Triethylsilyltrifluoromethansulfonat

Triethylsilyl trifluoromethanesulphonate

HCID 2733308CAS 79271-56-0

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Grundinformationen

Standard-SMILES: CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F
InChIKey: STMPXDBGVJZCEX-UHFFFAOYSA-N
Summenformel: C7H15F3O3SSi
Durchschnittliche Molmasse: 264,34 g/mol
Monoisotopische Masse: 264,04632653

Namen und Bezeichner

Bevorzugter Name: Triethylsilyl trifluoromethanesulphonate
IUPAC: triethylsilyl trifluoromethanesulfonate
Lokaler Name: Triethylsilyltrifluoromethansulfonat
Englischer Name: Triethylsilyl trifluoromethanesulfonate
Summenformel: C7H15F3O3SSi
Molmasse: 264.34

Namen und Synonyme

79271-56-0Triethylsilyl trifluoromethanesulphonateEINECS 279-124-4DTXSID00229597RefChem:899556DTXCID50152088279-124-4Triethylsilyl trifluoromethanesulfonateTriethylsilyl TriflatetriethylsilyltrifluoromethanesulfonateMFCD00000407Trifluoromethanesulfonic Acid Triethylsilyl Ester

Weitere Namen anzeigen

TES-OTFDKSI108DKSI136DKFELEX0305TESOTf 97%TES TRIFLATETriethyl(trifluoromesyloxy)silaneTriethylsilyl trifluoromethanesulfote

Methanesulfonic acid, trifluoro-, triethylsilyl esterS17625TESOTfEt3SiOTfTriethylsilyltriflateSCHEMBL36993STMPXDBGVJZCEX-UHFFFAOYSA-CS-B0887

Datenbank-Bezeichner

CAS: 79271-56-0
PubChem CID: 2733308
DTXSID: DTXSID00229597
EC Number: 279-124-4
Nikkaji: J267.450E

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 51,8 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 6
Frei drehbare Bindungen: 5
Schwere Atome: 15
Formalladung: 0
Komplexität: 281

Physikochemische Eigenschaften

Siedepunkt: 85 · 85-86 °C/12 mmHg (lit.)
Dichte: 1.169 g/mL · 1.169 g/mL at 25 °C (lit.)
Brechungsindex: 20 · n20/D 1.389(lit.)
Flammpunkt: 162 °F · 162 °F
storage temp.: Inert atmosphere,Room Temperature
Löslichkeit: 2 Cl2 · Triethylsilyl Trifluoromethanesulfonate is readily sol hydrocarbons, dialkyl ethers, halogenated solvents. CH2Cl2 is employed most commonly. Reactions in 1,2-dichloroethane proceed faster than those in CCl4 or Et2O. Protic solvents and THF react with trialkylsilyl triflates and are therefore not suitable.
Aggregatzustand: Fuming Liquid
Wichte: 1.169 · 1.169
Farbe: Clear colorless to light brown
Wasserlöslichkeit: Miscible with dichloromethane, hydrocarbons, dialkyl ethers and halogenated solvents. Immiscible with water.
BRN: 3590541 · 3590541
Stabilität: Moisture Sensitive and Hygroscopic, Moisture Sensitive And Hygroscopic
InChI: 1S/C7H15F3O3SSi/c1-4-15(5-2,6-3)13-14(11,12)7(8,9)10/h4-6H2,1-3H3
InChIKey: STMPXDBGVJZCEX-UHFFFAOYSA-N
SMILES: CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F
CAS Datenbank: 79271 · 79271-56-0(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Corr. 1 (100%)

Sicherheitsdaten

F: 10-21
wgk: 3
tsca: No
ridadr: UN 3265 8/PG 2
hs_code: 29319090
risk_code: 34-14
hazard_code: C,F
hazard_note: Corrosive/Flammable
safety_code: 26-36/37/39-45-27
hazard_class: 8
packing_group: II
Speicherklasse: 8A - Combustible corrosive hazardous materials
Hazard Classifications: Skin Corr. 1B

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenTriethylsilyl Trifluoromethanesulfonate can be used as potent silylating agent and as Lewis acid catalyst. Triethylsilyl ethers are generally more stable towards hydrolysis than are trimethylsilyl ethers, and consequently the Et3Si moiety has gained increasing use as a protecting group for alcohols. However, since it is often difficult to silylate sterically hindered hydroxyl groups using Et3SiCl, triethylsilyl perchlorate and triethylsilyl triflate (Et3SiOTf) were introduced to overcome this problem. Jefford has reported that condensation reactions of 2-trimethylsiloxyfuran with aldehydes can be catalyzed by Et3SiOTf to give mainly the threo addition product (eq 8).

Darstellung

synthetischeTriethylsilyl Trifluoromethanesulfonate can be prepared by reacting chlorotriethylsilane with trifluoromethanesulfonic acid followed by distillation.