136-90-3

Basic information

• Product Name: 4-AMINO-2-METHYLANISOLE
• Synonyms: 4-AMino-2-Methylanisole[4-Methoxy-3-Methylaniline];3-Methyl-4-methoxybenzenamine;4-AMINO-2-METHYLANISOLE;4-METHOXY-3-METHYLANILINE;3-Methyl-4-methoxyaniline;4-methoxy-3-methylbenzenamine;BenzenaMine, 4-Methoxy-3-Methyl-
• CAS NO: 136-90-3
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Mol File: 136-90-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 57-60℃
• Boiling Point: 252.03°C (rough estimate)
• Flash Point: 106.1 °C
• Appearance: /
• Density: 1.0630 (rough estimate)
• Refractive Index: 1.5360 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 5.32±0.10(Predicted)
• CAS DataBase Reference: 4-AMINO-2-METHYLANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-2-METHYLANISOLE(136-90-3)
• EPA Substance Registry System: 4-AMINO-2-METHYLANISOLE(136-90-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 136-90-3(Hazardous Substances Data)

Usage

Uses

4-Methoxy-3-methylaniline is used in preparation of triamine pyrimidine derivatives as antitumor agents.

Synthesis

The synthesis of 4-methoxy-3-methylaniline is as follows:4-Methoxy-3-methyl-phenylamine10% Palladium on carbon (10% Pd/C) (1.5 g) was added to a solution of 1 -methoxy-2- methyl-4-nitrobenzene (9.5 g, 57 mmol) in methanol (100 ml_). The mixture was stirred under a hydrogen atmosphere (1 atm.) at room temperature for 16 h. The mixture was filtered through a pad of CELITE and the filtrate was evaporated in vacuo to yield 4- methoxy-3-methylphenylamine (8.0 g, 57 mmol, 100%).

InChI:InChI=1/C8H11NO/c1-6-5-7(9)3-4-8(6)10-2/h3-5H,9H2,1-2H3

Upstream product

• 50741-92-9 2-methyl-4-nitroanisole 
• 7439-89-6 iron 
• 578-58-5 2-methylmethoxybenzene 
• 14786-82-4 4-hydroxy-2-methylanisole 
• 108-39-4 3-methyl-phenol 
• 99-53-6 2-methyl-4-nitrophenol 
• 2835-96-3 4-amino-2-methylphenol 
• 16375-90-9 4-acetamido-2-methylphenol 
• 31910-25-5 N-(4-methoxy-3-methylphenyl)acetamide 
• 620-25-7 N-(3-methylphenyl)hydroxylamine 
• 67-56-1 methanol 
• 4113-72-8 1-azido-3-methylbenzene 

Downstream Products

• 1416353-75-7 C₃₁H₂₄N₂O 
• 1416353-73-5 6-methoxy-7-methyl-1-phenyl-9-(pyridin-2-yl)-9H-carbazole 
• 1416353-76-8 6-methoxy-7-methyl-1-phenyl-9H-carbazole 
• 1447016-66-1 (S)-2-tert-butoxy-2-((R)-5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-7-methyl-2-oxo-1-m-tolyl-1,2-dihydroquinolin-6-yl)acetic acid 
• 1447016-37-6 (S)-2-tert-butoxy-2-((R)-5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-7-methyl-2-(3-(trifluoromethyl)benzyloxy)quinolin-6-yl)acetic acid 
• 1447016-99-0 (R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 
• 1403666-04-5 7-(4-chlorophenyl)-6-methoxy-5-methylbenzo[d]thiazol-2-amine 
• 1403665-81-5 (S)-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)acetic acid 
• 1403666-00-1 (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol 

Relevant articles and documents

Transition metal-diene complexes in organic synthesis, Part 22. The iron-mediated quinone imine cyclization: A general route to 3-hydroxycarbazoles

Electrophilic aromatic substitution of 4-methoxyarylamines 2 by the tricarbonyliron-complexed cyclohexadienylium cations 1 leading to the iron complexes 3 is described. Chemoselective oxidation of the arylamine moiety of the complexes 3 to the quinone imine and iron-mediated quinone imine cyclization using appropriate oxidizing reagents (activated manganese dioxide or thallium(III) trifluoroacetate) led to the tricarbonyliron-complexed 4b,8a-dihydrocarbazol-3-ones 5. Demetalation of 5 with trimethylamine N-oxide at room temperature occurred with concomitant aromatization of the organic ligand and provided a broad access to the 3-hydroxy-9H-carbazoles 7.

C-H Amination of Arenes with Hydroxylamine

This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.