2586-62-1

Usage

Uses

1. Used in Analytical Chemistry:
1-Bromo-2-methylnaphthalene is used as a test compound for the determination of halogenated hydrocarbons at trace levels by supercritical fluid chromatography-microwave-induced plasma mass spectrometry. This application takes advantage of its unique chemical properties to accurately measure and analyze trace amounts of similar compounds in various samples.
2. Used in Environmental Monitoring:
In environmental science, 1-Bromo-2-methylnaphthalene serves as a test compound for monitoring and detecting halogenated hydrocarbons in the environment. This is crucial for assessing pollution levels and understanding the impact of these compounds on ecosystems.
3. Used in Chemical Synthesis:
1-Bromo-2-methylnaphthalene undergoes asymmetric cross-coupling reactions with its corresponding Grignard reagent using a nickel catalyst. This process is utilized in the formation of non-racemic 2,2′-dimethyl-1,1′-binaphthyl, which is an important intermediate in the synthesis of various organic compounds.
4. Used in Sensor Technology:
Dynamic phosphorescence quenching of 1-bromo-2-methylnaphthalene without deoxygenation has been employed for selective sensing of Cu(II) at ngml-1 levels. This application highlights its potential use in developing sensitive and selective sensors for detecting metal ions in various industries, including water treatment and environmental monitoring.

InChI:InChI=1/C11H9Br/c1-8-6-7-9-4-2-3-5-10(9)11(8)12/h2-7H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 7553-56-2 iodine 
• 91-57-6 2-Methylnaphthalene 
• 75-15-0 carbon disulfide 
• 1575-96-8 2-methyl-1-naphthoic acid 
• 2246-44-8 1-amino-2-methylnaphthalene 

Downstream Products

• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 39070-93-4 (4-methoxyphenyl)(2-methylnaphthalen-1-yl)methanone 
• 29304-63-0 2-methyl-1-phenylnaphthalene 
• 103989-84-0 2-methyl-1-naphthylboronic acid 
• 29574-51-4 6,6-dimethyl-6H-dibenzopyran 
• 91-57-6 2-Methylnaphthalene 
• 93870-58-7 1-(2'-methylphenyl)-2-methylnaphthalene 
• 573-99-9 1-Fluoro-2-methylnaphthalene 
• 1004984-14-8 1-(2-isopropylphenyl)-2-methylnaphthalene 
• 910784-96-2 1-(2-methoxyphenyl)-2-methylnaphthalene 
• 814254-89-2 1-(2',6'-dimethylphenyl)-2-methylnaphthalene 
• 2246-44-8 1-amino-2-methylnaphthalene 
• 1254105-11-7 C₁₈H₁₃F₃ 
• 1309657-42-8 1-(2-methyl-1-naphthyl)-2-(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene 

Relevant academic research and scientific papers

Improved efficiency and product selectivity in the photo-Claisen-type rearrangement of an aryl naphthylmethyl ether using a microreactor/flow system

Ultraviolet (UV) irradiation of 2-[(2,4,6-trimethylphenoxy)methyl]-1- (methoxycarbonyl)naphthalene promotes a photochemical reaction that gives a cyclohexa-2,4-dienone product arising from a photo-Claisen-type ortho-rearrangement and a phenol derivative arising from a meta-rearrangement, along with 1-methoxycarbonyl-2-methylnaphthalene and 1,2-bis[1-(methoxycarbonyl) naphthalen-2-yl]ethane. When this process is carried out in a microreactor/flow system, its efficiency is dramatically enhanced and selectivity of products is improved. The effects on efficiency and product selectivity caused by the microreactor/flow system are attributed to more efficient light absorption and the suppression of secondary reactions.

Selective benzylic bromination of 2-methylnaphthalene

A practical synthesis of 2-(bromomethyl)naphthalene (1) by selective benzylic bromination of 2-methylnaphthalene (2) with bromine in heptane in the presence of lanthanum acetate hydrate is described.

