17484-36-5

Usage

Uses

Used in Organic Synthesis:
4-Methyl-3-nitroanisole is used as a key intermediate in the synthesis of a wide range of organic compounds. Its unique structure allows for the formation of various derivatives, making it a valuable asset in the development of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
4-Methyl-3-nitroanisole is used as a starting material for the synthesis of 4-fluoro and 2-fluoro-substituted acetylcholinesterase inhibitors. These inhibitors play a crucial role in the treatment of various neurological disorders, such as Alzheimer's disease and myasthenia gravis, by modulating the levels of acetylcholine in the brain.
Used in Catalyst Synthesis:
4-Methyl-3-nitroanisole has been employed as an external standard in the synthesis of antibody catalysts using the bait and switch hapten strategy. This approach involves the use of a temporary functional group, or "bait," which is later replaced with the desired functional group, or "switch." The use of 4-methyl-3-nitroanisole in this process aids in the development of highly specific and efficient antibody catalysts for various applications.

InChI:InChI=1/C8H9NO3/c1-6-3-4-7(12-2)5-8(6)9(10)11/h3-5H,1-2H3

Upstream product

• 106-49-0 p-toluidine 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 
• 2042-14-0 4-methyl-5-nitrophenol 
• 104-93-8 p-methylanizole 
• 134-19-0 2-methoxy-4-nitro-5-methyl aniline 
• 74-88-4 methyl iodide 
• 5344-78-5 4-bromo-3-nitroanizole 
• 544-97-8 dimethyl zinc(II) 
• 119-32-4 4-Methyl-3-nitroanilin 
• 106-44-5 p-cresol 
• 621-02-3 di-p-tolyl carbonate 
• 108-24-7 acetic anhydride 
• 67-56-1 methanol 

Downstream Products

• 27077-78-7 4-methyl-2,3-dinitroanisole 
• 57559-52-1 4-methoxy-2-nitrobenzyl bromide 
• 33844-21-2 2-nitro-4-methoxybenzoic acid 
• 22996-21-0 4-methoxy-2-nitro-benzaldehyde 
• 62492-42-6 4-chloro-5-methoxy-2-methylaniline 
• 50868-72-9 5-methoxy-o-toluidine 
• 16792-46-4 (4-methoxy-2-nitro-phenyl)-pyruvic acid 
• 3189-13-7 6-methoxylindole 
• 112251-88-4 4-methyl-2,5-dinitroanisole 
• 112251-86-2 4-methyl-3,4-dinitrocyclohexa-2,5-dienone 
• 112251-94-2 (Z)-3-methoxy-6-methyl-5,6-dinitrocyclohexa-2,4-dienyl acetate 
• 20876-30-6 (4-methoxy-2-nitro-phenyl)-acetic acid 
• 16732-73-3 6-Methoxyindole-2-carboxylic acid 
• 7169-01-9 2,4-dimethoxy-3-nitro-benzoic acid 

Relevant academic research and scientific papers

A reassessment of mycophenolic acid as a lead compound for the development of inhibitors of chikungunya virus replication

Mycophenolic acid (MPA) has been previously reported as an inhibitor of the chikugunya virus (CHIKV) with an EC50 value of 0.2 μM. We used MPA as a lead compound designing and synthesizing a series of isatins and benzolactones in a typical medicinal chemistry program. The synthesis and testing of 19 derivatives produced compounds with no desired activity which prompted us to retest the lead compound, MPA. We can reveal that MPA shows no anti-CHIKV activity and therefore needs to be reassessed as a lead compound for this target.

TETRAHYDRO-PYRIDOAZEPIN-8-ONES AND RELATED COMPOUNDS FOR THE TREATMENT OF SCHIZOPHRENIA

Compounds of formula 1 are disclosed, wherein G, D, A, Q, Y, Z, and R1 through R10 are defined in the specification. Also provided are descriptions of processes for preparing compounds of formula 1, intermediates used in making the same, and pharmaceutical compositions containing such compounds and their use in the treatment of central nervous system disorders and other disorders.

Negishi-type coupling of bromoarenes with dimethylzinc

Treatment of bromoarenes with dimethylzinc in the presence of a palladium catalyst provides a high-yielding route to methylarenes. The process accommodates a wide range of aromatic substituents and, in the majority of cases, is free of side reactions.

ipso NITRATION. XXIX. NITRATION OF SUBSTITUTED 4-METHYLANISOLES AND PHENOLS

Nitration of 2-chloro-4-methylanisole (1a) in acetic anhydride gives (Z)-4-chloro-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2a), 2-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone (3a), and 2-chloro-4-methyl-6-nitroanisole (4a).Similarly 2-bromo-4-methylanisole (1b) gives (Z)-4-bromo-3-methoxy-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate (2b), 2-bromo-4-methyl-4-nitrocyclohexa-2,5-dienone (3b), and 2-bromo-4-methyl-6-nitroanisole (4b), whereas 4-methyl-2-nitro-anisole (1c) gives (Z)-3-methoxy-6-methyl-4,6-dinitrocyclohexa-2,4-dienyl acetate (2c), (Z)-3-methoxy-6-methyl-2,6-dinitrocyclohexa-2,4-dienyl acetate (7), and 4-methyl-2,6-dinitroanisole (4c).Nitration of 3-chloro-4-methylanisole (9a) gives 3-chloro-4-methyl-4-nitrocyclohexa-2,5-dienone (10a), 3-chloro-4-methyl-2-nitro anisole (11a), and 5-chloro-4-methyl-2-nitroanisole (12a), and 4-methyl-3-nitroanisole (9c) gives (Z)-3-methoxy-6-methyl-5,6-dinitrocyclohexa-2,4-dienyl acetate (13), 4-methyl-2,3-dinitroanisole (11c), and 4-methyl-2,5-dinitroanisole (12c).Nitration of 2-chloro-4-methylphenol (14) in chloroform gives 3a and 2-chloro-4-methyl-6-nitrophenol (5a), and 3-chloro-4-methylphenol (15) gives dienone 10a, 3-chloro-4-methyl-2-nitrophenol (16), and 5-chloro-4-methyl-2-nitrophenol (17).

Convenient Synthesis of 6-Methoxyindole and 6-Methoxytryptophyl Bromide

A preparatively convenient synthesis of 6-methoxyindole (7) and 6-methoxytryptophylbromide (11) is presented starting with p-cresol (1).Regioselective nitration of p-cresol carbonate (2) followed by hydrolysis of the carbonate and methylation gives 4-methoxy-2-nitrotoluene (5) which is converted to 7 by esterification, reduction and bromination yields 6-methoxytryptophyl bromide (11).The overall yield of 7 and 11 from p-cresol is 43percent and 25percent respectively.

ipso-Nitration: Formation of Nitronium Acetate Adducts in the Nitration of p-Acetamido-, p-Halogeno-, and p-Methoxy-toluenes, and α-p-Tolyloxyisobutyric acid

Low-temperature nitration of the title compounds in acetic anhydride gives 1,2-nitronium acetate adducts, except p-fluorotoluene which gives both 1,2 and 1,4 adducts and α-p-tolyloxyisobutyric acid which gives a spiro adduct.