6264-98-8

Usage

Uses

Used in Dye and Pigment Manufacturing:
m-(o-Toluidino)phenol is used as a chemical intermediate for the production of dyes and pigments. Its aromatic amine structure contributes to the color properties of these compounds, making it a valuable component in the industry.
Used in Chemical Research:
m-(o-Toluidino)phenol is also used as a research compound in various chemical studies. Its unique structure and properties make it an interesting subject for scientific investigation, potentially leading to new applications and discoveries in the field of chemistry.

InChI:InChI=1/C13H13NO/c1-10-5-2-3-8-13(10)14-11-6-4-7-12(15)9-11/h2-9,14-15H,1H3

Upstream product

• 95-53-4 o-toluidine 
• 108-46-3 recorcinol 
• 16419-60-6 2-Methylphenylboronic acid 
• 591-27-5 m-Hydroxyaniline 
• 95-46-5 2-methylphenyl bromide 
• 95-49-8 2-methylchlorobenzene 
• 762-04-9 Diethyl phosphonate 
• 102-85-2 tri-n-butyl phosphite 
• 10294-56-1 phosphorous acid 
• 101-02-0 triphenyl phosphite 

Downstream Products

• 107456-48-4 N-(3-methoxyphenyl)-2-methylaniline 
• 20178-49-8 tetradecahydroacridine 
• 260-94-6 acridine 
• 108801-83-8 3',6'-di-o-toluidino-spiro[phthalan-1,9'-xanthen]-3-one 

Relevant academic research and scientific papers

Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols

Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc)2/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)2/Cs2CO3 system and benzoic acid as an additive. These ligand-free conditions and “open-flask” chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.

Orthogonal Cu- and Pd-based catalyst systems for the O- and N-arylation of aminophenols

O- or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu- and Pd-based catalyst systems for the selective O- and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3- and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N′-dimethyl-1,2- cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3- and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.

Manufacture of arylamines

Arylamines are manufactured by reacting alcohols with amines in the presence of phosphorus-III compounds. The arylamines I manufactured by the process of the invention are intermediates for the manufacture of crop protection agents, optical brighteners, especially amino-coumarin derivatives, and dyes, especially of the xanthene, pyronine, rhodamine, oxazine, azo, triphenylmethane and diphenylmethane series.