10262-65-4

Basic information

• Product Name: 2-Bromoacetyl-6-methoxynaphtalene
• Synonyms: 2-Bromoacetyl-6-methoxynaphtalene;2-bromoacetyl-6-methoxynaphthalene;2-Bromo-1-(6-methoxy-naphthalen-2-yl)-ethanone;2-bromo-1-(6-methoxy-2-naphthyl)ethanone;2-Bromo-6'-methoxy-2'-acetonaphthone;Ibuprofen Impurity 20
• CAS NO: 10262-65-4
• Molecular Formula: C₁₃H₁₁BrO₂
• Molecular Weight: 279.12924
• Mol File: 10262-65-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 110.0 to 114.0 °C
• Boiling Point: 387.2 °C at 760 mmHg
• Flash Point: 188 °C
• Appearance: /
• Density: 1.451 g/cm³
• Vapor Pressure: 3.35E-06mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: 2-Bromoacetyl-6-methoxynaphtalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromoacetyl-6-methoxynaphtalene(10262-65-4)
• EPA Substance Registry System: 2-Bromoacetyl-6-methoxynaphtalene(10262-65-4)

Safety Data

• RIDADR: 3261
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 10262-65-4(Hazardous Substances Data)

Usage

Uses

2-(Bromoacetyl)-6-methoxynaphthalene is used in the preparation of 2-(2-arylmorpholino)ethyl esters of ibuprofen hydrochlorides as COX-2 and serotonin reuptake inhibitors.

InChI:InChI=1/C13H11BrO2/c1-16-12-5-4-9-6-11(13(15)8-14)3-2-10(9)7-12/h2-7H,8H2,1H3

Upstream product

• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 93-04-9 2-Methoxynaphthalene 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 878796-46-4 2-(2,6-dichlorobenzyl)-4-(6-methoxy-2-naphthyl)-1,3-thiazole 
• 1195951-03-1 C₂₁H₁₈O₅ 
• 1195950-95-8 C₂₇H₂₉NO₆ 
• 877379-61-8 ethyl 2-benzoyl-4-(6-methoxy-2-naphthyl)-4-oxobutanoate 
• 62244-94-4 (6-Methoxy-2-naphthacyl)-benzoat 
• 1243257-38-6 2-[2-(6-methoxynaphthalen-2-yl)morpholino-4-yl]ethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-acetate hydrochloride 
• 1603829-38-4 2-(6-methoxynaphthalen-2-yl)-5-(p-tolyl)indolizine 
• 1195951-07-5 C₂₈H₁₉Cl₂N₇O₃ 
• 1195951-11-1 C₃₄H₃₁Cl₂N₃O₅ 

Relevant articles and documents

Measurement of pH values in human tissues by two-photon microscopy

pH values go live! A ratiometric two-photon (TP) probe (NP1, see scheme) that has a significant TP action cross-section, high photostability, negligible toxicity, and can estimate pH values in live cells and human tissues by two-photon microscopy is described. NP1 can detect the difference in pH between live cells from the gastroesophageal junction (GEJ) and the lower esophageal sphincter of patients with and without esophagitis (see image). Copyright

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

Synthesis and evaluation of 2-(2-arylmorpholino)ethyl esters of ibuprofen hydrochlorides as COX-2 and serotonin reuptake inhibitors

Based on the positive effects of COX-2 inhibitors on depressive symptoms and the desirable physicochemical and biological properties of the morpholine group, a series of novel 2-(2-arylmorpholino)ethyl esters of ibuprofen hydrochlorides were designed, synthesized, and tested for their COX-2 inhibitory and serotonin reuptake inhibitory activities in vitro. The structure-activity relationships of the 2-(2-arylmorpholino)ethyl esters of ibuprofen hydrochlorides as dual COX-2 and serotonin reuptake inhibitors were determined and discussed in detail. The biological assays indicated that five of the compounds possess good COX-2 selectivity (selectivity index COX-1/COX-2 42.8-158.1). The compound 2-[2-(4-benzyloxyphenyl)morpholino]ethyl 2-(4-iso-butylphenyl)-propanoate hydrochloride (1k) shows better COX-2 inhibitory activity (IC50 = 0.78 μM) than ibuprofen (IC 50 = 7.6 μM), and it simultaneously possesses favorable serotonin reuptake inhibitory activity. A series of novel 2-(2-arylmorpholino)ethyl esters of ibuprofen were tested for their COX-2 inhibitory and serotonin reuptake inhibitory activities in vitro. Most of the compounds possess good COX-2 selectivity. Compound 1k shows better COX-2 inhibitory activity than ibuprofen and possesses favorable serotonin reuptake inhibitory activity. According to the results of the biological assays, 2-arylmorpholine-substituted ibuprofen could be used as a core structure to design novel dual COX-2 and serotonin reuptake inhibitors.