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Merck
CN

195529

三甲基碘硅烷

97%

别名:

TMIS, 碘代三甲硅烷

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线性分子式:
(CH3)3SiI
化学文摘社编号:
分子量:
200.09
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
240-171-0
Beilstein/REAXYS Number:
1731136
MDL number:
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产品名称

三甲基碘硅烷, 97%

InChI key

CSRZQMIRAZTJOY-UHFFFAOYSA-N

InChI

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

SMILES string

C[Si](C)(C)I

assay

97%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.471 (lit.)

bp

106 °C (lit.)

density

1.406 g/mL at 25 °C (lit.)

storage temp.

−20°C

Quality Level

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Application

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。

General description

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。

pictograms

FlameCorrosion

signalword

Danger

hcodes

Hazard Classifications

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

supp_hazards

存储类别

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

法规信息

危险化学品
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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?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)
Tetrahedron Letters, 45, 3607-3607 (2004)

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