939-26-4

Basic information

• Product Name: 2-(Bromomethyl)naphthalene
• Synonyms: 2-(BROMOMETHYL)NAPHTHALENE;2-BMN;BROMOMETHYLNAPTHALENE-2;2-Bromomethylnaphthalene98%;2-(Bromomethyl)naphthalene,96%;Naphthalene, 2-(bromomethyl)-;2-naphthylmethyl bromide;2-(Bromomethyl)naphthalene 96%
• CAS NO: 939-26-4
• Molecular Formula: C₁₁H₉Br
• Molecular Weight: 221.09
• EINECS: 213-359-5
• Product Categories: Naphthalene derivatives;Aryl;C9 to C12;Halogenated Hydrocarbons;Naphthalene series
• Mol File: 939-26-4.mol
• Article Data: 59

Chemical Properties

• Melting Point: 51-54 °C(lit.)
• Boiling Point: 213 °C100 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Slightly yellow to light beige/Fine Crystalline Powder
• Density: 1.3971 (rough estimate)
• Vapor Pressure: 0.00304mmHg at 25°C
• Refractive Index: 1.6411 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Very Slightly)
• Water Solubility: Soluble in water (reacts), and chloroform.
• BRN: 636546
• CAS DataBase Reference: 2-(Bromomethyl)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Bromomethyl)naphthalene(939-26-4)
• EPA Substance Registry System: 2-(Bromomethyl)naphthalene(939-26-4)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-43-36/37/38-36
• Safety Statements: 26-28-36/37/39-45-37-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 939-26-4(Hazardous Substances Data)

Usage

Description

2-(Bromomethyl)naphthalene, also known as 2-BMN, is an organic compound that features a naphthalene ring with a bromine atom attached to a methyl group. It is a versatile intermediate in various chemical reactions and synthesis processes.

Uses

Used in Organic Synthesis:
2-(Bromomethyl)naphthalene is used as a key intermediate for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes. Its unique structure allows for a wide range of chemical reactions, making it a valuable building block in the development of new molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(Bromomethyl)naphthalene is used as a starting material for the synthesis of various drug candidates. Its reactivity and structural features enable the creation of novel therapeutic agents with potential applications in treating various diseases and conditions.
Used in Agrochemical Industry:
2-(Bromomethyl)naphthalene is employed as a raw material in the development of agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the synthesis of compounds that can effectively control pests and weeds, contributing to increased crop yields and agricultural productivity.
Used in Dye Industry:
In the dye industry, 2-(Bromomethyl)naphthalene is used as an intermediate for the production of various dyes and pigments. Its ability to participate in different chemical reactions enables the creation of a wide range of colorants for use in textiles, plastics, and other applications.
Used in Synthesis of 2-(Fluoromethyl)naphthalene:
2-(Bromomethyl)naphthalene can be employed as a starting material in the synthesis of 2-(fluoromethyl)naphthalene, which is an important compound with potential applications in various fields, such as pharmaceuticals and materials science.
Used in Synthesis of 2-Naphthylmethyl Azide:
2-(Bromomethyl)naphthalene is used as a precursor in the synthesis of 2-naphthylmethyl azide, a compound that can be further utilized in the preparation of various organic molecules and pharmaceutical agents.
Used in Synthesis of 2-Naphthalenecarboxaldehyde:
2-(Bromomethyl)naphthalene serves as a starting material for the synthesis of 2-naphthalenecarboxaldehyde, an important intermediate in the production of various organic compounds and pharmaceuticals.
Used in Synthesis of Diselenide:
2-(Bromomethyl)naphthalene can be employed as a precursor in the synthesis of diselenide, a compound with potential applications in the development of new materials and pharmaceutical agents.
Used in Synthesis of Bis(2-naphthalenylmethyl):
2-(Bromomethyl)naphthalene is used as a starting material in the synthesis of bis(2-naphthalenylmethyl), a compound that can be further utilized in the preparation of various organic molecules and pharmaceutical agents.
Used in Synthesis of 1H-1,2,3-Triazole:
2-(Bromomethyl)naphthalene can be employed as a precursor in the synthesis of 1H-1,2,3-triazole, a heterocyclic compound with potential applications in various fields, such as pharmaceuticals and materials science.
Used in Synthesis of 4,4′-(1,4-Phenylene)bis[1-(2-naphthalenylmethyl):
2-(Bromomethyl)naphthalene is used as a starting material in the synthesis of 4,4′-(1,4-phenylene)bis[1-(2-naphthalenylmethyl), a compound with potential applications in the development of new materials and pharmaceutical agents.

Purification Methods

Dissolve the bromo compound in toluene, wash it with saturated aqueous NaHCO3, dry (Mg SO4), evaporate, fractionally distil the residue and recrystallise the solidified distillate from EtOH. [Chapman & Williams J Chem Soc 5044, 1952, Bergmann & Szmuszkovicz Bull Soc Chim Fr 20 566 1953, Beilstein 5 IV 1698.]

