O-304
[CAS# 1261289-04-6]

Identification

• Classification: Biochemical >> Inhibitor >> PI3K/Akt/mTOR inhibitor (PI3K/Akt/mTOR) >> AMPK inhibitor
• Name: O-304
• Synonyms: 4-chloro-N-(2-(4-chlorobenzyl)-3-oxo-2,3-dihydro-1,2,4-thiadiazol-5-yl)benzamide
• Molecular Formula: C₁₆H₁₁Cl₂N₃O₂S
• Molecular Weight: 380.25
• CAS Registry Number: 1261289-04-6
• SMILES: C1=CC(=CC=C1CN2C(=O)N=C(S2)NC(=O)C3=CC=C(C=C3)Cl)Cl

Properties

• Density: 1.5±0.1 g/cm³ Calc.^*
• Index of refraction: 1.698 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

2-Chlorothiophenol is an organosulfur compound with a benzene ring bearing a thiol (–SH) at position 1 and a chlorine atom at position 2, giving it the molecular formula C₆H₅ClS. It is a reactive, pale yellow liquid or solid with a strong, unpleasant odor and finds utility as a synthetic intermediate.

The compound does not occur naturally and is synthesized via controlled chlorination of thiophenol or through nucleophilic aromatic substitution on chlorinated aromatics. Its bifunctionality—comprising both thiol and chloro substituents—makes it a versatile building block in further organic transformations. The thiol group allows facile oxidation, alkylation, and coupling reactions, while the chlorine atom enables selective aromatic nucleophilic substitution by nucleophiles like amines or thiols.

In pharmaceutical and agrochemical synthesis, 2‑chlorothiophenol derivatives have been explored for bioactivity such as antimicrobial, enzyme inhibitory, and antifungal properties. The thiol group can form coordination bonds with metal ions or cysteine residues in proteins, leading to biological modulation, while the chloro substituent contributes lipophilicity and electronic tuning.

In materials and surface chemistry, aryl thiols like this compound are valuable for functionalizing gold surfaces to create self‑assembled monolayers (SAMs). These SAMs are used in sensor technologies, nanotechnology, and studies of interfacial phenomena, as sulfur establishes strong bonds with gold surfaces, enabling controlled molecular assemblies.

Physicochemical characterization reveals that the compound is flammable, moisture-sensitive, and reactive, particularly with oxidizing agents. Handling requires strict safety measures due to the potent odor and potential for toxicity. It acts as an irritant and must be manipulated in fume hoods with appropriate protective equipment including gloves and goggles. Storage in sealed, dry conditions is necessary to avoid hydrolysis or oxidation.

Analytical techniques confirm its structure and purity. In nuclear magnetic resonance, the aromatic ring and thiol proton show characteristic chemical shifts. Infrared spectroscopy displays a strong absorption band near 2550–2600 cm^–1 corresponding to the S–H stretch, along with C–Cl and aromatic skeletal vibrations. Mass spectrometry supports the molecular weight and fragmentation profile.

Environmental considerations include its volatility and potential to form odor issues if released. Due to its reactivity, it is unlikely to bioaccumulate, but it must be contained to prevent exposure. Industrial handling facilities incorporate ventilation and containment to manage emissions.

In research settings, 2‑chlorothiophenol serves as a key intermediate in the synthesis of more complex molecules. Medicinal chemists use the scaffold to build libraries of heterocycles and potential therapeutics, exploiting the reactivity at both the thiol and aryl chloride positions. In materials science, the compound has been used to modify nanoparticles, gold surfaces, and polymers to introduce thiol functionalities for crosslinking or binding purposes.

The discovery and development of 2‑chlorothiophenol reflect the broader trend in organic chemistry towards multifunctional intermediates that can undergo diverse reactions. Its synthesis showcases classical chlorination and thiol chemistry, while its applications span from small‑molecule bioactive compound construction to advanced materials.

In summary, 2‑chlorothiophenol is a synthetic aromatic thiol notable for its dual functional reactivity, which underpins its role as a versatile chemical intermediate. Its applications in pharmaceutical synthesis, agrochemical design, and materials functionalization have been enabled by its unique chemical properties, though they demand careful handling owing to safety and environmental considerations.