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195529

Sigma-Aldrich

Iodtrimethylsilan

Iodotrimethylsilane

97%

Synonym(e):

TMIS, Trimethyliodsilan

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CHF 49.60
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CHF 114.00
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CHF 263.00

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5 G
CHF 49.60
25 G
CHF 114.00
100 G
CHF 263.00

About This Item

Lineare Formel:
(CH3)3SiI
CAS-Nummer:
16029-98-4
Molekulargewicht:
200.09
Beilstein:
1731136
EG-Nummer:
240-171-0
MDL-Nummer:
MFCD00001028
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24851696
NACRES:
NA.22

CHF 49.60

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Qualitätsniveau

300

Assay

97%

Form

liquid

Enthält

copper as stabilizer

Brechungsindex

n20/D 1.471 (lit.)

bp

106 °C (lit.)

Dichte

1.406 g/mL at 25 °C (lit.)

Lagertemp.

−20°C

SMILES String

C[Si](C)(C)I

InChI

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

InChIKey

CSRZQMIRAZTJOY-UHFFFAOYSA-N

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Allgemeine Beschreibung

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]

Anwendung

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]

Zubehör

Produkt-Nr.
Beschreibung
Preisangaben

Piktogramme

FlameCorrosion
GHS02,GHS05

Signalwort

Danger

H-Sätze

H225,H314

Gefahreneinstufungen

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

Zusätzliche Gefahrenhinweise

EUH014

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

-23.8 °F - closed cup

Flammpunkt (°C)

-31 °C - closed cup

Persönliche Schutzausrüstung

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

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCW6931
MKCV4191
MKCQ8371
MKCN4247
MKCL5508

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Die Dokumentenbibliothek aufrufen

Iodotrimethylsilane?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
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
Tetrahedron Letters, 35, 5445-5445 (1994)
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
Erick J Rendón-Ramirez et al.
Viral immunology, 28(5), 248-254 (2015-04-30)
There is a strong interest in finding adequate biomarkers to aid in the diagnosis and prognosis of influenza A (H1N1)pdm09 virus infection. In this study, serum levels of inflammatory cytokines and laboratory markers were evaluated to assess their usefulness as
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Questions

1–4 of 4 Questions  

  1. 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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  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.
      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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  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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