20933-24-8

Basic information

• Product Name: 2-BROMO-6-METHOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE
• Synonyms: 2-BROMO-6-METHOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE;2-bromo-6-methoxy-3,4-dihydronaphthalen;2-broMo-6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one;2-broMo-6-Methoxy-1-tetralone;2-Bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)
• CAS NO: 20933-24-8
• Molecular Formula: C₁₁H₁₁BrO₂
• Molecular Weight: 255.1078
• Mol File: 20933-24-8.mol

Chemical Properties

• Melting Point: 78-79 °C(Solv: ethanol (64-17-5))
• Boiling Point: 367.642 °C at 760 mmHg
• Flash Point: 176.144 °C
• Appearance: /
• Density: 1.491 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 2-BROMO-6-METHOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-6-METHOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE(20933-24-8)
• EPA Substance Registry System: 2-BROMO-6-METHOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE(20933-24-8)

Safety Data

• Hazardous Substances Data: 20933-24-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research and Synthesis:
2-Bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure, featuring a bromine atom, a methoxy group, and a ketone group, makes it a valuable building block in the development of new chemical entities with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one is used as a starting material for the synthesis of novel drug candidates. Its structural features, including the bromine atom and the methoxy group, can be exploited to design and develop new molecules with potential therapeutic properties. 2-BROMO-6-METHOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONE may also be used in the synthesis of bioactive molecules targeting specific receptors or enzymes, contributing to the discovery of new drugs for the treatment of various diseases.
Used in Material Science:
2-Bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one can be utilized in the field of material science for the development of new materials with specific properties. Its unique structure and functional groups can be incorporated into polymers, coatings, or other materials to impart desired characteristics such as improved stability, enhanced reactivity, or specific interactions with other molecules.
Used in Analytical Chemistry:
In analytical chemistry, 2-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one can be employed as a reference compound or a standard for the development and validation of analytical methods. Its distinct structure and properties can be used to evaluate the performance of chromatographic, spectroscopic, or other analytical techniques, ensuring accurate and reliable results in chemical analysis.
Overall, while the specific applications of 2-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one may be limited, its unique structure and functional groups make it a valuable compound for chemical research, synthesis, and potential use in various industries such as pharmaceuticals, material science, and analytical chemistry.

InChI:InChI=1/C11H11BrO2/c1-14-8-3-4-9-7(6-8)2-5-10(12)11(9)13/h3-4,6,10H,2,5H2,1H3

Upstream product

• 107-06-2 1,2-dichloro-ethane 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 

Downstream Products

• 138047-60-6 2-(4-Hydroxy-4-phenylpiperidino)-6-methoxy-1-tetralone 
• 1208110-09-1 (2S)-6-methoxy-1'-[2-(3-methoxyphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one 
• 1208110-12-6 (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1Hspiro[naphthalene-2,2'-piperidin]-1-one 
• 1208110-11-5 (2S)-6-methoxy-1'-[2-(3-methoxyphenyl)ethyl]-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride 
• 1208110-05-7 (2S)-1'-[2-(2-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride 
• 1208110-14-8 (2S)-1'-[2-(3-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride 
• 1208109-99-2 (2S)-1'-[2-(4-fluorophenyl)ethyl]-6-methoxy-3,4-dihydro-1H-spiro[naphthalene-2,2'-piperidin]-1-one hydrochloride 
• 1208110-27-3 C₂₄H₂₆F₃NO₄S 
• 1307812-93-6 N-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide 
• 1370525-11-3 C₂₁H₂₂O₅ 
• 872857-72-2 acetic acid 2-bromo-6-methoxy-3,4-dihydro-naphthalen-1-yl ester 
• 1011794-38-9 1-(p-tolyl)-2-benzoylimino-4,5-dihydro-7-methoxy-1H-naphtho[1,2-d]thiazole 
• 100298-28-0 (R)-6-Methoxy-2-[(S)-3-oxo-2-(toluene-4-sulfonyl)-cyclopentyl]-3,4-dihydro-2H-naphthalen-1-one 
• 100298-28-0 (S)-6-Methoxy-2-[(S)-3-oxo-2-(toluene-4-sulfonyl)-cyclopentyl]-3,4-dihydro-2H-naphthalen-1-one 

Relevant articles and documents

Highly Enantioselective Synthesis of Fused Tri- and Tetrasubstituted Aziridines: aza-Darzens Reaction of Cyclic Imines with α-Halogenated Ketones Catalyzed by Bifunctional Phosphonium Salt

The first enantioselective aza-Darzens reaction of cyclic imines with α-halogenated ketones was realized under mild reaction conditions by using amino-acid-derived bifunctional phosphonium salts as phase-transfer promoters. A variety of structurally dense tri- and tetrasubstituted aziridine derivatives, containing benzofused heterocycles as well as spiro-structures, were readily synthesized in high yields with excellent diastereo- and enantioselectivities (up to >20:1 d.r. and >99.9 % ee). The highly functionalized aziridine products could be easily transformed into different classes of biologically active compounds.

