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tert-Butyldimethylsilyl chloride

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tert-Butyldimethylsilyl chloride Basic information

Product Name:
tert-Butyldimethylsilyl chloride
Synonyms:
  • t-butylchlorodimethyl-silan
  • SILANE TBM2
  • SILANE, CHLORO(1,1-DIMETHYLETHYL)DIMETHYL-
  • T-BUTYLDIMENHYLSILYL CHLORIDE
  • t-butyl dimethyl chlorsilane
  • T-BUTYLDIMETHYLCHLOROSILANE
  • T-BUTYLDIMETHYLSILYL CHLORIDE
  • TBDMSCI
CAS:
18162-48-6
MF:
C6H15ClSi
MW:
150.72
EINECS:
242-042-4
Product Categories:
  • Pharmaceutical intermediates
  • Organics
  • Alkyldimethylsilylation (GC Derivatizing Reagents)
  • organosilicon compounds
  • Miscellaneous Reagents
  • pharma material
  • FINE Chemical & INTERMEDIATES
  • blocks
  • BuildingBlocks
  • Coupling Reagent
  • N-Protecting Reagents
  • Protecting and Derivatizing Reagents
  • Protection and Derivatization
  • Silicon-Based
  • Analytical Chemistry
  • Biochemistry
  • GC Derivatizing Reagents
  • Monochlorosilanes
  • Nucleosides, Nucleotides & Related Reagents
  • Protecting Agents for Hydroxyl and Amino Groups
  • Protecting Agents, Phosphorylating Agents & Condensing Agents
  • Protection & Derivatization Reagents (for Synthesis)
  • Reagents for Oligosaccharide Synthesis
  • Si (Classes of Silicon Compounds)
  • Si-Cl Compounds
  • Silicon Compounds (for Synthesis)
  • Blocking Agents
  • Chloro Silanes
  • Protective Agents
  • Silylating Agents
  • Silylation (GC Derivatizing Reagents)
  • Synthetic Organic Chemistry
  • bc0001
Mol File:
18162-48-6.mol
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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
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 
white solid
Specific Gravity
1.225
color 
white
Water Solubility 
Soluble in chloroform and ethyl acetate. Insoluble in water.
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
Sensitive 
Moisture Sensitive
BRN 
505999
Exposure limits
ACGIH: 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)
InChIKey
BCNZYOJHNLTNEZ-UHFFFAOYSA-N
LogP
2.5 at 20℃
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)
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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
Toxicity
mouse,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

  • Language:English Provider:TBDMCS
  • Language:English Provider:SigmaAldrich
  • Language:English Provider:ACROS
  • Language:English Provider:ALFA
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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-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) 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%.

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.

Application

Tert-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.

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.

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.

Flammability and Explosibility

Flammable

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.]

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