580-13-2

Basic information

• Product Name: 2-Bromonaphthalene
• Synonyms: BETA-NAPHTHYL BROMIDE;BETA-BROMONAPHTHALENE;BROMONAPHTHALENE(2-);2-BROMONAPHTHALENE;2-bromo-naphthalen;2-Naphthyl bromide;Naphthalene, 2-bromo-;naphthalene,2-bromo-
• CAS NO: 580-13-2
• Molecular Formula: C₁₀H₇Br
• Molecular Weight: 207.07
• EINECS: 209-452-5
• Product Categories: Aromatic Compounds;FINE Chemical & INTERMEDIATES;Naphthalene derivatives;White crystal powder;Aryl;C9 to C12;Halogenated Hydrocarbons;B;Bioactive Small Molecules;Building Blocks;C9 to C12;Cell Biology;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;Naphthalene series
• Mol File: 580-13-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 52-55 °C(lit.)
• Boiling Point: 281-282 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear light yellow to orange-brown/Liquid
• Density: 1,605 g/cm3
• Vapor Pressure: 0.00565mmHg at 25°C
• Refractive Index: 1.6382
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble50mg/mL, clear, colorless to yellow
• Water Solubility: slightly soluble
• Merck: 14,1426
• BRN: 1858110
• CAS DataBase Reference: 2-Bromonaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromonaphthalene(580-13-2)
• EPA Substance Registry System: 2-Bromonaphthalene(580-13-2)

Safety Data

• Hazard Codes: Xn,Xi,T
• Statements: 22-36-39/23/24/25-23/24/25-36/37/38-20/21/22
• Safety Statements: 26-36-45-36/37
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 580-13-2(Hazardous Substances Data)

Usage

Chemical Properties

White or pale yellow powder

Uses

2-Bromonaphthalene is used as a raw material in the preparation of biaryls through Suzuki cross coupling reaction. Further, it plays a vital role in the preparation of dyes. It is also used to study potential tumorigenicity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 32, p. 1607, 1967 DOI: 10.1021/jo01280a069Tetrahedron Letters, 26, p. 5939, 1985 DOI: 10.1016/S0040-4039(00)98266-2

General Description

Reaction of 2-bromonaphthalene with cuprous cyanide in N-methylpyrrolidone has been investigated. Nanosecond time-resolved resonance Raman spectra of the T1→Tn transition of 2-bromonaphthalene in methanol solvent has been investigated.

Purification Methods

Purify 2-bromonaphthalene by fractional elution from a chromatographic column of activated alumina. Crystallise it from EtOH. [Beilstein 5 IV 1667.]

InChI:InChI=1/C10H7Br/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

Upstream product

• 91-20-3 naphthalene 
• 875-83-2 sodium 2-naphtholate 
• 13590-47-1 bromochlorocarbene 
• 95-13-6 1-indene 
• 2243-83-6 2-naphthaloyl chloride 
• 7726-95-6 bromine 
• 7705-08-0 iron(III) chloride 
• 7732-18-5 water 
• 64-19-7 acetic acid 
• 19125-84-9 1,6-dibromonaphthalene 
• 10035-10-6 hydrogen bromide 
• 90-11-9 1-Bromonaphthalene 
• 7664-39-3 hydrogen fluoride 
• 52358-73-3 1,3-dibromonaphthalene 

Downstream Products

• 62062-39-9 1-naphthalen-1-yl-piperidine 
• 5465-85-0 N-(2-naphthyl)piperidine 
• 91-20-3 naphthalene 
• 18271-22-2 N-(naphthalen-2-yl)benzamide 
• 5395-85-7 N-[2]naphthyl-salicylamide 
• 106031-63-4 Hydroxy-naphthalen-2-yl-phenyl-acetic acid methyl ester 
• 2039-70-5 (E)-2-styrylnaphthalene 
• 613-46-7 2-naphthalenecarbonitrile 
• 612-78-2 2,2'-binaphthalene 
• 19420-29-2 2-phenoxynaphthalene 
• 4185-62-0 2-bromo-1-nitronaphthalene 
• 102153-49-1 2-bromo-8-nitronaphthalene 
• 134-32-7 1-amino-naphthalene 
• 91-59-8 naphthalen-2-ylamine 

Relevant articles and documents

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Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Acceptorless Dehydrogenation of Hydrocarbons by Noble-Metal-Free Hybrid Catalyst System

A hybrid catalysis that comprises an acridinium photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst-enabled acceptorless dehydrogenation of hydrocarbons is reported. The cationic nickel complex played a critical role in the reactivity. This is the first example of acceptorless dehydrogenation of hydrocarbons by base metal catalysis under mild reaction conditions of visible light irradiation at room temperature.

A mild and ligand-free Ni-catalyzed silylation via C-OMe cleavage

Metal-catalyzed transformations that forge carbon-heteroatom bonds are of central importance in organic synthesis. Despite the formidable potential of aryl methyl ethers as coupling partners, the scarcity of metal-catalyzed C-heteroatom bond formations via C-OMe cleavage is striking, with isolated precedents requiring specialized, yet expensive, ligands, high temperatures, and π-extended backbones. We report an unprecedented catalytic ipso-silylation of aryl methyl ethers under mild conditions and without recourse to external ligands. The method is distinguished by its wide scope, which includes the use of benzyl methyl ethers, vinyl methyl ethers, and unbiased anisóle derivatives, thus representing a significant step forward for designing new C-heteroatom bond formations via C-OMe scission. Applications of this transformation in orthogonal silylation techniques as well as in further derivatizations are also described. Preliminary mechanistic experiments suggest the intermediacy of Ni(0)-ate complexes, leaving some doubt that a canonical catalytic cycle consisting of an initial oxidative addition of the C-OMe bond to Ni(0) species comes into play.