tert-Butyldimethylchlorosilane, 97%

Description

Chemical Properties

· Formula : C₆H₁₅ClSi
· Formula weight : 150.73
· Melting Point : 86-89°
· Boiling Point : 124-126°
· Flash point : 22°(72°F)
· Density : 0.81
· Sensitivity : Moisture Sensitive. Ambient temperatures.
· Form : Crystals
· Solubility : Soluble in chloroform and ethyl acetate. Insoluble in water.

Literature References
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.

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.

Other References:
· Beilstein: 505999
· UN#: UN2921

GHS Hazard and Precautionary Statements
Hazard Statements : H228-H314-H318
Flammable solid.Causes severe skin burns and eye damage.Causes serious eye damage.

Precautionary Statements : 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.

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위험 및 안전 코드
위험 문구 : 11-34
Highly flammable.Causes burns.

안전 문구 : 16-26-36/37/39-45
Keep away from sources of ignition - No smoking.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.Wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).

· TSCA : 예
· RTECS : VV2000000