50617-73-7

Usage

Uses

Used in Dye Manufacturing Industry:
N-Methyl-m-phenylenediamine is used as a key intermediate for the production of azo dyes, which are widely used in various applications such as textiles, plastics, and printing inks. Its diazonium derivative is crucial for the synthesis of these dyes, making it an essential component in the dye manufacturing process.
Used in Chemical Research:
N-Methyl-m-phenylenediamine is used as a reagent in various chemical reactions and research studies. Its unique chemical structure allows for the exploration of new reaction pathways and the development of novel compounds with potential applications in various industries.
Used in Safety and Handling Protocols:
Due to its reactivity and potential health risks, N-Methyl-m-phenylenediamine is used as a case study for the development of safety protocols and handling procedures in the chemical industry. This ensures that workers are protected from exposure to hazardous substances and that the environment is safeguarded from potential contamination.

Upstream product

• 108-45-2 m-phenylenediamine 
• 616-38-6 carbonic acid dimethyl ester 
• 7006-52-2 3-chloro-N-methylaniline 
• 99-09-2 3-nitro-aniline 
• 619-26-1 N-methyl-3-nitroaniline 

Downstream Products

• 14814-75-6 N,N'-dimethyl-1,3-phenylenediamine 
• 86518-02-7 tert-butyldimethyl-<3-(N-methylamino)anilino>silane 
• 1018830-32-4 C₁₈H₁₆N₄S₂ 
• 95-80-7 4-methylbenzene-1,3-diamine 

Relevant academic research and scientific papers

Nickel-catalyzed monoarylation of ammonia

Structurally diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni-catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported protocol. Proof-of-principle experiments established that air-stable [(JosiPhos)NiCl2] precatalysts can be employed successfully in such transformations. Lighten Up: The substrate scope of the title reaction includes (hetero)aryl chloride, bromide, and tosylate electrophiles. The versatility and potential scalability of the reported method is demonstrated by the use of either commercially available stock solutions of ammonia or ammonia gas.

An examination of the palladium/Mor-DalPhos catalyst system in the context of selective ammonia monoarylation at room temperature

An examination of the [{Pd(cinnamyl)Cl}2]/Mor-DalPhos (Mor-DalPhos=di(1-adamantyl)-2-morpholinophenylphosphine) catalyst system in Buchwald-Hartwig aminations employing ammonia was conducted to better understand the catalyst formation process and to guide the development of precatalysts for otherwise challenging room-temperature ammonia monoarylations. The combination of [{Pd(cinnamyl)Cl}2] and Mor-DalPhos afforded [(κ 2-P,N-Mor-DalPhos)Pd(η1-cinnamyl)Cl] (2), which, in the presence of a base and chlorobenzene, generated [(κ2-P,N- Mor-DalPhos)Pd(Ph)Cl] (1 a). Halide abstraction from 1 a afforded [(κ3-P,N,O-Mor-DalPhos)Pd(Ph)]OTf (5), bringing to light a potential stabilizing interaction that is offered by Mor-DalPhos. An examination of [(κ2-P,N-Mor-DalPhos)Pd(aryl)Cl] (1 b-f) and related precatalysts for the coupling of ammonia and chlorobenzene at room temperature established the suitability of 1 a in such challenging applications. The scope of reactivity for the use of 1 a (5 mol %) encompassed a range of (hetero)aryl (pseudo)halides (X=Cl, Br, I, OTs) with diverse substituents (alkyl, aryl, ether, thioether, ketone, amine, fluoro, trifluoromethyl, and nitrile), including chemoselective arylations. Copyright

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

A P,N-Ligand for palladium-catalyzed ammonia arylation: Coupling of deactivated aryl chlorides, chemoselective arylations, and room temperature reactions

(Figure Presented) Amazing ammonia: A new air-stable P,N-ligand (Mor-DalPhos) is reported that enables the palladium-catalyzed crosscoupling of ammonia to a variety of aryl chloride and aryl tosylate substrates with high chemoselectivity and, for the first time, at room temperature (see scheme; Ad = adamantyl, Ts=para-toluenesulfonyl).

Highly selective zeolite-catalysed mono-N-alkylation of arylenediamines by dialkyl carbonates

Arylenediamines are mono-N-alkylated by dialkyl carbonates in the presence of NaY zeolite catalyst in a regioselective and nontoxic process.