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:

99% ^*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

3-methyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate

3-ethyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate

Refernces

• 1、 Poesche. "-". . p. 568,571. Retrieved 1966.
• 2、 -. "Method for continuously synthesizing benzothiadiazole compound". Paragraph 0020-0024. . Retrieved 2020/06/02.
• 3、 Trusova, Marina E.,Krasnokutskaya, Elena A.,Postnikov, Pavel S.,Choi, Younghwa,Chi, Ki-Whan,Filimonov, Victor D.. "A green procedure for the diazotization-iodination of aromatic amines under aqueous, strong-acid-free conditions". experimental part. p. 2154 - 2158. Retrieved 2011/08/05.