272-43-5

Usage

Uses

Used in Pharmaceutical Industry:
Thieno[3,4-b]pyrazine is used as a building block for the synthesis of pharmaceutical compounds due to its potential biological and pharmacological activities. It is being studied for its potential as a drug candidate for various diseases, offering a promising avenue for the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, Thieno[3,4-b]pyrazine is utilized as a component in the creation of agrochemicals, leveraging its chemical properties to enhance the effectiveness of these products in agricultural applications.
Used in Materials Science:
Thieno[3,4-b]pyrazine is employed as a functional organic semiconductor material in materials science. Its unique electronic properties make it a candidate for use in the development of advanced materials with specific optical and electronic characteristics, contributing to innovations in areas such as electronics and optoelectronics.
Overall, Thieno[3,4-b]pyrazine's diverse applications across different industries underscore its significance in organic chemistry and its potential to drive advancements in pharmaceuticals, agrochemicals, and materials science.

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

Upstream product

• 78637-85-1 thiophene-3,4-diamine 
• 131543-46-9 Glyoxal 
• 52431-30-8 2,5-dibromo-3,4-dinitrothiophene 
• 90069-81-1 thiophene-3,4-diamine dihydrochloride 

Downstream Products

• 1188306-70-8 5,7-bis(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine 
• 1422391-62-5 2,5,7-tris(3-hexylthiophen-2-yl)thieno[3,4-b]pyrazine 

Relevant academic research and scientific papers

In Situ Oxidation Synthesis of p-Type Composite with Narrow-Bandgap Small Organic Molecule Coating on Single-Walled Carbon Nanotube: Flexible Film and Thermoelectric Performance

Although composites of organic polymers or n-type small molecule/carbon nanotube (CNT) have achieved significant advances in thermoelectric (TE) applications, p-type TE composites of small organic molecules as thick surface coating layers on the surfaces of inorganic nanoparticles still remain a great challenge. Taking advantage of in situ oxidation reaction of thieno[3,4-b]pyrazine (TP) into TP di-N-oxide (TPNO) on single-walled CNT (SWCNT) surface, a novel synthesis strategy is proposed to achieve flexible films of TE composites with narrow-bandgap (1.19 eV) small molecule coating on SWCNT surface. The TE performance can be effectively enhanced and conveniently tuned by poly(sodium-p-styrenesulfonate) content, TPNO/SWCNT mass ratio, and posttreatment by various polar solvents. The maximum of the composite power factor at room temperature is 29.4 ± 1.0 μW m?1 K?2. The work presents a way to achieve flexible films of p-type small organic molecule/inorganic composites with clear surface coating morphology for TE application.

Donor-Acceptor-Donor Thienopyrazine-Based Dyes as NIR-Emitting AIEgens

Organic Near-Infrared luminophores have found broad application as functional materials, but the development of efficient NIR emitters is still a challenging goal. Here we report on a new class of thieno[3,4-b]pyrazine-based NIR emitting materials with Aggregation Induced Emission (AIE) properties. The dyes feature a donor–acceptor–donor (D?A?D) structure, with a thienopyrazine acceptor core connected to two triarylamine donor groups bearing a tetraphenylethylene (TPE) moiety. Fast and efficient synthesis allowed the modular preparation of three dyes of tunable absorption and emission profiles. These constructs were extensively characterized by spectroscopic studies in different solvents, which revealed intense light-harvesting ability and emissions in the deep-red and NIR region with large Stokes shift values. Remarkably, the dyes exhibited AIE properties, retaining emissive ability in the aggregate state, thus emerging as attractive materials for their potential application in the development of luminescent devices.

Delay fluorescent compound and using the same and display device having the organic light-emitting diode (by machine translation)

The present invention provides a delay fluorescent compound and the use of the compound of the organic light-emitting diode and the display device, the delay fluorescent compound is a type 1 or type 2 delay fluorescent compound : [formula 1] ; [Formula 2] . (by machine translation)

Palladium-catalyzed direct C-H arylation of thieno[3,4-b]pyrazines: Synthesis of advanced oligomeric and polymeric materials

The first examples are reported of an efficient regioselective direct C-H arylation of thieno[3,4-b]pyrazine (TP) and its 2,3-dimethyl derivative with bromoalkylthiophenes (BATs), under Heck experimental conditions using Pd(OAc)2/Bu4NBr as the catalytic system, giving rise to a variety of valuable aryl-substituted thienopyrazines. The obtained results suggested that the 2-position of the TP moiety is less reactive towards C-H arylation than the 5-and 7-positions. Moreover, the 3-position of the TP moiety showed almost no significant reactivity when all other positions were arylated. The C-H arylation of 2,3-dimethyl-TP with an excess amount of BATs proceeded smoothly, affording the corresponding diarylated thienopyrazine derivatives in excellent yields, without any additional products. Compared to usual cross-coupling reactions, the present synthetic methodology has been used to prepare interesting donor-acceptor π-conjugated polymeric materials in a facial manner in a simple way. Microwave-assisted polymerization proved to be efficient for obtaining reasonable molecular weight copolymers ranging from 18.8 to 24.3 kg mol-1. Incorporating the thienopyrazine unit into polyhexylthiophene chains affected the photophysical and electrochemical properties. The optical band gaps were estimated to be in the range of 1.63-1.06 eV. All copolymers exhibited a diffraction peak at around 2θ = 5.72° corresponding to a d spacing of 15.43 A, which was assigned to an interchain spacing between polymer main chains similar to that found in P3HT. Moreover, a peak around 2θ = 23.09 (3.84 A) was also observed and is believed to be related to π-π stacking of the polymer backbones.

Thieno[3,4-b]pyrazines: Synthesis, structure, and reactivity

A general synthetic route has been developed for the efficient preparation of 2,3-disubstituted thieno[3,4-b]-pyrazines. These methods eliminate problems in the preparation of the precursor 3,4-diaminothiophene and utilize α-diones prepared through the reaction of the appropriate organocuprates with oxalyl chloride. This combination allows the convenient preparation of thieno[3,4-b]pyrazine and its 2,3-disubstituted analogues (where substituent = methyl, hexyl, octyl, decyl, dodecyl, and phenyl) in high yield. Characterization of the structure and reactivity of this class of compounds is also described, including the results of structural, electrochemical, and pKa studies.

Synthese de nouveaux systemes heterocycliques thiopheniques azotes a partir du diamino-3,4 thiophene

The synthesis of thiophenic bicyclic and tricyclic heterocycles are described. 3,4-Diaminothiophene reacted with carbondisulfide in alkaline medium to yield the tautomeric form of 2-mercaptothienoimidazole.Thienopyrazines and thieno1,