Shaanxi BLOOM Tech Co., Ltd. is one of the most experienced manufacturers and suppliers of 4-mercaptopyridine cas 4556-23-4 in China. Welcome to wholesale bulk high quality 4-mercaptopyridine cas 4556-23-4 for sale here from our factory. Good service and reasonable price are available.
4-Mercaptopyridine, also known as 4-Pyridinethiol. Pure product is a white to light yellow solid. It can be soluble in water, but its solubility is not high. At room temperature, only about 6 grams of this compound can be dissolved in 100 grams of water. However, as the temperature increases, its solubility also increases accordingly. Under heating, more 4Mercaptopyridine can dissolve in water. The molecular structure contains one sulfur atom and one nitrogen atom. The sulfur atom is connected to two hydrogen atoms and one nitrogen atom, forming a five membered ring. This five membered ring is connected to another nitrogen atom, forming the final pyridine structure. It is a compound containing thiol groups and therefore has some special chemical properties. It is prone to complex reactions with heavy metal ions, generating stable complexes. It can be used for the separation and enrichment of heavy metal ions, as well as labeling and detection in protein electrophoresis and immunoassay.
|
|
 |
|
Chemical Formula |
C5H5NS |
|
Exact Mass |
111.01 |
|
Molecular Weight |
111.16 |
|
m/z |
111.01 (100.0%), 112.02 (5.4%), 113.01 (4.5%) |
|
Elemental Analysis |
C, 54.02; H, 4.53; N, 12.60; S, 28.84 |
4-Mercaptopyridine is a sulfur-containing organic compound that has wide applications in many fields due to its unique molecular structure and chemical properties.
Electrochemistry
As an electroactive substance to construct high-performance electrochemical devices, such as batteries, supercapacitors, and sensors. Due to its pyridine ring and thiol group in its molecular structure, it can undergo redox reactions and has electrochemical activity. Therefore, electrochemical devices based on 4 Mercaptopyridine can be charged and discharged at low voltage, and have excellent electrochemical performance and cycling stability.
Materials Science
To synthesize organic functional materials and nanostructured materials. Due to the presence of a pyridine ring and a thiol group in its molecular structure, it can undergo chemical reactions with other molecules or groups to generate new organic or nanostructured materials. For example, it can react with polymers to generate polymer materials with specific functions and properties. In addition, it can also be used to modify the surface of nanoparticles to alter their physical and chemical properties.
Biology
To study the structure and function of biomolecules, as well as explore the interactions between biomolecules. Due to its ability to undergo complex reactions with heavy metal ions, it can be used to study the roles and effects of metal ions in biomolecules. In addition, it can also be used for labeling and detecting biomolecules such as proteins, nucleic acids, and sugars. For example, it can bind to antibodies for labeling and detection in immunoassay.
Drug development
Serve as a ligand for designing novel drugs. Due to its pyridine ring and thiol group in its molecular structure, it can strongly interact with biomolecules, thereby affecting their function and activity. Therefore, ligands based on 4 Mercaptopyridine can be used to develop anticancer drugs, antibacterial drugs, and other therapeutic drugs. In addition, it can also be used to regulate the metabolic processes of biomolecules for the treatment of various diseases.
Other fields
In addition to the above-mentioned fields, it can also be used for applications in other fields. For example, it can be used as a catalyst for the synthesis of polymer materials and organic compounds. In addition, it can also be used to study physical and chemical properties and quantum chemical calculations.
in Coordination Chemistry
4-Mercaptopyridine (4-MPy) is a versatile ligand in coordination chemistry due to its ability to coordinate with both transition metals and rare earth metals, forming complexes with diverse structures and properties. These metal complexes have garnered significant interest for their potential applications in catalysis, magnetic materials, and luminescent materials. Below is a detailed exploration of its coordination behavior, structural diversity, and applications.
The reactivity of 4-MPy stems from its two potential donor atoms: the nitrogen of the pyridine ring and the sulfur of the thiol group. Depending on the metal ion and reaction conditions, 4-MPy can exhibit multiple coordination modes:
- Monodentate Coordination: The ligand may bind through either the nitrogen or sulfur atom alone, though nitrogen coordination is often favored due to its stronger basicity.
- Bidentate Coordination: Both the nitrogen and sulfur atoms can participate in bonding, forming chelating rings that enhance the stability of the complex.
- Bridging Coordination: In polymeric or extended structures, 4-MPy can act as a bridge between two or more metal centers, contributing to the formation of coordination polymers or metal-organic frameworks (MOFs).
