255835-91-7

Basic information

• Product Name: 4-(2,6-dimethylphenyl)morpholine
• Synonyms: 4-(2,6-dimethylphenyl)morpholine
• CAS NO: 255835-91-7
• Molecular Formula: C12H17NO
• Molecular Weight: 191.26948
• Mol File: 255835-91-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(2,6-dimethylphenyl)morpholine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,6-dimethylphenyl)morpholine(255835-91-7)
• EPA Substance Registry System: 4-(2,6-dimethylphenyl)morpholine(255835-91-7)

Safety Data

• Hazardous Substances Data: 255835-91-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2,6-dimethylphenyl)morpholine is used as a building block for the synthesis of various biologically active molecules and pharmaceuticals. Its unique chemical structure and properties make it a promising candidate for the development of new drugs.
Used in Agricultural Industry:
4-(2,6-dimethylphenyl)morpholine is used as a precursor in the development of new pesticides. Its chemical properties allow it to be incorporated into compounds that can effectively control pests and protect crops.
Used in Manufacturing Industry:
4-(2,6-dimethylphenyl)morpholine is used as an intermediate in the production of various useful compounds. Its versatility and unique structure make it a valuable component in the synthesis of a wide range of products.
Overall, 4-(2,6-dimethylphenyl)morpholine plays a significant role in the field of chemical research and has promising potential in various industrial applications.

Upstream product

• 110-91-8 morpholine 
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• 576-22-7 2-Bromo-m-xylene 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 1003858-51-2 2-(2,6-dimethylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 576-26-1 2.6-dimethylphenol 

Relevant articles and documents

Pd-NHC catalyzed biaryl coupling by direct C-H activationA novel strategy for the synthesis of dibenzocyclooctane lignans

Cross-coupling reactions, such as Buchwald-Hartwig arylamination and direct intramolecular biaryl coupling by C-H activation, were carried out using various Palladium-N-heterocyclic carbenes (Pd-NHC) as catalysts. The yields were good to excellent. The la

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%.

Synergistic Ligand Effect between N-Heterocyclic Carbene (NHC) and Bicyclic Phosphoramidite (Briphos) Ligands in Pd-Catalyzed Amination

A synergistic ligand effect between NHC and phosphorus ligands in Pd-catalyzed Buchwald-Hartwig amination reactions was demonstrated with tunable π-acceptor bicyclic bridgehead phosphoramidite (briphos) ligands. The catalytic activity of NHC-Pd-L (L = phosphorus ligand) precatalysts depends on the electronic properties of L. A NHC-Pd-L catalyst with an N-cyclohexyl-substituted briphos ligand was found to be highly efficient. A series of C-N bond coupling reactions between primary or secondary amines and aryl chlorides were performed with high yields under mild reaction conditions.

An easily available N-heterocyclic carbene–palladium(II) catalyst for Buchwald–Hartwig amination of aryl chlorides

Abstract: An easily available N-heterocyclic carbene–palladium(II) complex was found to be an efficient catalyst for the Buchwald–Hartwig amination of aryl chlorides. Both secondary and primary amines were tolerated under the same reaction conditions. Under the optimal conditions, all reactions proceeded successfully to give the desired products in good to high yields within hours. Graphical Abstract: [Figure not available: see fulltext.]

Practical catalytic method for synthesis of sterically hindered anilines

A practical catalytic method for the synthesis of sterically hindered anilines is described. The amination of aryl and heteroaryl boronic esters is accomplished using a catalyst prepared in situ from commercially available and air-stable copper(i) triflat

Palladium-catalysed amination of aryl- and heteroaryl halides using tert-butyl tetraisopropylphosphorodiamidite as an easily accessible and air-stable ligand

The phosphorus compound tert-butyl tetraisopropylphosphorodiamidite, prepared from bis(diisopropylamino)chlorophosphine, is an excellent ligand for palladium-catalysed Buchwald-Hartwig amination of aryl- and heteroaryl chlorides and bromides. Based on its ready accessibility and air-stability, this amination protocol is a practical approach to the synthesis of industrially important aryl- and heteroarylamines. Copyright

Skeleton decoration of NHCs by amino groups and its sequential booster effect on the palladium-catalyzed Buchwald-Hartwig amination

A challenging synthetic modification of PEPPSI-type palladium pre-catalysts consisting of a stepwise incorporation of one and two amino groups onto the NHC skeleton was seen to exert a sequential enhancement of the electronic donor properties. This appears to be positively correlated with the catalytic performances of the corresponding complexes in the Buchwald-Hartwig amination. This is illustrated, for example, by the quantitative amination of 4-chloroanisole by morpholine within 2 h at 25°C with a 2 mol% catalyst/substrate ratio or by a significant reduction of catalytic loading (down to 0.005 mol%) for the coupling of aryl chlorides with anilines (max TON: 19600).

Modular synthesis of functionalisable alkoxy-tethered N-heterocyclic carbene ligands and an active catalyst for buchwald-hartwig aminations

Modular syntheses of functionalised, alkoxy-tethered 1,3-bis(2,4,6- trimethylphenyl)imidazolium (IMes*H+) and 1,3-bis(2,6- diisopropylphen-l)imidazolium (IPr*H+) derivatives 1,3-bis(4-alkyl- -2,4,6-trimethylphenyl)imidazolium (IXyOR*H+) and 1,3-bis(4-alkyl-oxy-2,6-diisopropylphenyl)imidazolium (IPrOR*H +) are reported. A reliable synthesis of the key starting material 4-amino-3,5-diisopropylphenol is also described. Etherification of hydroxydecorated ligand intermediates before formation of the imidazolium core and subsequent modification, or direct etherification of the versatile synthon IPrOH·HCl, allowed access to various linker types including triethoxysilyl, primary amino and norbornenyl, which are not accessible by other methods. An IPrOR-palladium(II) complex was prepared, and its catalytic activity was evaluated in challenging Buchwald- Hartwig aminations of aryl chlorides. This precatalyst displayed excellent activity and selectivity under mild reaction conditions, achieving in some cases a 10-fold improvement in TOF relative to the IPr-based version. An unexpected activity profile was observed wherein sterically demanding anilines were coupled more easily than those lacking orthosubstitution.

N-heterocyclic carbene-palladium(II)-4,5-dihydrooxazole complexes: Synthesis and catalytic activity toward amination of aryl chlorides

A series of novel N-heterocyclic carbene-palladium(II)-4,5-dihydrooxazole (NHC-PdII-Ox) complexes 3 were successfully synthesized from commercially available imidazolium salts 1, PdCl2, and 4,5-dihydrooxazoles 2 in a one-step process, and these complexes showed efficient catalytic activity toward the amination of aryl chlorides. Both secondary and primary amines were tolerated under the same reaction conditions. Under the optimal reaction conditions, the expected coupling products were obtained in moderate to high yields.