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190500

Sigma-Aldrich

tert-Butyldimethylsilyl chloride

reagent grade, 97%

Synonyme(s) :

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

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About This Item

Formule linéaire :
(CH3)3CSi(CH3)2Cl
Numéro CAS:
18162-48-6
Poids moléculaire :
150.72
Beilstein:
505999
Numéro CE :
242-042-4
Numéro MDL:
MFCD00000501
Code UNSPSC :
12352103
ID de substance PubChem :
24851442
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Qualité

reagent grade

Niveau de qualité

200

Essai

97%

Forme

solid

pb

125 °C (lit.)

Pf

86-89 °C (lit.)

Chaîne SMILES 

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

InChI

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

Clé InChI

BCNZYOJHNLTNEZ-UHFFFAOYSA-N

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Catégories apparentées

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]

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

19905

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

394882

N-tert-butyldiméthylsilyl-N-méthyltrifluoroacétamide, >97%

375934

N-tert-butyldiméthylsilyl-N-méthyltrifluoroacétamide avec 1 % de tert-butyldiméthylchlorosilane, ≥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-Butyldiméthylsilyl)imidazole, ≥95%

33092-U

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

06735

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

56563

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

77626

N-tert-butyldiméthylsilyl-N-méthyltrifluoroacétamide, derivatization grade (GC derivatization), LiChropur™, ≥98.0% (GC)

00942

N-tert-butyldiméthylsilyl-N-méthyltrifluoroacétamide avec 1 % de tert-butyldiméthylchlorosilane, LiChropur™, ≥95.0% (GC)

44795

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

901741

Bis(triphenyl-λ5-phosphanylidene)ammonium hydrogendifluoride

Pictogrammes

FlameCorrosionEnvironment
GHS02,GHS05,GHS09

Mention d'avertissement

Danger

Mentions de danger

H228,H314,H411

Classification des risques

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

Code de la classe de stockage

4.1B - Flammable solid hazardous materials

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

71.6 °F - closed cup

Point d'éclair (°C)

22 °C - closed cup

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Certificats d'analyse (COA)

Lot/Batch Number
STBL1946
SDBB2849
STBL3012
STBL2764
STBL1529

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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]
Journal of the Chemical Society. Chemical Communications, 125-125 (1993)
Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups, 1999
Makino T and Toyota S
Bulletin of the Chemical Society of Japan, 78(5), 917-928 (2005)
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Questions

1–8 sur 8 questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 réponse

    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 réponse

    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. What is the Department of Transportation shipping information for this product?

    1 réponse

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

    1 réponse

    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 réponse

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

    1 réponse

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

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

    1 réponse

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

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

    1 réponse

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

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