This adaptability allows 4-MPy to stabilize a wide range of metal complexes with varying geometries, from mononuclear to polynuclear species.
Numerous metal complexes of 4-MPy have been synthesized and structurally characterized, providing insights into their coordination environments and properties.
- Silver(I) Complexes: The synthesis of silver(I) 4-MPy complexes often involves the reaction of AgNO₃ with 4-MPy in solution. These complexes typically exhibit linear or trigonal planar geometries around the silver center, with the ligand coordinating through nitrogen or sulfur. For instance, [Ag(4-MPy)₂]NO₃ has been reported, where 4-MPy acts as a monodentate N-donor ligand.
- Cadmium(II) Complexes: Cadmium(II) forms more complex structures with 4-MPy due to its higher coordination number. Polymeric cadmium(II) 4-MPy complexes have been synthesized, featuring the ligand in a bridging mode, linking Cd²⁺ ions into one-dimensional chains or two-dimensional layers. The crystal structures reveal that the sulfur atom often participates in bonding, in addition to nitrogen, leading to bidentate or bridging coordination.
Spectroscopic techniques, such as NMR, IR, and UV-Vis spectroscopy, are employed to probe the electronic environment of the complexes, while X-ray crystallography provides definitive structural information.
4-MPy-based metal complexes have shown promise as catalysts in various organic transformations. The ligand's ability to modulate the electronic properties of the metal center enhances its catalytic activity and selectivity.
- Oxidation Reactions: Some 4-MPy metal complexes have been explored as catalysts for the oxidation of alcohols to aldehydes or ketones. The sulfur atom may play a role in stabilizing reactive intermediates or facilitating oxygen transfer.
- C-C Coupling Reactions: Transition metal complexes of 4-MPy have been investigated for their potential in cross-coupling reactions, such as Suzuki or Heck reactions, due to their ability to activate aryl halides or olefins.
The tunability of the coordination environment allows for the optimization of catalytic performance by varying the metal ion or ligand substituents.
Certain 4-MPy metal complexes exhibit interesting magnetic properties, making them candidates for molecular magnets or spin crossover materials.
- Polynuclear Complexes: Complexes containing multiple metal ions bridged by 4-MPy ligands can display magnetic coupling between the metal centers, leading to phenomena such as ferromagnetism or antiferromagnetism.
- Spin Crossover Behavior: Some iron(II) 4-MPy complexes have been reported to undergo spin transitions, where the metal ion switches between high-spin and low-spin states in response to temperature or light, with potential applications in data storage or sensing.
The design of such materials relies on controlling the ligand field strength and intermolecular interactions within the complex.
4-MPy metal complexes also show potential in luminescent applications, such as sensors, OLEDs, or bioimaging agents.
- Lanthanide Complexes: Rare earth metal complexes of 4-MPy, particularly those containing europium(III) or terbium(III), can exhibit intense luminescence due to the antenna effect, where the ligand absorbs light and transfers the energy to the metal ion, which then emits at a characteristic wavelength.
- Transition Metal Complexes: Some copper(I) or zinc(II) 4-MPy complexes have been found to emit in the visible region, with potential applications in lighting or display technologies.
The photophysical properties of these complexes can be fine-tuned by modifying the ligand structure or the metal environment
Core Synthesis Process and Mechanism
The industrial production of 4-mercaptopyridine mainly follows the mainstream route of the substitution reaction between 4-chloropyridine and thioamidocarboxylate. This reaction is carried out in polar solvents (such as DMF) at 80-120℃ for 6-12 hours. The thioanionic sulfur of the thioamidocarboxylate attacks the 4-carbon of 4-chloropyridine, and the chloride ion acts as the leaving group to be replaced, generating the target product. This route has readily available raw materials (4-chloropyridine is a common chemical product), mild reaction conditions, and the reaction rate can be improved by optimizing the solvent ratio (such as mixing DMF with toluene). The post-treatment process adopts the water precipitation crystallization method. The crude product is re-crystallized with ethanol, and the purity can reach over 98%, making it suitable for large-scale production.
