5,6-Dibromo-2,1,3-benzothiadiazole

Base Information

• Chemical Name: 5,6-Dibromo-2,1,3-benzothiadiazole
• CAS No.: 18392-81-9
• Molecular Formula: C6H2Br2N2S
• Molecular Weight: 293.969
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20453175
• Nikkaji Number: J2.584.272C
• Wikidata: Q82274233
• Mol file: 18392-81-9.mol

Synonyms:5,6-Dibromo-2,1,3-benzothiadiazole;18392-81-9;5,6-Dibromobenzo[c][1,2,5]thiadiazole;SCHEMBL15417096;DTXSID20453175;MFCD20257910;5,6-Dibromobenzo[1,2,5]thiadiazole;AKOS005186842;DS-19404;CS-0157816;D4064;C73541;A903549

Chemical Property of 5,6-Dibromo-2,1,3-benzothiadiazole

Chemical Property:

• Melting Point: 131.0 to 135.0 °C
• Boiling Point: 334.5±22.0 °C(Predicted)
• PKA: -1.97±0.50(Predicted)
• PSA: 54.02000
• Density: 2.229±0.06 g/cm3(Predicted)
• LogP: 3.21630
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Toluene
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 293.82850
• Heavy Atom Count: 11
• Complexity: 142

Purity/Quality:

98% ^*data from raw suppliers

5,6-Dibromo-2,1,3-benzothiadiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CC2=NSN=C21)Br)Br

Technology Process of 5,6-Dibromo-2,1,3-benzothiadiazole

There total 6 articles about 5,6-Dibromo-2,1,3-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%

4,5-dibromo-1,2-diaminobenzene (49764-63-8) → 5,6‐dibromo‐2,1,3‐benzothiadiazole (18392-81-9)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; for 5h; Cooling with ice; Reflux;

DOI:10.1039/c2ob25680k

Reference yield:

1,2-diamino-benzene (95-54-5) → 5,6‐dibromo‐2,1,3‐benzothiadiazole (18392-81-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / pyridine

2: 89 percent / Br₂, acetic acid, sodium acetate

3: 83.5 percent / sulfuric acid

4: 76 percent / thionyl chloride, pyridine / 3 h / Heating

With pyridine; thionyl chloride; sulfuric acid; bromine; sodium acetate; acetic acid;

Reference yield:

1,2-bis-(p-methylphenylsulfonamido)-benzene (49633-28-5) → 5,6‐dibromo‐2,1,3‐benzothiadiazole (18392-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / Br₂, acetic acid, sodium acetate

2: 83.5 percent / sulfuric acid

3: 76 percent / thionyl chloride, pyridine / 3 h / Heating

With pyridine; thionyl chloride; sulfuric acid; bromine; sodium acetate; acetic acid;

upstream raw materials:

1,2-dinitro-4,5-dibromobenzene

4,5-dibromo-1,2-diaminobenzene

1,2-bis-(p-methylphenylsulfonamido)-benzene

N-[4,5-dibromo-2-(p-tolylsulfonylamino)phenyl]-4-methylbenzenesulfonamide

Downstream raw materials:

4,5-dibromo-1,2-diaminobenzene

Refernces

• 1、 Shang, Hong,Xue, Zheng,Wang, Kang,Liu, Huibiao,Jiang, Jianzhuang. "Multinuclear Phthalocyanine-Fused Molecular Nanoarrays: Synthesis, Spectroscopy, and Semiconducting Property". . p. 8644 - 8651. Retrieved 2017.
• 2、 Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria. "Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2". supporting information. . Retrieved 2021/06/09.
• 3、 Aslan, Joseph M.,Boston, David J.,MacDonnell, Frederick M.. "Photodriven Multi-electron Storage in Disubstituted RuII Dppz Analogues". . p. 17314 - 17323. Retrieved 2016/01/26.