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Merck
CN

238902

Sigma-Aldrich

2-(三甲基硅烷基)乙氧甲基氯

technical grade

别名:

(2-氯甲氧基乙基)三甲基硅烷, SEM-Cl, SEM-氯化物, 氯甲基三甲基硅乙基醚

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About This Item

线性分子式:
(CH3)3SiCH2CH2OCH2Cl
CAS号:
分子量:
166.72
Beilstein:
3587289
EC 号:
MDL编号:
UNSPSC代码:
12352101
PubChem化学物质编号:
NACRES:
NA.22

等级

technical grade

质量水平

形式

liquid

折射率

n20/D 1.435 (lit.)

bp

170-172 °C (lit.)
57-59 °C/8 mmHg (lit.)

密度

0.942 g/mL at 25 °C (lit.)

储存温度

−20°C

SMILES字符串

C[Si](C)(C)CCOCCl

InChI

1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3

InChI key

BPXKZEMBEZGUAH-UHFFFAOYSA-N

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一般描述

在 Bruce Lipshutz 教授的教授和产品门户网站上了解更多信息。

应用

在 laterifluorone 的合成中作为苯酚保护基团。
用于制备 SEM-醚,SEM-醚又可被 BBr3 除去,并且发生环化反应生成 benzo-oxapane。

特点和优势

方便的羟基保护试剂。SEM-醚可在很宽的 pH 范围内稳定存在,在温和非质子条件下可被氟离子选择性裂解。

象形图

FlameCorrosion

警示用语:

Danger

危险声明

危险分类

Flam. Liq. 3 - Skin Corr. 1B

WGK

WGK 3

闪点(°F)

114.8 °F

闪点(°C)

46 °C

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)

输入产品批号来搜索 分析证书(COA) 。批号可以在产品标签上"批“ (Lot或Batch)字后找到。

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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. Why is Product 238902 2-(Trimethylsilyl)ethoxymethyl chloride, such a popular hydroxyl protecting agent?

    2-(Trimethylsilyl)ethoxymethyl chloride is widely used in the protection of alcohols because the SEM ethers are easily prepared.  They are stable to a number of synthetic transformations, and they are easily removed.

  4.  What are the advantaged of using Product 238902, 2-(Trimethylsilyl)ethoxymethyl chloride, in carbohydrate chemistry?

    In carbohydrate chemistry, the SEM group has shown distinct advantages over other groups such as the 2-methoxyethoxymethyl (MEM) group, because the SEM group is removed under milder acidic conditions. 

  5. Are SEM protected carboxylic acids like Product 238902 stable enough for chromatography?

    SEM protected carboxylic acids are stable enough for chromatography but are readily deprotected without affecting either acid of base-sensitive functionalities. 

  6. How is the SEM group, Product 238902, 2-(Trimethylsilyl)ethoxymethyl chloride, used in the protection of nitrogen atoms in heterocyclic compounds?

    In SEM protected indole, the aminal oxygen is used to direct lithiation to the 2-position.  A similar approach has been used for pyrroles and imidazoles.

  7. 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.

  8. 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. 

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

    Ask a Scientist here.

The Journal of Organic Chemistry, 55, 5180-5180 (1990)
Tetrahedron Letters, 36, 1683-1683 (1995)
K C Nicolaou et al.
Journal of the American Chemical Society, 126(17), 5493-5501 (2004-04-29)
The total synthesis of 1-O-methyllateriflorone (2) is described. The construction of the cage-like domain of the molecule involved a biomimetic Claisen/Diels-Alder cascade, whereas the novel spiroxalactone framework was generated by an intramolecular Michael reaction within precursor 16a involving the carboxylate
Tetrahedron Letters, 47, 5909-5909 (2006)

相关内容

Prof. Bruce Lipshutz and co-workers have developed designer surfactants to allow several classes of transformations (e.g. Suzuki-Miyaura, Olefin Metathesis, 1,4-Addition to Enones, etc.) to be performed in water.

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