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

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride  Struktur
141556-45-8
CAS-Nr.
141556-45-8
Englisch Name:
1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
Synonyma:
IMes.HCl;IMESCL;1,3-DiMesityl-1H-iMidazol-3-iuM chloride;1,3-Bis(mesityl)imidazolium chloride;1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE;1,3-Bisimidazolium chloride;1,3-DIMESITYLIMIDAZOLIUM CHLORIDE;1,3-DimesitylimidazoliumChloride>1,3-Dimesitylimidazoliumchloride,96%;1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLI&
CBNumber:
CB5707153
Summenformel:
C21H25ClN2
Molgewicht:
340.89
MOL-Datei:
141556-45-8.mol

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride 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
Wasserl?slichkeit
Slightly soluble in water.
InChIKey
OTOSIXGMLYKKOW-UHFFFAOYSA-M
CAS Datenbank
141556-45-8(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi
R-S?tze: 36/37/38
S-S?tze: 26-36
WGK Germany  3
TSCA  No
HS Code  29332900
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" />
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P271 Nur im Freien oder in gut belüfteten R?umen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P302+P352 BEI BERüHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckm??ig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.

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

R-S?tze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze 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.
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 of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
Reaction of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride
Reaction of 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride

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

Upstream-Materialien

Downstream Produkte


1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 253)Lieferanten
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Xilinglab Co., Ltd.
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  • 1,3-DIMESITYLIMIDAZOLIUM CHLORIDE
  • 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
  • 1,3-(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
  • N,N'-(2,4,6-TRIMETHYLPHENYL)DIHYDROIMADAZOLIUM CHLORIDE
  • 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLI&
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazoliumchloride,min.95%
  • 1,3-BIS-(2,4,6-TRIMETHYLPHENYL)-1H-IMIDAZOLIUM CHLORIDE
  • 1,3-Bis-(2,4,6-trimethyl-phenyl)-3H-imidazol-1-ium chloride
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride, min. 97%
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride,95%
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride,97%
  • [1,3-bis(2,4,6-triMethylphenyl)-3H-1$l^{5},3-iMidazol-1-yliuM-2-yl]chloranuide
  • 1,3-Bis(2,4,6-triMethylphenyl)iMidazoliuMchloride,Min.97%
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolium Chloride IMes.HCl
  • 1,3-bis(2,4,6-triMethylphenyl)iMidazol-1-iuM,chloride
  • 1,3-Dimesitylimidazoliumchloride,96%
  • 1,3-Dihydro-1,3-dimesityl-2H-imidazol-2-ylidene monohydrochloride
  • 1,3-Bis(2,4,6-trimethyphenyl)imidazolium chloride
  • 1,3-bis(2,4,6-trimethylphenyl)imidazol-1-ium
  • 1,3-Bisimidazolium chloride
  • 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-1-ium
  • 1,3-DimesitylimidazoliumChloride>
  • 1H-Imidazolium, 1,3-bis(2,4,6-trimethylphenyl)-, chloride (1:1)
  • 1,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chlori...
  • TIANFU CHEM 1,3-BIS(2,4,6-TRIMETHYLPHENYL)IMIDAZOLIUM CHLORIDE
  • 1,3-BIS(2,4,6-TRIMETHYLPHENYL)-4,5-DIHYDROIMIDAZOLIUM CHLORIDE
  • IMes.HCl
  • 1,3-DiMesityl-1H-iMidazol-3-iuM chloride
  • 1,3-Bis(mesityl)imidazolium chloride
  • IMESCL
  • 1,3-bis(2,4,6-trimethylphenyl)-1H-Imidazolium chloride (1:1)
  • 1,3-bis (2,4,6-trimethylphenyl) imidazole chloride
  • 1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride,98%
  • 1,3-Dimesityl-1H-imidazol-3-ium chloride , IMes.HCl
  • 141556-45-8
  • C21H25N2Cl
  • C21H25ClN2
  • NHC Compounds
  • Catalysis and Inorganic Chemistry
  • organic amine
  • Imidazolium Compounds
  • Ligands
  • N-Heterocyclic Carbene Ligands
  • Synthetic Organic Chemistry
  • Catalysis and Inorganic Chemistry
  • Chemical Synthesis
  • NHC Compounds
  • API intermediates
  • Achiral Nitrogen
  • NHC
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