylsilane (Tetrahedron, 38, 2225 (1982)). The amide linkages in the peptide backbone are not cleaved.
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Protocols & Articles

Articles

Activating Reagents and Protecting Groups

The use of activating agents and protecting groups in organic synthesis is necessary to prevent unwanted side reactions from occurring when using other common reagents such as oxidizing or reducing a...
Chemfiles Volume 1 Article 3
Keywords: Organic synthesis

Peer-Reviewed Papers
15

References

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