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190500

Sigma-Aldrich

tert-Butyldimethylsilyl chloride

reagent grade, 97%

Synonym(s):

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

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About This Item

Linear Formula:
(CH3)3CSi(CH3)2Cl
CAS Number:
18162-48-6
Molecular Weight:
150.72
Beilstein:
505999
EC Number:
242-042-4
MDL number:
MFCD00000501
UNSPSC Code:
12352103
PubChem Substance ID:
24851442
NACRES:
NA.22
Pricing and availability is not currently available.

grade

reagent grade

Quality Level

200

Assay

97%

form

solid

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.[1][2] It is also used in the preparation of isoxazoline N-oxides from α-bromonitroalkanes and olefins.[3] 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.[4]

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Product No.
Description
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19905

tert-Butyl(chloro)dimethylsilane, ≥95.0% (GC)

394882

N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide, >97%

375934

N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide with 1% tert-Butyldimethylchlorosilane, ≥95%

473464

tert-Butylchlorodimethylsilane solution, 50 wt. % in toluene

384429

tert-Butyldimethylsilyl chloride solution, 1.0 M in methylene chloride

372951

tert-Butyldimethylsilyl chloride solution, 1.0 M in THF

226149

tert-Butyldimethylsilyl trifluoromethanesulfonate, reagent grade, 98%

250236

1-(tert-Butyldimethylsilyl)imidazole, ≥95%

33092-U

tert-Butyldimethylsilylimidazole solution, TBDMSIM in DMF, pkg of 10 × 1 mL

06735

tert-Butyldimethylsilyl chloride, for GC derivatization, LiChropur™, ≥99.0% (GC)

56563

tert-Butyldimethylsilyl trifluoromethanesulfonate, for GC derivatization, LiChropur™, ≥98.0% (T)

77626

N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide, for GC derivatization, LiChropur™, ≥98.0% (GC)

00942

N-tert-Butyldimethylsilyl-N-methyltrifluoroacetamide with 1% tert-Butyldimethylchlorosilane, for GC derivatization, LiChropur™, ≥95.0% (GC)

44795

N,O-Bis(tert-butyldimethylsilyl)acetamide, for GC derivatization, LiChropur™, ≥98.0% (GC)

901741

Bis(triphenyl-λ5-phosphanylidene)ammonium hydrogendifluoride

Signal Word

Danger

Hazard Statements

H228,H314,H411

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 - closed cup

Flash Point(C)

22 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
STBL1946
STBL3012
STBL2764
STBL1529
STBK0725

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New approach for the synthesis of isoxazoline-N-oxides
Kunetsky RA, et al.
Organic Letters, 5(25) (2003)
Greene, T.W. Wuts, P.G.M.
Protective Groups in Organic Synthesis (1991)
Roman A Kunetsky et al.
Organic letters, 5(25), 4907-4909 (2003-12-05)
A strategy for the synthesis of isoxazoline-N-oxides (cyclic five-membered nitronates) from primary nitro compounds and olefins is described. The key step of the process involves 1,3-dipolar cycloaddition of corresponding 1-bromosilyl nitronates with alkenes. [reaction: see text]
Ag/ZnO/graphene-tert-butyldimethylsilyl chloride hybrid nanocomposite as highly efficient catalyst for hydrogen production
Attia YA
Materials Express, 6(3) (2016)
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)
View All Related Papers

Questions

1–8 of 8 Questions  

  1. 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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  2. 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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  3. How else can Product 190500, tert-Butyldimethylsilyl chloride, silylating reagent be used?

    1 answer

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

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  4. What types of compounds can Product 190500, tert-Butyldimethylsilyl chloride, be used as a protecting reagent for?

    1 answer

    1. This product is a versatile protecting reagent for amines, amides, and especially alcohols.

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  5. How can Product 190500, tert-Butyldimethylsilyl chloride, be used as a silylating reagent?

    1 answer

    1. 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.

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

    1 answer

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

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  7. 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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  8. What is the solubility of Product 190500, tert-Butyldimethylsilyl chloride?

    1 answer

    1. It is soluble in organic solvents such as chloroform, toluene, tetrahydrofuran (THF), and dichloromethane.  It reacts with water.

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