136-90-3 Usage
Description
4-AMINO-2-METHYLANISOLE, also known as 4-Methoxy-3-methylaniline, is an organic compound with the molecular formula C7H10NO. It is a derivative of aniline, featuring a methyl group and a methoxy group attached to the benzene ring, with an amino group at the para position. 4-AMINO-2-METHYLANISOLE is known for its potential applications in the pharmaceutical and chemical industries due to its unique structural properties.
Uses
Used in Pharmaceutical Industry:
4-AMINO-2-METHYLANISOLE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds, specifically in the preparation of triamine pyrimidine derivatives. These derivatives have demonstrated potential as antitumor agents, making 4-AMINO-2-METHYLANISOLE a valuable component in the development of novel cancer treatments.
In the context of cancer research and drug development, 4-AMINO-2-METHYLANISOLE serves as a key building block for creating new molecules with potential antitumor activities. Its unique structure allows for the formation of various triamine pyrimidine derivatives, which can be further modified and optimized to enhance their therapeutic effects against different types of cancer.
The use of 4-AMINO-2-METHYLANISOLE in the pharmaceutical industry highlights its importance as a versatile and promising compound for the development of innovative cancer therapies. As research continues to explore its potential applications, it is likely that this compound will play a significant role in the advancement of cancer treatment options.
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%).
Check Digit Verification of cas no
The CAS Registry Mumber 136-90-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 6 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 136-90:
(5*1)+(4*3)+(3*6)+(2*9)+(1*0)=53
53 % 10 = 3
So 136-90-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO/c1-6-5-7(9)3-4-8(6)10-2/h3-5H,9H2,1-2H3
136-90-3Relevant articles and documents
Transition metal-diene complexes in organic synthesis, Part 22. The iron-mediated quinone imine cyclization: A general route to 3-hydroxycarbazoles
Knolker,Bauermeister,Pannek,Wolpert
, p. 397 - 408 (1995)
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
See, Yi Yang,Sanford, Melanie S.
supporting information, p. 2931 - 2934 (2020/04/09)
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
Liu, Jianzhong,Wu, Kai,Shen, Tao,Liang, Yujie,Zou, Miancheng,Zhu, Yuchao,Li, Xinwei,Li, Xinyao,Jiao, Ning
supporting information, p. 563 - 567 (2017/01/18)
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.
