COMMERCIAL
16029-98-4

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TRIMETHYLIODOSILANE

Product Code: SIT8564.0

Cas No: 16029-98-4

R&D quantities:

2.5 kg
$1,387.50
100 g
$242.00
25 g
$75.00
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

    • Boiling Point: 106-7°

    EINECS Number: 240-171-0

    Molecular Weight: 200.10

    Alternative Name: TRIMETHYLSILYL IODIDE

    Specific Gravity: 1.470

    Flashpoint: -2°C (28°F)

    HMIS Key: 3-4-1-X

    Hydrolytic Sensitivity: 8: reacts rapidly with moisture, water, protic solvents

    Formula: C3H9ISi

    Refractive Index: 1.4742

    TSCA: TSCA

    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.

    Fieser:

    Additional Properties: Dipole moment: 2.46 debye
    ?Hform: -52.2 kcal/mole
    Stabilized with copper granules
    Vapor pressure, 25°: 40 mm