TRIMETHYLIODOSILANE

Product Code: SIT8564.0
CAS No: 16029-98-4
SDS Sheets: EU | US
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16029-98-4
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25 g
$90.00
100 g
$291.00
2.5 kg
$1,665.00
25 kg
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250 kg
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Product data and descriptions listed are typical values, not intended to be used as specification.

  • Einecs Number

    240-171-0
  • Synonyms

    TRIMETHYLSILYL IODIDE
  • HMIS

    3-4-1-X
  • Molecular Formula

    C3H9ISi
  • Molecular Weight (g/mol)

    200.1
  • TSCA

    Yes
  • Boiling Point (˚C/mmHg)

    106-107
  • Density (g/mL)

    1.470
  • Flash Point (˚C)

    -2 °C
  • Refractive Index @ 20˚C

    1.4742

Additional Properties

  • Hydrolytic Sensitivity

    8: reacts rapidly with moisture, water, protic solvents

    • Application

    Key reviews.1,2
    Reagent for cleavage of ethers, esters, lactones.3
    Used to dechlorinate aryl chlorides.4
    Allylates aldehydes in the presence of allyl chloride and tin tetraiodide (SNT7946).5

    Reference

    1. Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis, Fuchs, P. L. Ed., John Wiley and Sons, Ltd., 2011, p. 325-336.
    2. Olah, G. et al. In Advances in Silicon Chemistry; Larson, G., Ed.; JAI Press: Greenwich, Co, 1991; Vol. 1, p.1.
    3. DePew, K. M. et al. J. Org. Chem. 1999, 121, 11953.
    4. Sako, M. et al. J. Org. Chem. 2001, 66, 3610.
    5. Masuyama, Y. et al. Tetrahedron Lett. 2005, 46, 2861.

    Safety

  • Packaged Over Copper
  • Packaging Under

    Nitrogen

    • Trimethylsilyl Blocking Agent

    Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.

    Trimethyliodosilane; Iodotrimethylsilane, Trimethylsilyl iodide; TMIS

  • Extremely reactive silylating agent
  • Used with HMDS for hindered alcohols
  • Forms enol silyl ethers with ketones and SIT8620.0
  • Nafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction times
  • Summary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochure

    • Silicon Chemistry, Articles

    Iodotrimethylsilane – Olah et al.

    Silicon Chemistry, Applied Technology

    Silicon Nitride and Silicon Nitride-Rich Thin Film Technologies: Trends in Deposition Techniques and Related Applications – Kaloyeros, Jove, Goff, & Arkles

    This article provides an overview of the state-of-the-art chemistry and processing technologies for silicon nitride and silicon nitride- rich films, i.e., silicon nitride with C inclusion, both in hydrogenated (SiNx:H and SiNx:H(C)) and non-hydrogenated (SiNx and SiNx(C)) forms. The emphasis is on emerging trends and innovations in these SiNx material system technologies, with focus on Si and N source chemistries and thin film growth processes, including their primary effects on resulting film properties. It also illustrates that SiNx and its SiNx(C) derivative are the focus of an ever-growing research and manufacturing interest and that their potential usages are expanding into new technological areas.