1,2,4-Thiadiazole

Base Information

• Chemical Name: 1,2,4-Thiadiazole
• CAS No.: 288-92-6
• Molecular Formula: C₂H₂N₂S
• Molecular Weight: 86.1173
• DSSTox Substance ID: DTXSID50182986
• Nikkaji Number: J5.457G
• Wikidata: Q27120311
• Metabolomics Workbench ID: 56316
• Mol file: 288-92-6.mol

Synonyms:1,2,4-Thiadiazole;288-92-6;CHEBI:39471;DTXSID50182986;Q27120311

Chemical Property of 1,2,4-Thiadiazole

Chemical Property:

• Vapor Pressure: 13.5mmHg at 25°C
• Melting Point: -33°C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 127.6°Cat760mmHg
• Flash Point: 39.2°C
• PSA: 54.02000
• Density: 1.317g/cm³
• LogP: 0.53810
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 85.99386925
• Heavy Atom Count: 5
• Complexity: 30.8

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NSC=N1
• General Description: 1,2,4-Thiadiazole, also known as 1-Thia-2,4-diazacyclopentadiene or 2,4-Diazathiophene, is a heterocyclic compound with notable biological and therapeutic applications. An efficient and eco-friendly synthesis method for its derivatives has been developed, involving ultrasound-initiated dimerization of primary thioamides with chloranil in water, yielding high product efficiency without metal catalysts or harsh conditions. This approach represents a rapid and sustainable alternative to conventional synthetic routes.

Technology Process of 1,2,4-Thiadiazole

There total 2 articles about 1,2,4-Thiadiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-bromo-1,2,4-thiadiazole (43201-13-4) → 1,2,4-thiadiazole (288-92-6)

Guidance literature:

With methanol; nickel; triethylamine; Hydrogenation;

Reference yield:

→ 1,2,4-thiadiazole (288-92-6)

Guidance literature:

upstream raw materials:

5-bromo-1,2,4-thiadiazole

Refernces

An Expeditious Ultrasound-Initiated Green Synthesis of 1,2,4-Thiadiazoles in Water

10.1007/s10593-020-02632-5

The research focuses on the development of an efficient, environmentally friendly method for synthesizing 1,2,4-thiadiazole derivatives, which are important heterocyclic compounds with a range of biological activities and therapeutic applications. The study introduces a metal- and catalyst-free protocol that utilizes the combination of water and ultrasound technique to achieve the dimerization of primary thioamide derivatives with chloranil, leading to the formation of 1,2,4-thiadiazoles. The optimized reaction conditions resulted in excellent yields within a short reaction time, demonstrating a significant improvement over traditional methods. The chemicals used in the process include primary thioamide derivatives, chloranil as the oxidizing agent, and water as the solvent, with other solvents like MeCN, THF, EtOH, 1,4-dioxane, CHCl3, CH2Cl2, DCE, and DMSO also tested for comparison. The study concludes that the ultrasound-initiated green synthesis in water is a valuable addition to existing methods for synthesizing substituted 3,5-diaryl-1,2,4-thiadiazoles, offering a rapid and efficient approach.