5438-74-4

Basic information

• Product Name: 4-Bromo-1-naphthaleneacetic acid
• Synonyms: 4-Bromo-1-naphthaleneacetic acid;2-(4-bromonaphthalen-1-yl)acetic acid
• CAS NO: 5438-74-4
• Molecular Formula: C₁₂H₉BrO₂
• Molecular Weight: 265.1027
• Mol File: 5438-74-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 430°Cat760mmHg
• Flash Point: 213.8°C
• Appearance: /
• Density: 1.585g/cm³
• Vapor Pressure: 3.7E-08mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 4-Bromo-1-naphthaleneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-1-naphthaleneacetic acid(5438-74-4)
• EPA Substance Registry System: 4-Bromo-1-naphthaleneacetic acid(5438-74-4)

Safety Data

• Hazardous Substances Data: 5438-74-4(Hazardous Substances Data)

Usage

General Description

4-Bromo-1-naphthaleneacetic acid is a synthetic organic compound that belongs to the class of naphthalene derivatives. It is a white to off-white solid with a molecular formula of C12H9BrO2. This chemical is commonly used as a plant growth regulator, mimicking the action of the natural plant hormone auxin. It is known to stimulate root formation and can also be used to prevent premature fruit drop in certain crops. Additionally, 4-Bromo-1-naphthaleneacetic acid has been studied for its potential use in promoting the growth and yield of various agricultural crops. However, it is important to handle this chemical with care as it may have toxic effects if mishandled or ingested.

InChI:InChI=1/C12H9BrO2/c13-11-6-5-8(7-12(14)15)9-3-1-2-4-10(9)11/h1-6H,7H2,(H,14,15)

Upstream product

• 86-87-3 naphth-1-yl acetic acid 
• 30098-50-1 2-(4-bromonaphth-1-yl)acetonitrile 
• 90-11-9 1-Bromonaphthalene 
• 79-11-8 chloroacetic acid 
• 108-24-7 acetic anhydride 
• 79996-99-9 1-bromo-4-bromomethyl-naphthalene 
• 90-12-0 1-Methylnaphthalene 
• 3163-27-7 2-(bromomethyl)naphthalene 

Downstream Products

• 86-87-3 naphth-1-yl acetic acid 
• 4022-43-9 2-(4-phenylnaphthalen-1-yl)acetic acid 
• 1423683-36-6 C₃₃H₂₉ClN₂O₅ 
• 1423683-38-8 C₃₁H₂₅ClN₂O₅ 
• 34841-59-3 ethyl 2-(4-bromonaphthalen-1-yl)acetate 

Relevant articles and documents

Catalytic Enantioselective Synthesis of Atropisomeric Biaryls: A Cation-Directed Nucleophilic Aromatic Substitution Reaction

A catalytic enantioselective nucleophilic aromatic substitution reaction which yields axially chiral biaryl derivatives in excellent yields with e.r. values of up to 97:3 has been developed. This process uses a chiral counterion to direct the addition of thiophenolate to a prochiral dichloropyrimidine by a tandem desymmetrization/kinetic resolution mechanism. The products can be derivatized to a range of atropisomeric structures without any reduction in enantioenrichment, thus offering access to unexplored chiral biaryl architectures.

Rational design of a pirinixic acid derivative that acts as subtype-selective PPARγ modulator

Peroxisome proliferator-activated receptor γ (PPARγ) is involved in glucose and lipid homeostasis. PPARγ agonists are in clinical use for the treatment of type 2 diabetes. Lately, a new class of selective PPARγ modulators (SPPARγMs) was developed, which are believed to show less side effects than full PPARγ agonists. We have previously shown that α-substitution of pirinixic acid, a moderate agonist of PPARα and PPARγ, leads to low micromolar active balanced dual agonists of PPARα and PPARγ. Herein we present modifications of pirinixic acid leading to subtype-selective PPARγ agonists and furthermore the development of a selective PPARγ modulator guided by molecular docking studies.

Synthesis and structure-antifungal activity relationships of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues: Further refinement of tentative pharmacophore group

Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well.