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tert-Butyldimethylchlorosilane, 97%

Name: tert-Butyldimethylchlorosilane, 97%
SKU: A13064.14
Price: 147.00 EUR

CAS: 18162-48-6 | C6H15ClSi | 150.721 g/mol

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Catalog number A13064.14

also known as A13064-14

Price (EUR)

147,00

Each

Quantity:

25 g

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Price (EUR)

147,00

Each

Chemical Identifiers

CAS18162-48-6

IUPAC Nametert-butyl(chloro)dimethylsilane

Molecular FormulaC6H15ClSi

InChI KeyBCNZYOJHNLTNEZ-UHFFFAOYSA-N

SMILESCC(C)(C)[Si](C)(C)Cl

Specifications

Specification Sheet

Appearance (Color)Colorless to white

FormCrystals or powder or crystalline powder or lumps or fused solid

Assay (GC)≥96.0%

CommentSpecification differs for U.S. and non-U.S. material where indicated

Melting Point (clear melt)84.0-94.0°C (non-U.S. specification)

tert-Butyldimethylchlorosilane is used to protect hydroxyl group in organic synthesis. It finds application in the synthesis of prostaglandin. It is also used as an auxiliary material for hypolipaemics such as lovastatin and simvastatin. It plays an important role in the preparation of isoxazolines N-oxides from alpha-bromonitroalkanes. It acts as a versatile protecting reagent for amines, amides and alcohols.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
tert-Butyldimethylchlorosilane is used to protect hydroxyl group in organic synthesis. It finds application in the synthesis of prostaglandin. It is also used as an auxiliary material for hypolipaemics such as lovastatin and simvastatin. It plays an important role in the preparation of isoxazolines N-oxides from alpha-bromonitroalkanes. It acts as a versatile protecting reagent for amines, amides and alcohols.

Solubility
Soluble in chloroform and ethyl acetate. Insoluble in water.

Notes
Moisture sensitive. Store in cool place. Incompatible with bases, metals, oxidizing agents and alcohols.

RUO – Research Use Only

General References:

Reagent for silylation of hydroxyl functions (see Appendix 4), giving silyl ethers more stable to aqueous hydrolysis e.g. during work-up, than TMS. Various conditions have been used for the introduction of the group:
Imidazole in DMF: J. Am. Chem. Soc., 94, 6190 (1972); Et₃N - DMAP: Tetrahedron Lett., 99 (1979); Org. Synth. Coll., 9, 136 (1998); N-ethyldiisopropylamine: Tetrahedron Lett., 25, 227 (1984); 1,1,3,3-tetramethylguanidine: J. Org. Chem., 49, 4657 (1984); K₂CO₃ (phase-transfer): Synth. Commun., 11, 545 (1981); DBU - superior to imidazole for thiols, amines and carboxylic acids: Tetrahedron Lett., 26, 475 (1985).
Cleavage is generally effected with fluoride ion e.g. TBAF in an aprotic system: J. Am. Chem. Soc., 94, 6190 (1972), or KF with a phase-transfer catalyst: J. Am. Chem. Soc., 90, 4462, 4464 (1968); 96, 2250 (1974); J. Chem. Soc., Chem. Commun., 514 (1979).
Many other reagents have been used, including:
Acidic ion-exchange resin: Tetrahedron Lett., 21, 137 (1980); NBS in DMSO: Synthesis, 234 (1980); BF₃ etherate: Synth. Commun., 9, 295 (1979); FeCl₃ or SnCl₂ in acetonitrile: Synth. Commun., 20, 757 (1990); K 10 clay in aqueous methanol: J. Org. Chem. 61, 9026 (1996); DMSO-water at 90°; many other groups unaffected: Tetrahedron Lett., 38, 495 (1997). See also Pyridinium p-toluenesulfonate, A15708, and Triethyl amine trihydrofluoride, L14417.
Zhao, W.; Gnanou, Y.; Hadjichristidis, N. Organocatalysis by hydrogen-bonding: a new approach to controlled/living polymerization of alfa-amino acid N-carboxyanhydrides. Polym. Chem. 2015, 6 (34), 6193-6201.
Garcia, M.; Bequette, B. J.; Moyes, K. M. Hepatic metabolic response of Holstein cows in early and mid lactation is altered by nutrient supply and lipopolysaccharide in vitro. J. Dairy Sci. 2015, 98 (10), 7102-7114.