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tert-Butyldimethylsilyl chloride

tert-Butyldimethylsilyl chloride Structure
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
Molecular Weight:
150.72
MOL File:
18162-48-6.mol
MSDS File:
SDS
Modify Date:
2024/5/14 14:43:53
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tert-Butyldimethylsilyl chloride 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

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS05,GHS07,GHS08,GHS09
Signal word  Danger
Hazard statements  H225-H304-H314-H336-H361d-H373-H411
Precautionary statements  P210-P280-P301+P310+P331-P301+P330+P331-P303+P361+P353-P305+P351+P338+P310
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,
NFPA 704
2
3 0

tert-Butyldimethylsilyl chloride price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 8.18642 tert-Butyldimethylchlorosilane for synthesis 18162-48-6 10G ₹5320 2022-06-14 Buy
Sigma-Aldrich(India) 8.18642 tert-Butyldimethylchlorosilane for synthesis 18162-48-6 25G ₹10460 2022-06-14 Buy
Sigma-Aldrich(India) 8.18642 tert-Butyldimethylchlorosilane for synthesis 18162-48-6 100G ₹12380 2022-06-14 Buy
Sigma-Aldrich(India) 473464 tert-Butylchlorodimethylsilane solution 50?wt. % in toluene 18162-48-6 50G ₹11006.78 2022-06-14 Buy
Sigma-Aldrich(India) 473464 tert-Butylchlorodimethylsilane solution 50?wt. % in toluene 18162-48-6 100G ₹23516.1 2022-06-14 Buy
Product number Packaging Price Buy
8.18642 10G ₹5320 Buy
8.18642 25G ₹10460 Buy
8.18642 100G ₹12380 Buy
473464 50G ₹11006.78 Buy
473464 100G ₹23516.1 Buy

tert-Butyldimethylsilyl chloride Chemical Properties,Uses,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.

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
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.

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 BIS(T-BUTYLDIMETHYLSILOXY)ETHANE Tert-Butyl N-(3-[(Tert-Butyldimethylsilyl)Oxy]-2-Oxopropyl)Carbamate 5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL (3-BROMOPROPOXY)-TERT-BUTYLDIMETHYLSILANE
2-(tert-Butyldimethylsilyl)thiophene
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tert-Butyldimethylsilyl chloride Spectrum

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18162-48-6(tert-Butyldimethylsilyl chloride)Related Search:

Pivaloyl chloride Chloro(chloromethyl)dimethylsilane Ammonium chloride Potassium chloride Dimethyl phthalate
Dimethyl sulfate DI-TERT-BUTYLDICHLOROSILANE Dimethyl sulfide Dimethyl sulfoxide ETHANE
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SILANE TBM2 T-BUTYLDIMENHYLSILYL CHLORIDE t-butyl dimethyl chlorsilane TBUME2SI-CL TERT-BUTYLDIMETHYLSILYL CHLORIDE T-butyldimethylsilyl chloride*crystalline 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 tert-Butylchlorodimethylsilane1.0M solution in dichloromethaneAcroSeal§3 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 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 Silane, t-butylchlorodimethyl- tbdmschloride TERT-BUTYLDIMETHYLSILYL CHLORIDE, 1.0M S OLUTION IN DICHLOROMETHANE TERT-BUTYLDIMETHYLCHLOROSILANE SOLUTION, ~1 M IN THF TERT-BUTYLDIMETHYLSILYL CHLORIDE, 1.0M S OLUTION IN TETRAHYDROFURAN TERT-BUTYLDIMETHYLCHLOROSILANE 98+% TERT-BUTYLL DIMETHYLCHOROSILANE t-butylchlorodimethyl-silane T-BUTYLDIMETHYLCHLOROSILANE, 2.85M IN TOLUENE T-BUTYLDIMETHYLCHLOROSILANE, 3M IN THF T-BUTYLDIMETHYLCHLOROSILANE, 1.0M IN METHYLENE CHLORIDE tert-Butyldimethylchlorosilane ,99% tert-Butylchlorodimethylsilane solution,tert-Butyldimethylchlorosilane, tert-Butyldimethylsilyl chloride, TBDMSCl solution tert-Butyldimethylsilychloride tert-Butyldimethylsilyl chloride,tert-Butyl(chloro)dimethylsilane, tert-Butyldimethylchlorosilane, TBDMSCl tert-Butyldimethylsilyl chloride solution,tert-Butylchlorodimethylsilane solution, tert-Butyldimethylchlorosilane, tert-Butyldimethylsilyl chloride, TBDMSCl solution