273-77-8

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

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

Downstream Products

• 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 
• 13599-78-5 5-Nitro-1,2,3-benzothiadiazol 
• 39269-36-8 Benzo-1,2,3-thiadiazol-1,1,2-trioxid 
• 29016-88-4 3-propyl-benzo[1,2,3]thiadiazolium; iodide 
• 79251-96-0 3-benzoyl-1H-4,1,2-benzothiadiazine 
• 154776-65-5 3-benzoyl-8-bromobenzothiadiazine 
• 154776-64-4 1-(4-Nitro-benzyl)-3-(4-nitro-phenyl)-1H-benzo[1,3,4]thiadiazine 
• 31859-99-1 7-nitro-1,2,3-benzothiadiazole 

Relevant academic research and scientific papers

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.

Method for continuously synthesizing benzothiadiazole compound

The invention discloses a method for continuously synthesizing a benzothiadiazole compound, comprising the following step: by using an o-mercaptoaniline compound, sodium nitrite and water as reactionsubstrates in a continuous flow reactor, a diazotization-coupling reaction is carried out at certain temperature under certain pressure to obtain the benzothiadiazole compound. By adopting the technology, no protonic acid participates, and water is used as a reactant and a solvent, so that the method is green and environment-friendly. The continuous flow reactor is used, online materials are small, the process is intrinsically safe, and the method is suitable for large-scale production.

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.

A green procedure for the diazotization-iodination of aromatic amines under aqueous, strong-acid-free conditions

A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential diazotization-iodination of aromatic amines with a reusable polymeric diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known diazotization-iodination methods. The method is also effective for the preparation of 1H-benzo[d][1,2,3]triazole and benzo[d][1,2,3]thiadiazole. Georg Thieme Verlag Stuttgart ? New York.

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.

Efficient solid phase synthesis of benzo[1,2,3]thiadiazoles and related structures

The first solid-phase synthesis of benzo[1,2,3]thiadiazoles was achieved by starting from resin bound ortho bromo or iodo triazenes and using a functionalization on cleavage. Two different synergistic methods including an anionic approach and a cross-coupling approach were used for the synthesis. The resulting diazonium compounds readily underwent electrophilic cyclization yielding benzothiadiazoles, when cleaving the arenethiol resins. Cleavage from the resin with diluted trifluoroacetic acid resulted spontaneously in the desired cyclization reaction.

New polysulfur-nitrogen heterocycles by thermolysis of 1, 3λ4δ2,2,4-benzodithiadiazines in the hydrocarbon and fluorocarbon series

In contrast to thermolysis of 1,3λ4δ2,2, 4-benzodithiadiazine (1) and its 5,6,7,8-tetrafluoro derivative 2 in dilute (10-3 M) hydrocarbon solutions, which leads to persistent 1,2,3-benzodithiazolyls in nearly quantitative

N-(AMIDINOPHENYL) CYCLOUREA ANALOGS AS FACTOR XA INHIBITORS

The present application describes N-(amidinophenyl)cyclourea analogs of formula I: STR1 which are useful as inhibitors of factor Xa.

CONVERSION OF CYCLIC TRITHIOCARBONATES TO THIOACETALS, INCLUDING 1,3-DITHIANE, BY REDUCTION WITH DIISOBUTYLALUMINIUM HYDRIDE (DIBAL)

Cyclic trithiocarbonates can be desulfurized with diisobutylaluminium hydride (DIBAL) to form the corresponding thioacetals.This new synthetic pathway was exploited for the preparation of several Umpolung reagents, including 1,3-dithiane.An efficient isolation of sodium trithocarbonate is described.

Bromination and Dehydrobromination in the Side Chains of 1,2,3-Thiadiazoles

The bromination of 1,2,3-thiadiazoles with N-bromosuccinimide (NBS) is investigated.The monobromides 3 and 4 and the dibromides 5 and 6 can be isolated.Several methods have been used for the introduction of double bonds by the elimination of HBr.Besides the elimination products 9, 11, 12, and 14 the substitution products 10, 13, 15, 16, and 17 are obtained.A lot of regio- and stereoselectivities can be observed.