74443-35-9

Usage

Uses

Used in Chemical Synthesis:
BIS-(2,6-DIMETHYL-PHENYL)-AMINE is used as a key intermediate in the synthesis of various polymers and materials, contributing to the development of a wide range of products.
Used in Dye Production:
In the dye industry, BIS-(2,6-DIMETHYL-PHENYL)-AMINE is used as a chemical intermediate for the production of dyes, enhancing color properties and performance in various applications.
Used in Pharmaceutical Manufacturing:
BIS-(2,6-DIMETHYL-PHENYL)-AMINE serves as an intermediate in the manufacturing of pharmaceuticals, playing a crucial role in the development of new drugs and medicines.
Used in Agricultural Chemicals:
BIS-(2,6-DIMETHYL-PHENYL)-AMINE is utilized in the production of agricultural chemicals, where it acts as an intermediate to help develop more effective and safer agrochemicals.
Used in Plastics and Rubber Industry:
BIS-(2,6-DIMETHYL-PHENYL)-AMINE is used as a precursor for the production of antioxidants, stabilizers, and UV absorbers, which are essential for improving the durability and performance of plastics and rubber products.

Upstream product

• 608-28-6 2,6-dimethyliodobenzene 
• 87-62-7 2,6-dimethylaniline 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 576-22-7 2-Bromo-m-xylene 
• 576-26-1 2.6-dimethylphenol 
• 81-20-9 2,6-dimethylnitrobenzene 
• 2192-33-8 2,6-dimethylbenzenediazonium tetrafluoroborate 

Relevant academic research and scientific papers

N-Heterocyclic Carbene Palladium(II) Amine Complexes: The Role of Primary Aryl- or Alkylamine Binding and Applications in the Buchwald-Hartwig Amination Reaction

N-heterocyclic carbene-palladium(II) amine complexes bearing primary aryl- or alkylamines were synthesized. The prepared complexes were characterized by single crystal X-ray diffraction as well as NMR spectroscopy. These complexes exhibited good catalytic activities for the Buchwald-Hartwig amination reaction of aryl chlorides to afford arylated anilines under mild conditions. All reactions were carried out in air and all starting materials were used as supplied without purification. 21 expected coupling products were obtained in moderate to high yields under optimum conditions.

Large-steric-hindrance N-heterocyclic carbene palladium complex, preparation method and application thereof, and synthesis method of sonidegib based on large-steric-hindrance N-heterocyclic carbene palladium complex

The invention belongs to the technical field of organic synthesis and chemical catalysis, and discloses a large-steric-hindrance N-heterocyclic carbene palladium complex, a preparation method thereof,an application of the complex in efficient catalysis of a C-N coupling reaction under a room-temperature air condition, and a synthesis method of sonidegib based on the complex. According to the large-steric-hindrance N-heterocyclic carbene palladium complex, diphenyl imidazole serves as a main ligand framework, functionalized allyl serves as an auxiliary ligand, the functionalized allyl is introduced beside a metal center of a catalyst to serve as an auxiliary ligand, the catalytic activity and stability are remarkably improved, the large-steric-hindrance N-heterocyclic carbene palladium complex can be applied to efficient catalysis of a CN coupling reaction, particularly, the CN coupling reaction can be efficiently catalyzed under the room temperature condition, and the yield can reachup to 99%. The invention also provides a method for synthesizing sonidegib by taking aryl/aliphatic amine and aryl chloride as reactants and a three-step method at room temperature under the catalysisof a palladium catalytic system, the synthetic method has few steps, and the total yield can reach 74.5%.

Synthesis of N-heterocyclic carbene-Pd(II)-5-phenyloxazole complexes and initial studies of their catalytic activity toward the Buchwald-Hartwig amination of aryl chlorides

Three new N-heterocyclic carbene (NHC)-Pd(II) complexes using 5-phenyloxazole as the ancillary ligand have been obtained in moderate to good yields by a one-pot reaction of the corresponding imidazolium salts, palladium chloride and 5-phenyloxazole under mild conditions. Initial studies showed that one of the complexes is an efficient catalyst for the Buchwald-Hartwig amination of aryl chlorides with various secondary and primary amines under the varied catalyst loading of 0.01-0.05 mol%, thus it will enrich the chemistry of NHCs and give an alternative catalyst for the coupling of challenging while cost-low aryl chlorides.

