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

A13064 tert-Butyldimethylchlorosilane, 97%

Codice CAS
18162-48-6
Sinonimi
tert-Butylchlorodimethylsilane
tert-Butyldimethylsilyl chloride

Dimensioni Prezzo ($) Quantità Disponibilità
5g 26,50
25g 79,60
100g 225,00
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tert-Butyldimethylchlorosilane, 97%

MDL
MFCD00000501
EINECS
242-042-4

Proprietà chimiche

Formula
C6H15ClSi
Peso formula
150.73
Punto di fusione
86-89°
Punto di ebollizione
124-126°
Punto di infiammabilità
22°(72°F)
Densità
0.81
Sensibilità
Moisture Sensitive
Solubilità
Soluble in chloroform and ethyl acetate. Insoluble in water.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H228-H314-H318

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

Dichiarazioni precauzionali: 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

Altri riferimenti

Beilstein
505999
Classe di rischio
4.1
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
Yes
RTECS
VV2000000

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  • L13303

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