101-16-6

Basic information

• Product Name: 3-Methoxydiphenylamine
• Synonyms: N1-phenyl-3-methoxyaniline;3-METHOXYDIPHENYLAMINE 97+%;DIPHENYLAMINE,3-METHOXY-;(3-Methoxyphenyl)phenylamine;N-(3-Methoxyphenyl)aniline;N-Phenyl-3-methoxyaniline;Phenyl(3-methoxyphenyl)amine;3-Methoxydiphenylami
• CAS NO: 101-16-6
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.25
• EINECS: 202-921-5
• Product Categories: Intermediates of Dyes and Pigments;M;Stains and Dyes;Stains&Dyes, A to
• Mol File: 101-16-6.mol

Chemical Properties

• Melting Point: 72-74°C
• Boiling Point: 160 °C / 2mmHg
• Flash Point: 132 °C
• Appearance: White to brown/Powder
• Density: 1.11 g/cm³
• Vapor Pressure: 0.000173mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: room temp
• CAS DataBase Reference: 3-Methoxydiphenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxydiphenylamine(101-16-6)
• EPA Substance Registry System: 3-Methoxydiphenylamine(101-16-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 101-16-6(Hazardous Substances Data)

Usage

Uses

Used in Dye and Stain Preparation:
3-Methoxydiphenylamine is used as a precursor in the synthesis of 3-methoxydiphenylamine-4-diazonium salts (MDP-4-DS) and the corresponding diazoresins. These compounds are employed as dyes and stains in various applications, providing color and contrast to different materials.
Used in Indicators:
3-Methoxydiphenylamine and its derivatives are used as indicators in various chemical and biological assays. They help in detecting the presence or absence of specific substances, as well as monitoring changes in pH or other environmental conditions.
Used in General Laboratory Applications:
3-Methoxydiphenylamine is utilized in general laboratory settings for a range of purposes, including the synthesis of other organic compounds, as a reagent in chemical reactions, and for educational purposes in teaching laboratories.
Used in Industrial Applications:
The diazonium salts and diazoresins derived from 3-methoxydiphenylamine find use in various industrial applications, such as in the textile industry for dyeing fabrics, in the plastics industry for coloration, and in the printing industry for ink production.

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

Upstream product

• 591-50-4 iodobenzene 
• 536-90-3 m-Anisidine 
• 108-86-1 bromobenzene 
• 588-16-9 m-methoxyacetanilide 
• 101651-37-0 N-(3-methoxyphenyl)acetanilide 
• 766-85-8 3-methoxy-1-iodobenzene 
• 62-53-3 aniline 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 766-51-8 2-Chloroanisole 
• 108-90-7 chlorobenzene 
• 2398-37-0 3-methoxyphenyl bromide 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 
• 103-84-4 Acetanilid 
• 66107-33-3 3-methoxyphenyl triflate 

Downstream Products

• 61174-11-6 4-methoxy-10H-phenothiazine 
• 1771-18-2 2-methoxy-10H-phenothiazine 
• 69829-28-3 (3-methoxy-4-nitroso-phenyl)-phenyl-amine 
• 112718-01-1 (3-methoxy-phenyl)-[2-(1-methyl-[2]piperidyl)-ethyl]-phenyl-amine 
• 6933-49-9 2-methoxy-9H-carbazole 
• 64053-59-4 N-chloroacetyl-N-phenyl-m-anisidine 
• 6933-50-2 4-methoxy-9H-carbazole 
• 105465-24-5 N,N'-diphenyl-N,N'-bis(3-methoxylphenyl)-[1,1'-biphenyl]-4,4'-diamine 
• 5840-10-8 1-amino-2-methoxy-4-(N-phenylamino)benzene 
• 883726-43-0 N,N-diethyl-N'-(3-methoxyphenyl)-N'-phenylurea 
• 83060-84-8 N,N-diethyl-2-anilino-6-methoxybenzamide 
• 207802-65-1 N,N-diethyl-2-(3-methoxyanilino)benzamide 
• 172834-72-9 3-Methoxy-acridine-9-carboxylic acid 2,3,6-trifluoro-phenyl ester 
• 344307-16-0 4-Hydroxy-1-phenyl-1,3-dihydro-indol-2-one 

Relevant articles and documents

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.]

