tert-Butyldimethylsilyl chloride Property

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)

Safety

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,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H304May be fatal if swallowed and enters airways

H314Causes severe skin burns and eye damage

H336May cause drowsiness or dizziness

H373May cause damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

tert-Butyldimethylsilyl chloride Chemical Properties,Usage,Production

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.]