273-77-8

Basic information

• Product Name: 1,2,3-BENZOTHIADIAZOLE
• Synonyms: 1,2,3-BENZOTHIADIAZOLE;AKOS 90367;BENZO[1,2,3]THIADIAZOLE;benzo[d][1,2,3]thiadiazole
• CAS NO: 273-77-8
• Molecular Formula: C₆H₄N₂S
• Molecular Weight: 136.17
• EINECS: 205-989-4
• Mol File: 273-77-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 295 °C (decomp)
• Boiling Point: 220.5 °C at 760 mmHg
• Flash Point: 90.8 °C
• Appearance: /
• Density: 1.368g/cm³
• Vapor Pressure: 0.167mmHg at 25°C
• Refractive Index: 1.705
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.83±0.50(Predicted)
• CAS DataBase Reference: 1,2,3-BENZOTHIADIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-BENZOTHIADIAZOLE(273-77-8)
• EPA Substance Registry System: 1,2,3-BENZOTHIADIAZOLE(273-77-8)

Safety Data

• Hazardous Substances Data: 273-77-8(Hazardous Substances Data)

Usage

Purification Methods

1,2,3-Benzothiadiazole crystallises from pet ether, and has at 264 and 306nm in hexane. [Overberger et al. J Org max Soc 24 1407 1959, Beilstein 27 III/IV 7113.]

InChI:InChI=1/C6H4N2S/c1-2-4-6-5(3-1)7-8-9-6/h1-4H

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 1141-88-4 2-Aminophenyl disulfide 
• 82172-31-4 4,7-Dibrom-4,5,6,7-tetrahydro-1,2,3-benzothiadiazol 
• 109287-03-8 1-acetylamino-2-benzenesulfonylmercapto-benzene 
• 34357-13-6 1,3λ⁴δ²,2,4-benzodithiadiazine 
• 109259-19-0 1-(acetyl-nitroso-amino)-2-benzenesulfonylmercapto-benzene 
• 26306-57-0 thiosulfuric acid S-(2-amino-phenyl) ester 
• 56382-72-0 Cyclohexeno-1,2,3-thiadiazol 

Downstream Products

• 31859-99-1 7-nitro-1,2,3-benzothiadiazole 
• 13599-78-5 5-Nitro-1,2,3-benzothiadiazol 
• 3710-65-4 3-methyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 3383-50-4 3-ethyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 3718-26-1 3-(2-hydroxy-ethyl)-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 29016-86-2 3-(3-methyl-butyl)-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 29016-84-0 3-pentyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 3718-25-0 3-propyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 29016-83-9 3-butyl-benzo[1,2,3]thiadiazolium; 2,4-dinitro-benzenesulfonate 
• 39269-36-8 Benzo-1,2,3-thiadiazol-1,1,2-trioxid 
• 934-36-1 2-thioxo-1,3-benzodithiole 
• 92013-95-1 2,3-Dihydro-2,2-diphenylbenzothiophene 
• 92-85-3 Thianthrene 
• 132-65-0 dibenzothiophene 

Relevant articles and documents

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Benzothiadiazole vs. Iso-benzothiadiazole: Synthesis, electrochemical and optical properties of d–a–d conjugated molecules based on them

This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoВТD) has higher values of ELUMO and energy band gap (Eg), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer–acceptor–π-spacer type compounds were obtained by means of the Stille reaction. Therefore, 6 new structures of this type have been synthesized. A detailed study of the optical and electrochemical properties of the obtained π-spacer–acceptor–π-spacer type compounds in comparison with isomeric structures based on benzo[c][1,2,5]thiadiazole (BTD) showed a red shift of absorption maxima with lower absorptive and luminescent capacity. However, the addition of the 2,2′-bithiophene fragment as a π-spacer resulted in an unexpected increase of the extinction coefficient in the UV/vis spectra along with a blue shift of both absorption maxima for the isoBTD-based compound as compared to the BTD-based compound. Thus, a thorough selection of components in the designing of appropriate compounds with benzo[d][1,2,3]thiadiazole as an internal acceptor can lead to promising photovoltaic materials.

Synthesis method of 1,2,3-diazosulfide compound

The invention discloses a synthesis method of a 1,2,3-diazosulfide compound. A o-aminothiophenol compound with a structure shown as a formula (I) and tert-butyl nitrite are taken as raw materials, and are subjected to intramolecular diazo-reaction to obtain the 1,2,3-diazosulfide compound with a structure shown as a formula (II); a reaction equation is as follows (shown in the description), wherein R=hydrogen, fluorine, chlorine, ester group, nitro or methyl. The synthesis method has the beneficial effects that (1) the operation is simple and convenient in a preparation process, an obtained product is easy for after-treatment, and large-scale industrialized production is suitable; (2) reaction conditions are mild; (3) the synthesis cost is lowered; (4) a reaction substrate is high in functional group tolerance, is wide in range and easy to prepare; (5) the reaction is efficient, the yield is high, and the reaction efficiency is higher after reaction amplification; (6) environment pollution is avoided, and environment friendliness is achieved.

7-AMINOFUROPYRIDINE DERIVATIVES

Compounds of Formula 1, as shown below and defined herein: pharmaceutically acceptable salts thereof, synthesis, intermediates, formulations, and methods of disease treatment therewith, including treatment of cancers, such as tumors driven at least in part by TAK1 or for which an appropriate TAK1 inhibitor is effective. This Abstract is not limiting of the invention.