956577-20-1

Basic information

• Product Name: 1,3-bis-(2,6-diisopropylphenyl)imidazolium bromide
• Synonyms: 1,3-bis-(2,6-diisopropylphenyl)imidazolium bromide
• CAS NO: 956577-20-1
• Molecular Weight: 469.508
• Mol File: 956577-20-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3-bis-(2,6-diisopropylphenyl)imidazolium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis-(2,6-diisopropylphenyl)imidazolium bromide(956577-20-1)
• EPA Substance Registry System: 1,3-bis-(2,6-diisopropylphenyl)imidazolium bromide(956577-20-1)

Safety Data

• Hazardous Substances Data: 956577-20-1(Hazardous Substances Data)

Upstream product

• 1187568-00-8 [SiBr₃(Idipp)]Br 
• 956972-12-6 1,3-bis(2,6-diiopropylphenyl)imidazol-2-ylidene borane 
• 1643-19-2 tetrabutylammomium bromide 
• 1940-57-4 9H-fluoren-9-yl bromide 
• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 

Downstream Products

• 1246013-92-2 [FeBr₃(THF)](bis(2,6-diisopropylphenyl)imidazolium)*THF 

Relevant articles and documents

Preventing Pd-NHC bond cleavage and switching from nano-scale to molecular catalytic systems: Amines and temperature as catalyst activators

Many reactions catalyzed by Pd complexes with N-heterocyclic carbene (NHC) ligands are performed in the presence of amines which usually act as coupling reagents or mild bases. However, amines can react with Pd/NHC complexes in a number of ways: enhancing molecular catalysis, causing the catalyst deactivation or triggering the ligandless modes of catalysis by producing NHC-free active palladium species. This study gains insight into conditions required for the efficient use of amines as activators of molecular Pd/NHC catalysis and preventing the undesirable reductive cleavage of the Pd-NHC bond in catalytic systems. Reactions of Pd/NHC complexes with various amines within a temperature range of 25-140 °C and thermal stability of the resulting amino-complexes are examined. The results indicate the major influence of the amine structure and reaction temperature on the catalyst transformation. In particular, thermal decomposition of Pd/NHC complexes with aliphatic amine ligands predominantly leads to reductive Pd-NHC bond cleavage, while deprotonation of the complexes with primary and secondary aliphatic amine ligands in the presence of strong bases at 25-60 °C promotes the activation of molecular Pd/NHC catalysis. Efficient Pd-PEPPSI complex-amine systems suitable for strong-base-promoted C-S cross-coupling reactions between aryl halides and thiols are suggested on the basis of these findings.

On the dual role of N-heterocyclic carbenes as bases and nucleophiles in reactions with organic halides

The synthetic consequences of different basicities, nucleophilicities, and sterics of N-heterocyclic carbenes have been studied in reactions of imidazolin-2-ylidenes with organic halides. Highly nucleophilic and less basic carbenes cleanly gave alkyli-deneimidazolines, the deoxy analogues of Breslow-type intermediates. More basic NHCs engaged in unwanted deprotonation or dehydrohalogenation reactions. Georg Thieme Verlag Stuttgart. New York.

SiBr2(Idipp): A stable n-heterocyclic carbene adduct of dibromosilylene

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