62012-54-8

Usage

Uses

Used in Organic Synthesis:
2-bromo-1-methoxynaphthalene is used as a building block for various chemical reactions, particularly in palladium-catalyzed cross-coupling reactions, due to its reactivity and the presence of a bromine atom and a methoxy group on the naphthalene ring.
Used in Pharmaceutical Production:
2-bromo-1-methoxynaphthalene is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications.
Used in Agrochemicals:
2-bromo-1-methoxynaphthalene is employed in the production of agrochemicals, where it serves as a precursor for the synthesis of active ingredients in pesticides and other agricultural chemicals.
Used in Organic Dyes and Materials Synthesis:
It is utilized in the synthesis of organic dyes and materials, where its unique properties contribute to the development of new materials with specific characteristics.
Used in Medicinal Chemistry:
2-bromo-1-methoxynaphthalene has potential applications in medicinal chemistry, where its structural and chemical properties can be leveraged to design and develop new therapeutic agents.
Used in Material Science:
2-bromo-1-methoxynaphthalene is also used in material science for the synthesis of materials with specific properties, such as conductivity, stability, or optical characteristics.
It is important to handle and use 2-bromo-1-methoxynaphthalene with caution due to its potential hazards and toxicity. Proper safety measures should be taken during its synthesis, storage, and application to minimize risks.

Upstream product

• 186581-53-3 diazomethane 
• 771-15-3 2-bromo-1-naphthol 
• 74-88-4 methyl iodide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 2216-69-5 1-Methoxynaphthalene 
• 90-15-3 α-naphthol 

Downstream Products

• 148491-01-4 3-iodo-1-methoxynaphthalene 
• 85051-83-8 2-(2'-methoxyphenoxy)-1-methoxynaphthalene 
• 19938-27-3 2-Methoxy-6-(1-methoxy-2-naphthoyl)-benzoesaeure 
• 19938-26-2 3-Methoxy-2-(1-methoxy-2-naphthoyl)-benzoesaeure 
• 1608458-02-1 C₁₈H₁₉ClO₂ 

Relevant academic research and scientific papers

Development of FABP4/5 inhibitors with potential therapeutic effect on type 2 Diabetes Mellitus

Fatty acid-binding protein 4 (FABP4) and fatty acid-binding protein 5 (FABP5) are promising therapeutic targets for the treatment of various metabolic diseases. However, the weak potency, low selectivity over FABP3, or poor pharmacokinetic profiles of currently reported dual FABP4/5 inhibitors impeded further research. Here, we described the characterization of a series of dual FABP4/5 inhibitors with improved metabolic stabilities and physicochemical properties based on our previous studies. Among the compounds, D9 and E1 exhibited good inhibitory activities against FABP4/5 and favorable selectivity over FABP3 in vitro. In cell-based assays, D9 and E1 exerted a decrease of FABP4 secretion, a strong anti-lipolytic effect in mature adipocytes, and suppression of MCP-1 expression in THP-1 macrophages. Moreover, D9 and E1 possessed good metabolic stabilities in mouse hepatic microsomes and acceptable pharmacokinetics profiles in ICR mice. Further in vivo experiments showed that D9 and E1 could potently decrease serum FABP4 levels and ameliorate glucose metabolism disorders in obese diabetic db/db mice. These results demonstrated that D9 and E1 could serve as lead compounds for the development of novel anti-diabetic drugs.

Aryl sulfamide compound, preparation method, pharmaceutical composition and uses thereof

The invention relates to the field of medicinal chemistry and pharmacotherapeutics, particularly to a compound represented by a general formula (I), a pharmaceutically acceptable salt, a prodrug molecule and a mixture thereof, a preparation method of the compound, a pharmaceutical composition containing the compound, and applications as an FABP4/FABP5 double-targeting inhibitor. The invention relates to applications of an aryl sulfamide compound in treatment of metabolic diseases and autoimmune diseases.

Identification of new dual FABP4/5 inhibitors based on a naphthalene-1-sulfonamide FABP4 inhibitor

Fatty acid binding protein 4 (FABP4) and fatty acid binding protein 5 (FABP5) are mainly expressed in adipocytes and/or macrophages and play essential roles in energy metabolism and inflammation. When FABP4 function is diminished, FABP5 expression is high

Selective Halogenation Using an Aniline Catalyst

Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.

Computational and DNMR investigation of the isomerism and stereodynamics of the 2,2′-binaphthalene-1,1′-diol scaffold

The relative stabilities of three conformational isomers of 2,2′-binaphthalene-1,1′-diol diisobutyrate and the energy barriers to rotation about the pivotal aryl-aryl bond and the two aryl-oxygen bonds were investigated by variable-temperature NMR spectroscopy in conjunction with DFT computations. The experimental and calculated data were found to be in very good agreement and provide new insights into the dynamic stereochemistry of BINOL-derived tropos ligands.

Chirality sensing of amines, diamines, amino acids, amino alcohols, and α-hydroxy acids with a single probe

A stereodynamic probe for determination of the absolute configuration and enantiomeric composition of chiral amines, diamines, amino alcohols, amino acids, and α-hydroxy carboxylic acids is described. The chirality sensing is based on spontaneous asymmetric transformation of the first kind with stereolabile binaphtholate boron and zinc complexes. The substrate binding and chiral amplification processes yield a distinctive chiroptical sensor output at high wavelength that can be used for rapid and accurate ee detection of minute sample amounts.

Impact of incorporating substituents onto the P-o-anisyl groups of DiPAMP ligand on the rhodium(I)-catalyzed asymmetric hydrogenation of olefins

The introduction of 1,2-bis[(o-anisyl)-(phenyl)phosphino]ethane (DiPAMP) as a P-stereogenic ligand for rhodium(I)-catalyzed hydrogenation by Knowles et al. came after their evaluation of several diphosphines. However, no in-depth study was carried out on incorporating various substituents on its P-o-anisyl groups. In this work, we have prepared a large series of enantiopure and closely related DiPAMP analogues possessing various substituents (MeO, TMS, t-Bu, Ph, fused benzene ring) on the o-anisyl rings. The new ligands were evaluated in rhodium-catalyzed hydrogenation of several model substrates: methyl α-acetamidoacrylate, methyl (Z)-α-acetamidocinnamate, methyl (Z)-β-acetamidocrotonate, dimethyl itaconate, and atropic acid. They displayed enhanced activities and increased enantioselectivities, particularly the P-(2,3,4,5-tetra-MeO-C6H)-substituted ligand (4MeBigFUS). Interestingly enough, 88% ee was obtained in the hydrogenation of atropic acid using the Rh-(4MeBigFUS) catalyst under mild conditions (10 bar H2, room temperature) versus 7% ee using Rh-DiPAMP. Conversely, the ligand possessing P-(2,6-di-MeO-C6H3) groups proved to slow down considerably the hydrogenation. X-Ray structures of their corresponding Rh complexes are presented and discussed.

An efficient and regioselective oxybromination of aromatic compounds using potassium bromide and oxone

A simple, efficient and regioselective method for oxybromination of aromatics is reported. The electrophilic substitution of bromine generated in situ from potassium bromide using oxone as an oxidant for the first time.