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/418/501/product-dating-information-06-25-mk.pdf
238902
2-(Trimethylsilyl)ethoxymethyl chloride
technical grade
Synonym(s):
(2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-Cl, SEM-chloride
Select a Size
| Size/SKU | Availability | Price |
|---|---|---|
1 g | Available to ship TODAYfromMILWAUKEE | $64.30 |
5 g | Available to ship TODAYfromMILWAUKEE | $169.00 $126.75 |
25 g | Available to ship TODAYfromMILWAUKEE | $804.00 $603.00 |
100 g | Available to ship TODAYfromMILWAUKEE | $1,950.00 $1,462.50 |
About This Item
grade
technical grade
Quality Segment
form
liquid
reaction suitability
reactivity: alcohol reactive, reactivity: amine reactive, reagent type: protection reagent
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
General description
Application
Features and Benefits
Disclaimer
1 of 1
This Item | |||
|---|---|---|---|
| description technical grade | description for electrochemical analysis, ≥99.0% | description 97% | description 95% |
| reaction suitability reactivity: amine reactive, reagent type: protection reagent, reactivity: alcohol reactive | reaction suitability - | reaction suitability - | reaction suitability - |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 200 |
| storage temp. −20°C | storage temp. - | storage temp. 2-8°C | storage temp. 2-8°C |
| form liquid | form crystals | form liquid | form liquid |
| density 0.942 g/mL at 25 °C (lit.) | density - | density 0.899 g/mL at 25 °C (lit.) | density 0.839 g/mL at 25 °C (lit.) |
| bp 170-172 °C (lit.), 57-59 °C/8 mmHg (lit.) | bp - | bp 162-163 °C/768 mmHg (lit.) | bp 62-63 °C/43 mmHg (lit.), 144-146 °C (lit.) |
Still not finding the right product?
Explore all of our products under 2-(Trimethylsilyl)ethoxymethyl chloride
Signal Word
Danger
Hazard Codes
Precautionary Statements
Hazard Classifications
Flam. Liq. 3 - Skin Corr. 1B
Storage Class
3 - Flammable liquids
WGK
WGK 3
Flash Point (°F)
114.8 °F - closed cup
Flash Point (°C)
46 °C - closed cup
PPE (personal protective equipment)
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
-
How can I determine the shelf life / expiration / retest date of this product?
1 answer-
Helpful?
-
-
How is shipping temperature determined? And how is it related to the product storage temperature?
1 answer-
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
Helpful?
-
-
Are SEM protected carboxylic acids like Product 238902 stable enough for chromatography?
1 answer-
SEM protected carboxylic acids are stable enough for chromatography but are readily deprotected without affecting either acid of base-sensitive functionalities.
Helpful?
-
-
Why is Product 238902 2-(Trimethylsilyl)ethoxymethyl chloride, such a popular hydroxyl protecting agent?
1 answer-
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.
Helpful?
-
-
What is the Department of Transportation shipping information for this product?
1 answer-
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.
Helpful?
-
-
What are the advantaged of using Product 238902, 2-(Trimethylsilyl)ethoxymethyl chloride, in carbohydrate chemistry?
1 answer-
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.
Helpful?
-
-
How is the SEM group, Product 238902, 2-(Trimethylsilyl)ethoxymethyl chloride, used in the protection of nitrogen atoms in heterocyclic compounds?
1 answer-
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.
Helpful?
-