CuII-β-cyclodextrin complex as a nanocatalyst for the homo-and cross-coupling of arylboronic acids under ligand-and base-free conditions in air: Chemoselective cross-coupling of arylboronic acids in water

We report here the transition-metal-catalyzed chemoselective cross-coupling of arylbroronic acids in high yields without using ligand or base. We have developed an efficient copper-catalyzed protocol for the homocoupling and cross-coupling of arylboronic acids. The protocol is also suitable for the cross-coupling of aliphatic primary amines with arylboronic acids. Aminophenols and primary amines bearing an alcoholic substituent on the aliphatic chain were coupled with arylboronic acids, and the products were obtained with high C-N coupling selectivity. An effective catalyst was Cu2-β- cyclodextrin, which is readily available and structurally simple, but has not previously been explored as a catalyst.

Copper-TBAF catalyzed arylation of amines and amides with aryl trimethoxysilane

A copper-catalyzed C-N bond forming reaction among aryl siloxane and primary, secondary amines as well as amides has been described. The reaction was conducted in the presence of P(C6F5)3 and 4 A molecular sieves in CHsub

Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes

Described herein is a novel palladium-catalyzed C-N bond-formation reaction employing aryltrimethylgermanes as the new arylating reagents. Primary/secondary amines or even amides could be smoothly arylated to provide the corresponding N-arylation products in moderate to excellent yields.

Palladium-Catalyzed Amination of Aryl Halides: Mechanism and Rational Catalyst Design

Palladium complexes of tri-o-tolyl phosphine and bis(diphenylphospino)ferrocene catalyze the reaction between aryl halides and either tin amides or amines in the presence of base to form aryl amines by halide substitution. This account describes our mechanistic and synthetic studies related to the amination reactions. These studies include kinetic behavior of the catalytic systems as well as direct observation of the primary stoichiometric reactions comprising the catalysis - including the rare C-N bond-forming reductive eliminations - and the mechanisms of these individual reactions. This paper also describes the development of tin-free amide sources and second generation amination catalysts that have resulted from our mechanistic understanding of the amination chemistry.

Improved synthesis of 2-methoxyphenothiazine

A procedure for synthesis of 2-methoxyphenothiazine (1) has been developed, starting from resorcinol and aniline by condensation, following methylation and cyclization. p-Toluenesulfonic acid and polysubstituted aromatics were employed as the catalyst of condensation and the solvent of cyclization, respectively, to improve the yield. The use of parallel experiments, statistical experimental design, and multivariate modeling made the total yield of the procedure as high as 74.2%. Copyright

Facile N-Arylation of Amines and Sulfonamides

(Matrix presented) A facile, transition-metal-free N-arylation procedure for amines and sulfonamides has been developed, which affords good to excellent yields of arylated products under very mild reaction conditions. A methoxy-substituted aryl triflate affords N-arylated products in high yields with excellent regioselectivity. This chemistry tolerates a variety of functional groups.

Copper-mediated aryl amination: In situ generation of an active copper(I) species

We have developed novel conditions for copper-mediated aryl amination by using a combination of easy-to-handle and inexpensive Cu(OAc) 2·H2O and phenylhydrazine. Georg Thieme Verlag Stuttgart . New York.

N -heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed amination between aryl chlorides and amides

We report herein that amides are excellent N-sources in the NHC-Pd(II)-Im complex 1 catalyzed amination of aryl chlorides. In the presence of KO tBu, various aryl chlorides and amides can react smoothly to give the corresponding aminated products in moderate to almost quantitative yields at room temperature within 6 h.

Nickel Dual Photoredox Catalysis for the Synthesis of Aryl Amines

In this work, a new dual photoredox nickel catalysis system has been utilized for the synthesize of aryl amines. Previously, our group has shown that a nickel catalyst in conjunction with a photosensitizer and a sacrificial electron donor can cross-couple C-C bonds via photoredox-assisted reductive coupling. Here we have built upon that system to develop a redox-neutral cross-coupling system for the formation of C-N bonds. The catalytic system is composed of just a nickel cross-coupling catalyst, a Ru photocatalyst, and base and is capable of coupling amines with aryl halides in good to excellent yields. Furthermore, it was found that these reactions are functional under ambient conditions with catalyst loadings of 1 mol %. Spectroscopic studies provide support that this amination mechanism proceeds via a nitrogen-based radical intermediate. This N-radical mechanism offers direct synthetic access to di- and triaryl amines from nickel photocatalysis.