2H-1,2,4-benzothiadiazine

Base Information

• Chemical Name: 2H-1,2,4-benzothiadiazine
• CAS No.: 255-18-5
• Molecular Formula: C7H6N2S
• Molecular Weight: 150.20100
• UNII: X7JFP65SVP
• DSSTox Substance ID: DTXSID50332969
• Nikkaji Number: J1.910.888K
• Wikipedia: Benzothiadiazine
• Mol file: 255-18-5.mol

Synonyms:2H-1,2,4-benzothiadiazine;X7JFP65SVP;255-18-5;4h-1,2,4-benzothiadiazine;1,2,4-benzothiadiazine;UNII-X7JFP65SVP;2H-Benzo[e]1,2,4-thiadiazine;SCHEMBL205451;DTXSID50332969;4h-benzo[e][1,2,4]thiadiazine

Chemical Property of 2H-1,2,4-benzothiadiazine

Chemical Property:

• Boiling Point: 303.3±25.0 °C(Predicted)
• PKA: 2.86±0.20(Predicted)
• PSA: 49.69000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 1.72110
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 150.02516937
• Heavy Atom Count: 10
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=CNS2
• General Description: 2H-1,2,4-Benzothiadiazine is a heterocyclic compound featuring a benzene ring fused to a 1,2,4-thiadiazine ring, which contains nitrogen and sulfur atoms. It serves as a key scaffold in medicinal chemistry, particularly for the synthesis of biologically active derivatives such as 1,2,4-benzothiadiazin-3(4H)-ones. These compounds are of pharmaceutical interest due to their potential applications as antiviral agents and other therapeutic uses. The structure allows for versatile functionalization, enabling the introduction of diverse substituents to modulate biological activity. Efficient synthetic methods, such as copper-catalyzed N–H/S–H functionalization, have been developed to access these derivatives under mild and environmentally benign conditions.

Refernces

Copper-catalyzed N[sbnd]H/S[sbnd]H functionalization: A strategy for the synthesis of benzothiadiazine derivatives

10.1016/j.tet.2017.02.063

The study titled "Copper-catalyzed N–H/S–H functionalization: A strategy for the synthesis of benzothiadiazine derivatives" by ?engül Dilem Do?an presents a novel copper-catalyzed method for synthesizing 1,2,4-benzothiadiazin-3(4H)-ones. The research highlights the direct construction of N–S bonds using readily available N-(2-mercaptophenyl)-N'-(phenyl)-ureas as starting materials. The copper catalyst, specifically copper(I) iodide, plays a crucial role in facilitating the N-H/S-H activation, leading to the formation of the desired benzothiadiazine derivatives under mild conditions. The reaction is performed in N,N-dimethylformamide (DMF) under molecular oxygen, showcasing high efficiency and step economy. The study demonstrates the versatility of the method by synthesizing a variety of benzothiadiazine derivatives with different substituents, including aromatic and aliphatic groups, without significant effects on the reaction outcome. The findings offer an efficient and environmentally benign approach to synthesizing biologically important benzothiadiazine compounds, which have applications in pharmaceuticals and as antiviral agents.