1157867-61-2

Basic information

• Product Name: 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-iMidazol-3-iuM chloride
• Synonyms: 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-iMidazol-3-iuM chloride;CAS:1157867-61-2
• CAS NO: 1157867-61-2
• Molecular Formula: C₃₅H₅₃N₂*Cl
• Molecular Weight: 537.26172
• Mol File: 1157867-61-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-iMidazol-3-iuM chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-iMidazol-3-iuM chloride(1157867-61-2)
• EPA Substance Registry System: 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-iMidazol-3-iuM chloride(1157867-61-2)

Safety Data

• Hazardous Substances Data: 1157867-61-2(Hazardous Substances Data)

Usage

Description

1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-imidazol-3-ium chloride is an organic compound characterized by its unique chemical structure, which features two pentan-3-yl groups attached to phenyl rings connected to an imidazolium core. This structure endows the compound with specific chemical properties that make it suitable for various applications in the field of organic synthesis.

Uses

1. Used in Organic Synthesis:
1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-imidazol-3-ium chloride is used as a reactant in organic synthesis for its ability to participate in various chemical reactions, such as electrophilic aromatic substitution, nucleophilic aromatic substitution, and other reactions involving the imidazolium core. Its unique structure allows it to act as a building block for the synthesis of more complex organic molecules with potential applications in various industries.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-imidazol-3-ium chloride may be used as a reactant for the synthesis of novel drug candidates. Its chemical properties and structural features can be exploited to design and develop new molecules with potential therapeutic applications.
3. Used in Material Science:
1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-imidazol-3-ium chloride can also be utilized in the field of material science, where it may be employed in the development of new materials with specific properties. For example, its incorporation into polymers or other materials could lead to the creation of materials with enhanced thermal stability, electrical conductivity, or other desirable characteristics.
4. Used in Chemical Research:
In the realm of chemical research, 1,3-Bis(2,6-di(pentan-3-yl)phenyl)-1H-imidazol-3-ium chloride serves as a valuable compound for studying various aspects of organic chemistry, such as reaction mechanisms, stereochemistry, and the influence of substituents on reactivity. Its unique structure provides researchers with a platform to explore new synthetic strategies and gain insights into the fundamental principles governing organic reactions.

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• 50-00-0 formaldehyd 
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Relevant articles and documents

Steric and electronic parameters of a bulky yet flexible N-heterocyclic carbene: 1,3-bis(2,6-bis(1-ethylpropyl)phenyl)imidazol-2-ylidene (IPent)

The free N-heterocyclic carbene IPent (1; IPent = 1,3-bis(2,6-bis(1- ethylpropyl)phenyl)imidazol-2-ylidene) was prepared from the corresponding imidazolium chloride salt (2). The steric and electronic parameters of 1 were determined by synthesis of the gold(I) chloride complex [Au(IPent)Cl] (3) and the nickel-carbonyl complex [Ni(IPent)(CO)3] (4), respectively. 3 and 4 were fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction studies on single crystals.

The Selective Cross-Coupling of Secondary Alkyl Zinc Reagents to Five-Membered-Ring Heterocycles Using Pd-PEPPSI-IHeptCl

The ability to cross-couple secondary alkyl centers is fraught with a number of problems, including difficult reductive elimination, which often leads to β-hydride elimination. Whereas catalysts have been reported that provide decent selectivity for the expected (non-rearranged) cross-coupled product with aryl or heteroaryl oxidative-addition partners, none have shown reliable selectivity with five-membered-ring heterocycles. In this report, a new, rationally designed catalyst, Pd-PEPPSI-IHeptCl, is demonstrated to be effective in selective cross-coupling reactions with secondary alkyl reagents across an impressive variety of furans, thiophenes, and benzo-fused derivatives (e.g., indoles, benzofurans), in most instances producing clean products with minimal, if any, migratory insertion for the first time. A wide variety of five-membered-ring heterocycles were successfully cross-coupled to secondary alkyl zinc reagents with the new precatalyst Pd-PEPPSI-IHeptCl, which features a bulky N-heterocyclic carbene ligand. This catalyst suppresses migratory-insertion (rearrangement) pathways, and the desired products are thus formed with high selectivity.

Large yet flexible N-heterocyclic carbene ligands for palladium catalysis

A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent ("Tent" for "tentacular") of which the well-known IMes (N,N′-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N′-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N′-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N′-bis(2,6- di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N′-bis(2,6-di(4-heptyl) phenyl)imidazol-2-ylidene) and INon (N,N′-bis(2,6-di(5-nonyl)phenyl) imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated. Tentacular NHCs: A straightforward, scalable eight-step synthesis of N-heterocyclic carbenes (NHCs) has been developed using inexpensive and readily available 2-nitro-m-xylene, allowing the preparation of a class of NHCs designated ITent ("Tent" for "tentacular"). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes, and the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.