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| | tert-Butyldimethylsilyl chloride Basic information |
| | tert-Butyldimethylsilyl chloride Chemical Properties |
| Melting point | 86-89 °C (lit.) | | Boiling point | 125 °C (lit.) | | density | 0.87 g/mL at 20 °C(lit.) | | refractive index | n20/D 1.46 | | Fp | 73 °F | | storage temp. | Store below +30°C. | | solubility | very sol nearly all common organic solvents such as
THF, methylene chloride, and DMF. | | form | Liquid | | color | Clear colorless | | Specific Gravity | 1.225 | | Water Solubility | Soluble in chloroform and ethyl acetate. Insoluble in water. | | Sensitive | Moisture Sensitive | | Hydrolytic Sensitivity | 7: reacts slowly with moisture/water | | BRN | 505999 | | InChIKey | BCNZYOJHNLTNEZ-UHFFFAOYSA-N | | CAS DataBase Reference | 18162-48-6(CAS DataBase Reference) | | NIST Chemistry Reference | Silane, chloro(1,1-dimethylethyl)dimethyl-(18162-48-6) | | EPA Substance Registry System | Silane, chloro(1,1-dimethylethyl)dimethyl- (18162-48-6) |
| | tert-Butyldimethylsilyl chloride Usage And Synthesis |
| Chemical Properties | tert-Butyldimethylsilyl chloride is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols.It is an organosilicon compound that can be used as a versatile protecting reagent for alcohols, amines, amides, and various carboxylic acids. | | Uses | tert-Butyldimethylsilyl Chloride is a chemical used to protect alcohols during organic synthesis. | | Uses | t-Butyldimethylchlorosilane is useful as an anion trapping reagent.
For example, TBDMSCl was found to be an efficient trap of
the lithio α-phenylthiocyclopropane anion.When dichlorothiophene
was treated with 2 equiv of n-butyllithium followed by
2 equiv of TBDMSCl the di-TBDMS-thiophene was isolated.
The lithium anions of primary (eq 1) and secondary (eq 2)
nitriles were trapped with TBDMSCl to give C,N-disilyl- and Nsilylketenimines
in excellent yields.
Silyl stannanes have been prepared by trapping tin anions with
TBDMSCl or other silyl chlorides. Alkynes treated with silyl stannanes
and catalytic tetrakis(triphenylphosphine)palladium(0) give
cis-silyl stannylalkenes in good yields.
| | Uses | 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. | | Preparation | tert-butyldimethylsilyl chloride (TBSCI, mp 86–89 °C) is expensive though it is readily prepared in high yield by the reaction of tert-butyllithium with dichlorodimethylsilane. | | Definition | ChEBI: Tert-butyldimethylsilyl chloride is a silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry applications. It has a role as a chromatographic reagent. | | Reactions | tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ethers:(Me3C)Me2SiCl + ROH → (Me3C)Me2SiOR + HCl
These silyl ethers hydrolyze much more slowly than the trimethylsilyl ethers. | | Hazard | Moderately toxic. | | Purification Methods | Fractionally distil it at atmospheric pressure. [Sommer & Tyler J Am Chem Soc 76 1030 1954, Corey & Venkateswarlu J Am Chem Soc 94 6190 1972, Beilstein 4 IV 4076.] |
| | tert-Butyldimethylsilyl chloride Preparation Products And Raw materials |
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