Chemical Structure and Physical Properties

2-Amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole (CAS 13078-30-3) belongs to the 1,3,4-thiadiazole family of five-membered heterocycles containing one sulfur and two adjacent nitrogen atoms. The compound carries a primary amino group at the 2-position and a para-methoxyphenyl (anisyl) group at the 5-position, giving the molecule a molecular formula of C₉H₉N₃OS and a molecular weight of approximately 207.25 g/mol.

The 1,3,4-thiadiazole ring is aromatic and planar, conferring considerable thermal and chemical stability. The amino substituent acts as a hydrogen-bond donor and nucleophilic handle, while the methoxy group on the phenyl ring donates electron density through resonance, modulating the electronic profile of the scaffold. These combined electronic features influence the compound's solubility, melting point, and reactivity in condensation and cycloaddition chemistry.

The compound typically appears as a pale yellow to off-white crystalline solid. Exact melting point and spectral data (¹H NMR, IR, MS) should be confirmed against the certificate of analysis supplied with each batch from Aladdin Scientific.

Synthesis and Reactivity as a Building Block

The 1,3,4-thiadiazole ring system is commonly constructed by the cyclodehydration of diacylhydrazines with phosphorus pentasulfide (P₄S₁₀) or Lawesson's reagent, or by the reaction of thiosemicarbazide derivatives with carboxylic acids under acidic conditions. The 4-methoxybenzoic acid (anisic acid) route is a straightforward approach to install the aryl substituent at C-5 of the thiadiazole ring.

The primary amino group at C-2 provides multiple avenues for downstream functionalization, including:

• Acylation and sulfonylation — reaction with acid chlorides or sulfonyl chlorides to yield amide or sulfonamide derivatives.
• Condensation with aldehydes and ketones — formation of Schiff bases (imines) useful in coordination chemistry and as further synthetic intermediates.
• Coupling reactions — the amino group can participate in diazotization followed by cross-coupling, or serve as a directing group in transition-metal-catalyzed reactions.
• Heterocycle annulation — the amino group adjacent to the thiadiazole ring allows for the construction of fused polyheterocyclic systems of pharmacological interest.

These reactions make 2-Amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole a productive scaffold for generating compound libraries in drug discovery programs.

Research Applications

Compounds incorporating the 1,3,4-thiadiazole scaffold have been extensively investigated in medicinal chemistry owing to the scaffold's documented association with diverse biological activities. Research areas where 2-Amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole and its derivatives have been explored include:

Antimicrobial research: 2-Aminothiadiazole derivatives have been studied for antibacterial and antifungal properties. The amino group and the electron-rich methoxyphenyl moiety are considered to contribute to interactions with microbial targets, although specific structure–activity relationships depend on the final derivative structure.

Anticancer lead generation: The thiadiazole nucleus has appeared in reported antiproliferative agents. Derivatives of 2-aminothiadiazoles have been examined as potential inhibitors of kinases and other enzyme targets relevant to oncology.

Coordination and materials chemistry: The amino and ring nitrogen atoms provide multiple coordination sites, making this compound a ligand precursor for metal complexes used in catalysis and sensor research.

Agrochemical research: Thiadiazole-containing structures appear in herbicidal and fungicidal compound classes, and aminothiadiazole building blocks serve as starting materials in the design of novel agrochemicals.

Note: Specific activity data for this exact compound should be sourced from peer-reviewed literature. Aladdin Scientific supplies this compound for research purposes only.

Handling, Storage, and Safety Considerations

As with all fine chemical reagents, appropriate laboratory safety practices should be followed when working with 2-Amino-5-(4-methoxyphenyl)-1,3,4-thiadiazole. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use.

Storage: Store in a tightly sealed container in a cool, dry, well-ventilated area away from incompatible materials such as strong oxidizers and strong acids. Specific storage temperature recommendations are detailed in the product SDS and on the product label.

Personal Protective Equipment (PPE): Standard laboratory PPE including chemical-resistant gloves, laboratory coat, and safety eyewear is recommended when handling this compound. Avoid inhalation of dust.

Disposal: Dispose of waste in accordance with local, regional, and national regulations governing chemical waste. Do not pour down the drain.

Researchers are advised to verify GHS hazard classification and precautionary statements from the current SDS, as classifications may be updated following new toxicological data.