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

A13064 tert-Butyldimethylchlorosilane, 97%

Número CAS
18162-48-6
Nombre Alternativo
tert-Butylchlorodimethylsilane
tert-Butyldimethylsilyl chloride

Tamaño Precio ($) Cantidad Disponibilidad
5g 23,50
25g 71,12
100g 201,15
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

tert-Butyldimethylchlorosilane, 97%

MDL
MFCD00000501
EINECS
242-042-4

Propiedades químicas

Fórmula
C6H15ClSi
Peso molecular
150.73
Punto de fusión
86-89°
Punto de ebullición
124-126°
Punto de inflamabilidad
22°(72°F)
Densidad
0.81
Sensibilidad
Moisture Sensitive
Solubilidad
Soluble in chloroform and ethyl acetate. Insoluble in water.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H228-H314-H318

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

Indicaciones de precaución: 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.

Otras referencias

Beilstein
505999
Clase de peligro
4.1
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2931.90
TSCA
Yes
RTECS
VV2000000

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