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tert-Butyldimethylsilyl chloride

Basic information Introduction Safety Related Supplier
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
  • Flash point: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
  • Specific Gravity1.225
  • color Clear colorless
  • Water Solubility Soluble in chloroform and ethyl acetate. Insoluble in water.
  • Sensitive Moisture Sensitive
  • Hydrolytic Sensitivity7: reacts slowly with moisture/water
  • Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
  • BRN 505999
  • InChIKeyBCNZYOJHNLTNEZ-UHFFFAOYSA-N
  • CAS DataBase Reference18162-48-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceSilane, chloro(1,1-dimethylethyl)dimethyl-(18162-48-6)
  • EPA Substance Registry SystemSilane, chloro(1,1-dimethylethyl)dimethyl- (18162-48-6)
Safety Information
MSDS
tert-Butyldimethylsilyl chloride Usage And Synthesis
  • IntroductionTriethylchlorosilane is a clear, colourless to yellowish, pungent smelling, caustic and flammable liquid. It can be dissolved in non-protonating solvents without decomposition.
    It may be used as silylating agent for dervatization of primary and secondary alcohols etc.. Also it may be used to protect allylic esters as silylketene acetal which is ore stable but less volatile derivates than trimethylchlorosilane.
  • Chemical PropertiesWhite solid
  • Physical propertiesmp 86–89°C; bp 125°C.
  • Usest-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.

  • UsesUsed to protect alcohols during organic synthesis.
  • DefinitionChEBI: 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 ap lications.
  • HazardModerately toxic.
  • Purification MethodsFractionally 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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