Trimethyl(2-(phenylsulfonyl)ethyl)silane

Base Information

• Chemical Name: Trimethyl(2-(phenylsulfonyl)ethyl)silane
• CAS No.: 73476-18-3
• Molecular Formula: C11H18 O2 S Si
• Molecular Weight: 242.414
• Hs Code.: 29310099
• DSSTox Substance ID: DTXSID20369308
• Wikidata: Q82156361
• Mol file: 73476-18-3.mol

Synonyms:Trimethyl(2-(phenylsulfonyl)ethyl)silane;73476-18-3;2-(benzenesulfonyl)ethyl-trimethylsilane;Phenyl 2-(trimethylsilyl)ethyl sulfone;trimethyl[2-(phenylsulfonyl)ethyl]silane;SCHEMBL8071225;DTXSID20369308;AKOS015889048;AG-G-90643;FT-0723049

Chemical Property of Trimethyl(2-(phenylsulfonyl)ethyl)silane

Chemical Property:

• Vapor Pressure: 0.000108mmHg at 25°C
• Melting Point: 51-52 °C(lit.)
• Refractive Index: 1.491
• Boiling Point: 347.4°C at 760 mmHg
• Flash Point: >230 °F
• PSA: 42.52000
• Density: 1.04g/cm³
• LogP: 3.87930
• Solubility.: sol all common ethereal, halocarbon, and hydrocarbon solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 242.07967752
• Heavy Atom Count: 15
• Complexity: 279

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CCS(=O)(=O)C1=CC=CC=C1
• Physical properties: mp 52 °C.
• Uses: (2-Phenylsulfonylethyl)trimethylsilane is widely used as reagent for the synthesis of mono- and 1,1-disubstituted alkenes via sulfone metalation, alkylation, and fluoride-induced elimination. A sequence involving metalation, alkylation, and fluoride-induced elimination of benzenesulfinate allows the conversion of (2) to a terminal alkene. An analogous sequence involving a double alkylation of (2) provides a 1,1-disubstituted alkene (eq 2). The lithio derivative of (2) has also been used to prepare cyclopropylidene derivatives, homoallylic alcohols, and allyl silanes via the Julia alkenation.

Technology Process of Trimethyl(2-(phenylsulfonyl)ethyl)silane

There total 13 articles about Trimethyl(2-(phenylsulfonyl)ethyl)silane 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: 99.2%

phenyl 2-(trimethylsilyl)ethyl sulfide (17988-59-9) → 1-benzenesulfonyl-2-trimethylsilylethane (73476-18-3)

Guidance literature:

With dihydrogen peroxide; In acetic acid; at 100 ℃; for 2h;

DOI:10.1016/S0040-4039(00)87234-2

Reference yield: 82.0%

methylphenylsulfonate (3112-85-4) + Chloromethyltrimethylsilane (2344-80-1) → 1-benzenesulfonyl-2-trimethylsilylethane (73476-18-3)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -40 ℃;

DOI:10.1016/0022-328X(85)87362-9

Reference yield: 12.0%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) + PVS (5535-48-8) → 1-benzenesulfonyl-2-trimethylsilylethane (73476-18-3)

Guidance literature:

1,1,1,2,2,2-hexamethyldisilane; PVS; With 1,10-Phenanthroline; copper(I) trifluoromethanesulfonate benzene; at 100 ℃; Inert atmosphere;

With toluene-4-sulfonic acid; In water; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.201200767

upstream raw materials:

phenyl 2-(trimethylsilyl)ethyl sulfide

cis-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene

trans-1-(benzylsulfonyl)-2-(trimethylsilyl)ethylene

methylphenylsulfonate

Downstream raw materials:

(2-Benzenesulfonyl-decyl)-trimethyl-silane

2-(phenylsulfonyl)-1-(trimethylsilyl)hexane

2-(phenylsulfonyl)-1,2-bis-(trimethylsilyl)ethane

2-(phenylsulfonyl)-1-(trimethylsilyl)octane