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238902

Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl chloride

technical grade

Synonym(s):

(2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-Cl, SEM-chloride

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1 G
€42.10
5 G
€142.00
25 G
€667.00
100 G
€1,880.00

€42.10

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1 G
€42.10
5 G
€142.00
25 G
€667.00
100 G
€1,880.00

About This Item

Linear Formula:
(CH3)3SiCH2CH2OCH2Cl
CAS Number:
76513-69-4
Molecular Weight:
166.72
Beilstein:
3587289
EC Number:
278-483-4
MDL number:
MFCD00009919
UNSPSC Code:
12352101
PubChem Substance ID:
24854351
NACRES:
NA.22
form:
liquid

€42.10

In StockDetails

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grade

technical grade

Quality Level

100

form

liquid

refractive index

n20/D 1.435 (lit.)

bp

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

density

0.942 g/mL at 25 °C (lit.)

functional group

chloro
ether

storage temp.

−20°C

SMILES string

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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General description

Learn More at the Professor and Product Portal of Professor Bruce Lipshutz.

Application

Phenol protecting group in the synthesis of laterifluorones.[1]
Used to prepare a SEM-ether which was, in turn, removed with BBr3 and cyclized to a benzo-oxapane.[2]

Features and Benefits

Convenient hydroxyl-protecting reagent. SEM-ethers are stable over a wide pH range, and can be selectively cleaved with fluoride ion under mild aprotic conditions.[3][4]

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

114.8 °F - closed cup

Flash Point(C)

46 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL5454
BCCL4773
BCCM0587
BCCK9919
BCCL2943

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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, 36, 1683-1683 (1995)
The Journal of Organic Chemistry, 55, 5180-5180 (1990)
Tetrahedron Letters, 47, 5909-5909 (2006)

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Lipshutz Group – Professor Product Portal

Designer surfactants enable diverse transformations like Suzuki-Miyaura, Olefin Metathesis, and 1,4-Addition to Enones in water by Prof. Bruce Lipshutz.

Questions

1–7 of 7 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. How is the SEM group, Product 238902, 2-(Trimethylsilyl)ethoxymethyl chloride, used in the protection of nitrogen atoms in heterocyclic compounds?

    1 answer

    1. 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.

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

    1 answer

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

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

    1 answer

    1. 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.

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

    1 answer

    1. 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.

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