2-Mercaptonicotinic acid
[CAS# 38521-46-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: 2-Mercaptonicotinic acid
• Synonyms: 2-Mercaptopyridine-3-carboxylic acid
• Molecular Formula: C₆H₅NO₂S
• Molecular Weight: 155.17
• CAS Registry Number: 38521-46-9
• EC Number: 629-602-7
• SMILES: C1=CNC(=S)C(=C1)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 263-265 °C (Expl.)
• Index of Refraction: 1.653, Calc.^*
• Boiling Point: 337.6±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 158.0±23.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: S26;S37/39

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Mercaptonicotinic acid, also known as 2-thionicotinic acid, is a sulfur-containing derivative of nicotinic acid. This chemical compound contains a thiol group (-SH) at the 2-position of the pyridine ring, which is substituted by a carboxylic acid group at the 3-position. The molecular formula of 2-mercaptonicotinic acid is C6H5NO2S, and it is primarily used in various chemical synthesis processes and in the development of coordination compounds.

The discovery of 2-mercaptonicotinic acid can be traced to the study of modified nicotinic acid derivatives, which have been extensively investigated for their diverse chemical and biological properties. The addition of a mercapto group to the pyridine ring increases the reactivity of the molecule, providing a functional group that can form coordination complexes with metal ions and participate in other chemical reactions.

2-Mercaptonicotinic acid has found applications in several fields, including materials science and catalysis. It has been used in the preparation of metal-ligand complexes. The thiol group in 2-mercaptonicotinic acid forms stable coordination bonds with various transition metals, making it useful in the synthesis of metal-organic frameworks (MOFs) and other metal-containing complexes that exhibit interesting electronic and catalytic properties.

In addition, this compound has been explored for its role in organic synthesis as a potential intermediate for the synthesis of other biologically active molecules. Its thiol group allows it to serve as a versatile building block in the design of new drugs, particularly in the development of agents targeting specific enzymes or biological pathways. The presence of both the pyridine ring and the thiol group enhances the potential for 2-mercaptonicotinic acid to participate in various chemical transformations.

The compound has also been researched for its potential biological activities. Some studies have shown that 2-mercaptonicotinic acid and its derivatives can exhibit antioxidant and anti-inflammatory properties, suggesting potential therapeutic applications. Additionally, the compound has been evaluated for its potential to act as a ligand in enzyme inhibition, potentially offering avenues for the development of novel therapeutic agents.

In summary, 2-mercaptonicotinic acid is a sulfur-containing derivative of nicotinic acid that has been studied for its utility in metal-ligand chemistry, organic synthesis, and potential biological applications. Its ability to form stable complexes with metal ions makes it a valuable tool in materials science and catalysis, while its reactivity offers promise in the design of new chemical entities for medicinal purposes.

References

2023. A novel electrochemical sensor based on a cerium oxide/graphene nanocomposite for the detection of 2-mercaptonicotinic acid. Analytical Methods, 15(40).
DOI: 10.1039/d3ay01337e

2022. 2-Mercaptonicotinic acid as a new ligand for the spectrophotometric determination of Fe(III) in the aqueous medium. Monatshefte für Chemie - Chemical Monthly, 153(10).
DOI: 10.1007/s00706-022-02981-5

2015. Synthesis and characterization of a novel 2-mercaptonicotinic acid (MNA) substituted porphyrin. Journal of Porphyrins and Phthalocyanines, 19(7).
DOI: 10.1142/S1088424615500535