1,3,4-Thiadiazole

Base Information

• Chemical Name: 1,3,4-Thiadiazole
• CAS No.: 289-06-5
• Molecular Formula: C2H2 N2 S
• Molecular Weight: 86.11568
• European Community (EC) Number: 869-482-5
• UNII: 14IAC3GH7G
• DSSTox Substance ID: DTXSID00183089
• Nikkaji Number: J622.733C
• Wikidata: Q27120327
• Metabolomics Workbench ID: 56317
• Mol file: 289-06-5.mol

Synonyms:1,3,4-thiadiazole

Chemical Property of 1,3,4-Thiadiazole

Chemical Property:

• Vapor Pressure: 13.5mmHg at 25°C
• Melting Point: 42.5°C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 127.6°Cat760mmHg
• PKA: -0.33±0.10(Predicted)
• Flash Point: 39.2°C
• PSA: 54.02000
• Density: 1.317g/cm³
• LogP: 0.53810
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 85.99386925
• Heavy Atom Count: 5
• Complexity: 26.8

Purity/Quality:

99% ^*data from raw suppliers

1,3,4-THIADIAZOLE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NN=CS1
• General Description: Thiadiazole is a heterocyclic compound containing sulfur and nitrogen atoms in its ring structure, with notable derivatives such as 1,3,4-thiadiazole and 1,2,4-thiadiazole. It serves as a key scaffold in medicinal chemistry, particularly in the synthesis of antiviral agents, as demonstrated by its incorporation into triazolopyrimidinediones with activity against hepatitis B virus. Additionally, thiadiazole derivatives are utilized in macrocyclic chemistry, forming thia crown ethers with potential applications in coordination and supramolecular chemistry. Its structural versatility allows for diverse functionalization, making it valuable in drug design and materials science.

Technology Process of 1,3,4-Thiadiazole

There total 14 articles about 1,3,4-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: 70.0%

dibutylamine (111-92-2) + 2,5-Dimercapto-1,3,4-thiadiazole (1072-71-5,132120-63-9) → 1,3,4-thiadiazole (289-06-5)

Guidance literature:

With dihydrogen peroxide; In water;

Reference yield: 70.0%

2,5-Dimercapto-1,3,4-thiadiazole (1072-71-5,132120-63-9) → 1,3,4-thiadiazole (289-06-5)

Guidance literature:

With dihydrogen peroxide; In water;

Reference yield: 44.0%

diformylhydrazine (628-36-4) → 1,3,4-thiadiazole (289-06-5)

Guidance literature:

With Lawessons reagent; In xylene; at 140 ℃; for 1h;

upstream raw materials:

2-bromo-1,3,4-thiadiazole

potassium dithioformate

2-mercapto-1,3,4-thiadiazole

formaldehyd

Downstream raw materials:

3-Benzyl-1,3,4-thiadiazolium-chlorid

3-(p-Bromphenacyl)-1,3,4-thiadiazolium-bromid

Oxindole

Refernces

Synthesis of 1,2,4-triazol-3-ylmethyl-, 1,3,4-oxa-, and -thiadiazol-2-ylmethyl-1H-[1,2,3]-triazolo[4,5-d]pyrimidinediones

10.1007/s00706-007-0649-7

The research focuses on the synthesis of novel heterocyclic compounds, specifically 1,2,4-triazol-3-ylmethyl-, 1,3,4-oxa-, and -thiadiazol-2-ylmethyl-1H-[1,2,3]-triazolo[4,5-d]pyrimidinediones, which are potentially useful as antiviral agents against hepatitis B virus. The experiments involved the synthesis of 1-carbethoxymethyl-4,6-dimethyl-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione and its subsequent reactions with hydrazine hydrate to yield a hydrazide. This hydrazide was further reacted with phenylisothiocyanate or carbon disulfide and KOH to produce thiosemicarbazide and oxadiazole derivatives. Various alkylation and cyclization reactions were performed to form the desired heterocyclic structures, including the formation of 1,3,4-thiadiazole, 5-mercapto-1,2,4-triazole, and 1,3,4-oxadiazole rings. The synthesized compounds were analyzed using techniques such as infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS) to confirm their structures. The reactants used in these syntheses included phenylisothiocyanate, carbon disulfide, alcoholic potassium hydroxide, dimethyl sulfate, ethyl chloroacetate, and various monosaccharide aldoses. The synthesized compounds were tested for their antiviral activity, with some showing moderate activities against hepatitis B virus.

Synthesis and Structural Aspects of (2,5)-1,3,4-Thiadiazolo and (3,5)-1,3,4-Thiadiazolino Thia Crown Ethers

10.1021/jo00391a045

The research focuses on the synthesis and structural aspects of (2,5)-1,3,4-thiadiazolo and (3,5)-1,3,4-thiadiazolino thia crown ethers. The study describes a general route to synthesize (2,5)-1,3,4-thiadiazolo thia crown ethers by reacting 2,5-dimercapto-1,3,4-thiadiazole dipotassium salt with oligoethylene glycol dihalides in ethanol under high-dilution conditions. The structures of the macrocycles were confirmed by 1H and 13C NMR spectroscopy, and one of the macrocycles was further characterized by single-crystal X-ray diffraction. The research also involves the synthesis of related open-chain models for further studies on the complexing behavior and chemical reactivity of 1,3,4-thiadiazole acyclic versus cyclic structures.