Among the alternative routes, the addition-elimination reaction of 4-bromopyridine with hydrogen sulfide has attracted attention due to the lower cost of the raw materials (the price of 4-bromopyridine is approximately 70% of that of 4-chloropyridine). This reaction is carried out in a high-pressure reactor using ethanol as the solvent, with H₂S gas being introduced, and the reaction is conducted at 100-150°C for 8-16 hours. The intermediate 4-mercaptopyridine hydrogen sulfate is precipitated after being neutralized by an alkaline solution, and the product is obtained after drying. However, this route requires high-pressure equipment, and the toxicity of H₂S (occupational exposure limit of 10 ppm) imposes extremely high requirements for safety control. Currently, only a few enterprises adopt this route.
Process Optimization and Technological Innovation
Continuous Flow Production Technology
Zhejiang Xinhecheng Company developed a UV light (365 nm) driven microchannel reactor, which shortened the traditional batch synthesis reaction time from 24 hours to 45 minutes, and increased the yield from 68% to 92%. The high specific surface area of the microchannel (>>5000 m²/m³) enhanced the mass transfer efficiency, while the UV light activated the reactant molecules, reducing the activation energy.
Green Chemical Process
The team from Jiangnan University used the modified transaminase (EcoAT-7) to achieve direct chloromethylation of the pyridine ring, avoiding the use of the highly toxic chloromethyl ether. The enzyme catalytic system reacted at 37°C and pH 7.5 for 4 hours, with a product selectivity of 95%, and won the "Green Chemistry Award" in 2024. This route complies with the EU REACH regulations on high concern substances (SVHC), providing a compliance solution for export enterprises.
Purification Technology Upgrade
Supercritical CO₂ extraction technology replaces traditional chromatographic purification equipment, enabling the domestic production of pharmaceutical-grade products. This technology utilizes the solubility characteristics of CO₂ at the critical point (31.1°C, 7.38 MPa) for selective extraction of impurities, with product purity exceeding 99.5%, and no risk of solvent residue.
Quality Control and Safety Standards
Key Quality Indicators
Pharmaceutical-grade 4-mercaptopyridine requires control of the mercaptan content (≥98.0%), heavy metal residues (<10 ppm), and microbial limits (<100 CFU/g). The HPLC method (C18 column, methanol-water mobile phase) is a commonly used detection method, with the detection wavelength at 254 nm.
Safety Operating Points
The reaction system needs to be protected by nitrogen gas to prevent mercaptan oxidation.
The H₂S tail gas is absorbed by alkaline solution and converted into sodium sulfide, with a recovery rate of up to 90%.
The drying process temperature needs to be below 60°C to avoid product decomposition.
Market Trends and Industry Chain Analysis
Demand Growth Driver:
As the key intermediate for EGFR inhibitor Osimertinib, the global demand for 4-mercaptopyridine exceeded 120 tons in 2024, with a year-on-year increase of 35%. The "New Pollutant Governance Action" in China restricted the use of chloromethyl ether, forcing enterprises to adopt green processes such as enzyme catalysis, and it is expected that the domestic production rate of pharmaceutical-grade products will increase to 60% from 2025 to 2027.
Raw Material Price Fluctuations:
The price of pyridine is affected by the demand for nicotine, with a 22% year-on-year increase in Q4 2024. The bio-based pyridine synthesis route (such as conversion of corn straw) has become a research hotspot. This route uses glucose as the raw material and is produced through microbial fermentation, with a cost 15% lower than the traditional petroleum route.
Geopolitical Impact:
The US "Biomanufacturing Act" restricts the export of 4-mercaptopyridine to US pharmaceutical enterprises, prompting domestic enterprises to establish overseas filling bases (such as Mexico). At the same time, Zehetinger's "Molecule Builder" AI platform can design alternative structures, forcing enterprises to accelerate the patent layout for downstream applications.
Future Technology Roadmap
2025-2027:
Achieve a fully green synthetic path using 100% bio-based raw materials (such as glucose fermentation to pyridine).
Collaborate with DeepMind to develop a performance prediction model for 4-mercaptopyridine derivatives, shortening the new drug development cycle to 18 months.
2028-2030:
Promote continuous flow-enzyme catalysis coupling technology, with single-line production capacity increasing to 500 tons per year.
Develop 4-mercaptopyridine-based MOFs materials to expand their application in gas storage and separation.
Hot Tags: 4-mercaptopyridine cas 4556-23-4, suppliers, manufacturers, factory, wholesale, buy, price, bulk, for sale, 2 5 Dihydroxybenzaldehyde, DIMETHYLPHOSPHINE OXIDE, 3 Nitrobenzaldehyde 99 , Methylamine hydrochloride powder, gs 441524 remdesivir, N N N Trimethylethylenediamine