Ethyl trifluoropyruvate

Bezeichnung:Ethyl trifluoropyruvate

CAS-Nr13081-18-0

Englisch Name:Ethyl trifluoropyruvate

CBNumberCB8333735

SummenformelC5H5F3O3

Molgewicht170.09

MOL-Datei13081-18-0.mol

Ethyl trifluoropyruvate physikalisch-chemischer Eigenschaften

Siedepunkt	42 °C(lit.)
Dichte	1.283 g/mL at 25 °C (lit.)
Dampfdruck	12.49hPa at 25℃
Brechungsindex	n20/D 1.341(lit.)
Flammpunkt	88 °F
storage temp.	Inert atmosphere,2-8°C
Löslichkeit	Miscible with dichloromethane.
Aggregatzustand	Liquid
Farbe	Clear colorless to pale yellow
BRN	2087388
Stabilität	Moisture Sensitive
InChI	InChI=1S/C5H5F3O3/c1-2-11-4(10)3(9)5(6,7)8/h2H2,1H3
InChIKey	KJHQVUNUOIEYSV-UHFFFAOYSA-N
SMILES	C(OCC)(=O)C(=O)C(F)(F)F
LogP	-0.05
CAS Datenbank	13081-18-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,C,Xi
R-Sätze:	10-22-36/37/38
S-Sätze:	26-37/39-16
RIDADR	UN 3272 3/PG 3
WGK Germany	3
Hazard Note	Corrosive
HazardClass	3
PackingGroup	III
HS Code	29183000
Speicherklasse	3 - Flammable liquids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

Ethyl trifluoropyruvate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Chemische Eigenschaften
Clear pale yellow liquid
Verwenden
Ethyl 3,3,3-trifluoropyruvate may be used in the preparation of N-heteroaryl(trifluoromethyl)hydroxyalkanoic acid esters.
Verwenden
Ethyl trifluoropyruvate acts as a building block in synthetic chemistry for the synthesis of fluorine containing compounds. It is also used as a reagent for the preparation of potential biologically active compounds like highly enantioselective organocatalytic hydroxyalkylation of indoles.
Verwenden
Ethyl Trifluoropyruvate is used as a reagent in the preparation of potential biologically active compounds such as in the highly enantioselective organocatalytic hydroxyalkylation of indoles .
Allgemeine Beschreibung
Ethyl 3,3,3-trifluoropyruvate is a trifluoromethylated compound. Enantioselective Friedel–Crafts alkylation of simple phenols and indoles with ethyl 3,3,3-trifluoropyruvate under different reaction conditions have been reported.
Synthese
To 58 mL (1.0 mL/mmol) of acetonitrile, 10 g (58 mmol, 1.0 eq) of ethyl 3,3,3-trifluorolactate was added and dissolved therein.Furthermore, 11 g (67 mmol, 1.2 eq) of NaClO.5H2O was added, followed by stirring at 20° C. for 30 minutes.As the reaction-terminated liquid was analyzed by 19F-NMR, conversion was 100%, and selectivity was 98%.To the reaction-terminated liquid, 0.38 g (1.5 mmol, 0.026 eq) of sodium thiosulfate pentahydrate was added, followed by stirring, thereby quenching the remaining oxidation agent.Furthermore, 0.33 g (3.9 mmol, 0.067 eq) of sodium hydrogencarbonate and 10 g (70 mmol, 1.2 eq) of sodium sulfate were added, followed by stirring and then removing solid matter by filtration.As the filtrate was quantified with internal standard method (internal standard substance: α,α,α-trifluorotoluene) by 19F-NMR, Ethyl trifluoropyruvate was contained by 56 mmol (quantitative yield: 97%).By a simple distillation (up to 48° C./0.5 kPa) of the filtrate, 7.6 g of Ethyl trifluoropyruvate was obtained. 19F-NMR purity was 99% (40 mmol), and the total yield was 69%.
Einzelnachweise
[1] Patent: US2018/50976, 2018, A1. Location in patent: Paragraph 0143; 0144; 0145; 0146; 0147; 0148; 0149; 0150

Ethyl trifluoropyruvate Upstream-Materialien And Downstream Produkte

Ethyl trifluoropyruvate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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