32721-06-5

Basic information

• Product Name: 2-(6-Bromonaphthalen-2-yl)acetic acid
• Synonyms: 2-(6-Bromonaphthalen-2-yl)acetic acid;6-Bromo-2-naphthaleneacetic acid
• CAS NO: 32721-06-5
• Molecular Formula: C₁₂H₉BrO₂
• Molecular Weight: 265.10266
• Mol File: 32721-06-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(6-Bromonaphthalen-2-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(6-Bromonaphthalen-2-yl)acetic acid(32721-06-5)
• EPA Substance Registry System: 2-(6-Bromonaphthalen-2-yl)acetic acid(32721-06-5)

Safety Data

• Hazardous Substances Data: 32721-06-5(Hazardous Substances Data)

Usage

Description

2-(6-bromonaphthalen-2-yl)acetic acid is a chemical compound with the molecular formula C13H10BrO2. It is a derivative of naphthalene and belongs to the class of arylacetic acids. 2-(6-bromonaphthalen-2-yl)acetic acid is characterized by the presence of a bromine atom attached to the naphthalene ring, which imparts unique chemical and physical properties to the molecule.

Uses

Used in Organic Synthesis:
2-(6-bromonaphthalen-2-yl)acetic acid is used as a building block in organic synthesis for the creation of various biologically active molecules. Its unique structure allows for the formation of diverse chemical entities with potential applications in different fields.
Used in Pharmaceutical Research:
In pharmaceutical research, 2-(6-bromonaphthalen-2-yl)acetic acid is utilized as a key intermediate in the synthesis of drugs with potential therapeutic benefits. Its structural features make it a valuable component in the development of new medications.
Used in Anti-inflammatory and Analgesic Applications:
2-(6-bromonaphthalen-2-yl)acetic acid has been studied for its potential anti-inflammatory and analgesic properties. Its ability to modulate inflammatory responses and alleviate pain makes it a promising candidate for the development of new treatments for inflammatory and pain-related conditions.
Used in Fluorescent Probes and Dyes Development:
Due to its fluorescent properties, 2-(6-bromonaphthalen-2-yl)acetic acid is used in the development of fluorescent probes and dyes for biological imaging applications. Its fluorescence can be harnessed to visualize and study biological processes at the molecular level, aiding in research and diagnostics.
Used in Biological Imaging Applications:
In biological imaging applications, 2-(6-bromonaphthalen-2-yl)acetic acid serves as a component in the creation of imaging agents that can be used to label and track specific biological targets. Its fluorescent characteristics enable the visualization of cellular and molecular events, contributing to a better understanding of biological systems.

Upstream product

• 305798-02-1 2-bromo-6-(bromomethyl)naphthalene 
• 151-50-8 potassium cyanide 
• 305798-03-2 2-(6-bromonaphthalen-2-yl)acetonitrile 
• 33626-98-1 methyl 6-bromo-2-naphthoate 
• 100751-63-1 (6-bromo-2-naphthy)methanol 
• 689290-84-4 2-bromo-6-(chloromethyl)naphthalene 
• 37796-78-4 2-bromo-6-methylnaphthalene 
• 37796-79-5 6-methylnaphthalen-2-amine 

Downstream Products

• 689290-86-6 4-[6-(2-hydroxyethyl)-2-naphthyl]benzonitrile 
• 693773-64-7 methanesulfonic acid 2-[6-(4-cyano-phenyl)-naphthalen-2-yl]-ethyl ester 
• 689290-83-3 4-(6-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-2-naphthyl)benzonitrile 
• 1423691-32-0 C₂₈H₂₄N₂O₄S 
• 1423685-07-7 C₂₇H₂₂N₂O₄S 

Relevant articles and documents

Three-component asymmetric catalytic ugi reaction - Concinnity from diversity by substrate-mediated catalyst assembly

The first chiral catalyst for the three-component Ugi reaction was identified as a result of a screen of a large set of different BOROX catalysts. The BOROX catalysts were assembled in situ from a chiral biaryl ligand, an amine, water, BH3×SMe2, and an alcohol or phenol. The catalyst screen included 13 different ligands, 12 amines, and 47 alcohols or phenols. The optimal catalyst system (LAP 8-5-47) provided α-amino amides from an aldehyde, a secondary amine, and an isonitrile with excellent asymmetric induction. The catalytically active species is proposed to be an ion pair that consists of the chiral boroxinate anion and an iminium cation. Harmonious arrangement of parts: A screen of BOROX catalysts that were generated in situ from 13 different ligands and 47 alcohols led to the identification of an effective combination for the catalytic asymmetric three-component Ugi reaction. Experimental results suggest that the catalyst is a chiral polyborate anion, which then forms an ion pair with the iminium cation that is generated from aldehyde and secondary amine.

Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones

A palladium-catalyzed intramolecular decarboxylative cyclization of α-aryl-γ-methylidene-δ-valerolactones, followed by olefin isomerization, has been developed to give fused polycyclic aromatic compounds under mild conditions. The process described here can be regarded as a formal decarboxylative allylic arylation without using a pre-formed organometallic nucleophile. The reaction can be conducted on a gram scale and the products thus obtained are further derivatized with ease.

An expedient and multikilogram synthesis of a naphthalenoid H3 antagonist

A facile and scaleable synthesis of potent and selective histamine H3 receptor antagonist 1 is described, starting from commercially available 6-bromo-naphthalene-2-carboxylic acid methyl ester 3a. The key intermediate, 2-(6-bromonaphthalen-2-yl)ethanol 5 was prepared in good yield (78%) and purity (99%) via a one-carbon homologation of 3a. The coupling of 5 with pyridazinone 12 was accomplished effectively by a copper-catalyzed cross-coupling reaction. Activation of the hydroxyl group of 4, followed by displacement reaction with 2(R)-methylpyrrolidine 13, afforded the free base of 1, which was subsequently converted to its corresponding salt The new process consisted of eight chemical steps and one salt formation step and required no Chromatographic purification throughout the synthesis. It has been successfully implemented on pilot plant scale to prepare over 10 kg quantities of the target compound 1 in 43% overall yield in high purity (99%) and with the desired physical properties.