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Merck
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安全信息

195529

Sigma-Aldrich

三甲基碘硅烷

97%

别名:

TMIS, 碘代三甲硅烷

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About This Item

线性分子式:
(CH3)3SiI
CAS号:
16029-98-4
分子量:
200.09
Beilstein:
1731136
EC 号:
240-171-0
MDL编号:
MFCD00001028
UNSPSC代码:
12352103
PubChem化学物质编号:
24851696
NACRES:
NA.22

质量水平

300

检测方案

97%

形式

liquid

包含

copper as stabilizer

折射率

n20/D 1.471 (lit.)

bp

106 °C (lit.)

密度

1.406 g/mL at 25 °C (lit.)

储存温度

−20°C

SMILES字符串

C[Si](C)(C)I

InChI

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

InChI key

CSRZQMIRAZTJOY-UHFFFAOYSA-N

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相关类别

一般描述

三甲基碘硅烷是用于各种有机反应的多用途试剂。用于某些化合物（如内酯，醚，缩醛和氨基甲酸酯）的脱烷基化反应以及用作三甲基硅烷基化剂，用于合成硅烷基亚氨酸酯、烷基和烯基硅烷等。在许多有机反应中，还可用作路易斯（Lewis）酸催化剂和还原剂。

三甲基碘硅烷是一种硬软试剂，很容易与含氧有机化合物（硬碱）反应，形成强硅氧键。

应用

最近报道用于将烯丙基以及苄基磷酸三酯转化为相应的碘化物的试剂。
用于引入 TMS 基团，如 TMS 烯醇醚。用于在三甲基锡基存在的条件下对 N-Cbz 基团进行选择性脱保护的重要试剂。
用于裂解醚、酯、氨基甲酸盐、缩酮和内酯的有效试剂。

象形图

FlameCorrosion
GHS02,GHS05

警示用语：

Danger

危险声明

H225,H314

危险分类

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

补充剂危害

EUH014

WGK

WGK 3

闪点(°F)

closed cup

闪点(°C)

closed cup

个人防护装备

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

法规信息

危险化学品

分析证书(COA)

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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.

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?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
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