2-(Trimethylsilyl)ethanesulfonamide

Base Information

• Chemical Name: 2-(Trimethylsilyl)ethanesulfonamide
• CAS No.: 125486-96-6
• Molecular Formula: C5H15 N O2 S Si
• Molecular Weight: 181.331
• European Community (EC) Number: 626-938-6
• DSSTox Substance ID: DTXSID10451665
• Nikkaji Number: J1.590.539E
• Wikidata: Q82271789
• Mol file: 125486-96-6.mol

Synonyms:2-(Trimethylsilyl)ethanesulfonamide;125486-96-6;2-(trimethylsilyl)ethane-1-sulfonamide;2-trimethylsilylethanesulfonamide;Ethanesulfonamide, 2-(trimethylsilyl)-;2-(TRIMETHYLSILYL)ETHANESULFONAMIDE, 90per cent;SES-NH2;C5H15NO2SSi;SCHEMBL28753;2-trimethylsilylethylsulfonamide;DTXSID10451665;MZASHBBAFBWNFL-UHFFFAOYSA-N;AMY34680;2-(trimethylsilyl)-ethanesulfonamide;Ethanesulfonamide,2-(trimethylsilyl)-;AKOS015908466;CS-W010749;PB47812;2-(Trimethylsilyl)ethanesulfonamide, 90%;AS-54103;FT-0723609;P17502;EN300-1601201;J-005233

Chemical Property of 2-(Trimethylsilyl)ethanesulfonamide

Chemical Property:

• Vapor Pressure: 0.0187mmHg at 25°C
• Melting Point: 81-87oC
• Boiling Point: 253oC at 760 mmHg
• Flash Point: 106.8oC
• PSA: 68.54000
• Density: 1.057g/cm3
• LogP: 2.39420
• Solubility.: Soluble in benzene, chloroform, dichloromethane, ether, methanol and toluene.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 181.05927643
• Heavy Atom Count: 10
• Complexity: 187

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(Trimethylsilyl)ethanesulfonamide 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CCS(=O)(=O)N
• Uses: 2-Trimethylsilylethanesulfonyl amide is a useful reagent for introduction of a SES-protected nitrogen functionality, which can be cleaved with fluoride ion. 2-(Trimethylsilyl)ethanesulfonamide is a source of nucleophilic nitrogen that can react in manifold ways with electrophiles prior to removal of SES group with fluoride ion. It participates in the following reactions: Preparation of N-Sulfonylimines, Mitsunobu Reactions, Azaglycosylation Chemistry, Preparation of Sulfodiimides, Preparation of (N-SES-imino)phenyliodinane etc. Useful reagent for introduction of a SES-protected nitrogen functionality, which can be cleaved with fluoride ion.

Technology Process of 2-(Trimethylsilyl)ethanesulfonamide

There total 2 articles about 2-(Trimethylsilyl)ethanesulfonamide 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: 88.0%

2-trimethylsilanyl-ethanesulfonyl chloride (106018-85-3) → 2-(trimethylsilyl)ethanesulfonamide (125486-96-6)

Guidance literature:

With ammonia; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/j.tet.2003.10.067

Reference yield: 67.0%

sodium β-trimethylsilylethanesulfonate (18143-40-3) → 2-(trimethylsilyl)ethanesulfonamide (125486-96-6)

Guidance literature:

sodium β-trimethylsilylethanesulfonate; With phosphorus pentachloride; In dichloromethane; at 20 ℃; for 0.5h;

With ammonia; In dichloromethane; at -10 ℃; for 0.25h;

DOI:10.1021/jo048519r

Reference yield: 98.0%

Ethyl 4-bromobenzoate (5798-75-4) + 2-(trimethylsilyl)ethanesulfonamide (125486-96-6) → 4-[2-(trimethylsilanyl)ethanesulfonylamino]benzoic acid ethyl ester (1045771-43-4)

Guidance literature:

With caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 ℃; for 15h;

DOI:10.1016/j.tetlet.2008.05.099

upstream raw materials:

2-trimethylsilanyl-ethanesulfonyl chloride

sodium β-trimethylsilylethanesulfonate

Downstream raw materials:

N-3)-O-(2,4-di-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-O-<(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>...

benzyl <<2-(trimethylsilyl)ethyl>sulfonyl>carbamate

2-Trimethylsilanyl-ethanesulfonic acid ((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-iodo-tetrahydro-pyran-2-yl)-amide

2-(trimethylsilyl)-N-(phenyl-λ³-iodanylidene)-ethanesulfonamide

Refernces

• 1、 Benohoud, Meryem,Leman, Loic,Cardoso, Silvia H.,Retailleau, Pascal,Dauban, Philippe,Thierry, Josiane,Dodd, Robert H.. "Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine". supporting information; experimental part. p. 5331 - 5336. Retrieved 2009/12/03.
• 2、 Aggarwal,Ferrara,O'Brien,Thompson,Jones,Fieldhouse. "Scope and limitations in sulfur ylide mediated catalytic asymmetric aziridination of imines: Use of phenyldiazomethane, diazoesters and diazoacetamides". . p. 1635 - 1643. Retrieved 2007/10/03.