Discovery, synthesis, and structure-activity relations of 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-ones as potassium-competitive acid blockers

With the aim to discover a gastric antisecretory agent more potent than the existing proton pump inhibitors, novel 3,4-dihydro-1H-spiro(naphthalene-2,2′-piperidin)-1-one derivatives, which could occupy two important lipophilic pockets (described as LP-1 and LP-2) of H+,K+-ATPase and can strongly bind to the K+-binding site, were designed based on a docking model. Among the compounds synthesized, compound 4d showed a strong H+,K+-ATPase-inhibitory activity and a high stomach concentration in rats, resulting in potent inhibitory action on histamine-stimulated gastric acid secretion in rats. Furthermore, 4d exerted significant inhibitory action on histamine-stimulated gastric-acid secretion in rats with a rapid onset and moderate duration of action after the administration. These findings may lead to a new insight into the drug design of potassium-competitive acid blockers.

Identification of Tricyclic Agonists of Sphingosine-1-phosphate Receptor 1 (S1P1) Employing Ligand-Based Drug Design

Fingolimod (1) is the first approved oral therapy for the treatment of relapsing remitting multiple sclerosis. While the phosphorylated metabolite of fingolimod was found to be a nonselective S1P receptor agonist, agonism specifically of S1P1 is responsible for the peripheral blood lymphopenia believed to be key to its efficacy. Identification of modulators that maintain activity on S1P1 while sparing activity on other S1P receptors could offer equivalent efficacy with reduced liabilities. We disclose in this paper a ligand-based drug design approach that led to the discovery of a series of potent tricyclic agonists of S1P1 with selectivity over S1P3 and were efficacious in a pharmacodynamic model of suppression of circulating lymphocytes. Compound 10 had the desired pharmacokinetic (PK) and pharmacodynamic (PD) profile and demonstrated maximal efficacy when administered orally in a rat adjuvant arthritis model.

Heterobicyclic sphingosine 1-phosphate analogs

Compounds that have agonist activity at one or more of the S1P receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at S1P receptors.

PPh3·HBr-DMSO mediated expedient synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters and α-bromo enals: Application to the synthesis of 2-methylsulfanyl-3(2 H)-furanones

An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3·HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl 3-catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described. Copyright

TETRACYCLIC HETEROCYCLE COMPOUNDS FOR TREATING HEPATITIS C VIRAL INFECTION

Tetracyclic heterocycle compounds of formula (I) and pharmaceutically acceptable salts thereof are provided, wherein A, A', G, R1, R15, U, V, V', W, W, X, X', Y and Y' are as defined in the invention. The pharmaceutical compositions comprising these compounds and the use of the compounds for treating hepatitis C virus (HCV) infection are also provided.

FUSED TETRACYCLIC HETEROCYCLE COMPOUNDS AND METHODS OF USE THEREOF FOR TREATMENT OF VIRAL DISEASES

The present invention discloses novel Fused Tetracyclic Heterocycle Compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, A', G, R1, R15, U, V, V', W, W', X, X', Y and Y' are as defined herein. The present invention also discloses compositions comprising at least one Fused Tetracyclic Heterocycle Compound, and methods of using the Fused Tetracyclic Heterocycle Compounds for treating or preventing HCV infection in a patient.

HETEROBICYCLIC SPHINGOSINE 1-PHOSPHATE ANALOGS

Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.

Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide

A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.

A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues

For the first time a reaction intermediate has been isolated giving further insight into the mechanism of thiazol-2-imine formation. The first step of the reaction requires a basic medium, while the second step is an acid mediated E1 elimination reaction. An efficient one-pot synthesis of substituted thiazol-2-imines have been achieved by the condensation of carbonyl compounds with thioureas and 1,3-disubstituted thioureas using 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). Unsymmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical ketones, which are mainly governed by the pKas of NH protons of thiourea, whereas symmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical carbonyl compounds owing to the regioselective bromination of ketones. The methodology is extended to access novel neurodegenerative drug candidate pifithrin-α analogues in good yields in shorter reaction time. This method is simple, versatile and is applicable for different 1,3-disubstituted thioureas as well as a range of carbonyl compounds.