Trifluormethansulfonsäure-tris(1-methylethyl)-silylester

Bezeichnung:Trifluormethansulfonsäure-tris(1-methylethyl)-silylester

CAS-Nr80522-42-5

Englisch Name:Triisopropylsilyl Trifluoromethanesulfonate

CBNumberCB5189874

SummenformelC10H21F3O3SSi

Molgewicht306.42

MOL-Datei80522-42-5.mol

Synonyma

Trifluormethansulfonsäure-tris(1-methylethyl)-silylester

Trifluormethansulfonsäure-tris(1-methylethyl)-silylester physikalisch-chemischer Eigenschaften

Siedepunkt	45-46 °C/0.03 mmHg
Dichte	1.14 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.415(lit.)
Flammpunkt	213 °F
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit	Miscible with chloroform and ethyl acetate.
Aggregatzustand	Liquid
Wichte	1.14
Farbe	Clear light brown to orange-brown
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
BRN	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	80522-42-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	34
S-Sätze:	26-36/37/39-45-28A-27
RIDADR	UN 3265 8/PG 2
WGK Germany	3
F	3-10-21
TSCA	No
HazardClass	8
PackingGroup	II
HS Code	29319090

Gefahreninformationscode (GHS)

Triisopropylsilyl Trifluoromethanesulfonate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
Chemische Eigenschaften
clear light brown to orange-brown liquid
Physikalische Eigenschaften
Colorless oil; bp 83–87 °C/1.7 mmHg; d 1.173 g cm?3.
Verwenden
Triisopropylsilyl trifluoromethanesulfonate is used as a reagent for the introduction of triisopropylsilyl(TIPS) group in organic synthesis. It is involved in the synthesis of 2-substituted benzothiopyran-4-ones and silyloxy acetylenes. As a protecting group in organic synthesis, it is utilized especially for the protection of primary amines. Furthermore, it plays an important role in Takahashi Taxol total synthesis or for chemical glycosylation reactions.
Verwenden
Triisopropylsilyl 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.
synthetische
To 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.
Reaktivität anzeigen
Triisopropylsilyl 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).
Einzelnachweise
[1] Rücker, C. “1,3‐Bis(triisopropylsilyl)propyne.” 2001. 0.
[2] Fumihiko Yoshimura. “Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ.” Synlett 29 1 (2017): 1816–1820.

Triisopropylsilyl Trifluoromethanesulfonate Upstream-Materialien And Downstream Produkte

Trifluormethansulfonsäure-tris(1-methylethyl)-silylester Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

80522-42-5, Triisopropylsilyl Trifluoromethanesulfonate Verwandte Suche:

Send Inquriy