1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

Bezeichnung:1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

CAS-Nr141556-45-8

Englisch Name:1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

CBNumberCB5707153

SummenformelC21H25ClN2

Molgewicht340.89

MOL-Datei141556-45-8.mol

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	>300 °C (lit.)
Siedepunkt	499.2°C (rough estimate)
Dichte	1.0279 (rough estimate)
Brechungsindex	1.5940 (estimate)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Aggregatzustand	Powder
Farbe	Off-white to beige
Wasserlöslichkeit	Slightly soluble in water.
InChIKey	OTOSIXGMLYKKOW-UHFFFAOYSA-M
CAS Datenbank	141556-45-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
TSCA	No
HS Code	29332900

Gefahreninformationscode (GHS)

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
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.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
off-white to beige powder
Verwenden
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride is used as a phosphine-free ligand in various metal-catalyzed coupling reactions, often with advantageous results in difficult cases. For use in the Pd-catalyzed cross-coupling of aryl Grignards with aryl chlorides (Kumada reaction). Many examples have been recorded of the use of NHC ligands in the Suzuki coupling reaction, for examples utilizing 1,3-dimesitylimidazol-2-ylidene, in the coupling of arylboronic acids with relatively unreactive aryl chlorides.
synthetische
In a flask, the imine(3 g, 10 mmol) was dissolved in tetrahydrofuran(25 ml), followed by dropwise addition of chloromethyl ethyl ether(1.04 g, 11 mmol). the mixture was stirred under N2 at 40 °C for 18 h, and then ethyl ether(25 ml) was added to separate white solid. The solid was filtered and washed with ethyl ether. Finally, the white solid was dried under vacuum affording 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride.
Reaktionen
Precursor to the nucleophilic carbene that serves as a bulky, electron-rich "phosphine mimic" for metal-catalyzed reactions.
(a) Palladium-catalyzed Suzuki cross-coupling of aryl chlorides.
(b) Palladium-catalyzed Kumada cross-coupling of aryl chlorides.
(c) Ruthenium-carbene catalysts for ring-closing metathesis.
(d) Suzuki coupling of aryltrimethylammonium salts.
(e) Sonogashira coupling of aryl bromides.
Precursor to a nucleophilic carbene that serves as catalyst.
Ligand for arylation of aldehydes.
Ligand for carbene catalyzed intermolecular arylation of C-H bonds.
Catalyst for boron conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls.
Ligand for dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes.
Precursor for carbene for conjugate silylation of alpha, beta-unsaturated carbonyls.
reaction suitability
reagent type: ligand

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Upstream-Materialien And Downstream Produkte

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