2586-62-1

Basic information

• Product Name: 1-BROMO-2-METHYLNAPHTHALENE
• Synonyms: 2-Methyl-1-bromonaphthalene;beta-Methyl-alpha-bromonaphthalene;1-BROMO-2-METHYLNAPHTHALENE;1-Bromo-2-methylnaphtalene;1-BROMO-2-METHYLNAPHTHALENE, TECH., 90%;1-Bromo-2-methylnaphthalene, 90-95%;NSC 36286;1-BroMo-2-Methylnaphthalene, 90-95% 100GR
• CAS NO: 2586-62-1
• Molecular Formula: C₁₁H₉Br
• Molecular Weight: 221.09
• EINECS: 219-966-1
• Product Categories: Naphthalene derivatives;Aryl;C9 to C12;Halogenated Hydrocarbons;Building Blocks;C9 to C12;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 2586-62-1.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 296 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow/Liquid
• Density: 1.418 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00195mmHg at 25°C
• Refractive Index: n20/D 1.648(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Not miscible in water.
• BRN: 2042531
• CAS DataBase Reference: 1-BROMO-2-METHYLNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-METHYLNAPHTHALENE(2586-62-1)
• EPA Substance Registry System: 1-BROMO-2-METHYLNAPHTHALENE(2586-62-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-11
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2586-62-1(Hazardous Substances Data)

Usage

Description

1-Bromo-2-methylnaphthalene is a clear yellow liquid that is a halogenated hydrocarbon derivative of naphthalene. It is characterized by the presence of a bromine atom at the first position and a methyl group at the second position in the naphthalene molecule.

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

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

Downstream Products

• 65814-06-4 N-(2-methyl-[1]naphthyl)-anthranilic acid 
• 838885-76-0 (2-methyl-[1]naphthyl)-o-tolyl-amine 
• 1575-96-8 2-methyl-1-naphthoic acid 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 19634-89-0 (R)-2,2'-dimethyl-1,1'-binaphthyl 
• 32587-64-7 (S)-(+)-2,2'-dimethyl-1,1'-binaphthyl 
• 19634-89-0 (S)-(+)-2,2'-dimethyl-1,1'-binaphtyl 
• 20944-85-8 2-methyl-1-naphthonitrile 
• 93322-81-7 2-methyl-1-phenylsulfonylnaphthalene 
• 36374-82-0 1-iodo-2-methylnaphthalene 
• 20717-79-7 1-bromo-2-naphthoic acid 
• 21450-90-8 (2-methyl-1-naphthyl)magnesium bromide 
• 52719-90-1 Bis(2.6-xylyl)-1-(2-methylnaphthyl)-methan 
• 50418-10-5 Dimesityl-1-(2-methylnaphthyl)boran 

Relevant articles and documents

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.

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.

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.

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.

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.