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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.)
vapor pressure 60-710Pa at 25℃
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 white solid
color white
Specific Gravity1.225
Water Solubility Soluble in chloroform and ethyl acetate. Insoluble in water.
Hydrolytic Sensitivity7: reacts slowly with moisture/water
Sensitive Moisture Sensitive
BRN 505999
Exposure limitsACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)
LogP2.5 at 20℃
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
Hazard Note Flammable/Corrosive/Moisture Sensitive
HazardClass 4.1
PackingGroup III
HS Code 29310095
Toxicitymouse,LDLo,intraperitoneal,1gm/kg (1000mg/kg),IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE,Personal Communication from G.D. Stoner, Dept. of Community Medicine, School of Medicine, Univ. of California, La Jolla, CA 92037, May 25, 1975Vol. 27MAY1975,
MSDS Information
TBDMCS English
SigmaAldrich English
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ALFA English
tert-Butyldimethylsilyl chloride Usage And Synthesis
Chemical Propertiestert-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.
Usestert-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.
DefinitionChEBI: 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.
Preparationtert-butyldimethylsilyl chloride (TBSCI) was synthesized by the reaction of tert-butyllithium with dichlorodimethylsilane.
The pentane solution of dichlorodimethylsilane was cooled to 0°C, and the pentane solution of tert-butyllithium was added dropwise with stirring under nitrogen. The temperature was maintained at 0 °C, stirred for 1.5 h and then heated to 25 °C, and the reaction was continued for 48 h. Distillation, collect 125 ℃ (97.5kPa) fractions, stand to solidify, and obtain tert-butyldimethylsilyl chloride. Yield 70%.
ApplicationTert-butyldimethylsilyl chloride is a sterically hindered organosilicon protective agent, which is widely used in the synthesis of original drugs. It is used as a protective group for hydroxyl in the synthesis of ribonucleosides, and is also an oxidant and decyanide.
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.
Tert-butyldimethylsilyl chloride Reaction
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.
Reactionstert-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.
HazardModerately toxic.
Flammability and ExplosibilityFlammable
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
Pivaloyl chloride Chloro(chloromethyl)dimethylsilane Ammonium chloride Potassium chloride Dimethyl phthalate Dimethyl sulfate DI-TERT-BUTYLDICHLOROSILANE Dimethyl sulfide Dimethyl sulfoxide ETHANE Calcium chloride Choline chloride Dimethyl carbonate Dichlorodimethylsilane Dichloromethylvinylsilane Dichloromethylsilane Polyvinyl chloride Dimethyl ether Tertiary Butyl Dimethyl Silyl Chloride