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195529

Iodotrimethylsilane

97%

Iodotrimethylsilane

Synonym(s):

TMIS, Trimethyliodosilane

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Size/SKUAvailabilityPrice
5 g

Estimated to ship onOctober 05, 2026fromMILWAUKEE

$54.70
25 g

Estimated to ship onOctober 05, 2026fromMILWAUKEE

$142.00
100 g

Estimated to ship onOctober 05, 2026fromMILWAUKEE

$318.00

About This Item

Linear Formula:
(CH3)3SiI
CAS Number:
Molecular Weight:
200.09
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
240-171-0
Beilstein/REAXYS Number:
1731136
MDL number:
Assay:
97%
Form:
liquid

$54.70


Estimated to ship onOctober 05, 2026Details


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Quality Segment

assay

97%

form

liquid

contains

copper as stabilizer

reaction suitability

reactivity: alcohol reactive, reagent type: protection reagent

refractive index

n20/D 1.471 (lit.)

bp

106 °C (lit.)

density

1.406 g/mL at 25 °C (lit.)

functional group

silyl

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

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

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

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

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bp

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pictograms

FlameCorrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

supp_hazards

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-23.8 °F - closed cup

flash_point_c

-31 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter



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Questions

1–4 of 4 Questions  
  1. 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.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    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

      Helpful?

  3. 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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  4. 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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Reviews

Active Filters

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

    wrong structure

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

    Helpful?