4900-63-4

Usage

Uses

1. Used in Pharmaceutical Industry:
1-METHOXY-4-NITRONAPHTHALENE is used as a reagent for the synthesis of UMI-77 (U700850), a small molecule inhibitor of Mcl-1. This inhibitor plays a significant role in blocking and attenuating the growth of pancreatic cancer cells, making it a valuable component in the development of anticancer treatments.
2. Used as an Anticancer Agent:
1-METHOXY-4-NITRONAPHTHALENE is also utilized as an anticancer agent, contributing to the development of novel therapies for various types of cancer. Its chemical properties allow it to be a key component in the synthesis of compounds that target cancer cells and inhibit their growth, ultimately aiding in the fight against cancer.

Synthesis Reference(s)

Synthesis, p. 70, 1985 DOI: 10.1055/s-1985-31110

Purification Methods

Purify it by chromatography on silica gel, then recrystallise it from MeOH or EtOH (yellow needles). [Hodgson & Habeshaw J Chem Soc 47 1942, Bunce et al. J Org Chem 52 4214 1987, Beilstein 6 H 616, 6 III 2938.]

InChI:InChI=1/C11H9NO3/c1-15-11-7-6-10(12(13)14)8-4-2-3-5-9(8)11/h2-7H,1H3

Upstream product

• 67-56-1 methanol 
• 605-61-8 1-chloro-4-nitronaphthalene 
• 91569-62-9 ethyl-(4-nitro-[1]naphthyl)-ether 
• 124-41-4 sodium methylate 
• 108-24-7 acetic anhydride 
• 2216-69-5 1-Methoxynaphthalene 
• 605-62-9 4-nitro-1-naphthol 
• 77-78-1 dimethyl sulfate 
• 509-14-8 tetranitromethane 
• 71-23-8 propan-1-ol 
• 64-17-5 ethanol 
• 13041-62-8 4-methoxy-1-naphthoic acid 
• 169178-80-7 1-methoxy-4-trinitromethylnaphthalene 
• 91-20-3 naphthalene 

Downstream Products

• 16430-99-2 1-amino-4-methoxynaphthalene 
• 871887-75-1 4-methoxy-N-phenyl-1-naphthalenamine 
• 108451-00-9 4-Methoxy-1-nitro-2-(p-tolylsulfonylmethyl)naphthalene 
• 73323-53-2 4-Benzyl-1-nitronaphthalene 
• 73323-56-5 cis-2-Benzyl-4-methoxy-1-nitro-1,2-dihydronaphthalene 
• 73323-59-8 trans-2-Benzyl-4-methoxy-1-nitro-1,2-dihydronaphthalene 
• 5961-55-7 4-methoxy-1-naphthalenecarbonitrile 
• 58-27-5 menadione 
• 69798-30-7 2-methyl-4-methoxy-1-naphthylamine 
• 95393-47-8 E-2-methyl-2,3-dihydro-1,4-naphthoquinone-1-oxime 
• 95393-42-3 E-2-methyl-4-methoxy-1-(2H)naphthalenone oxime 
• 77416-45-6 r-1-bromo-1-nitro-t-2-benzyl-1,2,3,4-tetrahydronaphthalen-4-one 
• 77416-44-5 r-1-bromo-1-nitro-t-2-phenethyl-1,2,3,4-tetrahydronaphthalen-4-one 
• 84-95-7 N,N-diethyl-1-naphthylamine 

Relevant academic research and scientific papers

Corey-Chaykovsky Cyclopropanation of Nitronaphthalenes: Access to Benzonorcaradienes and Related Systems

Nitronaphthalene derivatives react as Michael acceptors in the Corey-Chaykovsky reaction with alkyl phenyl selenones and alkyl diphenyl sulfonium salts. Mechanistic studies reveal that sterically demanding substituents at the carbanionic center favor formation of cyclopropanes and suppress competitive β-elimination to the alkylated products. The transformation, demonstrated also on heterocyclic nitroquinoline and nitroindazolines, is an example of transition metal-free dearomatization method.

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing ?-conjugated molecules.

Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration

Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C-Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C-H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under mild conditions occurred predominantly at the electron-rich position. The resulting product having methoxy and bromo groups can be utilized as a building block for the synthesis of unsymmetrically substituted 9-silafluorene-containing π-conjugated molecules.

Direct nitration method of electron-enriched aromatic hydrocarbons

The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.

A Facile Synthesis of Benzo[h]quinolines via Silica-TsOH-P2O5 Promoted Condensation of 1-Naphthylamines with 1,3-Diketones under Solvent Free Conditions

A facile synthesis of benzo[h]quinolines has been developed via improved Combes reaction. A combination of silica gel, p-toluenesulfonic acid and phosphorus pentoxide was utilized to promote the condensation of 1-naphthylamines with 1,3-diketones under solvent free conditions. In this case, silica gel was used as reaction media, p-toluenesulfonic acid and phosphorus pentoxide were acted as catalyst and dehydrating agent, respectively.

The relevance of Ki calculation for bi-substrate enzymes illustrated by kinetic evaluation of a novel lysine (K) acetyltransferase 8 inhibitor

Histone acetyltransferases (HATs) are important mediators of epigenetic post-translational modifications of histones that play important roles in health and disease. A disturbance of these modifications can result in disease states, such as cancer or inflammatory diseases. Inhibitors of HATs (HATi) such as lysine (K) acetyltransferase 8 (KAT8), could be used to study the epigenetic processes in diseases related to these enzymes or to investigate HATs as therapeutic targets. However, the development of HATi is challenged by the difficulties in kinetic characterization of HAT enzymes and their inhibitors to enable calculation of a reproducible inhibitory potency. In this study, a fragment screening approach was used, enabling identification of 4-amino-1-naphthol, which potently inhibited KAT8. The inhibitor was investigated for enzyme inhibition using kinetic and calorimetric binding studies. This allowed for calculation of the Ki values for both the free enzyme as well as the acetylated intermediate. Importantly, it revealed a striking difference in binding affinity between the acetylated enzyme and the free enzyme, which could not be revealed by the IC50 value. This shows that kinetic characterization of inhibitors and calculation of Ki values is crucial for determining the binding constants of HAT inhibitors. We anticipate that more comprehensive characterization of enzyme inhibition, as described here, is needed to advance the field of HAT inhibitors.

Nitrogen Dioxide Catalyzed Oxidative Thiocyanation of Arenes with Ambient Air as the Terminal Oxidant

NO2 is an effective catalyst for the oxidative thiocyanation of arenes. This unique catalyst is inexpensive and separated easily from the final products because of its low boiling point. The mild reaction conditions allow a series of arenes and thiophenes to be thiocyanated smoothly in moderate to high yields. A preliminary mechanistic investigation suggests that the present reaction may proceed through a radical pathway.

Oxidative dimerization of 4-methoxynaphthylamines in the presence of semiconductors

Three types of 4-methoxynaphthylamines 4a-c were oxidized by treatment with metal oxides under molecular oxygen (O2). 4-Methoxy-1-naphthylamine 4a and 4,6-dimethoxy-1-naphthylamine 4b, on treatment with TiO2 under O2, gave mainly 2-amino-1,4-naphthoquinone derivatives 5a and 5b, respectively whereas 4,8-dimethoxy-1-naphthylamine 4c afforded an unique carbazole 6c as the major product.

Aromatic nitration in liquid Ag0.51K0.42Na 0.07NO3

(Figure Presented) Aromatic molecules have a strong affinity for silver(I) and dissolve to a limited extent in Ag0.51K0.42Na 0.07NO3, a low-melting eutectic mixture of silver, potassium, and sodium nitrates. Aromatic nitration in this inorganic ionic liquid leads to products which arise from nonelectrophilic substitution pathways.

Nitration of some aromatic compounds by sodium nitrate in the presence of benzyltriphenylphosphonium peroxodisulfate

A simple, mild, and regioselective method for the nitration of some aromatic compounds using sodium nitrate in the presence of benzyltriphenylphosphonium peroxodisulfate in acetonitrile as solvent is reported. Mild reaction conditions and good to excellent yields of the products are the noteworthy advantages of the method. Copyright Taylor & Francis Group, LLC.