5-Nitro-2,1,3-benzothiadiazole

Base Information

• Chemical Name: 5-Nitro-2,1,3-benzothiadiazole
• CAS No.: 16252-88-3
• Molecular Formula: C6H3N3O2S
• Molecular Weight: 181.175
• NSC Number: 169218
• UNII: K2T9C5FVT8
• DSSTox Substance ID: DTXSID60167385
• Nikkaji Number: J774.174J
• Wikidata: Q83036741
• ChEMBL ID: CHEMBL206713
• Mol file: 16252-88-3.mol

Synonyms:5-nitro-2,1,3-benzothiadiazole;16252-88-3;5-nitrobenzo[c][1,2,5]thiadiazole;5-nitrobenzo-2,1,3-thiadiazole;5-(Hydroxy(oxido)amino)-2,1,3-benzothiadiazole;K2T9C5FVT8;NSC169218;UNII-K2T9C5FVT8;NSC 169218;CHEMBL206713;NSC-169218;2,1,3-Benzothiadiazole, 5-nitro-;Maybridge1_005863;Oprea1_705286;SCHEMBL922633;HMS558C11;DTXSID60167385;BXZPSERJJMAPSV-UHFFFAOYSA-N;BDBM50182129;MFCD00114840;RDP 00064;AKOS003197175;AM806177;AS-61005;CS-0316448;EU-0066875;SR-01000389716;SR-01000389716-1

Chemical Property of 5-Nitro-2,1,3-benzothiadiazole

Chemical Property:

• Vapor Pressure: 0.000867mmHg at 25°C
• Refractive Index: 1.746
• Boiling Point: 314.3 °C at 760 mmHg
• Flash Point: 143.9 °C
• PSA: 99.84000
• Density: 1.627 g/cm³
• LogP: 2.12270
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 180.99459752
• Heavy Atom Count: 12
• Complexity: 196

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NSN=C2C=C1[N+](=O)[O-]

Technology Process of 5-Nitro-2,1,3-benzothiadiazole

There total 9 articles about 5-Nitro-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: 93.2%

4-Nitrophenylene-1,2-diamine (99-56-9) → 5-nitro-2,1,3-benzothiadiazole (16252-88-3)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 65 ℃; for 3h;

Reference yield: 89.0%

4-nitro-aniline (100-01-6,104810-17-5) → 5-nitro-2,1,3-benzothiadiazole (16252-88-3)

Guidance literature:

With trithiazyl trichloride; In benzene; Ambient temperature;

Reference yield: 83.0%

6-nitro-2,1,3-benzothiadiazole 1-oxide (1436420-31-3) → 5-nitro-2,1,3-benzothiadiazole (16252-88-3)

Guidance literature:

With pyridine; sulfur monochloride; In acetonitrile;

DOI:10.1016/j.tetlet.2013.03.134

upstream raw materials:

N-phenylsulfinylamine

4-Nitrophenylene-1,2-diamine

benzene

4-nitro-aniline

Downstream raw materials:

benzo[1,2,5]thiadiazol-5-ylamine

N-(7-chloro-benzo[1,2,5]thiadiazol-5-yl)-phthalamic acid

5-amino-4-nitrobenzo[1,2,5]thiadiazole

benzo[1,2,5]thiadiazol-5-ol

Refernces

• 1、 Konstantinova,Knyazeva,Gatilov, Yu. V.,Zlotin,Rakitin. "Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release". . p. 95 - 101. Retrieved 2018/04/27.
• 2、 Konstantinova, Lidia S.,Knyazeva, Ekaterina A.,Obruchnikova, Natalia V.,Gatilov, Yuri V.,Zibarev, Andrey V.,Rakitin, Oleg A.. "Reactions of vicinal nitroamines with sulfur monochloride - A short and convenient route to fused 1,2,5-thiadiazoles and their N-oxides". . p. 3075 - 3078. Retrieved 2013/06/27.