1711-66-6

Basic information

• Product Name: 2,1,3-BENZOTHIADIAZOLE-4,5-DIAMINE
• Synonyms: 2,1,3-BENZOTHIADIAZOLE-4,5-DIAMINE;2,1,3-Benzothiadiazole-2-SIV-4,5-diamine;4,5-Diamino-2,1,3-benzothiadiazole;4,5-Diaminobenzothiadiazole;BENZO[1,2,5]THIADIAZOLE-4,5-DIAMINE
• CAS NO: 1711-66-6
• Molecular Formula: C₆H₆N₄S
• Molecular Weight: 166.2
• Mol File: 1711-66-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 168-169℃
• Boiling Point: 372.3°C at 760 mmHg
• Flash Point: 178.9°C
• Appearance: /
• Density: 1.597
• Vapor Pressure: 9.73E-06mmHg at 25°C
• Refractive Index: 1.866
• CAS DataBase Reference: 2,1,3-BENZOTHIADIAZOLE-4,5-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,1,3-BENZOTHIADIAZOLE-4,5-DIAMINE(1711-66-6)
• EPA Substance Registry System: 2,1,3-BENZOTHIADIAZOLE-4,5-DIAMINE(1711-66-6)

Safety Data

• Hazardous Substances Data: 1711-66-6(Hazardous Substances Data)

Usage

Type of compound

Nitrogen-containing aromatic heterocyclic compound

Common uses

Synthesis of organic semiconductors, building block for polymeric materials in organic electronics

Applications

Organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), organic field-effect transistors (OFETs)

Unique properties

Electronic and optical properties suitable for organic electronics

Stability

High thermal and chemical stability

Importance

Versatile and valuable compound in the field of organic electronic materials

InChI:InChI=1/C6H6N4S/c7-3-1-2-4-6(5(3)8)10-11-9-4/h1-2H,7-8H2

Upstream product

• 2274-89-7 5-chloro-4-nito-2,1,3-benzothiadiazole 
• 72023-79-1 5-bromo-4-nitro-benzo[1,2,5]thiadiazole 
• 21110-91-8 5-acetamidobenzo-2,1,3-thiadiazole 
• 874-37-3 benzo[1,2,5]thiadiazol-5-ylamine 
• 70061-35-7 5-bromo-[1,2,5]thiadiazolo[3',4':3,4]benzo[1,2-c][1,2,5]oxadiazole 3-oxide 
• 70015-81-5 4-bromo-6,7-(2',1',3'-oxadiazole)benzo-2,1,3-thiadiazole 
• 2274-65-9 4,7-dibromo-5-nitrobenzo[c][1,2,5]thiadiazole 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 6583-06-8 4-nitro-1,2,3-benzothiadiazole 
• 33066-35-2 [1,2,5]thiadiazolo[3',4':3,4]benzo[1,2-c][1,2,5]oxadiazole 
• 1915-85-1 4-Amino-5-nitrobenzo<1.2.5>thiadiazol 
• 30536-22-2 5-amino-4-nitrobenzo[1,2,5]thiadiazole 
• 873995-19-8 4-phenylazo-benzo[1,2,5]thiadiazol-5-ylamine 
• 16252-88-3 5-nitro-2,1,3-benzothiadiazole 

Downstream Products

• 71919-01-2 7-(4-methoxyphenyl)-6H-imidazo<4,5-e>-2,1,3-benzothiadiazole 
• 129485-63-8 7,9-diphenyl-8-dihydro-1,5-diazepino<6,7-e>-2,1,3-benzothiadiazole 
• 187336-66-9 4H-imidazo[4.5-e][2.1.3]benzothiadiazol-5(6H)-one 
• 129485-61-6 7-benzyl-6(8)H-imidazo<4,5-e>-2,1,3-benzothiadiazole 
• 129485-73-0 7-(2-Chloro-phenyl)-6H-imidazo[4',5':3,4]benzo[1,2-c][1,2,5]thiadiazole 
• 77728-94-0 7-(p-chlorophenyl)-6H-imidazo<4,5-e>-2,1,3-benzothiadiazole 
• 77728-92-8 7-phenyl-(4-phenyl)-6H-imidazo<4,5-e>-2,1,3-benzothiadiazole 
• 19546-85-1 6(8)H-imidazo<4,5-e>-2,1,3-benzothiadiazole 
• 129485-72-9 7-o-Tolyl-6H-imidazo[4',5':3,4]benzo[1,2-c][1,2,5]thiadiazole 
• 129485-65-0 7,8-Bis-(4-methoxy-phenyl)-2-thia-1,3,6,9-tetraaza-cyclopenta[a]naphthalene 

Relevant articles and documents

Synthesis and reaction of furazanobenzothiadiazole and related compounds

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Multifunctional Imidazobenzothiadiazole Probe Displaying Solvatofluorochromism and Ability To Form Ion-Pair Complexes in Solid State and in Solution

Fluorescent solid 5-pyridylimidazobenzothiadiazole displays a remarkable solvatofluorochromism and with Zn(AcO)2 and Cd(AcO)2, either in solution or under solvent-free conditions, forms ion-pair complexes that in the solid state can be discriminated and separated by fluorescence measurements and selective extraction with diethyl ether or chloroform. (Chemical Equation Presented).

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.

Benzo[1,2-c:3,4-c′]bis[1,2,5]selenadiazole, [1,2,5]selenadiazolo-[3, 4-e]-2,1,3-benzothiadiazole, furazanobenzo-2,1,3-thiadiazole, furazanobenzo-2,1,3-selenadiazole and related heterocyclic systems

The first synthesis of benzo[1,2-c:3,4- c′]bis[1,2,5]selenadiazole has been developed starting from commercially available 4-nitrobenzo-2,1,3- selenadiazole. Improved syntheses of the related heterocycles [1,2,5]selenadiazolo[3,4-e]-2,1,3-benzothiadiazole, furazanobenzo-2,1,3- thiadiazole and furazanobenzo-2,1,3-selenadiazole are also reported.