10541-78-3

Basic information

• Product Name: 2-METHOXY-N-METHYANILINE
• Synonyms: N-METHYL-O-ANISIDINE;2-METHOXY-N-METHYANILINE;2-METHOXY-N-METHYLANILINE;(2-METHOXY-PHENYL)-METHYL-AMINE;2-Methoxy-N-Methyaniline ,97%;N-Methyl-2-anisidine;2-METHOXY-N-METHYANI;2-Methoxy-N-Methylaniline 97%
• CAS NO: 10541-78-3
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Product Categories: Amines;C8;Nitrogen Compounds
• Mol File: 10541-78-3.mol
• Article Data: 29

Chemical Properties

• Melting Point: 30-34 °C(lit.)
• Boiling Point: 115 °C
• Flash Point: 209 °F
• Appearance: /
• Density: 1.032g/cm³
• Vapor Pressure: 0.22mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.80±0.10(Predicted)
• CAS DataBase Reference: 2-METHOXY-N-METHYANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-N-METHYANILINE(10541-78-3)
• EPA Substance Registry System: 2-METHOXY-N-METHYANILINE(10541-78-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37/39
• WGK Germany: 2
• Hazardous Substances Data: 10541-78-3(Hazardous Substances Data)

Usage

General Description

2-Methoxy-N-methylaniline, also known as o-toluidine, is a chemical compound belonging to the class of anilines. 2-METHOXY-N-METHYANILINE is commonly used as an intermediate in the synthesis of dyes, organic pigments, and pharmaceuticals. Its main application is in the production of ortho-toluidine-derived dyes and pesticides. However, exposure to o-toluidine has been linked to harmful effects on human health, such as damage to the liver, kidneys, and central nervous system. Therefore, protective measures should be taken when handling this chemical compound.

InChI:InChI=1/C8H11NO/c1-9-7-5-3-4-6-8(7)10-2/h3-6,9H,1-2H3

Upstream product

• 483-64-7 methyl 3-methoxy-2-(methylamino)benzoate 
• 23896-88-0 formic acid o-anisidide 
• 485-27-8 3-methoxy-2-methylamino-benzoic acid 
• 90-04-0 2-methoxy-phenylamine 
• 74-88-4 methyl iodide 
• 124-41-4 sodium methylate 
• 77-78-1 dimethyl sulfate 
• 50-00-0 formaldehyd 
• 93-26-5 2-methoxyacetanilide 
• 85680-36-0 1,3,5-tris(o-methoxyphenyl)-1,3,5-triazacyclohexane 
• 10034-85-2 hydrogen iodide 
• 1226-64-8 1,3-bis-(2-methoxy-phenyl)-thiourea 
• 100-66-3 methoxybenzene 
• 592489-13-9 1,3-dimethyl-2-(2-methoxyphenylimino)imidazolidine 

Downstream Products

• 100390-66-7 N-(2-methoxyphenyl)-N-methyl-3-oxobutanamide 
• 10121-94-5 2-methoxy-N-methyl-4-phenylazo-aniline 
• 15258-52-3 N-allyl-N-methyl-o-anisidine 
• 102012-71-5 3-(2-benzyloxy-ethyl)-4-hydroxy-8-methoxy-1-methyl-1H-quinolin-2-one 
• 20451-54-1 N-(2-methoxyphenyl)-N-methylnitrous amide 
• 857600-62-5 2-methoxy-N-methyl-4-nitro-N-nitroso-aniline 
• 611-24-5 o-(N-methylamino)phenol 
• 151657-66-8 N-benzyl-N-methyl-o-anisidine 
• 21744-84-3 4-methyl-4H-benzo[1,4]oxazin-3-one 
• 77747-62-7 N-chloroacetyl-N-methyl-o-anisidine 
• 21226-38-0 benzenesulfonic acid-(N-methyl-o-anisidide) 
• 133368-88-4 2-(N-methyl-o-anisidino)-ethanol 
• 700-75-4 2-methoxy-N,N-dimethyl-benzenamine 
• 70329-19-0 tri-N-methyl-o-anisidinium; iodide 

Relevant articles and documents

Evaluation of 4-phenylamino-substituted naphthalene-1,2-diones as tubulin polymerization inhibitors

A series of 4-phenylamino-substituted naphthalene-1,2-dione derivatives were prepared and evaluated as effective antiproliferative agents. MTT assays showed that the compounds with a methyl group on the nitrogen linker exhibited potent antiproliferative activities against human cancer cells. The mechanistic study revealed that these compounds could induce mitochondrial depolarization, which resulted in intracellular ROS production, and they also acted as tubulin polymerization inhibitors. Moreover, the typical compound could arrest A549 cells in the G2/M phase, resulting in cellular apoptosis and induced mitotic arrest in A549 cells through disrupting microtubule dynamics.

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Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

DIRECT C-H AMINATION AND AZA-ANNULATION

In some aspects, the present disclosure provides methods of aminating an aromatic compound comprising reacting an aminating agent with an aromatic compound in the presence of a rhodium catalyst. In some embodiments, the methods may comprise aminating an aromatic compound which contains multiple different functional groups. The methods described herein may also be used to create bicyclic system comprising reacting an intramolecular aminating agent with an aromatic ring to obtain a second ring containing a nitrogen atom. In another aspect, the methods described herein may also be used to create a cyclic aliphatic cyclic/poly cyclic amine system comprising a reacting an intramolecular aminating agent by insertion into a C(sp3)-H bond.