Tert-Butyldimethylsilyl chloride

Base Information

• Chemical Name: Tert-Butyldimethylsilyl chloride
• CAS No.: 18162-48-6
• Deprecated CAS: 132560-73-7,187979-91-5,187979-91-5
• Molecular Formula: C6H15ClSi
• Molecular Weight: 150.724
• Hs Code.: 29310095
• European Community (EC) Number: 242-042-4
• UNII: 550OPF5Z9F
• DSSTox Substance ID: DTXSID4038843
• Nikkaji Number: J47.875J
• Wikipedia: Tert-Butyldimethylsilyl_chloride
• Wikidata: Q1916937
• Mol file: 18162-48-6.mol

Synonyms:t-butyldimethylchlorosilane;t-butyldimethylchlorsilane;TBMCS cpd

Chemical Property of Tert-Butyldimethylsilyl chloride

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 12.089mmHg at 25°C
• Melting Point: 86-89 °C
• Refractive Index: n20/D 1.46
• Boiling Point: 125 °C at 760 mmHg
• Flash Point: 22.8 °C
• PSA: 0.00000
• Density: 0.862 g/cm³
• LogP: 3.23040
• Storage Temp.: Store at 5°C
• Sensitive.: Moisture Sensitive
• Solubility.: very sol nearly all common organic solvents such as THF, methylene chloride, and DMF.
• Water Solubility.: Soluble in chloroform and ethyl acetate. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 150.0631547
• Heavy Atom Count: 8
• Complexity: 81

Purity/Quality:

99%min ^*data from raw suppliers

tert-Butyldimethylsilyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,F,T
• Hazard Codes: C,F,T,Xn
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chlorosilanes
• Canonical SMILES: CC(C)(C)[Si](C)(C)Cl
• Description: Tert-Butyldimethylsilyl chloride (TBDMSCl), also known as TBSCl or tert-butyldimethylsilyl chloride. Tert-Butyldimethylsilyl chloride is a synthetic compound primarily used in organic synthesis and various chemical reactions.
• Chemical Composition and Structure: Tert-Butyldimethylsilyl chloride contains tert-butyl and dimethylsilyl functional groups attached to a silicon atom, with a chloride ion.
• Uses and Mechanism of Action: In organic synthesis, TBDMSCl is utilized as a silylating agent to protect hydroxy groups in alcohols, thus facilitating various reactions without interference from these groups.; It is used in the preparation of 5-halo-1,2,3-triazoles via aerobic oxidative halogenations and 6-silyloxy-6-alkylfulvenes through in situ trapping of enolates.^[1]; TBDMSCl is also employed in the synthesis of silyl ethers from carboxylic acids under solvent-free conditions.; In catalysis, it serves as a precursor for silicon substrates in the modification of nanocomposites, enhancing catalytic activity for hydrogen production and dye degradation.; Additionally, TBDMSCl is utilized in the development of fluorogenic probes for fluoride ion detection, exploiting the cleavage of tert-butyldimethylsilyl ethers.
• Analysis Method: The effects and reactions involving TBDMSCl are analyzed using techniques such as X-ray crystallographic analysis, theoretical calculations, fluorescence spectroscopy, NMR spectroscopy, IR spectroscopy, and thin-layer chromatography. These methods help elucidate the structures, mechanisms, and outcomes of reactions involving TBDMSCl.^[2]
• References: [1] Three-component assembly of 5-halo-1,2,3-triazoles via aerobic oxidative halogenation; DOI 10.1016/j.tetlet.2013.08.089; [2] Reaction of germabenzenylpotassium with TBDMSCl: Unusual trimerization of germabenzene skeletons; DOI 10.1080/10426507.2020.1804187

Technology Process of Tert-Butyldimethylsilyl chloride

There total 25 articles about Tert-Butyldimethylsilyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.8%

tert-butyldimethylsilane (29681-57-0) + 3-Chloro-2-methylpropene (563-47-3) → tert-butyldimethylsilyl chloride (18162-48-6)

Guidance literature:

palladium diacetate;

Reference yield: 99.6%

→ tert-butyldimethylsilyl chloride (18162-48-6)

Guidance literature:

Reference yield: 96.0%

tert-butyl(dimethyl)(phenylseleno)silane (72726-46-6) → diphenyl diselenide (1666-13-3) + tert-butyldimethylsilyl chloride (18162-48-6)

Guidance literature:

With chlorine; In tetrachloromethane;

DOI:10.1021/jo00320a012

upstream raw materials:

tert.-butyl lithium

dimethylsilicon dichloride

tert-butyldimethylfluorosilane

tert-butyldimethylsilanol

Downstream raw materials:

tert-butyldimethyl(phenoxy)silane

tert-butyldimethylsilanol

N-(cyclohexaneylidenemethylene)-1-(1,1-dimethylethyl)-1,1-dimethylsilanamine

tert-butyl(1,3-dithian-2-yl)dimethylsilane

Refernces

• 1、 Miqueu,Sotiropoulos,Pfister-Guillouzo,Romanenko. "First gas-phase generation of a cis chloroiminoarsane ClAs NSiMe and a cis chloroiminophosphane ClP NSiMe Bu. Characterization by photoelectron spectroscopy". . p. 930 - 938. Retrieved 2001.
• 2、 Pongkittiphan, Veerachai,Theodorakis, Emmanuel A.,Chavasiri, Warinthorn. "Hexachloroethane: a highly efficient reagent for the synthesis of chlorosilanes from hydrosilanes". scheme or table. p. 5080 - 5082. Retrieved 2009/12/01.
• 3、 -. "Production processes for triorganomonoalkoxysilanes and triorganomonochlorosilanes". Page/Page column 27. . Retrieved 2008/06/13.