Basic information
- Standard SMILES
CC(C)(C)[Si](C)(C)Cl- InChIKey
BCNZYOJHNLTNEZ-UHFFFAOYSA-N- Molecular formula
- C6H15ClSi
- Average molar mass
- 150.72 g/mol
- Monoisotopic mass
- 150.06315469
Overview
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.
Names & identifiers
- Preferred name
- tert-Butyldimethylsilyl chloride
- IUPAC
- tert-butyl-chloro-dimethylsilane
- English name
- tert-Butyldimethylsilyl chloride
- Molecular formula
- C6H15ClSi
- Molecular weight
- 150.72
Names & synonyms
Tert-Butyldimethylsilyl chloride18162-48-6tert-Butyldimethylchlorosilanet-ButyldimethylchlorosilaneTBDMS chlorideSilane, chloro(1,1-dimethylethyl)dimethyl-Chloro-tert-butyldimethylsilane2-(chlorodimethylsilyl)-2-methylpropane550OPF5Z9FCHEBI:85071TBMCS cpdt-butyldimethylchlorsilane
Show more names
TBDMSCLTBSCITBDMSCItert-ButyldimethylsilylTBDMCl
RefChem:188237242-042-4tert-Butylchlorodimethylsilanetert-Butyl(chloro)dimethylsilaneTBSCltert-butyl-chloro-dimethylsilaneTBS-Clt-butyldimethylsilyl chloride
Database identifiers
- CAS
18162-48-6- PubChem CID
- 28928
- DTXSID
DTXSID4038843- ChEBI
CHEBI:85071- UNII
- 550OPF5Z9F
- EC Number
- 242-042-4
- Nikkaji
- J47.875J
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 81
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Chlorosilanes
SpringerMaterials PropertiesSchoenflies notation
Physical DescriptionWhite hygroscopic solid; [Merck Index] White crystals with a pungent odor; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 86 · 86-89 °C (lit.)
- Boiling point
- 125 °C · 125 °C (lit.)
- Density
- 0.87 g/mL · 0.87 g/mL at 20 °C(lit.)
- vapor pressure
- 60 · 60-710Pa at 25℃
- refractive index
- 20 · n20/D 1.46
- Flash point
- 73 °F · 73 °F
- storage temp.
- 30 °C · 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 · 1.225
- Water Solubility
- Soluble in chloroform and ethyl acetate. Insoluble in water.
- Hydrolytic Sensitivity
- 7 · 7: reacts slowly with moisture/water
- Sensitive
- Moisture Sensitive
- BRN
- 505999 · 505999
- InChI
- 1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3
- InChIKey
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N
- SMILES
- CC(C)(C)[Si](C)(C)Cl
- LogP
- 2.5 at · 2.5 at 20℃
- CAS DataBase Reference
- 18162 · 18162-48-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- BDCS
- FDA UNII
- 550 OPF5Z9F · 550OPF5Z9F
- 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)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 225 · H225-H304-H314-H336-H361d-H373-H411
- Precautionary statements
- 210 · P210-P280-P301+P310+P331-P301+P330+P331-P303+P361+P353-P305+P351+P338+P310
- Hazard Codes
- C,F,T,Xn
- Risk Statements
- 22 · 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 · 26-36/37/39-46-62-45-25-16-28-27-33-29-53-36/37
- RIDADR
- 2925 · UN 2925 4.1/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 2000000 · VV2000000
- F
- 10 · 10-21
- Hazard Note
- Flammable/Corrosive/Moisture Sensitive
- TSCA
- TSCA listed
- HazardClass
- 4.1 · 4.1
- PackingGroup
- III
- HS Code
- 29310095 · 29310095
- Storage Class
- 4.1 B · 4.1B - Flammable solid hazardous materials
- Hazard Classifications
- 2 Eye · Aquatic Chronic 2Eye Dam. 1Flam. Sol. 1Skin Corr. 1A
- Toxicity
- 1 gm/kg · 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,
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1.0 Kg (2.2 lbs)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 23.7% (56 of 236) of reports.
Danger
H228 (57.6%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P260, P261, P264, P264+P265, P271, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P363, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 236 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Silane, chloro(1,1-dimethylethyl)dimethyl-
Status: Active Update: 30-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/28118
Silane, t-butylchlorodimethyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes decreased immune response in intraperitoneal lethal-dose studies of mice (LDLo = 1,000 mg/kg); [RTECS] Corrosive; [Merck Index] Reacts with water producing hydrochloric acid; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract; [Alfa Aesar MSDS] See Chlorotrimethylsilane.
Hazard Classes and CategoriesFlam. Sol. 1 (57.6%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 10-21
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- VV2000000
- ridadr
- UN 2925 4.1/PG 2
- 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,
- risk_code
- 22-35-40-34-10-19-11-67-65-63-48/20-20/21/22-45-23/24/25-37-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS08,GHS09
- hazard_code
- C,F,T,Xn
- hazard_note
- Flammable/Corrosive/Moisture Sensitive
- safety_code
- 26-36/37/39-46-62-45-25-16-28-27-33-29-53-36/37
- hazard_class
- 4.1
- Storage Class
- 4.1B - Flammable solid hazardous materials
- packing_group
- III
- Hazard statements
- H225-H304-H314-H336-H361d-H373-H411
- Limited Quantities
- 1.0 Kg (2.2 lbs)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 2Eye Dam. 1Flam. Sol. 1Skin Corr. 1A
- Precautionary statements
- P210-P280-P301+P310+P331-P301+P330+P331-P303+P361+P353-P305+P351+P338+P310
Chemistry & industry
Uses & manufacturing
UsesUsed as a reagent; [Merck Index]
General Manufacturing InformationSilane, chloro(1,1-dimethylethyl)dimethyl-: ACTIVE
Applications
Usestert-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 methods
Preparationtert-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%.
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Additional notes
DefinitionChEBI: 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.
Related reactions
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