1,2,3-Benzothiadiazole

Base Information

• Chemical Name: 1,2,3-Benzothiadiazole
• CAS No.: 273-77-8
• Molecular Formula: C6H4N2S
• Molecular Weight: 136.177
• Hs Code.: 2934999090
• European Community (EC) Number: 205-989-4
• NSC Number: 111919
• UNII: R3PA3EL3RP
• DSSTox Substance ID: DTXSID00181747
• Nikkaji Number: J101.214B
• Wikipedia: 1,2,3-Benzothiadiazole
• Wikidata: Q83052364
• Mol file: 273-77-8.mol

Synonyms:1,2,3-benzothiadiazole;2,1,3-benzothiadiazole;benzo-1,2,3-thiadiazole;benzothiadiazole

Chemical Property of 1,2,3-Benzothiadiazole

Chemical Property:

• Vapor Pressure: 0.167mmHg at 25°C
• Melting Point: 295 °C (decomp)
• Refractive Index: 1.705
• Boiling Point: 220.5 °C at 760 mmHg
• PKA: -2.83±0.50(Predicted)
• Flash Point: 90.8 °C
• PSA: 54.02000
• Density: 1.368g/cm³
• LogP: 1.69130
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 136.00951931
• Heavy Atom Count: 9
• Complexity: 107

Purity/Quality:

97% ^*data from raw suppliers

1,2,3-Benzothiadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=NS2

Technology Process of 1,2,3-Benzothiadiazole

There total 12 articles about 1,2,3-Benzothiadiazole 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: 96.0%

2-amino-benzenethiol (137-07-5) → benzo[1,2,3]thiadiazole (273-77-8)

Guidance literature:

2-amino-benzenethiol; With toluene-4-sulfonic acid; In water; at 20 ℃; for 0.5h;

With potassium iodide; In water; at 20 ℃; for 0.25h;

DOI:10.1055/s-0030-1260046

Reference yield: 90.0%

4,7-Dibrom-4,5,6,7-tetrahydro-1,2,3-benzothiadiazol (82172-31-4) → benzo[1,2,3]thiadiazole (273-77-8)

Guidance literature:

With triethylamine; Heating;

Reference yield: 62.0%

N-(2-iodophenyldiazenyl)piperazinyl-N-methylpolystyrene, molecular mass: C86H87N4I, loading: 0.49 mmol/g (59 percent) → benzo[1,2,3]thiadiazole (273-77-8)

Guidance literature:

N-(2-iodophenyldiazenyl)piperazinyl-N\-methylpolystyrene, molecular mass: C₈₆H₈₇N₄I, loading: 0.49 mmol/g (59 percent); With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at -40 - 20 ℃; for 1h;

With sulfur; In tetrahydrofuran; at 20 ℃; for 12h;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1039/b504900h

upstream raw materials:

thiosulfuric acid S-(2-amino-phenyl) ester

1-(acetyl-nitroso-amino)-2-benzenesulfonylmercapto-benzene

2-amino-benzenethiol

2-Aminophenyl disulfide

Downstream raw materials:

7-nitro-1,2,3-benzothiadiazole

5-Nitro-1,2,3-benzothiadiazol

2-thioxo-1,3-benzodithiole

2,3-Dihydro-2,2-diphenylbenzothiophene

Refernces

SAR of the arylpiperazine moiety of obeline somatostatin sst₁ receptor antagonists

10.1016/j.bmcl.2007.04.078

The research investigates the structure–activity relationship (SAR) of over 50 derivatives of octahydrobenzo[g]quinoline (obeline)-type somatostatin sst1 receptor antagonists, with a focus on modifying the arylpiperazine moiety. The goal was to enhance the sst1 receptor affinities to a subnanomolar level while improving selectivities over the sst2 receptor subtype, without compromising the favorable drug-like properties of the lead molecule. Key chemicals used include various heteroaryl moieties, substituted phenylpiperazines, and cyclic secondary amines. The study found that the best derivatives achieved subnanomolar sst1 affinities and >10,000-fold selectivities over sst2, with promising pharmacokinetic properties. Notably, the introduction of a 4-cyano substituent and a 2-pyridone moiety significantly improved sst1 affinity, while benzothiadiazole derivatives also showed high affinity and selectivity. The research concludes that the arylpiperazine moiety is crucial for optimizing the binding properties of obeline-type sst1 receptor antagonists.