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195529

Sigma-Aldrich

Iodotrimethylsilane

Iodotrimethylsilane

97%

Synonym(s):

TMIS, Trimethyliodosilane

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About This Item

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
Pricing and availability is not currently available.

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

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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.[1][1]

[1]Iodotrimethylsilane is a hard-soft reagent that reacts readily with organic compounds containing oxygen (a hard base) forming a strong siliconoxygen bond.[2]

Application

Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.[3]
For the introduction of the TMS group, e.g., TMS enol ethers.[4] Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.[5]
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.[6]

accessory

Product No.
Description
Pricing

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225,H314

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW6931
MKCV4191
MKCQ8371
MKCN4247
MKCL5508

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Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
Iodotrimethylsilane?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
Tetrahedron Letters, 35, 5445-5445 (1994)
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
Go Hirai et al.
Bioorganic & medicinal chemistry letters, 14(10), 2647-2651 (2004-04-28)
Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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  3. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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.

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  4. What is known of the mechanism of reactions involving product 195529, Iodotrimethylsilane?

    1 answer

    1. 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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    • Review 1
    • Votes 0
    1 out of 5 stars.

    wrong structure

    The structure of the mentioned title and CAS No. do not match.

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