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190500

Sigma-Aldrich

tert-Butyldimethylsilyl chloride

reagent grade, 97%

Sinónimos:

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

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5 G
$60.00
25 G
$112.00
100 G
$216.00
500 G
$1,000.00
1 KG
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5 G
$60.00
25 G
$112.00
100 G
$216.00
500 G
$1,000.00
1 KG
Preguntar

About This Item

Fórmula lineal:
(CH3)3CSi(CH3)2Cl
Número de CAS:
18162-48-6
Peso molecular:
150.72
Beilstein:
505999
Número CE:
242-042-4
Número MDL:
MFCD00000501
Código UNSPSC:
12352103
ID de la sustancia en PubChem:
24851442
NACRES:
NA.22

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grado

reagent grade

Nivel de calidad

200

Ensayo

97%

Formulario

solid

bp

125 °C (lit.)

mp

86-89 °C (lit.)

cadena SMILES

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

InChI

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

Clave InChI

BCNZYOJHNLTNEZ-UHFFFAOYSA-N

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Aplicación

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

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tert-Butyldimethylsilyl trifluoromethanesulfonate, reagent grade, 98%

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

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

77626

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00942

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

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

901741

Bis(triphenyl-λ5-phosphanylidene)ammonium hydrogendifluoride

Palabra de señalización

Danger

Frases de peligro

H228,H314,H411

Clasificaciones de peligro

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

Código de clase de almacenamiento

4.1B - Flammable solid hazardous materials

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

71.6 °F - closed cup

Punto de inflamabilidad (°C)

22 °C - closed cup

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Certificados de análisis (COA)

Lot/Batch Number
STBL1946
SDBB2849
STBL3012
STBL2764
STBL1529

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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]
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)
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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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. 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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  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.

      Helpful?

  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. 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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  7. 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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  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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