16252-88-3

Usage

Uses

Used in Organic Synthesis:
5-NITRO-2,1,3-BENZOTHIADIAZOLE is used as a building block in the synthesis of organic materials such as polymers, dyes, and pharmaceuticals due to its strong electron-accepting properties and versatile chemical structure.
Used in Electronic Devices:
5-NITRO-2,1,3-BENZOTHIADIAZOLE is used in the development of organic semiconductors for electronic devices, leveraging its strong electron-accepting properties to enhance the performance of these devices.
Used in Medicinal Chemistry:
5-NITRO-2,1,3-BENZOTHIADIAZOLE has potential applications in the field of medicinal chemistry for the development of new drugs, owing to its bioactive properties and reactive nature, which make it a valuable compound for designing and synthesizing novel pharmaceutical agents.
Used in Chemical Research:
5-NITRO-2,1,3-BENZOTHIADIAZOLE is utilized in various chemical research applications, where its unique properties and reactivity are explored for the advancement of scientific knowledge and the development of innovative materials and compounds.

InChI:InChI=1/C6H3N3O2S/c10-9(11)4-1-2-5-6(3-4)8-12-7-5/h1-3H

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 100-01-6 4-nitro-aniline 
• 1436420-31-3 6-nitro-2,1,3-benzothiadiazole 1-oxide 
• 97-02-9 2,4-Dinitroanilin 
• 85786-52-3 di-μ-chlorobis[bis(5-nitro-2,1,3-benzothiadiazole)chlorocopper] 
• 222851-56-1 N-phenylsulfinylamine 
• 71-43-2 benzene 

Downstream Products

• 874-37-3 benzo[1,2,5]thiadiazol-5-ylamine 
• 14960-49-7 N-(7-chloro-benzo[1,2,5]thiadiazol-5-yl)-phthalamic acid 
• 30536-22-2 5-amino-4-nitrobenzo[1,2,5]thiadiazole 
• 768-10-5 benzo[1,2,5]thiadiazol-5-ol 
• 1360067-57-7 7-benzyl-6-methyl-8-phenyl-7H-[1,2,5]thiadiazolo[3,4-e]isoindole 
• 1360067-54-4 7-benzyl-8-methyl-6-phenyl-7H-[1,2,5]thiadiazolo[3,4-e]isoindole 
• 100264-68-4 7,8-diphenyl-[1,2,5]thiadiazolo[3,4-f]quinoxaline 
• 182012-46-0 4-nitro-benzenesulfonic acid benzo[1,2,5]thiadiazol-5-ylamide 
• 182012-50-6 sulfanilic acid benzo[1,2,5]thiadiazol-5-ylamide 
• 21110-91-8 5-acetamidobenzo-2,1,3-thiadiazole 
• 100191-31-9 6-chloro-benzo[1,2,5]thiadiazol-5-ylamine 
• 59127-46-7 4-Nitrobenzo<1.2-c:3,4-c'>bis<1.2.5>thiadiazol 
• 211-16-5 benzo[1,2-c:3,4-c']bis(1,2,5)thiadiazole 
• 300531-10-6 Ethyl 6-phenylpyrrolo[3,4-e][2,1,3]benzothiadiazole-8-carboxylate 

Relevant academic research and scientific papers

Benzothiadiazole compound and preparation method and use thereof

The present invention relates to a benzothiadiazole compound represented by the following formula I, and a preparation method and use thereof, the benzothiadiazole compound has the biological activityof inhibiting protein-tyrosine-phosphatase SHP2, can be used as a tool compound to study the biological functional relevance of the protein-tyrosine-phosphatase SHP2 in a cell signal transduction process, and provides a new means for prevention and treatment of cancer and metabolic and immune diseases.

Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release

A convenient one-pot synthesis of nitro derivatives of 2,1,3-benzothiadiazole 1-oxides by the reaction of o-nitroanilines with sulfur monochloride was developed. The structural features of 4-nitrobenzothiadiazole and its N-oxide were considered. High in vitro release of nitric oxide (69%) was found for a 6-nitro-2,1,3-benzothiadiazole sample by the Griess assay, which indicated good prospects for this class of compounds.

Luminescent ruthenium polypyridyl complexes with extended 'dppz' like ligands as DNA targeting binders and cellular agents

Four new Ru(ii) polypyridyl complexes that contain an extended aromatic moiety derived from pyrazino[2,3-h]dipyrido[3,2-a:2′,3′-c]phenazine and either 1,10-phenanthroline (phen) or 1,4,5,8-tetraazaphenanthrene (TAP) have been synthesized, their solid state X-ray crystal structure determined and their photophysical and biological properties evaluated. Their interactions with DNA have been studied, and they have been tested for their potential as photodynamic therapeutic (PDT) agents in the treatment of cancer. A practical modification of a method by Carter, Rodriguez and Bard has been introduced and used to calculate binding parameters for the complexes which show a strong affinity for DNA with binding constants in the order of 107 M1 (in 10 mM phosphate buffer). The complexes containing phen as an ancillary ligand become emissive upon binding to DNA (“light switch effect”), but do not show selective cytotoxicity upon light irradiation. On the other hand, the TAP complexes, which show an inverse “light switch effect” (emission quenched upon binding to DNA), are strongly photo-toxic suggesting their use in Photodynamic Therapy (PDT). In HeLa cells the best PDT agent shows an IC50 value (light) = 4 μM vs. IC50 value (dark) = 62 μM.

