23003-22-7

Basic information

• Product Name: 2-MERCAPTO-PYRIDIN-3-OL
• Synonyms: 3-Hydroxy-2-mercaptopyridine;3-Hydroxy-2-pyridinethione;3-Hydroxypyridine-2(1H)-thione;2-Mercapto-3-pyridinol,97%;2-MERCAPTO-PYRIDIN-3-OL;3-hydroxypyridine-2-thiol;2-Mercapto-3-pyridinol;2(1H)-Pyridinethione,3-hydroxy-(8CI,9CI)
• CAS NO: 23003-22-7
• Molecular Formula: C₅H₅NOS
• Molecular Weight: 127.16
• EINECS: 245-375-3
• Product Categories: THIOL;PYRIDINE;pharmacetical
• Mol File: 23003-22-7.mol

Chemical Properties

• Melting Point: 141 °C
• Boiling Point: 235.9 °C at 760 mmHg
• Flash Point: 96.5 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 0.00884mmHg at 25°C
• Refractive Index: 1.709
• PKA: 8.01±0.20(Predicted)
• CAS DataBase Reference: 2-MERCAPTO-PYRIDIN-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MERCAPTO-PYRIDIN-3-OL(23003-22-7)
• EPA Substance Registry System: 2-MERCAPTO-PYRIDIN-3-OL(23003-22-7)

Safety Data

• Hazardous Substances Data: 23003-22-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2-Mercapto-pyridin-3-ol is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its thiol group allows for the formation of stable metal complexes, making it a valuable component in the development of new drugs and pesticides.
Used in Metal Coordination Chemistry:
Due to its thiol group, 2-mercapto-pyridin-3-ol serves as a potential chelating agent in metal coordination chemistry. It can form stable complexes with various metal ions, which can be applied in areas such as catalysis, sensors, and materials science.
Used in Antioxidant and Anti-inflammatory Research:
2-Mercapto-pyridin-3-ol has been investigated for its potential antioxidant and anti-inflammatory properties. Its ability to scavenge free radicals and modulate inflammatory responses makes it a promising candidate for the development of therapeutic agents targeting oxidative stress and inflammation-related diseases.
Used in Disease and Condition Treatment:
2-Mercapto-pyridin-3-ol has been studied for its potential use in the treatment of various diseases and conditions. Its diverse biological activities, including antioxidant, anti-inflammatory, and metal-chelating properties, suggest its potential in addressing a range of health issues, although further research is needed to fully understand its therapeutic potential and safety profile.

InChI:InChI=1/C5H5NOS/c7-4-2-1-3-6-5(4)8/h1-3,7H,(H,6,8)

Upstream product

• 6602-32-0 2-bromo-pyridin-3-ol 
• 84719-32-4 3-Hydroxy-2(1H)-pyridinone 
• 6602-28-4 3-hydroxypyridine N-oxide 

Downstream Products

• 35191-20-9 8-hydroxy-2-methyl-3-oxo-2,3-dihydro-thiazolo[3,2-a]pyridinylium betaine 
• 23003-39-6 8-Hydroxy-dihydrothiazolo<3,2-a>-pyridinium-3-carboxylat 
• 23003-45-4 2,3-dihydrothiazolo<3,2-a>pyridylium-8-olate 
• 35143-55-6 8-hydroxy-3-oxo-2,3-dihydro-thiazolo[3,2-a]pyridinylium betaine 
• 32637-37-9 2-(methylsulfanyl)pyridin-3-ol 
• 76349-09-2 3-acetoxy-2(1H)-thiopyridone 
• 131353-13-4 2-thioxopyrid-3-yl cyclohexylcarbamate 
• 35143-57-8 8-hydroxy-3-oxo-2-phenyl-2,3-dihydro-thiazolo[3,2-a]pyridinylium betaine 
• 65424-02-4 1,4-Benzoxathiino<3,2-b>pyridine 
• 32002-92-9 8-acetoxy-3-oxo-2-phenyl-2,3-dihydro-thiazolo[3,2-a]pyridinylium betaine 
• 72719-73-4 7-(trifluoromethyl)-1-azaphenoxathiin 10,10-dioxide 

Relevant articles and documents

A THIONATION PROCESS AND A THIONATING AGENT

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N

A thionation process and a thionating agent

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.

Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.

NOVEL BENZOXATHIIN DERIVATIVE

Disclosed is a compound represented by the formula (I) below and a pharmaceutically acceptable salt thereof. This compound is useful for treatment of obesity, diabetes and the like. [In the formula (I), Ar represents a benzene ring or the like; X1 represents a nitrogen atom, a sulfur atom or the like; R1 represents an aryl group or the like; X2 represents a group represented by the following formula (II): (wherein R4 and R5 respectively represent a lower alkyl group or the like, and m represents a number of 2-4) or the like; one of X and Y represents an oxygen atom and the other represents a sulfanyl group or the like; and X3-X6 respectively represent -CH-, a nitrogen atom or the like.

Sulfonylureas

N-Pyridylsulfonyl-N'-pyrimidinylureas of formula I STR1 wherein R1 is methyl or methoxy and R2 is hydrogen or methyl; and the salts of those compounds with mines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence selective herbicidal and growth-regulating properties.

Deoxydative Thiation of 3-Substituted Pyridine N-Oxides with 4-Methoxytoluene-α-thiol: A Divergent Route to Pyridinethiols

Synthesis of 3-substituted 2-pyridinethiols was achieved by thiation of pyridine N-oxides with 4-methoxytoluene-α-thiol in the presence of diethylcarbamoyl chloride followed by cleavage of the resulting sulfides.The case of substitution was shown to be affected by nucleophilicity of the N-oxide oxygen.Addition of zinc bromide to the reaction, a need for triethylamine, decreased most of the yield for thiation products but the formation of 3-methoxy-2-methoxybenzylthiopyridine was only improved.A plausible mechanism of the substitution, particularly β-thiation to the N-oxide function, is discussed compared with the regiochemistry observed in the reaction with diethoxyphosphoryl chloride instead of diethylcarbamoyl chloride.The debenzylation to pyridinethiol was also found to be dependent on the electron-density in the pyridine ring.

1,3-Dipolar Character of Six-membered Aromatic Rings. Part 55. 3-Hydroxypyridine-2-thiones: Betaines, Cycloadditions, and Other Reactions

1-Methyl-2-methylthio-3-oxidopyridinium, 2-allylthio-1-methyl-3-oxidopyridinium, and 1--2-methylthio-3-oxidopyridinium undergo 1,3-dipolar cycloaddition to electron-deficient alkenes giving azabicyclooctene adducts having 1-alkylthio substituents.Quaternisation and tropone formation are investigated. 3-Hydroxypyridine-2-thione is cycloalkylated between sulphur and oxygen by substituted 1,1-dichloromethanes and certain α-haloacetyl chlorides. 1-(2-Pyridylmethyl)-3-oxidopyridinium gives azabicyclooctene cycloadducts with electron-deficient alkenes.The stereochemistry of all cycloadducts is deduced from the n.m.r.spectra.

NOVEL HETEROCYCLIC SYSTEMS, PART 4: A SIMPLE, CONVENIENT SYNTHESIS OF 3-HYDROXYPYRIDINE-2-THIONE, AND THE PREPARATION OF TWO NOVEL TRICYCLIC BETAINES.

Fusion of P4S10 with 3-hydroxy-2-pyridone gives 3-hydroxypyridine-2-thione as the major product, along with significant amounts of two isomeric tricyclic betaines - the first examples of their class.