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

A13064 tert-Butyldimethylchlorosilane, 97%

CAS-Nummer
18162-48-6
Synonyme
tert-Butylchlorodimethylsilane
tert-Butyldimethylsilyl chloride

Größe Preis ($) Menge Verfügbarkeit
5g 23,50
25g 71,12
100g 201,15
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

tert-Butyldimethylchlorosilane, 97%

MDL
MFCD00000501
EINECS
242-042-4

Chemische Eigenschaften

Formel
C6H15ClSi
Molmasse
150.73
Schmelzpunkt
86-89°
Siedepunkt
124-126°
Flammpunkt
22°(72°F)
Dichte
0.81
Sensitivität
Moisture Sensitive
Löslichkeit
Soluble in chloroform and ethyl acetate. Insoluble in water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H228-H314-H318

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

Sicherheitshinweise: 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.

Weitere Referenzen

Beilstein
505999
Gefahrenklasse
4.1
Verpackungsgruppe
II
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
VV2000000

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