2,2'-Dithiosalicylic acid
[CAS# 119-80-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Thiol/thiophenol
• Name: 2,2'-Dithiosalicylic acid
• Synonyms: 2,2'-Dithiodibenzoic acid
• Molecular Formula: C₁₄H₁₀O₄S₂
• Molecular Weight: 306.35
• CAS Registry Number: 119-80-2
• EC Number: 204-352-8
• SMILES: C1=CC=C(C(=C1)C(=O)O)SSC2=CC=CC=C2C(=O)O

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 283-286 °C (Expl.)
• Index of Refraction: 1.736, Calc.^*
• Boiling Point: 493.1±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 252.0±24.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1A	H317
Skin sensitization	Skin Sens.	1B	H317
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2,2'-Dithiosalicylic acid is a chemical compound that consists of two salicylic acid units connected by a sulfur-sulfur (disulfide) bond. It is categorized as a dithioderivative of salicylic acid, a class of compounds that exhibit various interesting chemical and biological properties due to the presence of sulfur atoms in their structure.

The discovery of 2,2'-dithiosalicylic acid is associated with the broader exploration of sulfur-containing organic compounds. Salicylic acid and its derivatives have long been studied for their biological activity and are well-known for their use in the pharmaceutical industry. The addition of sulfur to the structure creates a new class of compounds with potential applications in medicine and materials science. The compound’s chemical structure consists of two phenolic rings, each bearing a carboxyl group, with a disulfide bridge between them, influencing its reactivity and stability.

The primary application of 2,2'-dithiosalicylic acid is in the field of coordination chemistry. The presence of sulfur atoms allows this compound to form stable complexes with various metal ions, including transition metals. These metal complexes are valuable in catalysis, as sulfur-containing ligands often enhance the reactivity and selectivity of the metal center. The ability of 2,2'-dithiosalicylic acid to coordinate with metals makes it useful in the synthesis of organometallic compounds, which can be employed in a variety of chemical processes.

Additionally, 2,2'-dithiosalicylic acid has been studied for its potential role in the design of new materials. Due to the presence of both phenolic and sulfur groups, this compound can be used as a building block for the creation of functionalized polymers, which can exhibit desirable properties such as enhanced stability or conductivity. These materials could have applications in electronics, coatings, and other industrial sectors where advanced materials are required.

The compound is also of interest in medicinal chemistry. Like other salicylic acid derivatives, 2,2'-dithiosalicylic acid may possess anti-inflammatory properties due to its structural similarity to aspirin, a well-known nonsteroidal anti-inflammatory drug (NSAID). The disulfide bridge could potentially affect the compound’s bioactivity, although more research is required to fully understand its therapeutic potential. Compounds with sulfur-containing functional groups are often investigated for their ability to modulate biological pathways and interact with biomolecules such as enzymes or receptors.

Furthermore, 2,2'-dithiosalicylic acid has shown potential in the development of analytical tools. Its ability to bind to various metal ions makes it useful in the detection and quantification of these metals in different chemical and biological samples. By forming complexes with metals, the compound can be used in sensing applications, such as environmental monitoring or biochemical analysis.

Safety considerations for handling 2,2'-dithiosalicylic acid are typical for sulfur-containing organic compounds. It should be handled with care to avoid exposure to the skin and eyes, as sulfur compounds can be irritating. Adequate ventilation and the use of personal protective equipment, including gloves and safety goggles, are recommended during handling.

In conclusion, 2,2'-dithiosalicylic acid is a sulfur-containing derivative of salicylic acid with applications in coordination chemistry, material science, and potentially in medicinal chemistry. Its unique structure, featuring a disulfide bridge between two phenolic groups, provides it with valuable reactivity and stability, making it a useful building block for the development of new materials and catalytic systems. Further studies may expand its applications, particularly in drug design and metal ion detection.

References

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2023. A review of self-healable natural rubber based on reversible bonds: fundamental, design principle and performance. Journal of Materials Science, 58.
DOI: 10.1007/s10853-022-08062-2