Tertiary Butyl Dimethyl Silyl Chloride

Product NameTertiary Butyl Dimethyl Silyl Chloride
CAS18162-48-6
MFC6H15ClSi
MW150.72
EINECS242-042-4
MOL File18162-48-6.mol

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
color	white
Specific Gravity	1.225
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)

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
F	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

Provider	Language
TBDMCS	English
SigmaAldrich	English
ACROS	English
ALFA	English

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.

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.

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%.

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.
Tert-butyldimethylsilyl chloride Reaction

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.

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.]