Trifluormethansulfonsäure-tris(1-methylethyl)-silylester

Triisopropylsilyl trifluoromethanesulfonate

HCID 2724529CAS 80522-42-5

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Grundinformationen

Standard-SMILES: CC(C)[Si](OS(=O)(=O)C(F)(F)F)(C(C)C)C(C)C
InChIKey: LHJCZOXMCGQVDQ-UHFFFAOYSA-N
Summenformel: C10H21F3O3SSi
Durchschnittliche Molmasse: 306,42 g/mol
Monoisotopische Masse: 306,09327672

Namen und Bezeichner

Bevorzugter Name: Triisopropylsilyl trifluoromethanesulfonate
IUPAC: tri(propan-2-yl)silyl trifluoromethanesulfonate
Lokaler Name: Trifluormethansulfonsäure-tris(1-methylethyl)-silylester
Englischer Name: Triisopropylsilyl Trifluoromethanesulfonate
Summenformel: C10H21F3O3SSi
Molmasse: 306.42

Namen und Synonyme

Triisopropylsilyl trifluoromethanesulfonate80522-42-5DTXSID10369150RefChem:386312DTXCID70320186638-988-6Triisopropylsilyl triflateTrifluoromethanesulfonic acid triisopropylsilyl estertriisopropylsilyltrifluoromethanesulfonatetriisopropylsilyl trifluoromethanesulphonateMFCD00009913tri(propan-2-yl)silyl trifluoromethanesulfonate

Weitere Namen anzeigen

TriisopropylsilylTriisopropyl trifluoromethane sulfonate(i-Pr)3SiOTfDKSI152DKFELEX0272SILANE IP3-TRIFLATE

triisopropylsilyl-trifluoromethanesulfonateC10H21F3O3SSiTIPS triflatetris(propan-2-yl)silyl trifluoromethanesulfonatetri-iso-propylsilyl trifluoromethane sulfonatetips-otfTIPSOTf; Triisopropyl(trifluoromethanesulfonato)silane; Triisopropylsilyl Triflate; TIPS Triflate; 1,1,1-Trifluoromethanesulfonic Acid Tris(1-methylethyl)silyl EsterTIPSOTf

Datenbank-Bezeichner

CAS: 80522-42-5
PubChem CID: 2724529
DTXSID: DTXSID10369150
UNII: R7C8KB3N7A
EC Number: 638-988-6
Nikkaji: J364.634C

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 51,8 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 6
Frei drehbare Bindungen: 5
Schwere Atome: 18
Formalladung: 0
Komplexität: 347

Physikochemische Eigenschaften

Siedepunkt: 45 · 45-46 °C/0.03 mmHg
Dichte: 1.14 g/mL · 1.14 g/mL at 25 °C (lit.)
Brechungsindex: 20 · n20/D 1.415(lit.)
Flammpunkt: 213 °F · 213 °F
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit: Miscible with chloroform and ethyl acetate.
Aggregatzustand: Liquid
Wichte: 1.14 · 1.14
Farbe: Clear light brown to orange-brown
BRN: 3591541 · 3591541
InChI: InChI=1S/C10H21F3O3SSi/c1-7(2)18(8(3)4,9(5)6)16-17(14,15)10(11,12)13/h7-9H,1-6H3
InChIKey: LHJCZOXMCGQVDQ-UHFFFAOYSA-N
SMILES: C(F)(F)(F)S(O[Si](C(C)C)(C(C)C)C(C)C)(=O)=O
CAS Datenbank: 80522 · 80522-42-5(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 49 reports by companies from 6 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 11-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33840

Hazard Classes and CategoriesSkin Corr. 1B (100%)

Sicherheitsdaten

F: 3-10-21
wgk: 3
tsca: No
ridadr: UN 3265 8/PG 2
hs_code: 29319090
risk_code: 34
hazard_code: C
safety_code: 26-36/37/39-45-28A-27
hazard_class: 8
packing_group: II
Speicherklasse: 8A - Combustible corrosive hazardous materials
Hazard Classifications: Skin Corr. 1B

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenTriisopropylsilyl Trifluoromethanesulfonate is a highly reactive silylating agent and Lewis acid capable of converting primary and secondary alcohols to the corresponding triisopropylsilyl ethers and converting ketones and lactones into their enol silyl ethers; protection of terminal alkynes; promoting conjugate addition of alkynylzinc compounds to α,β-enones; preparation of (triisopropylsilyl)diazomethane, participating in the following (but not limited to) reactions: Silylation of Alcohols, Formations of Enol Silyl Ethers, Alkynyltriisopropylsilanes, Conjugate Addition of Alkynylzinc Bromides, (Triisopropylsilyl)diazomethane, Triisopropylsiloxycarbonyl (Tsoc) and BIPSOP Protecting Groups for Amines, TIPS Protection for Oxazoles/Regioselective Trapping of C-2 Oxazole Anions, Benzannulation Using Triisopropylsilyl Vinyl Ketenes, Cyclization of 1-Silyloxy-1,5-diynes, Desymmetrization of Tartaric Acid Esters etc.

Darstellung · 1 Eintrag

synthetischeTo 38.2 g (0.242 mol) of triisopropylsilane at 0°C under argon is added 23.8 mL (0.266 mol) of trifluoromethanesulfonic acid dropwise. The solution is stirred at 22°C for 16 h, at which time no further hydrogen gas evolves (removed through a bubbler). The resulting product is distilled through a 30-cm vacuum jacketed Vigreux column under reduced pressure: 71.7 g (97% yield) of TIPS triflate; bp 83–87°C/1.7 mmHg.