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190500 Aldrich

tert-Butyldimethylsilyl chloride

reagent grade, 97%

Synonym: tert-Butyl(chloro)dimethylsilane, tert-Butyldimethylchlorosilane, TBDMSCl

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Properties

Related Categories Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents More...
grade   reagent grade
InChI Key   BCNZYOJHNLTNEZ-UHFFFAOYSA-N
assay   97%
bp   125 °C(lit.)
mp   86-89 °C(lit.)

Description

Frequently Asked Questions

Frequently Asked Questions are available for this Product.

Packaging

1 kg in glass bottle

5, 25, 100, 500 g in glass bottle

Application

Versatile protecting reagent for amines, amides, and especially alcohols, among others. Can be selectively removed in the presence of a t-BuPh2Si-protected alcohol.
Used in a preparatrion of isoxazoline N-oxides from α-bromonitroalkanes.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2925 8(4.1) / PGII
WGK Germany 
2
RTECS 
VV2000000
Flash Point(F) 
71.6 °F
Flash Point(C) 
22 °C

Frequently Asked Questions

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. These documents are located on the product detail page under Useful Links & Tools. Click on the following link to search for a Certificate of Analysis. Please click the following link to see the details on our Product Dating Information.
How do I get lot-specific information or a Certificate of Analysis?
A Certificate of Analysis is available by lot number and can be obtained through our Advanced Search Option: http://www.sigmaaldrich.com/catalog/AdvancedSearchPage.do
What is the solubility of Product 190500, tert-Butyldimethylsilyl chloride?
It is soluble in organic solvents such as chloroform, toluene, tetrahydrofuran (THF), and dichloromethane.  It reacts with water. 
What types of compounds can Product 190500, tert-Butyldimethylsilyl chloride, be used as a protecting reagent for?
This product is a versatile protecting reagent for amines, amides, and especially alcohols.
How can Product 190500, tert-Butyldimethylsilyl chloride, be used as a silylating reagent?
When this compound was initially used as a silylation agent, it was found by E. J. Corey (J. Am. Chem. Soc. 1972, 94, 6192) to react very slowly and to give unsatisfactory yields with alcohols. Even forcing silylation techniques (excess silyl chloride, dry pyridine, elevated temperatures) were not successful. The use of 2.5 eq. imidazole as catalyst with 1.2 eq. of tert-butyldimethylsilyl chloride and dimethylformamide as solvent proved to be effective, and resulted in the mild conversion of various alcohols to tert-butyldimethylsilyl ethers in high yield.
Is Product 190500, tert-Butyldimethylsilyl chloride, packaged under inert atmosphere?
Since this product is readily hydrolyzed, we do package this product under nitrogen atmosphere.
How else can Product 190500, tert-Butyldimethylsilyl chloride, silylating reagent be used?
This silylating agent can be used to determine conformation of cholesterol derivatives.
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. 
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, or search here. 
My question is not addressed here, how can I contact Technical Service for assistance?
Use the option to the right to "Ask a Question" by email of a Technical Service Scientist.
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Protocols & Articles

Articles

Activating Reagents and Protecting Groups

The use of activating agents and protecting groups in organic synthesis is necessary to prevent unwanted side reactions from occurring when using other common reagents such as oxidizing or reducing a...
Chemfiles Volume 1 Article 3
Keywords: Organic synthesis

Peer-Reviewed Papers
15

References

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