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195529

Sigma-Aldrich

Iodotrimethylsilane

Iodotrimethylsilane

97%

Synonyme(s) :

TMIS, Trimethyliodosilane

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5 G
71,10 $
25 G
210,00 $
100 G
672,00 $

About This Item

Formule linéaire :
(CH3)3SiI
Numéro CAS:
16029-98-4
Poids moléculaire :
200.09
Beilstein:
1731136
Numéro CE :
240-171-0
Numéro MDL:
MFCD00001028
Code UNSPSC :
12352103
ID de substance PubChem :
24851696
Nomenclature NACRES :
NA.22

71,10 $

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Devis pour commande en gros

Essai

97%

Forme

liquid

Contient

copper as stabilizer

Indice de réfraction

n20/D 1.471 (lit.)

pb

106 °C (lit.)

Densité

1.406 g/mL at 25 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

C[Si](C)(C)I

InChI

1S/C3H9ISi/c1-5(2,3)4/h1-3H3

Clé InChI

CSRZQMIRAZTJOY-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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]

À utiliser avec

Réf. du produit
Description
Tarif

Pictogrammes

FlameCorrosion
GHS02,GHS05

Mention d'avertissement

Danger

Mentions de danger

H225,H314

Classification des risques

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

Risques supp

EUH014

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

-23.8 °F - closed cup

Point d'éclair (°C)

-31 °C - closed cup

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCW6931
MKCV4191
MKCQ8371
MKCN4247
MKCL5508

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Iodotrimethylsilane?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
Tetrahedron Letters, 35, 5445-5445 (1994)
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
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
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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/449/386/product-dating-information-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

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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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Reviews

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  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.

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