2-(Bromomethyl)naphthalene

Base Information

• Chemical Name: 2-(Bromomethyl)naphthalene
• CAS No.: 939-26-4
• Molecular Formula: C11H9Br
• Molecular Weight: 221.096
• Hs Code.: 29033036
• European Community (EC) Number: 213-359-5
• DSSTox Substance ID: DTXSID10239864
• Nikkaji Number: J149.364G
• Wikidata: Q72447437
• Mol file: 939-26-4.mol

Synonyms:2-(Bromomethyl)naphthalene;939-26-4;2-Bromomethylnaphthalene;Naphthalene, 2-(bromomethyl)-;2-Bromomethyl naphthalene;2-Naphthylmethyl bromide;C11H9Br;MFCD00004123;.beta.-(Bromomethyl)naphthalene;EINECS 213-359-5;2-Menaphthyl bromide;2-(bromomethyl)napthalene;(Naphthalen-2-yl)methyl bromide;beta-(Bromomethyl)naphthalene;beta-Naphthylmethyl bromide;2-bromomethynaphthalene;2-Bromomethylnapthalene;2-Bromomethyinaphthalene;2-bromomethyl-napthalene;2-Bromomethyl napthalene;Naphth-2-ylmethylbromide;2-bromomethyl-naphthalene;2-naphthyl methyl bromide;naphth-2-ylmethyl bromide;2-(bromomethyl)-napthalene;2-naphthalenylmethyl bromide;2-(bromomethyl) naphthalene;2-(bromomethyl)-naphthalene;SCHEMBL44621;.beta.-Naphthylmethyl bromide;naphthalen-2-yl-methyl-bromide;DTXSID10239864;2-(Bromomethyl)naphthalene, 96%;CS-B1312;STR04041;AKOS005067452;AC-4571;BP-30159;AM20041431;B1524;FT-0608743;EN300-82277;A24578;A843991;AB-131/40897099;W-100223;F0001-2257;2-naphthylmethyl bromide;-(Bromomethyl)naphthalene;-Naphthylmethyl bromide

Chemical Property of 2-(Bromomethyl)naphthalene

Chemical Property:

• Appearance/Colour: White to cream solid
• Vapor Pressure: 0.00304mmHg at 25°C
• Melting Point: 51-54 °C(lit.)
• Refractive Index: 1.663
• Boiling Point: 293.3 °C at 760 mmHg
• Flash Point: 151.8 °C
• PSA: 0.00000
• Density: 1.444 g/cm³
• LogP: 3.73470
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Very Slightly)
• Water Solubility.: Soluble in water (reacts), and chloroform.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 219.98876
• Heavy Atom Count: 12
• Complexity: 144

Purity/Quality:

98.0% ^*data from raw suppliers

2-(Bromomethyl)naphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-43-36/37/38-36
• Safety Statements: 26-28-36/37/39-45-37-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)CBr
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. 2-(Bromomethyl)naphthalene (2-BMN) can be employed as a starting material in the synthesis of 2-(fluoromethyl)naphthalene , 2-naphthylmethyl azide , 2-naphthalenecarboxaldehyde , diselenide, bis(2-naphthalenylmethyl) , 1H-1,2,3-triazole, 4,4′-(1,4-phenylene)bis[1-(2-naphthalenylmethyl).

Technology Process of 2-(Bromomethyl)naphthalene

There total 30 articles about 2-(Bromomethyl)naphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-Naphthalenemethanol (1592-38-7) → 2-bromomethylnaphthyl bromide (939-26-4)

Guidance literature:

With pyridine; phosphorus tribromide; In benzene; at 55 ℃; for 6h;

Reference yield: 94.0%

2-(dimethoxymethyl)naphthalene (77196-31-7) → 2-bromomethylnaphthyl bromide (939-26-4)

Guidance literature:

With triethylsilane; Acetyl bromide; tin(II) bromide; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1246/bcsj.64.1410

Reference yield: 94.0%

β-naphthaldehyde (66-99-9) → 2-bromomethylnaphthyl bromide (939-26-4)

Guidance literature:

With polymethylhydrosiloxane; dimethylbromosulphonium bromide; In chloroform; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2007.07.125

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

2-Methylnaphthalene

2-Naphthalenemethanol

Downstream raw materials:

β-naphthaldehyde

[2]naphthylmethyl-o-tolyl ether

2-(mercaptomethyl)naphthalene

2-methyl-3-[2]naphthylmethyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester

Refernces

Synthesis and biophysical evaluation of 2′,4′-Constrained 2′O-Methoxyethyl and 2′,4′-Constrained 2′O-Ethyl nucleic acid analogues

10.1021/jo902560f

The research focuses on the synthesis and biophysical evaluation of 20,40-constrained 20O-methoxyethyl (cMOE) and 20,40-constrained 20O-ethyl (cEt) nucleic acid analogues. The purpose of this study was to develop nucleoside modifications that combine the structural elements of 2O-methoxyethyl (MOE) and locked nucleic acid (LNA) to improve the potency and therapeutic index of antisense oligonucleotides while mitigating the hepatotoxicity associated with LNA. The key chemicals used in the synthesis include diacetone allofuranose, 2-bromomethyl naphthalene, tert-butyldiphenylsilyl chloride, and various nucleobases such as uracil, adenine, and guanine. The researchers employed a cycloetherification strategy to synthesize the cMOE and cEt nucleoside phosphoramidites, utilizing a 2-naphthylmethyl protecting group that provided crystalline intermediates and enabled clean deprotection under mild conditions. The biophysical evaluation revealed that cMOE- and cEt-containing oligonucleotides exhibited hybridization and mismatch discrimination attributes similar to LNA but with significantly improved resistance to exonuclease digestion. The study concludes that these modifications offer a promising approach for enhancing the stability and efficacy of antisense oligonucleotides, potentially leading to more effective and safer therapeutic applications.