59866-97-6

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-NAPHTHALENE-1-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic properties.
Used in Dye Industry:
In the dye industry, 5-BROMO-NAPHTHALENE-1-CARBOXYLIC ACID METHYL ESTER is used as a precursor in the production of dyes, where its chemical structure allows for the creation of dyes with unique color characteristics.
Used in Fine Chemicals Production:
5-BROMO-NAPHTHALENE-1-CARBOXYLIC ACID METHYL ESTER is utilized as a building block in the synthesis of fine chemicals, contributing to the development of high-quality specialty chemicals for various applications.
Safety Considerations:
It is important to handle 5-BROMO-NAPHTHALENE-1-CARBOXYLIC ACID METHYL ESTER with care due to its potential hazards. Proper safety measures should be followed when working with 5-BROMO-NAPHTHALENE-1-CARBOXYLIC ACID METHYL ESTER to ensure the safety of personnel and the environment.

Upstream product

• 16726-67-3 5-bromo-1-naphthalenecarboxylic acid 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 84532-82-1 5-bromo-1-naphthoyl chloride 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 86-55-5 1-naphthalenecarboxylic acid 

Downstream Products

• 91804-21-6 methyl 5-cyano-1-naphthylcarboxylate 
• 20366-57-8 (5-bromo-naphthalen-1-yl)-methanol 
• 865798-97-6 5-(2-amino-phenylsulfanyl)-naphthalene-1-carboxylic acid methyl ester 
• 51934-37-3 5-methoxy-1-naphthoic acid 
• 280135-08-2 5-(4-trifluoromethoxybenzyloxy)methyl-1-naphthaldehyde 
• 3839-20-1 5-cyanonaphthalene-1-carboxylic acid 
• 20366-59-0 1-bromo-5-methylnaphthalene 
• 4527-60-0 5-methyl-1-naphthoic acid 
• 42589-78-6 (+/-)-1.5-Dicarboxymethylacenaphthen 

Relevant academic research and scientific papers

Europium amphiphilic naphthalene based complex for the enhancement of linearly polarized luminescence in Langmuir-Blodgett films

Linearly polarized luminescence (LPL) in films of europium ions was induced by using naphthoic acid adopted alkyl chain (NaphC15), which plays the roles of both surfactant and photo-antenna. The synthesis of NaphC15 was newly developed, and the Eu complex composed in a 1:3 ratio of Eu3+ ion and NaphC15 was synthesized in the powder form for comparison. The structural aspects of LB films with a layered scheme were obtained from the measurements of synchrotron XRPD, X-ray photoelectron spectroscopy and waveguide polarized absorption spectra. Luminescence of europium in the film is more intense than that in the powdered complex. The luminescence efficiency calculated from the observed luminescence lifetimes and quantum yields also supported their structure-enhanced luminescence. Finally, we revealed that the LPL was sensitized by the electronic dipole moment localized on the NaphC15 moieties aligned independently in the Langmuir-Blodgett films.

From Acenaphthenes to (+)-Delavatine A: Visible-Light-Induced Ring Closure of Methyl (α-Naphthyl) Acrylates

Disclosed herein is a visible light mediated cyclization of methyl (α-naphthyl) acrylates and heteroaromatic analogues yielding substituted acenaphthenes and azaacenaphthenes. This highly functional-group-tolerant transformation was put to the test in an enantioselective formal synthesis of delavatine A. Mechanistic details were elucidated by DFT-calculations revealing an unusual intramolecular H-transfer mediated by a primary amine. The generality of this transformation enables a novel synthetic strategy of five membered ring annulation at an advanced stage, allowing reliance upon naphthalene chemistry up to the point of acenaphthene construction.

COMPOUNDS FOR BINDING PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9)

The present disclosure relates to novel compounds, methods, and compositions capable of binding to PCSK9, thereby modulating PCSK9 proprotein convertase enzyme activity. The compounds of the disclosure include compounds Formula (I).

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.

Synthesis, antitumor and DNA photocleaving activities of novel naphthalene carboxamides: Effects of different thio-heterocyclic rings and aminoalkyl side chains

Two kinds of thio-heterocyclic fused naphthalene carboxamides, 3a-b, 4a-b, were designed, synthesized and quantitatively evaluated as efficient antitumor and DNA photocleaving agents. Compound 3a or 3b, having the thiophene ring, intercalated into DNA mor

Photogeneration of 1,5-naphthoquinone methides via excited-state (formal) intramolecular proton transfer (ESIPT) and photodehydration of 1-naphthol derivatives in aqueous solution

The photochemistry of naphthols 1, 2, 4, 5 and 9, and phenol 10 has been studied in aqueous solution with the primary aim of exploring the viability of such compounds for naphthoquinone and quinone methide photogeneration, along the lines already demonstr

Glucagon antagonists/inverse agonists

Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof are disclosed. The compounds act to antagonize the action of the glucagon peptide hormone.

Optimization of alkylidene hydrazide based human glucagon receptor antagonists. Discovery of the highly potent and orally available 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1h-indol-4ylmethylene]hydrazide

Highly potent human glucagon receptor (hGluR) antagonists have been prepared employing both medicinal chemistry and targeted libraries based on modification of the core (proximal) dimethoxyphenyl group, the benzyl ether linkage, as well as the (distal) benzylic aryl group of the lead 2, 3-cyano-4-hydroxybenzoic acid (3,5-dimethoxy-4-isopropylbenzyloxybenzylidene)hydrazide. Electron-rich proximal aryl moieties such as mono- and dimethoxy benzenes, naphthalenes, and indoles were found to be active. The SAR was found to be quite insensitive regarding the linkage to the distal aryl group, since long and short as well as polar and apolar linkers gave highly potent compounds. The presence of a distal aryl group was not crucial for obtaining high binding affinity to the hGluR. In many cases, however, the affinity could be further optimized with substituted distal aryl groups. Representative compounds have been tested for in vitro metabolism, and structure - metabolism relationships are described. These efforts lead to the discovery of 74, NNC 25-2504, 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide, with low in vitro metabolic turnover. 74 was a highly potent noncompetitive antagonist of the human glucagon receptor (IC50 = 2.3 nM, KB = 760 pM) and of the isolated rat receptor (IC50 = 430 pM, KB = 380 pM). Glucagonstimulated glucose production from isolated primary rat hepatocytes was inhibited competitively by 74 (Ki = 14 nM). This compound was orally available in dogs (Fpo = 15%) and was active in a glucagon-challenged rat model of hyperglucagonemia and hyperglycemia.

Discovery of novel, orally active dual NK1/NK2 antagonists

Exploration of the SAR around selective NK2 antagonists, SR48968 and ZD7944, led to the discovery that naphth-1-amide analogues provide potent dual NK1 and NK2 antagonists. ZD6021 inhibited binding of [3H]-NKA or [3H]-SP to human NK1 and NK2 receptors, with high-affinity (Ki=0.12 and 0.62 nM, respectively). In functional assays ZD6021 had, at 10-7 M, in human pulmonary artery pKB=8.9 and in human bronchus pKB=7.3, for NK1 and NK2, respectively. Oral administration of ZD6021 to guinea pigs dose-dependently attenuated ASMSP induced extravasation of plasma proteins, ED50=0.5 mg/kg, and NK2 mediated bronchoconstriction, ED50=13 mg/kg.