Benzyloxycalix[8]arene supported Pd-NHC cinnamyl complexes for Buchwald-Hartwig C-N cross-couplings

The scalable synthesis of Pd-NHC cinnamyl complexes supported on benzyloxycalix[8]arene is reported. These catalysts are very active for Buchwald-Hartwig cross-coupling reactions, allowing the coupling of aryl chlorides and bromides with a wide variety of alkyl and aryl amines using low catalytic loadings. The supported complexes also successfully afforded attractive unsymmetrical triarylamines, and in one case, promoted the synthesis of an unprecedented Pd-catalyzed C-H activation product. Thanks to the calixarenic support, the target products could be isolated with low levels of residual palladium, and in some cases, even below the restrictive toxic metal standards applied by the pharmaceutical industry. Through an easy to implement procedure, these perfectly characterised catalysts thus combine the best of homogeneous and heterogeneous catalysis: high efficiency (similar to or even better than the corresponding homogeneous complexes) and low Pd leaching levels expected from heterogeneous catalysts.

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines

The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.

Direct Synthesis of Diphenylamines from Phenols and Ammonium Formate Catalyzed by Palladium

Arylamines are commercially and synthetically useful compounds with a wide variety of applications. Their preparation has been traditionally achieved using metal-catalyzed C?N coupling reactions with aryl halides. In this work, 17 different diarylamines are prepared from phenols by using ammonium formate as the aminating reagent. Phenolic compounds are more desirable feedstocks, owing to their availability from lignin, making them valuable biorenewable alternatives to aryl halides. Ammonium formate is found to be a convenient surrogate for ammonia and a useful aminating reagent for phenols. Diarylamine products are obtained in good to excellent yields while only water and CO2 are generated as byproducts of the transformation.

Facile Buchwald-Hartwig coupling of sterically encumbered substrates effected by PNP ligands

The diphosphinoamine ligands [(Ph2P)2N(Ar); 1 (Ar = C6H5), 2 (Ar = 2,6-iPr2C6H3)] were effectively utilized in Buchwald-Hartwig coupling of a range of sterically demanding substr

Sterically Hindered Amination of Aryl Chlorides Catalyzed by a New Carbazolyl-Derived P,N-Ligand-Composed Palladium Complex

A family of 2-(9 H -carbazol-9-yl)phenyl-based phosphine ligands were synthesized and their efficacy in promoting the steric hindered Buchwald-Hartwig amination was evaluated. In the presence of Pd(OAc) 2 (0.03-1.0 molpercent) associated with t

N-Heterocyclic carbene-palladacyclic complexes: synthesis, characterization and their applications in the C-N coupling and α-arylation of ketones using aryl chlorides

N-Heterocyclic carbene-palladacyclic complexes 3 were successfully achieved in a one-pot procedure under mild conditions. The structure of 3a was unambiguously confirmed by X-ray single crystal diffraction and it was an active catalyst in the Buchwald-Hartwig amination and α-arylation of ketones even at very low catalyst loadings (0.01 mol%).

Pd-PEPPSI-IPentAn Promoted Deactivated Amination of Aryl Chlorides with Amines under Aerobic Conditions

We report herein a highly efficient Pd-catalyzed amination by "bulky-yet-flexible" Pd-PEPPSI-IPentAn complexes. The relationship between the N-heterocyclic carbenes (NHCs) structure and catalytic properties was discussed. Sterically hindered (hetero)aryl chlorides and a variety of aliphatic and aromatic amines can be applied in this cross-coupling, which smoothly proceeded to provide desired products. The operationally simple protocol highlights the rapid access to CAr-N bond formation under mild conditions without the exclusion of air and moisture.