2-(Trimethylsilyl)ethane-1-sulfonyl chloride

HCID 9837086

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Grundinformationen

CAS: 106018-85-3
Standard-SMILES: C[Si](C)(C)CCS(=O)(=O)Cl
InChIKey: BLPMCIWDCRGIJV-UHFFFAOYSA-N
Summenformel: C5H13ClO2SSi
Durchschnittliche Molmasse: 200,76 g/mol
Monoisotopische Masse: 200,00940487

Namen und Bezeichner

Bevorzugter Name: 2-(Trimethylsilyl)ethane-1-sulfonyl chloride
IUPAC: 2-trimethylsilylethanesulfonyl chloride
Englischer Name: 2-(Trimethylsilyl)ethanesulfonyl chlori&
Summenformel: C5H13ClO2SSi
Molmasse: 200.76

Namen und Synonyme

2-(trimethylsilyl)ethane-1-sulfonyl chlorideRefChem:462634628-168-62-(Trimethylsilyl)ethanesulfonyl chloride106018-85-32-trimethylsilylethanesulfonyl ChlorideMFCD092651532-Trimethylsilanyl-ethanesulfonyl Chloride2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI2-(TRIMETHYLSILYL)ETHANESULFONYL CHLORI&SES-ClEthanesulfonylchloride, 2-(trimethylsilyl)-

Weitere Namen anzeigen

06018-85-32-(trimethylsilyl)ethylsulfonylchloro2-(TRISMETHYLSILYL)ETHANESULPHONYLCHLORIDE2-Trimethylsilylethylsulfonyl chloride, SES-Cl

Ethanesulfonyl chloride, 2-(trimethylsilyl)-C5H13ClO2SSiSCHEMBL1115359DTXSID20431554BLPMCIWDCRGIJV-UHFFFAOYSA-N2-(trimethylsilyl)ethylsulfonylchlorideAKOS0063362392-trimethylsilanylethanesulfonyl chloride

Datenbank-Bezeichner

CAS: 106018-85-3
PubChem CID: 9837086
DTXSID: DTXSID20431554
EC Number: 628-168-6
Nikkaji: J1.512.977H

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 42,5 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 3
Schwere Atome: 10
Formalladung: 0
Komplexität: 187

Physikochemische Eigenschaften

Siedepunkt: 146.8 °C/760 · 146.8 °C/760 mmHg
Dichte: 1.059 g/mL · 1.059 g/mL at 25 °C
Brechungsindex: 20 · n20/D 1.4444
Flammpunkt: 21 °C · 21 °C
storage temp.: 2 · 2-8°C
Löslichkeit: Sol most common organic solvents.
InChI: 1S/C5H13ClO2SSi/c1-10(2,3)5-4-9(6,7)8/h4-5H2,1-3H3
InChIKey: BLPMCIWDCRGIJV-UHFFFAOYSA-N
SMILES: C[Si](C)(C)CCS(Cl)(=O)=O

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesFlam. Liq. 2 (100%)

Sicherheitsdaten

wgk: 3
ridadr: UN 1993 3/PG 2
hs_code: 2931900090
risk_code: 11-36/37/38
hazard_code: F,Xi
safety_code: 26
Speicherklasse: 3 - Flammable liquids
Hazard Classifications: Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Anwendungen · 1 Eintrag

Verwendenβ-Trimethylsilylethanesulfonyl Chloride is used in the protection of primary and secondary amines as their sulfonamides, which are cleaved by fluoride ion. It participates in the reations of Protection of Amines, SESCl in Synthesis, N-Alkylation, Deprotection Conditions, Formation of 2-Trimethylsilylethanesulfonylimines, the (N-SES-Imino) Phenyliodinane or SESN=IPh Reagent, SES-N3, etc.

Darstellung · 1 Eintrag

synthetische|-Trimethylsilylethanesulfonyl Chloride can be most conveniently synthesized from commercially available vinyltrimethylsilane (eq 1). Radical addition of sodium bisulfite to the vinyl group catalyzed by t-butyl perbenzoate yields the sulfonate salt which can be directly converted to SESCl with phosphorus(V) chloride. The chloride can then be purified by distillation. The intermediate sulfonate salt is commercially available. The chloride can also be prepared in 62% yield from the salt using sulfuryl chloride and triphenylphosphine (eq 2). A less convenient procedure to synthesize SESCl using |-trimethylsilylethylmagnesium chloride and sulfuryl chloride has also been developed (eq 3).