InChI:InChI=1/C11H9Br/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8H2

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 91-57-6 2-Methylnaphthalene 
• 1592-38-7 2-Naphthalenemethanol 
• 613-54-7 2-Bromo-2'-acetonaphthone 
• 774197-64-7 3-(2-naphthylmethoxy)-3-bromoaziridine 
• 66-99-9 β-naphthaldehyde 
• 2459-25-8 methyl naphthalene-2-carboxylate 
• 93-09-4 naphthalene-2-carboxylate 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 33223-85-7 2-methyl-1,2,3,4-tetrahydronaphthalen-2-ol 
• 6571-72-8 1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene 
• 7726-95-6 bromine 
• 77196-31-7 2-(dimethoxymethyl)naphthalene 

Downstream Products

• 1076-67-1 2-(mercaptomethyl)naphthalene 
• 102448-36-2 2-methyl-3-[2]naphthylmethyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester 
• 103046-01-1 1-[2]naphthylmethyl-2-oxo-cyclohexanecarboxylic acid benzyl ester 
• 109036-07-9 2-[2]naphthylmethyl-cyclohexane-1,3-dione 
• 111663-81-1 5-methyl-1-[2]naphthylmethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 114225-16-0 diethyl-benzyl-[2]naphthylmethyl-ammonium; bromide 
• 111664-17-6 3-methyl-1-[2]naphthylmethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 855220-51-8 2-methyl-2-[2]naphthylmethyl-1-phenyl-butan-1-one 
• 7498-57-9 2-naphthaleneacetonitrile 
• 68299-60-5 2-((naphthalen-2-yl)methyl)phenol 
• 38418-15-4 benzoic acid 2-naphthalenylmethyl ester 
• 57277-25-5 (naphthalen-2-ylmethyl)phosphonic acid diethyl ester 
• 68299-61-6 4-Hydroxy-1-(naphthyl-⁽²⁾-methyl)-benzol 
• 68299-58-1 β-naphthylmethyl phenyl ether 

Relevant articles and documents

A general and efficient method to form self-assembled cucurbit[n]uril monolayers on gold surfaces

A general protocol based on spontaneous adsorption of cucurbit[n]uril (CB[n]) molecules through a strong multivalence interaction between CB[n] and gold is described, by which the formation of self-assembled CB[n] monolayers on gold surfaces can be efficiently achieved. The Royal Society of Chemistry.

Fluorescence response of anthracene modified D-π-A heterocyclic chromophores containing nitrogen atom to mechanical force and acid vapor

Three new 9-vinyl anthracene derivatives functionalized naphthalene (ANNP), quinoline (ANQL) and quinoxaline (ANQX) have been synthesized, and they exhibit excellent solid state luminescence. Optical properties and quantum chemical calculations indicate the absence of D-π-A structure in ANNP, and the presence of typical D-π-A structures in ANQL and ANQX. Though the differences between the three molecules are marginal, their stimuli-responsive behaviors are contrasting. Non-heteroatom-assisted ANNP has no clear chromic property. In contrast, heteroatom-assisted ANQL and ANQX show a clear response to external stimuli such as mechanical force (mechanofluorochromism) and protons (acidofluorochromism). On one hand, both of them exhibit contrasting MFC effects. Upon grinding, emission wavelength shifts are 16 nm and 28 nm, respectively. ANQX shows a large spectral change, which might be originated from nitrogen atom induced ICT process and twisted molecular conformation. On the other hand, two molecules show difference acidofluorochromic response. The presence of nitrogen atom leads to the formation of a stable complex between target molecule and TFA. The solution and film of ANQX achieve a fast response to TFA with high sensitivity and low detection limit. The present results suggest that the anthracene modified D-π-A heterocyclic chromophores containing nitrogen atom can achieve fluorescence response to mechanical forces and acid vapor.

Bioisosteric Modification of To042: Synthesis and Evaluation of Promising Use-Dependent Inhibitors of Voltage-Gated Sodium Channels

Three analogues of To042, a tocainide-related lead compound recently reported for the treatment of myotonia, were synthesized and evaluated in vitro as skeletal muscle sodium channel blockers possibly endowed with enhanced use-dependent behavior. Patch-clamp experiments on hNav1.4 expressed in HEK293 cells showed that N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine, the aryloxyalkyl bioisostere of To042, exerted a higher use-dependent block than To042 thus being able to preferentially block the channels in over-excited membranes while preserving healthy tissue function. It also showed the lowest active transport across BBB according to the results of P-glycoprotein (P-gp) interacting activity evaluation and the highest cytoprotective effect on HeLa cells. Quantum mechanical calculations and dockings gave insights on the most probable conformation of the aryloxyalkyl bioisostere of To042 in solution and the target residues involved in the binding, respectively. Both approaches indicated the conformations that might be adopted in both the unbound and bound state of the ligand. Overall, N-[(naphthalen-1-yl)methyl]-4-[(2,6-dimethyl)phenoxy]butan-2-amine exhibits an interesting toxico-pharmacological profile and deserves further investigation.

Promotion of Appel-type reactions by N-heterocyclic carbenes

N-Heterocyclic carbenes (NHCs) have been extensively used as a versatile class of catalysts and ligands in organocatalytic and organometallic chemistry. However, there are only a small number of synthetic applications where they act as reagents. Here we demonstrate that NHCs can be used as stoichiometric redox reagents for Appel-type halogenation reactions of alcohols. This new reactivity reveals a fresh and interesting aspect and enriches the chemistry of NHCs in an underexplored area. The potential of performing this chemical transformation at the catalytic level using an NHC-oxide derivative is also investigated.