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18162-48-6 - tert-Butyldimethylchlorosilane, 97% - tert-Butylchlorodimethylsilane - tert-Butyldimethylsilyl chloride - A13064 - Alfa Aesar

A13064 tert-Butyldimethylchlorosilane, 97%

Numéro CAS
18162-48-6
Synonymes
tert-Butylchlorodimethylsilane
tert-Butyldimethylsilyl chloride

Dimensions Prix ($) Quantité Disponibilité
5g 23,50
25g 71,12
100g 201,15
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tert-Butyldimethylchlorosilane, 97%

MDL
MFCD00000501
EINECS
242-042-4

Propriétés chimiques

Formule
C6H15ClSi
Poids formulaire
150.73
Point de fusion
86-89°
Point d'ébullition
124-126°
Point d'éclair
22°(72°F)
Densité
0.81
Sensibilité
Moisture Sensitive
Solubilité
Soluble in chloroform and ethyl acetate. Insoluble in water.

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.

Notes

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-P310

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 or doctor/physician.

Autres références

Beilstein
505999
Classe de danger
4.1
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
Yes
RTECS
VV2000000

Recommandé

  • A10221

    Imidazole, 99%
  • A10588

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  • A10973

    N,N'-Dicyclohexylcarbodiimide, 99%
  • A14708

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

    Tetra-n-butylammonium fluoride trihydrate, 98%

Consulté récemment

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