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重要文件

195529

Sigma-Aldrich

三甲基碘硅烷

Iodotrimethylsilane

97%

同義詞:

TMIS, 碘代三甲硅烷

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About This Item

線性公式:
(CH3)3SiI
CAS號碼:
分子量::
200.09
Beilstein:
1731136
EC號碼:
MDL號碼:
分類程式碼代碼:
12352103
PubChem物質ID:
NACRES:
NA.22
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品質等級

化驗

97%

形狀

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.)

儲存溫度

−20°C

SMILES 字串

C[Si](C)(C)I

InChI

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

InChI 密鑰

CSRZQMIRAZTJOY-UHFFFAOYSA-N

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一般說明

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。[1][1]

[1]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。[2]

應用

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。[3]
用于引入 TMS 基团,如 TMS 烯醇醚。[4]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。[5]
用于裂解醚、酯、氨基甲酸盐、缩酮和内酯的有效试剂。[6]

象形圖

FlameCorrosion

訊號詞

Danger

危險聲明

危險分類

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

安全危害

儲存類別代碼

3 - Flammable liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

-23.8 °F - closed cup

閃點(°C)

-31 °C - closed cup

個人防護裝備

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


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分析證明 (COA)

Lot/Batch Number

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存取文件庫

Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
Tetrahedron Letters, 35, 5445-5445 (1994)
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
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)

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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