623-09-6

Basic information

• Product Name: 4-Amino-N-methylaniline
• Synonyms: 4-AMINO-N-METHYLAMINE;4-AMINO-N-METHYLANILINE;N-METHYL-P-PHENYLENEDIAMINE;n-methyl-1,4-benzenediamine;N-METHYL-1,4-PHENYLENEDIAMINE;p-methylaminoaniline;4-AMINO-N-METHYLAMINE 98+%;4-(Methylamino)aniline
• CAS NO: 623-09-6
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• EINECS: 210-770-1
• Mol File: 623-09-6.mol
• Article Data: 17

Chemical Properties

• Melting Point: 36°C
• Boiling Point: 217.6°C (rough estimate)
• Flash Point: 127.1 °C
• Appearance: /
• Density: 1.0343 (rough estimate)
• Refractive Index: 1.5103 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 7.01±0.10(Predicted)
• CAS DataBase Reference: 4-Amino-N-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-N-methylaniline(623-09-6)
• EPA Substance Registry System: 4-Amino-N-methylaniline(623-09-6)

Safety Data

• Hazardous Substances Data: 623-09-6(Hazardous Substances Data)

Usage

General Description

4-Amino-N-methylaniline, also known as N-methylaniline-4-amine, is a chemical compound with the molecular formula C7H10N2. It is a derivative of aniline, where the amino group is located at the para position and there is a methyl group attached to the nitrogen atom. 4-Amino-N-methylaniline is commonly used as an intermediate in the synthesis of various dyes and pigments, as well as in the production of pharmaceuticals and agrochemicals. It is a colorless to pale yellow liquid with a distinct amine odor, and it can be harmful if inhaled or swallowed. In the environment, 4-Amino-N-methylaniline may pose a risk to aquatic organisms and can persist for a long time in soil and water. Therefore, proper handling, storage, and disposal of this chemical are important to minimize its potential impact on human health and the environment.

InChI:InChI=1/C7H10N2/c1-9-7-4-2-6(8)3-5-7/h2-5,9H,8H2,1H3

Upstream product

• 7647-01-0 hydrogenchloride 
• 618-40-6 1-Methyl-1-phenylhydrazine 
• 60-29-7 diethyl ether 
• 95348-27-9 butane-2,3-dione-mono-[methyl-(4-nitro-phenyl)-hydrazone] 
• 22110-09-4 toluene-4-sulfonic acid-(4-amino-N-methyl-anilide) 
• 7664-93-9 sulfuric acid 
• 932-96-7 N-methyl(p-chloroaniline) 
• 67-56-1 methanol 
• 106-50-3 1,4-phenylenediamine 
• 62-53-3 aniline 
• 74-89-5 methylamine 
• 106-40-1 4-bromo-aniline 
• 540-37-4 p-aminoiodobenzene 
• 64-18-6 formic acid 

Downstream Products

• 860554-97-8 N-methyl-N,N'-p-phenylene-bis-benzamide 
• 93320-66-2 1-[4-(Methyl-nitroso-amino-)-phenylazo]-[2]naphthol 
• 31568-57-7 C₂₁H₂₈N₂O 
• 911297-26-2 (S)-(4-{[2-hydroxy-2-(4-nitro-3-trifluoromethylphenylcarbamoyl)propyl]methylamino}phenyl)carbamic acid tert-butyl ester 
• 1111628-56-8 1-[2,3-di(tert-butoxycarbonyl)guanidino]-4-(N-methyl)benzene 
• 1111628-52-4 2-(4-methylamino-phenylimino)-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester 
• 1227195-07-4 N⁽¹⁾-(4-(2,4-dimethylthiazol-5-yl)pyrimidin-2-yl)-N₄-methylbenzene-1,4-diamine 
• 1432308-14-9 C₁₉H₁₆N₄O 
• 1987887-92-2 methyl (Z)-3-(((4-(methylamino)phenyl)amino)(phenyl)methylene)-2-oxoindoline-6-carboxylate 
• 39970-26-8 N-[4-(formylamino)phenyl]-N-methylformamide 
• 31033-16-6 N-[4-(Methanesulfonyl-methyl-amino)-phenyl]-N-methyl-methanesulfonamide 
• 57839-20-0 2-[5-Hydroxy-4-methyl-2-(4-methylamino-phenylamino)-phenylamino]-acetamide 
• 57838-85-4 N-[3-Hydroxy-2,4-dimethyl-6-(4-methylamino-phenylamino)-phenyl]-acetamide 
• 57839-05-1 N-[5-Hydroxy-4-methyl-2-(4-methylamino-phenylamino)-phenyl]-acetamide 

Relevant articles and documents

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Virtual screening guided design, synthesis and bioactivity study of benzisoselenazolones (BISAs) on inhibition of c-met and its downstream signalling pathways

c-Met is a transmembrane receptor tyrosine kinase and an important therapeutic target for anticancer drugs. In this study, we designed a small library containing 300 BISAs molecules that consisted of carbohydrates, amino acids, isothiourea, tetramethylthiourea, guanidine and heterocyclic groups and screened c-Met targeting compounds using docking and MM/GBSA. Guided by virtual screening, we synthesised a series of novel compounds and their activity on inhibition of the autophosphorylation of c-Met and its downstream signalling pathway proteins were evaluated. We found a panel of benzisoselenazolones (BISAs) obtained by introducing isothiourea, tetramethylthiourea and heterocyclic groups into the C-ring of Ebselen, including 7a, 7b, 8a, 8b and 12c (with IC50 values of less than 20 μMin MET gene amplified lung cancer cell line EBC-1), exhibited more potent antitumour activity than Ebselen by cell growth assay combined with in vitro biochemical assays. In addition, we also tested the antitumour activity of three cancer cell lines without MET gene amplification/activation, including DLD1, MDA-MB-231 and A549. The neuroblastoma SK-N-SH cells with HGF overexpression which activates MET signalling are sensitive to MET inhibitors. The results reveal that our compounds may be nonspecific multitarget kinase inhibitors, just like type-II small molecule inhibitors. Western blot analysis showed that these inhibitors inhibited autophosphorylation of c-MET, and its downstream signalling pathways, such as PI3K/AKT and MARK/ERK. Results suggest that bensoisoselenones can be used as a scaffold for the design of c-Met inhibiting drug leads, and this study opens up new possibilities for future antitumour drug design.

Single-Site Cobalt Catalysts at New Zr12(μ3-O)8(μ3-OH)8(μ2-OH)6 Metal-Organic Framework Nodes for Highly Active Hydrogenation of Nitroarenes, Nitriles, and Isocyanides

We report here the synthesis of a robust and porous metal-organic framework (MOF), Zr12-TPDC, constructed from triphenyldicarboxylic acid (H2TPDC) and an unprecedented Zr12 secondary building unit (SBU): Zr12(μ3-O)8(μ3-OH)8(μ2-OH)6. The Zr12-SBU can be viewed as an inorganic node dimerized from two commonly observed Zr6 clusters via six μ2-OH groups. The metalation of Zr12-TPDC SBUs with CoCl2 followed by treatment with NaBEt3H afforded a highly active and reusable solid Zr12-TPDC-Co catalyst for the hydrogenation of nitroarenes, nitriles, and isocyanides to corresponding amines with excellent activity and selectivity. This work highlights the opportunity in designing novel MOF-supported single-site solid catalysts by tuning the electronic and steric properties of the SBUs.