Catalytic Asymmetric Dearomatizing Redox Cross Coupling of Ketones with Aryl Hydrazines Giving 1,4-Diketones

An asymmetric Bronsted acid catalyzed dearomatizing redox cross coupling reaction has been realized, in which aryl hydrazines react with ketones to deliver 1,4-diketones, bearing an all-carbon quarternary stereocenter in high enantiopurity.

Convenient ring-bromination of alkylnaphthalenes using N-bromosuccinimide in acetonitrile

1-Alkyl- and 2-alkylnaphthalenes are conveniently brominated in the 4- and 1-positions respectively using N-bromosuccinimide (NBS) in acetonitrile. The reactions are easy to perform and give higher chemical yields and better regioselectivity compared to brominations employing bromine/dichloromethane.

Intramolecular photocycloaddition reactions of 2- and 4-(5-arylpent-4-enyl)-1-cyanonaphthalenes

Photoreactions of 1-cyanonaphthalene derivatives containing 5-arylpent-4-enyl groups at C-2 or C-4 of the naphthalene ring were investigated. Photoreactions of C-2 derivatives in benzene or CH3CN generated intramolecular [2 + 2] and [3 + 2] photocycloadducts. Substances bearing electron-rich and electron-poor phenyl groups produced respective [2 + 2] and [3 + 2] photocycloadducts preferentially. In contrast, photoreactions of C-4 linked 1-cyanonaphthalenes produced intramolecular [4 + 2] photocycloadducts as main products along with stereoisomers of tricyclic compounds as minor products. The formation of [4 + 2] photocycloadducts was promoted by using benzophenone or Michler's ketone triplet photosensitization, and quenched by O2 or ferrocene. Intramolecular singlet exciplexes, which serve as important intermediates in the mechanistic pathways for these reactions, governed the site-selectivities in photoreactions of both of the 2- and 4-(5-arylpent-4-enyl)-1-cyanonaphthalenes. In addition, [4 + 2] photocycloadducts were observed to undergo di-π-methane rearrangement under irradiation conditions to produce angular triquinane derivatives.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Synthesis of N-Substituted Condensed Tetrahydropyridine-Based Enaminones via Palladium-Catalyzed Intramolecular C–N Cross-coupling

A number of β-enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β-diketones. Two general protocols for their palladium-catalyzed intramolecular C–N cross-coupling were established to give corresponding N-substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends the applicability of novel, recently established, palladium precatalysts to new substrates.

Applications of Selenonium Cations as Lewis Acids in Organocatalytic Reactions

The use of trisubstituted selenonium salts as organic Lewis acids in electrophilic halogenation and aldol-type reactions has been developed. The substrate scope is broad. The reaction conditions are mild and compatible with various functionalities. This study opens a new avenue for the development of nonmetallic Lewis acid catalysis.

Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.

The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).

Synthesis of pentacyclic compounds via intramolecular [3 + 2] photocycloaddition of cycloalkene linked naphthalenes

Intramolecular photocycloaddition reactions of cycloalkene linked naphthalenes lead to formation of pentacyclic compounds in a high yielding and stereoselective manner. Intramolecular [2 + 2] cycloadducts are formed initially in photoreactions of cycloalkene linked 1-cyanonaphthalenes. The initially formed intramolecular [2 + 2] cycloadducts absorb light at wavelengths used to promote the photochemical reactions and, as a result, they undergo efficient photocycloreversion to regenerate the starting substrates. In a less efficient competing process, the cycloalkene linked 1-cyanonaphthalenes react to form [3 + 2] intramolecular photoadducts, which do not absorb incident light under the conditions used. Consequently, these photoadducts become the major products in these processes. The relative configuration of the major diastereomers of the pentacyclic products formed from photoreactions of cyclopentene linked naphthalenes (cis-cis) differ from those (cis-trans) arising from the cyclooctene linked substrates. The results of theoretical calculations, which show that steric factors govern the preferred facial mode of intramolecular addition, are in good agreement with the stereochemical course of these photoreactions.