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Usage

Uses

Used in Chemical Production:
2,6-Diphenylaniline is used as an intermediate for the production of dyes, pigments, and pharmaceuticals. Its chemical structure allows it to be a key component in the synthesis of these compounds, contributing to their color and properties.
Used in Corrosion Inhibition:
2,6-Diphenylaniline also has potential applications as a corrosion inhibitor for metal surfaces. Its ability to protect metals from corrosion makes it a valuable asset in industries where metal preservation is crucial.
Safety Considerations:

Upstream product

• 156021-09-9 [1-(2,2-Dichloro-1-phenyl-cyclopropyl)-meth-(E)-ylidene]-(1-phenyl-ethyl)-amine 
• 90-41-5 2-phenylaniline 
• 108-90-7 chlorobenzene 
• 877764-42-6 2,6-(diphenyl)phenyl azide 

Downstream Products

• 1331830-93-3 1-([1,1':3',1''-terphenyl]-2'-yl)-3-((1R,2R)-2-aminocyclohexyl)thiourea 
• 1245912-81-5 N-(2,4,6-triisopropylphenyl)-[1,1':3',1''-terphenyl]-2'-amine 
• 82777-09-1 2′-iodo-1,1′:3′,1″-terphenyl 

Relevant academic research and scientific papers

Catalytic C(sp2)?H amination reactions using dinickel imides

C?H amination reactions are valuable transformations for the construction of C?N bonds. Due to their relatively high bond dissociation energies, C(sp2)?H bonds are generally not susceptible toward direct nitrene insertion, necessitating alternative mechanisms for C?H activation. Here, we report that cationic dinuclear (NDI)Ni2 (NDI = naphthyridine?diimine) complexes catalyze intramolecular nitrene insertions into aryl and vinyl C(sp2)? H bonds. Mechanistic studies suggest that a bridging imido ligand supported at a Ni2 site induces C?H activation by a 1,2-addition pathway to generate an azametallacyclic intermediate. This organometallic mechanism contrasts with the electrocyclization/1,2-shift mechanism proposed for analogous transformations using Rh2 catalysts. The implications of these mechanistic differences for the stereoselectivity and chemoselectivity of C?H amination are described.

Direct intermolecular aniline ortho- arylation via benzyne intermediates

A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of enantiopure binaphthyldiamine affords a product with >99% ee.

Thermal Rearrangement of N-Arylmethyl- and N-Alkyl-2,2-dihalogenocyclopropyl Imines

An extended study of the thermal isomerization of 1-substituted 2,2-dihalogenocyclopropyl imines is reported.The thermolysis of N-arylmethyl-2,2-dichlorocyclopropanecarbaldimines 15a-h produces 2-aryl- 16a-h and 2-aryl-4-chloro-pyridine derivatives 17a-h, while N-cyclopropyl imines 15i, j yielded N-alyklchloropyrroles.The 2,2-dibromocyclopropane analogue undergoes thermolysis at lower temperatures.An ionic mechanism triggered by the halide ion dissociation is proposed for the thermal rearrangement on the basis of a study using deuterated imine 15m, and the effects of additives and solvents.On the other hand, difluorocyclopropyl imine undergoes a homolytic cleavage of cyclopropane 1,3-bond with lower activation energy than the dichlorocyclopropyl imine, and afforded the N-alykl-3-fluoropyrrole derivative preferentially.