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    tert-Butyldimethylsilyl chloride

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    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 Gravity1.225
    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
    Hazard Codes C,F,T,Xn
    Risk Statements 22-35-40-34-10-19-11-67-65-63-48/20-20/21/22-45-23/24/25-37-36/37/38
    Safety Statements 26-36/37/39-46-62-45-25-16-28-27-33-29-53-36/37
    RIDADR UN 2925 4.1/PG 2
    WGK Germany 2
    RTECS VV2000000
    10-21
    Hazard Note Flammable/Corrosive/Moisture Sensitive
    TSCA Yes
    HazardClass 4.1
    PackingGroup III
    HS Code 29310095
    MSDS Information
    ProviderLanguage
    TBDMCS English
    SigmaAldrich English
    ACROS English
    ALFA English
    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.]
    Tag:tert-Butyldimethylsilyl chloride(18162-48-6) Related Product Information
    tert-Butylchlorodiphenylsilane 2-Chloro-2-methylpropane Triethylsilane TERT-BUTYL VINYL ETHER Butylated hydroxyanisole Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester TERT-BUTYLDIMETHYL(2-PROPYNYLOXY)SILANE TERT-BUTYLDIMETHYLSILYL (S)-(-)-GLYCIDY& Fattyalkyl dimethyl amine Pivaloyl chloride Chloro(chloromethyl)dimethylsilane Ammonium chloride Potassium chloride Dimethyl phthalate Dimethyl sulfate DI-TERT-BUTYLDICHLOROSILANE Dimethyl sulfide Dimethyl sulfoxide