28419-11-6

Basic information

• Product Name: 3,5-DIBROMO-4-PYRIDINOL
• Synonyms: 3,5-DIBROMOPYRIDIN-4-OL;4-HYDROXY-3,5-DIBROMOPYRIDINE;3,5-DibroMopyridin-4(3H)-one;3,5-Dibromo-1H-pyridin-4-one
• CAS NO: 28419-11-6
• Molecular Formula: C₅H₃Br₂NO
• Molecular Weight: 252.89
• Mol File: 28419-11-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3,5-DIBROMO-4-PYRIDINOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIBROMO-4-PYRIDINOL(28419-11-6)
• EPA Substance Registry System: 3,5-DIBROMO-4-PYRIDINOL(28419-11-6)

Safety Data

• Hazardous Substances Data: 28419-11-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-DIBROMO-4-PYRIDINOL is used as a chemical intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Agrochemical Industry:
In the agrochemical sector, 3,5-DIBROMO-4-PYRIDINOL is utilized as a building block in the creation of agrochemicals, playing a part in the formulation of pesticides and insecticides to protect crops.
Used in Fine Chemicals Industry:
3,5-DIBROMO-4-PYRIDINOL serves as an intermediate in the production of fine chemicals, which are essential in various specialized applications, including the creation of complex organic molecules.
Used in Antimicrobial Agents:
Leveraging its antimicrobial and antifungal properties, 3,5-DIBROMO-4-PYRIDINOL is used in the development of antimicrobial agents, helping to combat microbial infections in various settings.
It is crucial to handle 3,5-DIBROMO-4-PYRIDINOL with caution due to its potential harmful effects if ingested, inhaled, or comes into contact with the skin.

Upstream product

• 108-96-3 4-pyridone 
• 117756-40-8 1H-Pyridin-4-one; compound with nitric acid 
• 130671-21-5 3-(3,5-Dibromo-4-oxo-4H-pyridin-1-yl)-propionitrile 
• 70149-39-2 3-bromo-4(1H)-pyridinone 

Downstream Products

• 1375275-05-0 diethyl-{3-[2-(4-trifluoromethylphenyl)naphthalen-1-yl]pyridin-4-yl}amine 
• 1375275-04-9 diethyl-{3-[2-(4-methoxyphenyl)naphthalen-1-yl]pyridin-4-yl}amine 
• 1375275-03-8 {3-[2-(3,5-dimethylphenyl)naphthalen-1-yl]pyridin-4-yl}diethylamine 
• 278600-41-2 diethyl{3-[2-(phenylmethoxy)naphthyl](4-pyridyl)}-amine 
• 278600-44-5 (+/-)-diethyl-[3-(2-phenylnaphthalen-1-yl)pyridin-4-yl]amine 
• 13626-17-0 3,5-dibromo-4-chloro-pyridine 

Relevant articles and documents

Discovery of 2,4-dimethoxypyridines as novel autophagy inhibitors

Autophagy is a catabolic process, which mediates degradation of cellular components and has important roles in health and disease. Therefore, small molecule modulators of autophagy are in great demand. Herein, we describe a phenotypic high-content screen for autophagy inhibitors, which led to the discovery of a dimethoxypyridine-based class of autophagy inhibitors, which derive from previously reported, natural product-inspired MAP4K4 inhibitors. Comprehensive structure-activity relationship studies led to a potent compound, and biological validation experiments indicated that the mode of action was upstream or independent of mTOR.

Theoretical prediction of selectivity in kinetic resolution of secondary alcohols catalyzed by chiral DMAP derivatives

The mechanism of esterification of the secondary alcohol 1-(1-naphthyl)ethanol 9 by isobutyric anhydride catalyzed by 4-pyrrolidinopyridine (PPY, 11) and a series of single enantiomer atropisomeric 4-dialkylaminopyridines 8a-g has been studied computationally at the B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level. Comparison of the levels of enantioselectivity predicted computationally with the results obtained experimentally allowed the method to be validated. The value of the approach is demonstrated by the successful prediction that a structural modification of an aryl group within the catalyst from phenyl to 3,5-dimethylphenyl would lead to improved levels of selectivity in this type of kinetic resolution (KR) reaction, as was subsequently verified following synthesis and evaluation of this catalyst (8d). Experimentally, the selectivity of this type of KR is found to exhibit a significant deuterium isotope effect (for 9 vs d1-9).

ALDOSTERONE SYNTHASE INHIBITORS

This invention relates to tricyclic triazole analogues of the formula I or their pharmaceutically acceptable salts, wherein the variable are defined herein. The inventive compounds selectively inhibit aldosterone synthetase. This invention also provides for pharmaceutical compositions comprising the compounds of Formula I or their salts as well as to methods for the treatment, amelioration or prevention of conditions that could be treated by inhibiting aldosterone synthetase.

