Trifluormethansulfonsaeureanhydrid

Bezeichnung:Trifluormethansulfonsaeureanhydrid

CAS-Nr358-23-6

Englisch Name:Trifluoromethanesulfonic anhydride

CBNumberCB5273333

SummenformelC2F6O5S2

Molgewicht282.14

MOL-Datei358-23-6.mol

Synonyma

Trifluormethansulfonsaeureanhydrid

Trifluormethansulfonsaeureanhydrid physikalisch-chemischer Eigenschaften

Schmelzpunkt	-80°C
Siedepunkt	81-83 °C (lit.)
Dichte	1.677 g/mL at 25 °C (lit.)
Dampfdichte	5.2 (vs air)
Dampfdruck	8 mm Hg ( 20 °C)
Brechungsindex	n20/D 1.321(lit.)
RTECS-Nr.	PB2772000
Flammpunkt	81-83°C
storage temp.	Store below +30°C.
Löslichkeit	Miscible with dichloromethane. Immiscible with hydrocarbons.
Aggregatzustand	Liquid
Wichte	1.677
Farbe	Clear colorless to light brown
Wasserlöslichkeit	reacts violently with water
Sensitive	Moisture Sensitive
BRN	1813600
Stabilität	Hygroscopic, Moisture Sensitive
InChIKey	WJKHJLXJJJATHN-UHFFFAOYSA-N
LogP	0.3 at 25℃
CAS Datenbank	358-23-6(CAS DataBase Reference)
NIST chemische Informationen	Trifluoromethanesulfonic anhydride(358-23-6)
EPA chemische Informationen	Methanesulfonic acid, trifluoro-, anhydride (358-23-6)

Sicherheit

Kennzeichnung gefährlicher	C
R-Sätze:	14-21/22-34-35-22-40
S-Sätze:	26-36/37/39-43-45-8
RIDADR	UN 3265 8/PG 2
WGK Germany	3
F	10-21
Hazard Note	Corrosive
TSCA	Yes
HazardClass	8
PackingGroup	I
HS Code	29049020
Toxizität	LD50 orally in Rabbit: 1012 mg/kg

Gefahreninformationscode (GHS)

Trifluoromethanesulfonic anhydride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R14:Reagiert heftig mit Wasser.
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.
R34:Verursacht Verätzungen.
R35:Verursacht schwere 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.
S43:Zum Löschen . . . (vom Hersteller anzugeben) verwenden (wenn Wasser die Gefahr erhöht, anfügen: "Kein Wasser verwenden").
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S8:Behälter trocken halten.
Beschreibung
Trifluoromethanesulfonic anhydride, also known as triflic anhydride, has proven to be an extraordinary reagent for a broad range of transformations. As a commercially and readily available reagent, It has been widely used in synthetic chemistry due to its high electrophilicity. Given its high affinity towards O-nucleophiles, reaction with alcohols, carbonyls, sulfur phosphorus- and iodine oxides towards the formation of the corresponding triflates is strongly favored. As one of the premier leaving groups in organic chemistry, the generated triflates then open the door to various downstream transformations, including (but not limited to) substitution reactions, cross-coupling processes, redox reactions, and rearrangements[1-2].
Chemische Eigenschaften
clear colorless to light brown liquid
Verwenden
Trifluoromethanesulfonic Anhydride is a strong electrophile used in chemical synthesis for introducing the triflyl group.
Verwenden
Trifluoromethanesulfonic anhydride is used to convert phenols and imine into triflic ester and NTf group. It is a strong electrophile used for the introduction of triflyl group in chemical synthesis. It serves as a reagent in the preparation of alkyl and vinyl triflates, and for the stereoselective synthesis of mannosazide methyl uronate donors. It acts as a catalyst for glycosylation with anomeric hydroxy sugars to prepare polysaccharides.
Definition
ChEBI: Triflic anhydride is an organosulfonic anhydride. It is functionally related to a triflic acid.
Reaktivität anzeigen
Electrophilic activation of tertiary and secondary amides with triflic anhydride (Tf2O; rifluoromethanesulfonic anhydride) under mild conditions gives rise to iminium and imino triflates, respectively, which could be utilized as versatile reagents to react with various C-, N-, O- and S-nucleophiles for the transformation of an amide function into different products. Other oxygen-containing nucleophiles, such as sulfoxides and phosphorus oxides, could also undergo nucleophilic attack with Tf2O to generate thionium triflate, electrophilic P-species, and phosphonium triflate. These highly active transient species could readily undergo nucleophilic substitution reactions for further diverse transformations. Furthermore, owing to the strong electrophilic property, Tf2O is prone to react with relatively weak nucleophiles such as nitrile groups or some nitrogen-containing heterocyclic compounds. In addition, Tf2O has also been used as an efficient radical trifluoromethylation and trifluorometh ylthiolation reagent through the release of SO2 or deoxygenation process for the synthesis of trifluoromethylated and trifluoromethylthiolated compounds[2].
Hazard
May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage.
Flammability and Explosibility
Not classified
Synthese
The synthesis of Trifluoromethanesulfonic anhydride is as follows:
A dry, 100-ml., round-bottomed flask is charged with 36.3 g. (0.242 mole) of trifluoromethanesulfonic acid (Note 1) and 27.3 g. (0.192 mole) of phosphorus pentoxide (Note 2). The flask is stoppered and allowed to stand at room temperature for at least 3 hours. During this period the reaction mixture changes from a slurry to a solid mass. The flask is fitted with a short-path distilling head and heated first with a stream of hot air from a heat gun and then with the flame from a small burner.
The flask is heated until no more trifluoromethanesulfonic anhydride distills, b.p. 82–115°, yielding 28.4–31.2 g. (83–91%) of the anhydride, a colorless liquid. Although this product is sufficiently pure for use in the next step, the remaining acid may be removed from the anhydride by the following procedure. A slurry of 3.2 g. of phosphorus pentoxide in 31.2 g. of the crude anhydride is stirred at room temperature in a stoppered flask for 18 hours. After the reaction flask has been fitted with a short-path distilling head, it is heated with an oil bath, yielding 0.7 g. of forerun, b.p. 74–81°, followed by 27.9 g. of the pure trifluoromethanesulfonic acid anhydride, b.p. 81–84° .
Lager
Store in a cool, dry, wellventilated area. Moisture sensitive.
läuterung methode
It can be freshly prepared from the anhydrous acid (11.5g) and P2O5 (11.5g, or half this weight) by setting aside at room temperature for 1hour, distilling off volatile products then distil it through a short Vigreux column. It is readily hydrolysed by H2O and decomposes appreciably after a few days to liberate SO2 and produce a viscous liquid. Store it dry at low temperatures. [Burdon et al. J Chem Soc 2574 1957, Beard et al. J Org Chem 38 373 1973, Beilstein 3 IV 35.]
Einzelnachweise
[1] Haoqi Zhang. “Trifluoromethanesulfonic Anhydride in Amide Activation: A Powerful Tool to Forge Heterocyclic Cores.” TCIMAIL (2021).
[2] Dr. Qixue Qin, Prof. Dr. Ning Jiao, Zengrui Cheng. “Recent Applications of Trifluoromethanesulfonic Anhydride in Organic Synthesis.” Angewandte Chemie 135 10 (2022).

Trifluoromethanesulfonic anhydride Upstream-Materialien And Downstream Produkte

Trifluormethansulfonsaeureanhydrid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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