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A13064 tert-Butyldimethylchlorosilane, 97%

Numéro de CAS
tert-Butyldimethylsilyl chloride

Stock No. Conditionnement Prix ($) Quantité Disponibilité
A13064-06 5g 26,50
A13064-14 25g 80,80
A13064-22 100g 228,00
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tert-Butyldimethylchlorosilane, 97%


Propriétés chimiques

Poids moleculaire
Point de fusion
Point d'ébullition
Point d'éclair
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Soluble in chloroform and ethyl acetate. Insoluble in water.


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.


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

Références bibliographiques

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 90o; many other groups unaffected: Tetrahedron Lett., 38, 495 (1997). See also Pyridinium p-toluenesulfonate, A15708, and Triethyl­amine 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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H228-H314-H318

Flammable solid. Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P210-P280-P305+P351+P338-P309-P310a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER/doctor

Autres références

Classe de danger
Groupe d'emballage
Code tarifaire harmonisé


  • A10221

    Imidazole, 99%
  • A10588

    Tetra-n-butylammonium fluoride, 1M soln. in THF
  • A10973

    N,N'-Dicyclohexylcarbodiimide, 99%
  • A14708

    Di-tert-butyl dicarbonate, 97+%
  • L13303

    Tetra-n-butylammonium fluoride trihydrate, 98%

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