13615-35-5

Usage

Uses

Used in Plant Growth Regulation:
Acetamide, N-(2-methyl-1-naphthalenyl)-, is used as a growth regulator in the agricultural industry for its ability to influence plant growth and development. As an impurity of the plant rooting hormone 1-Naphthaleneacetamide, it plays a role in enhancing root growth and overall plant health.
Used in Chemical Synthesis:
In the chemical industry, Acetamide, N-(2-methyl-1-naphthalenyl)is used as an intermediate in the synthesis of various compounds, including pharmaceuticals and other specialty chemicals. Its unique structure makes it a valuable building block for creating novel molecules with potential applications in different sectors.
Used in Research and Development:
Acetamide, N-(2-methyl-1-naphthalenyl)is also utilized in research and development for studying the properties and behavior of naphthalene-based compounds. Its role in understanding the structure-activity relationships of related molecules can contribute to the discovery of new compounds with specific applications in various industries.

Upstream product

• 2246-44-8 1-amino-2-methylnaphthalene 
• 108-24-7 acetic anhydride 
• 110678-73-4 1-(2-methyl-1-naphthyl)-4,5-bis(trimethylsilyl)-1,2,3-triazole 
• 881-03-8 1-nitro-2-methylnaphthalene 
• 98154-51-9 1-azido-2-methylnaphthalene 
• 10387-40-3 potassium thioacetate 
• 106469-17-4 N-(2-Methyl-1,4-dihydro-naphthalen-1-yl)-acetamide 

Downstream Products

• 83-68-1 2-methyl-naphthalene-1,4-diyldiamine 
• 50870-10-5 3-methyl-[1]naphthylamine 
• 13615-38-8 2-methyl-4-nitronaphthalene 
• 13615-40-2 3-methylnaphthalen-1-ol 
• 13615-36-6 1-Acetylamino-2-methyl-4-nitro-naphthalin 
• 5465-56-5 4-nitro-2-methyl-[1]naphthylamine 

Relevant academic research and scientific papers

Methylterrylene isomers

2-Methyl and 3-methylterrylenes have been obtained by Suzuki coupling of 3-bromoperylene and corresponding methylnaphthylboronic acids or esters, giving methylnaphthylperylene isomers, followed by Scholl cyclodehydrogenation; the latter reaction gave also the other cyclodehydrogenation isomers 10- (respectively, 9-) methylbenzo[4,5]indeno[1,2,3-cd]perylene.

One-step reductive amidation of nitro arenes: Application in the synthesis of Acetaminophen

A novel thioacetate mediated one-step reductive acetamidation of aryl nitro compounds was developed and applied to an efficient synthesis of acetaminophen. The reaction also proceeds well without a solvent in the presence of a catalytic amount of surfactant.

ONE-POT REDUCTIVE ACETAMIDATION OF ARYL NITRO COMPOUNDS

The present invention provides a method for the reductive acetamidation of an aryl nitro compound by reacting a substituted acid with an aryl nitro compound and adding a catalytic amount of a base with the substituted acid and the aryl nitro compound to form an acetamidation aryl nitro compound. The acetamidation aryl nitro compound is then purified.

Photolysis of 1-Aryl-1,2,3-triazoles; Rearrangement via !H-Azirines

The preparation and photolysis of a series of 1-(1-naphthyl)-1,2,3-triazoles, (2)-(5), and of 1-(2-methyl-1-naphthyl)-1,2,3-triazoles, (6)-(9), with and without electron-withdrawing groups (CO2R, CONH2, CN, CHO, COPh) in the triazole ring, are described.In the first series, triazoles (3) with two electron-withdrawing groups, and triazoles (4) with one such group at C-4, mostly give good yields of the expected benzindoles (10) and 11 respectively.Triazoles (5) with the electron-withdrawing group at C-5 also give benzindoles but these are now mixtures of the expected (12) and rearranged indoles (11).Photolysis of the 1-phenyltriazoles (21) and (22) follows the same pattern, those with the electron-withdrawing group at C-5 rearranging to give mixtures of indoles (23) and (24).This is explained by a mechanism (Scheme 3) in which the less stable carbene intermediate (13) rearranges to the more stable carbene (15) via the 1H-azirine (14), in competition with its direct cyclisation.This provides the first evidence for antiaromatic 1H-azirines as intermediates in a photochemical reaction.Photolysis of the 2-methylnaphthyl compounds follows a different path: diester (7b) and dinitrile (7d) give high yields of the deeply coloured 9-methyl-1H-benzoquinoline derivatives (25a) and (25b) respectively, the first stable examples of this ring system to be isolated.Photolysis of the nitrile (8c) gives 9b-methyl-9bH-benzindole-3-carbonitrile (28), a rare example of a stable indole with a ring junction substituent. 1,2-Shifts in the carbenes are only observed with the bis(trimethylsilyl)triazoles (2d) and (6f), in keeping with the known rapid migration of trimethylsilyl groups to carbene centres.

Direct Photoamination of Arenes with Ammonia and Primary Amines in the Presence of Electron Acceptors

Direct photoamination of phenanthrene, 9-methoxyphenanthrene, anthracene, naphthalene, and several substituted naphthalenes with ammonia or primary amines in the presence of m-dicyanobenzene occurs to give aminated dihydroarenes in fairly good yields. m-Dimethoxybenzene and biphenyl are photoaminated in lower yields.A suggested mechanism for the photoamination involves the nucleophilic attack of ammonia and amines on aromatic cation radicals generated by photochemical electron transfer to m-dicyanobenzene.The present photoamination is applied to direct introduction of various functionalized primary amines containing the vinyl, cyano, hydroxy, acetylamino, and ethoxycarbonyl groups.

Methylterrylene isomers

2-Methyl and 3-methylterrylenes have been obtained by Suzuki coupling of 3-bromoperylene and corresponding methylnaphthylboronic acids or esters, giving methylnaphthylperylene isomers, followed by Scholl cyclodehydrogenation; the latter reaction gave also the other cyclodehydrogenation isomers 10- (respectively, 9-) methylbenzo[4,5]indeno[1,2,3-cd]perylene.