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tert-Butyldimethylsilyl chloride

Product Name
tert-Butyldimethylsilyl chloride
CAS No.
18162-48-6
Chemical Name
tert-Butyldimethylsilyl chloride
Synonyms
TBSCL;TBDMSCL;TERT-BUTYLCHLORODIMETHYLSILANE;T-BUTYLDIMETHYLSILYL CHLORIDE;TBDMSCI;TERT-BUTYLDIMETHYLCHLOROSILANE;tert-Butyldimethylsilyl;SILANE, CHLORO(1,1-DIMETHYLETHYL)DIMETHYL-;TBDMCl;T-BUTYLDIMETHYLCHLOROSILANE
CBNumber
CB3763003
Molecular Formula
C6H15ClSi
Formula Weight
150.72
MOL File
18162-48-6.mol
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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)
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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,
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.18642
Product name
tert-Butyldimethylchlorosilane
Purity
for synthesis
Packaging
25g
Price
$175
Updated
2024/03/01
Sigma-Aldrich
Product number
8.18642
Product name
tert-Butyldimethylchlorosilane
Purity
for synthesis
Packaging
100g
Price
$333
Updated
2024/03/01
Sigma-Aldrich
Product number
06735
Product name
tert-Butyldimethylsilyl chloride
Purity
for GC derivatization, ≥99.0% (GC)
Packaging
10g
Price
$109
Updated
2022/05/15
TCI Chemical
Product number
B0995
Product name
tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
Purity
>98.0%(GC)
Packaging
5g
Price
$25
Updated
2024/03/01
TCI Chemical
Product number
B0995
Product name
tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
Purity
>98.0%(GC)
Packaging
25g
Price
$74
Updated
2024/03/01
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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.]

tert-Butyldimethylsilyl chloride Preparation Products And Raw materials

Raw materials

tert-Butyllithium Pentane Dichlorodimethylsilane

Preparation Products

beta-Methyl vinyl phosphate (MAP) (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one 2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside Calcipotriene Trifluoromethanesulfonic acid tert-butyldimethylsilyl ester 2-CYANOPYRIDINE-4-CARBOXALDEHYDE 4-Mercaptophenylboronic acid Montelukast 4-(HYDROXYMETHYL)PICOLINITRILE 5-(AMINOMETHYL)-1-METHYLPYRROLIDIN-2-ONE Simvastatin
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View Lastest Price from tert-Butyldimethylsilyl chloride manufacturers

Jinan Finer Chemical Co., Ltd
Product
tert-Butyldimethylsilyl chloride 18162-48-6
Price
US $5.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500mt/year
Release date
2023-08-31
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
tert-Butyldimethylsilyl chloride 18162-48-6
Price
US $55.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-06-03
hebei hongtan Biotechnology Co., Ltd
Product
tert-Butyldimethylsilyl chloride 18162-48-6
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000kg
Release date
2024-05-14

18162-48-6, tert-Butyldimethylsilyl chlorideRelated Search:

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

  • t-butylchlorodimethyl-silan
  • SILANE TBM2
  • SILANE, CHLORO(1,1-DIMETHYLETHYL)DIMETHYL-
  • T-BUTYLDIMENHYLSILYL CHLORIDE
  • t-butyl dimethyl chlorsilane
  • T-BUTYLDIMETHYLCHLOROSILANE
  • T-BUTYLDIMETHYLSILYL CHLORIDE
  • TBDMSCI
  • TBDMSCL
  • TBDMCl
  • TBDMCS
  • TBUME2SI-CL
  • TBSCL
  • TERT-BUTYLDIMETHYLSILYL CHLORIDE
  • TERT-BUTYLDIMETHYLCHLOROSILANE
  • TERT-BUTYLCHLORODIMETHYLSILANE
  • T-butyldimethylsilyl chloride*crystalline
  • tert-Butyldimethylsilyl chloride~TBDMSCl~TBSCl
  • tert-Butyl Dimethylchlorosilane (TBDMSCl)
  • chloro-dimethyl-tert-butyl-silane
  • Tert-butyldimethylsilyl chloride, TBSCI
  • TERT-BUTYLDIMETHYLSILYL CHLORIDE, 50 WT. % SOLUTION IN TOLUENE
  • TERT-BUTYLDIMETHYLCHLOROSILANE SOLUTION, ~50% IN TOLUENE
  • TERT-BUTYLDIMETHYLCHLOROSILANE SOLUTION, 50% IN METHYL. CHL.
  • tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
  • tert-Butyldimethylchlorosilane, 97+%
  • tert-Butyldimethylchlorosilane, tert-Butyldimethylsilyl chloride, TBDMSCl solution
  • tert-Butyldimethylchlorosilane, tert-Butyldimethylsilyl chloride, TBDMSCl
  • tert-Butyl(chloro)dimethylsilane, tert-Butyldimethylchlorosilane, TBDMSCl
  • t-BUTYLDIMETHYLCHLOROSILANE, 2.85M in toluene, 49-50% solution
  • t-BUTYLDIMETHYLCHLOROSILANE, 3M in tetrahydrofuran
  • tert-Butyldimethylchlorosilane, tert-Butyldimethylsilyl chloride, Silane TBM2-Tol Sol., TBDMSCl solution
  • tert-Butyldimethylchlorosilane, tert-Butyldimethylsilyl chloride, Silane TBM2, TBDMSCl
  • t-Butyldimethylchlorosilane, min. 97%
  • tert-Butylchlorodimethylsilane1.0M solution in dichloromethaneAcroSeal§3
  • tert-Butylchlorodimethylsilane,98%
  • tert-Butyldimethylsilyl
  • t-Butyldimethylchlorosilane,min.97%
  • TERT-BUTYLDIMETHYLCHLOROSILANE, 1.0 M IN METHYLENE CHLORIDE
  • 2.85M IN TOLUENE (CA. 49.5%)
  • TERT-BUTYLDIMETHYLCHLOROSILANE, 3M IN THF
  • tert-Butylchlorodimethylsilane, 1.0M solution in dichloromethane
  • tert-ButyldimethylchlorosilaneTBSCl
  • tert-BUTYLDIMETHYLCHLOROSILANE 98%
  • TERT-BUTYLDIMETHYLSILYL CHLORIDE (TBDMSCL)
  • Tert-Butyldimethylchlorosilane50%W/WInToluene
  • Tertbutyldimethylchlorosilane,ProtectiveReagent,
  • Tbdmscl(Tert-ButyldimethylsilylChloride)
  • Tert-ButyldimethylchlorosilaneTbms
  • TBSCl (Tert-butyldimethylsilyl chloride)
  • BDCS
  • BDCS SILYLATION REAGENT
  • CB2790
  • chloro(1,1-dimethylethyl)dimethyl-silan
  • chloro(1,1-dimethylethyl)dimethyl-Silane
  • chloro-tert-butyldimethyl-silan
  • Chloro-tert-butyldimethylsilane
  • Dimethyl-tert-butylchlorosilane