PYRIDINE AND PYRIMIDINE BASED COMPOUNDS AS WNT SIGNALING PATHWAY INHIBITORS FOR THE TREATMENT OF CANCER

The present invention relates to pyridine and pyrimidine based compounds, pharmaceutical compositions comprising these compounds and their potential use as therapeutic agents for the treatment and / or prevention of cancer.

Microwave-assisted synthesis of 4-amino-3,5-dihalopyridines

4-Amino-3,5-dihalopyridines have been efficiently prepared via microwave-assisted nucleophilic aromatic substitution of 3,4,5-trihalopyridines using 1-1.1 equiv of primary and secondary amines. The reaction is also applicable to electron rich arylamines.

Pyridinone diketo acids: inhibitors of HIV replication

A new class of diketo acids constructed on pyridinone scaffolds, designed as inhibitors of HIV replication through inhibition of HIV integrase, is described. These compounds are useful in the prevention or treatment of infection by HIV and in the treatment of AIDS and ARC, either as the compounds, or as pharmaceutically acceptable salts, with pharmaceutically acceptable carriers, used alone or in combination with antivirals, immunomodulators, antibiotics, vaccines, and other therapeutic agents, especially other anti-HIV compounds (including other integrase-based anti-HIV agents). Methods of treating AIDS and ARC and methods of treating or preventing infection by HIV are also described.

Chiral catalysts for asymmetric acylation and related transformations

A chiral catalyst comprising a 3,4-disubstituted pyridine, or a salt, N functionalized derivative, dimer or oligomer thereof, wherein the 3-substituent is substantially hindered from rotation about the bond (sp2-sp2 biaryl axis) link

Axially chiral analogues of 4-(dimethylamino)pyridine: Novel catalysts for nonenzymatic enantioselective acylations

A concise seven-step synthesis of atropisomeric 3-aryl analogues of DMAP from 4-pyridone 8 has been developed. A representative compound of this class, biaryl (±)-15, has been resolved using CSP HPLC and shown to be an efficient nucleophilic catalyst for kinetic resolution of a series of secondary alcohols on both an analytical and preparative scale (stereoselectivity factors, s = 8.9-29).

Equilibration of N-(2-cyanoethyl)pyridinium cations with substituted pyridines and acrylonitrile. A change in rate-determining step in an E1cb reaction

The rates of equilibration of N-(2-cyanoethyl)pyridinium cations (1) with the corresponding pyridines and acrylonitrile have been measured in aqueous solutions of ionic strength 0.1 at 25 °C. Second-order rate constants (kOH) have been obtained for the hydroxide ion catalyzed elimination reactions of 16 ring-substituted 1 having pyridine leaving groups of pKBH in the range 1.5-9.7. Bronsted plots of log kOH vs pKBH are "concave down" with two distinct linear regions having β1g = -0.30 (for pKBH 1g = -0.93 (for pKBH > 5.8). This observation is consistent with a change in rate-determining step within an E1cb reaction mechanism from rate-determining deprotonation of 1 (i.e., (E1cb)irrev) for pKBH rev) for pKBH > 5.8. This interpretation is supported by 1H NMR spectral observations in basic D2O, which show no incorporation of deuterium into the acrylonitrile product for pKBH BH > 5.8. Rates of nucleophilic attack of pyridines and pyridinone anions (pKBH > 6) upon acrylonitrile have also been measured. These display a linear Br?nsted plot of βnuc = 0.20. Combination of β1g and βnuc gives βeq = 0.13 for the Michael-type addition of pyridinium cations to acrylonitrile to produce 1. Although the rates of the addition of pyridines of pKBH nuc = 0.20 for pyridines of pKBH > 5.8 to rate-determining protonation of the carbanionic intermediate with βnuc = 0.83 for pyridine nucleophiles of pKBH irrev region but is extremely weak under the current experimental conditions.

Kinetics and mechanism of the bromination of 4-pyridone and related derivatives in aqueous solution

The kinetics of bromination of 4-pyridone and selected derivatives have been measured in aqueous solutions in the pH range 0-9, at 25 deg C.The tautomeric system 4-pyridone 4-hydroxypyridine (1a 2a) reacts with bromine via the predominant (pyridone) tautomer at pH 6. 3-Bromo-4-pyridone behaves similary.The kinetics also reveal that the facile dibromination of 4-pyridone occurs because at most pH's the monobromo derivative is actually more reactive towards bromine by virtue of its lower pKa values.From the point of view of reactivity the 4-pyridones and their anions behave as substituted phenoxide ions. 4-Methoxypyridine does not undergo bromination under comparable conditions, but rather forms a complex with bromine.