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190500

Sigma-Aldrich

tert-Butyldimethylsilyl chloride

reagent grade, 97%

Synonym(s):
TBDMSCl, tert-Butyldimethylchlorosilane, tert-Butyl(chloro)dimethylsilane
Linear Formula:
(CH3)3CSi(CH3)2Cl
CAS Number:
Molecular Weight:
150.72
Beilstein:
505999
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

reagent grade

assay

97%

bp

125 °C (lit.)

mp

86-89 °C (lit.)

SMILES string

CC(C)(C)[Si](C)(C)Cl

InChI

1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3

InChI key

BCNZYOJHNLTNEZ-UHFFFAOYSA-N

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Application

tert-Butyldimethylsilyl chloride (TBDMSCl) is an organosilicon compound that can be used as a versatile protecting reagent for alcohols, amines, amides, and various carboxylic acids. It is also used in the preparation of isoxazoline N-oxides from α-bromonitroalkanes and olefins. TBDMSCl is used as a precursor that forms a silicon substrate for Ag/ZnO/graphene-based nanocomposites to form effective photocatalytic system for hydrogen production.

Packaging

5, 25, 100, 500 g in glass bottle
1 kg in glass bottle

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1 - Flam. Sol. 1 - Skin Corr. 1A

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 2

Flash Point(F)

71.6 °F

Flash Point(C)

22 °C

Certificate of Analysis

Certificate of Origin

  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. 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. 

  4. 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.

  5. 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.

  6. Is Product 190500, tert-Butyldimethylsilyl chloride, packaged under inert atmosphere?

    Since this product is readily hydrolyzed, we do package this product under nitrogen atmosphere.

  7. How else can Product 190500, tert-Butyldimethylsilyl chloride, silylating reagent be used?

    This silylating agent can be used to determine conformation of cholesterol derivatives.

  8. 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.

  9. 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. 

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

    Ask a Scientist here.

Greene, T.W. Wuts, P.G.M.
Protective Groups in Organic Synthesis (1991)
New approach for the synthesis of isoxazoline-N-oxides
Kunetsky RA, et al.
Organic Letters, 5(25) (2003)
Journal of the Chemical Society. Chemical Communications, 125-125 (1993)
Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)
Firouzabadi H, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 166(1) (2000)
Ag/ZnO/graphene-tert-butyldimethylsilyl chloride hybrid nanocomposite as highly efficient catalyst for hydrogen production
Attia YA
Materials Express, 6(3) (2016)

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