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Merck
CN

748854

Sigma-Aldrich

碘三甲基硅烷 溶液

1 M in dichloromethane

别名:

三甲基碘硅烷 溶液, TMSI, 碘代三甲硅烷

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关于此项目

经验公式（希尔记法）:
C3H9ISi
分子量:
200.09
UNSPSC代码:
12352101
NACRES:
NA.22

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表单

liquid

质量水平

100

浓度

1 M in dichloromethane

折射率

n20/D 1.433

密度

1.334 g/mL at 25 °C

储存温度

2-8°C

相关类别

一般描述

Iodotrimethylsilane [(CH3)3SiI] is an important and versatile organosilicon reagent with wide applications in organic synthesis. It is used as a neutral nucleophilic reagent, trimethylsilylating agent, Lewis acid catalyst, reducing agent and dehydrating agent in many organic reactions.

应用

Iodotrimethylsilane can be used as:
  • A reagent in the hydroiodation of ynamides to yield the important building blocks (E)-α-iodoenamides.
  • A reagent in the synthesis of (1-iodovinyl) arenes by hydroiodation of trimethylsilyl ethynylarenes.

警示用语：

Danger

危险分类

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

靶器官

Central nervous system

补充剂危害

EUH014

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

-23.8 °F

闪点(°C)

-31 °C

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCW3104
MKCV4304
MKCV6894
MKCQ8317
MKCP8384

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    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. 

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

    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.

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Iodotrimethylsilane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2005)
Regio-and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 54(10), 1309-1311 (2013)
One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 53(28), 3585-3589 (2012)

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