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Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-nitro-1-naphthoate is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to be chemically modified and incorporated into the structures of various drugs. Its presence in the synthesis process can contribute to the development of new medications with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, Methyl 3-nitro-1-naphthoate is used as a precursor in the production of certain agrochemicals, such as pesticides and herbicides. Its chemical structure allows for the creation of compounds that can effectively control or eliminate unwanted plant species or pests.
Used in Material Science:
Methyl 3-nitro-1-naphthoate is utilized in the development of new materials, potentially due to its ability to be integrated into polymers or other composites, enhancing their properties or creating novel materials with specific characteristics.
Used in Dye Industry:
Methyl 3-nitro-1-naphthoate is also used in the dye industry, where it may serve as a starting material for the synthesis of various dyes. Its chemical structure can be manipulated to produce dyes with different color characteristics and properties suitable for various applications.

InChI:InChI=1/C12H9NO4/c1-17-12(14)11-7-9(13(15)16)6-8-4-2-3-5-10(8)11/h2-7H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 4507-84-0 3-nitro-1-naphthoic acid 
• 67-56-1 methanol 
• 3027-38-1 3-nitro-1,8-naphthalic anhydride 
• 54978-07-3 3-nitro-1-naphthalenecarboxylic acid chloride 

Downstream Products

• 4507-84-0 3-nitro-1-naphthoic acid 
• 343-53-3 1-bromo-3-fluoro-naphthalene 
• 575-07-5 3-fluoronaphthalene-1-carboxylic acid 
• 954410-00-5 methyl 3-[(3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)piperazin-1-yl]-1-naphthoate 
• 954410-14-1 C₃₈H₃₈FN₅O₅ 
• 954410-12-9 methyl 3-((3S)-3-(azidomethyl)-4-{[1-(3-ethoxyphenyl)-2-(2-fluoro-4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazin-1-yl)-1-naphthoate 
• 954410-06-1 [(2S)-1-{[1-(3-ethoxyphenyl)-2-(2-fluoro-4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-4-(4-{[(triisopropylsilyl)oxy]methyl}-2-naphthyl)piperazin-2-yl]methyl acetate 
• 79996-92-2 (3-bromonaphthalen-1-yl)methanol 

Relevant academic research and scientific papers

Substituted Imidazole 4-Carboxamides as Cholecystokinin-1 Receptor Modulators

Certain novel substituted imidazole 4-carboxamides are ligands of the human cholecystokinin receptor and, in particular, are selective ligands of the human cholecystokinin-1 receptor (CCK-1R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of CCK-1R, such as obesity, and diabetes.

SUBSTITUTED IMIDAZOLE 4-CARBOXAMIDES AS CHOLECYSTOKININ-1 RECEPTOR MODULATORS

Certain novel substituted imidazole 4-carboxamides are ligands of the human cholecystokinin receptor and, in particular, are selective ligands of the human cholecystokinin-1 receptor (CCK-1R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of CCK-1R, such as obesity, and diabetes.

The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis

The mercury-mediated decarboxylation (Pesci reaction) of several substituted naphthoic anhydrides has been investigated by microwave synthesis. A laboratory microwave reactor was found to be ideal for small-scale preparations of this slow reaction, reducing reaction times from typically four days to less than 1 h for the three-step process. The ionic reaction medium rapidly heated to high temperatures under microwave heating and could be efficiently maintained by low microwave power settings. Generation of stoichiometric CO2 was safely contained within the reaction tubes. A simplified reaction procedure has been developed. For substituted naphthoic anhydrides, 1H NMR analysis of the naphthoate ester derivatives indicated no change in the regioisomer ratio compared to previously reported thermal values.

(Aminoalkyl)indole isothiocyanates as potential electrophilic affinity ligands for the brain cannabinoid receptor

A series of (aminoalkyl)indole compounds, naphthalene analogs of pravadoline (1), has been shown to exhibit cannabinoid agonist activities such as antinociception in animals, inhibition of adenylate cyclase in brain membranes, and binding to the cannabinoid receptor. These pravadoline analogs were selected for the preparation of potential electrophilic affinity ligands based on the synthesis of isothiocyanate derivatives. One isothiocyanatonaphthalene derivative (8) displaced [3H]CP-55940 binding to a rat brain P2 membrane preparation with an IC50 of 690 nM, which was 10- fold less potent than the parent molecule (IC50 = 73 nM). Isothiocyanate substitution at various positions on the naphthalene moiety of the desmethyl analog 10 gave compounds that displaced [3H]CP-55940 with IC50 values between 400 and 1000 nM, compared with 46 nM for the parent compound 10. However, 6-isothiocyanato substitution on the indole ring of the desmethyl analog provided isothiocyanate 12 that displaced [3H]CP-55940 binding with an IC50 of 160 nM. After pretreatment of brain membranes with this high- affinity isothiocyanato ligand followed by washing out the ligand, the membranes were depleted of 90% of the cannabinoid receptor binding capacity. Loss of receptor binding capacity was half-maximal at 300 nM of the derivative under standard assay conditions. As a control, pretreatment with the parent compound at concentrations that were 20 times the K(d) failed to alter subsequent binding activity. This study demonstrates that an isothiocyanato (aminoalkyl)indole (12) can behave as an affinity ligand which binds irreversibly to the cannabinoid receptor in brain and which precludes subsequent binding of the cannabinoid ligand [3H]CP-55940.

Study of Reactions Leading to Sulfine Formation. 3. Competition of Reaction Pathways in the Reaction of Methoxide Ion with Methyl 1-Naphthylmethanesulfinates

In CD3O1-/CD3OD methyl 1-naphthylmethanesulfinates, NpCH2S(O)OCH3 (2), undergo both exchange of CH3O by CD3O by substitution at the sulfinyl group and elimination to form the sulfine, NpCH=S=O.With use of methyl (2-methoxy-1-naphthyl)methanesulfinate (2a) it has been shown that formation of the sulfine takes place by an (E1cB)irrev mechanism.The rates of substitution (ks) and elimination (ke) of a series of 2 have been determined in CD3O1-/CD3OD by 1H NMR spectroscopy, and the effect of several reaction variables on the competition between substitution and elimination has been examined.Salient results are as follows: (1) the rate of elimination is markedly increased by the presence of electron-withdrawing substituents on the aromatic ring, but the rate of substitution is increased only modestly by the same substituents; (2) substituents at the 2-position of the naphthyl group cause a large decrease in ks (steric hindrance to substitution at S=O) but have little effect on ke (elimination rate not sensitive to steric requirements of ortho substituents); (3) the activation energy for elimination is almost 9 kcal/mol greater than the activation energy for substitution.This large difference in activation energy contrasts with the 1-2 kcal/mol difference for elimination vs substitution found14 with alkyl halides.