Reactions of vicinal nitroamines with sulfur monochloride - A short and convenient route to fused 1,2,5-thiadiazoles and their N-oxides

A convenient synthetic approach to fused 1,2,5-thiadiazoles and their N-oxides from vicinal nitroamines and sulfur monochloride has been developed.

Synthesis and coplanarity-dependent HOMO-LUMO separation of π-conjugated dimers

Three series of dimers containing pyrrolo[3,4-e][2,1,3]benzothiadiazole units have been prepared by application of the Pd-catalyzed Suzuki coupling. The dependence of the HOMO-LUMO separation on coplanarity has been evaluated by means of electronic absorption spectra and cyclic voltammetry. The pyrrole dimer 5c shows a narrow HOMO-LUMO separation owing to its intrinsically planar structure, as confirmed by 1H NMR. The Royal Society of Chemistry 2000.

A new facet of the reaction of nitro heteroaromatic compounds with ethyl isocyanoacetate

Nitro heteroarenes react with ethyl isocyanoacetate in the presence of 1,8-diazabicyclo[5.4.0]undecene (DBU) to give pyrroles or pyrimidine N-oxide depending on the structure of the starting nitro compounds. For example, 4-nitro-2,1,3-benzothiadiazole 3a reacted with ethyl isocyanoacetate to give ethyl 2,1,3-benzothiadiazolo[3,4-c]pyrrole-2-carboxylate 4a (33%), while a similar reaction with 5-nitro-2,1,3-benzothiadiazole 3b gave the corresponding compound 4b (21%) as a sole product. A plausible mechanism for these reactions is presented.

MEHRFACH THIADIAZOL-UEBERBRUECKTE BENZOL- UND P-BENZOCHINON-RADIKALANIONEN UND IHRE Cr-, Mo- UND W-PENTACARBONYL-KOMPLEXE

Stable radical anions of bis(thiadiazolo)-p-benzoquinone as well as of bis- and tris(thiadiazolo)benzene derivatives form on one-electron reduction using potassium/ cryptand in THF solution.According to the assigned ESR spectra, their electron-rich sulfur centers exhibit especially large spin populations.On addition of THF soluble alkalimetal salts, the ESR signals vanish, whereas with metal hexacarbonyls Me(CO)6 paramagnetic mono- (Me = W) and di(metalpentacrbonyl) (Me = Cr, Mo, W) complexes result, for which HMO-McLachlan calculations suggest preferred coordination at the N centers of the same thiadiazol bridge.

FRIES REACTION AND DAKIN REARRANGEMENT IN BENZO-2,1,3-THIADIAZOLES

The Fries rearrangement of 4- and 5-acetoxybenzo-2,1,3-thiadiazoles has given 4-hydroxy-7-acetyl- and 5-hydroxy-4-acetylbenzo-2,1,3-thiadiazoles, which on oxidation afford mixtures of 5-chloro-4,7-dioxo- and 5,6-dichloro-4,7-dioxobenzo-2,1,3-thiadiazole and of 6-chloro-4,5-dioxo- and 6,7-dichloro-4,5-dioxobenzo-2,1,3-thiadiazole.Reaction of 6,7-dichloro-4,5-dioxobenzo-2,1,3-thiadiazole with ortho-phenylenediamine gives 4,5-dichloro-2,1,3-thiadiazolophenazine.

The Crystal Structures of the Benzobisthiadiazole and of the Semihomologous Selenadiazolo-2,1,3-benzothiadiazole

The X-ray structure analyses of the title compounds 1 and 2 were performed. 1: monoclinic, C2/c, a = 9.532(2), b = 11.469(2), c = 7.030(3) Angstroem, β = 110.58(2) deg, Z = 4; 2: monoclinic, P21/a, a = 7.650(2), b = 7.729(2), c = 12.948(3) Angstroem, β = 74.26(2) deg, Z = 4.The structure of 1 was solved by direct methods, that of 2 by Patterson- and successive Fourier-synthesis techniques.The least squares refinement converged for 894 independent reflections with I>2?I to an R-value of 0.032 (Rw = 0.035) in the case of 1 and for 1440 independent reflections to on R-value of 0.045 (Rw = 0.045) in the case of 2.The bond lengths in the thiadiazole rings in 1 and 2 and also in the Se-homologous ring in 2 indicate to a quasi-aromatic ?-system, whereas the aromatic character of the central benzene ring in 1 and 2 is strongly disturbed.The substitution of one S by the homologous Se in 2 induces significant changes of comparable bond lengths in 1 and 2.In the crystal structures of both compounds molecular layers and columnar stacks are formed.Quasi-polimers in form of ribbon like structures are established in 1 by short S***N contacts and in 2 by short Se***N contacts.In 2 (SeN2)x-chains are formed. - Key words: Chalkogen-Diimides, Thia(selena)diazoles, quasi-Aromatic ?-Systems, Columnar Structures, Intermolecular S(Se)***N Contacts