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
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.
N-Bromosuccinimide Price
- Product number
- 8.18642
- Product name
- tert-Butyldimethylchlorosilane
- Purity
- for synthesis
- Packaging
- 25g
- Price
- $180
- Updated
- 2025/07/31
- Product number
- 8.18642
- Product name
- tert-Butyldimethylchlorosilane
- Purity
- for synthesis
- Packaging
- 100g
- Price
- $342
- Updated
- 2025/07/31
- Product number
- 06735
- Product name
- tert-Butyldimethylsilyl chloride
- Purity
- for GC derivatization, ≥99.0% (GC)
- Packaging
- 10g
- Price
- $109
- Updated
- 2022/05/15
- Product number
- B0995
- Product name
- tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $25
- Updated
- 2025/07/31
- Product number
- B0995
- Product name
- tert-Butyldimethylchlorosilane [tert-Butyldimethylsilylating Agent]
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $74
- Updated
- 2025/07/31
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
Synthesis
507-20-0
75-78-5
18162-48-6
Example 3: To a 500 mL four-necked flask equipped with a reflux condenser, a dosing funnel, a thermometer, and a mechanical stirrer was added 12.2 g (0.5 mol) of magnesium powder under nitrogen protection. After drying, tert-butyl Grignard reagent was prepared by adding 250 mL of anhydrous tetrahydrofuran and 46.3 g (0.5 mol) of chlorotert-butane under stirring. At room temperature, 0.34 g (0.004 mol) of sodium thiocyanate was added to the reaction system as a catalyst, followed by the slow dropwise addition of 64.5 g (0.5 mol) of dimethyldichlorosilane. The reaction was exothermic and the system temperature was raised to 60°C. After maintaining reflux stirring for 3 h, the reaction mixture was diluted by adding 100 mL of hexane and filtered to remove insoluble material. The solvent was removed from the filtrate by distillation under reduced pressure, followed by distillation at atmospheric pressure to give 59 g (78% yield) of the colorless liquid product tert-butyldimethylchlorosilane.
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.]
References
[1] Patent: US5068386, 1991, A
[2] Tetrahedron Letters, 1989, vol. 30, # 46, p. 6393 - 6394
tert-Butyldimethylsilyl chloride Preparation Products And Raw materials
Raw materials
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View Lastest Price from tert-Butyldimethylsilyl chloride manufacturers
- Product
- Tert-butyldimethylsilyl chloride 18162-48-6
- Price
- US $1.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200000KG
- Release date
- 2025-09-12
- Product
- tert-Butyldimethylsilyl chloride 18162-48-6
- Price
- US $19.90/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-14
- 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