42140-95-4

Usage

Aromatic heterocyclic organic compound

Contains a thiazole ring fused with a thiophene ring

Building block

Commonly used in the synthesis of various pharmaceuticals and agrochemicals

Potential properties

Antioxidant, antifungal, and antibacterial

Application in materials development

Used in the development of new materials for organic light-emitting diodes (OLEDs) and organic semiconductors due to its electron-donating and electron-accepting abilities

Versatile properties

Unique structure and versatile properties make it a valuable component in the fields of chemistry, materials science, and pharmaceutical research.

Upstream product

• 24044-05-1 2-thiophen-2-yl-thiazole-4,5-dicarboxylic acid 
• 20300-02-1 thiophene-2-carbothioamide 
• 7252-83-7 1-bromo-2,2-dimethoxyethane 
• 288-47-1 1,3-thiazole 
• 881-89-0 phenyl thiophene-2-carboxylate 
• 3034-53-5 2-bromo-1,3-thiazole 
• 1003-31-2 thiophene-2-carbonitrile 
• 60705-34-2 4,5-dihydro-2-(2-thienyl)-1,3-thiazole 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 37496-13-2 2-(trimethylstannyl)thiophene 
• 193978-23-3 2-thiopheneboronic acid pinacol ester 
• 1003-09-4 2-bromothiophene 
• 188290-36-0 thiophene 
• 96-50-4 2-thiazolylamine 

Downstream Products

• 54987-01-8 2,5-di-(2-thienyl)thiazole 

Relevant academic research and scientific papers

Synthesis of Benzothiadiazole Derivatives by Applying C-C Cross-Couplings

The benzothiadiazole moiety has been extensively exploited as a building block in the syntheses of efficient organic semiconducting materials during the past decade. In this paper, parallel synthetic routes to benzothiadiazole derivatives, inspired by previous computational findings, are reported. The results presented here show that various C-C cross-couplings of benzothiadiazole, thiophene, and thiazole derivatives can be efficiently performed by applying Xantphos as a ligand of the catalyst system. Moreover, improved and convenient methods to synthesize important chemical building blocks, e.g., 4,7-dibromo-2,1,3-benzothiadiazole, in good to quantitative yields are presented. Additionally, the feasibility of Suzuki-Miyaura and direct coupling methods are compared in the synthesis of target benzothiadiazole derivatives. The computational characterization of the prepared benzothiadiazole derivatives shows that these compounds have planar molecular backbones and the possibility of intramolecular charge transfer upon excitation. The experimental electrochemical and spectroscopic studies reveal that although the compounds have similar electronic and optical properties in solution, they behave differently in solid state due to the different alkyl side-group substitutions in the molecular backbone. These benzothiadiazole derivatives can be potentially used as building blocks in the construction of more advanced small molecule organic semiconductors with acceptor-donor-acceptor motifs. (Chemical Equation Presented).

Pd-Catalyzed Decarbonylative C?H Coupling of Azoles and Aromatic Esters

A decarbonylative C?H coupling of azoles and aromatic esters by palladium catalysis is described. Our previously reported Ni-catalyzed C?H coupling of azoles and aromatic esters has a significant drawback regarding the substrate scope. Herein, we employ p

Synthesis of heteroaryl compounds through cross-coupling reaction of aryl bromides or benzyl halides with thienyl and pyridyl aluminum reagents

An efficient method for synthesis of useful biaryl building blocks containing 2-thienyl, 3-thienyl, 2-pyridyl, and 3-pyridyl moieties was provided through cross-coupling reactions of aryl bromides or benzyl halides with heteroaryl aluminum reagents in the presence of Pd(OAc)2 and (o-tolyl)3P. The coupling reaction also worked efficiently with heteroaryl bromides affording series of heterobiaryl compounds. The reaction of phenylbromide with in situ prepared 3-pyridyl aluminum was demonstrated to afford the product 8a in high yield. Additionally, the catalytic system was also suited well for the coupling reaction of benzyl halides with pyridyl aluminum reagents to afford series of pyridyl-arylmethane.

DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles

Strong as an Ox: 2-Thiazoles and 2-oxazoles are formed by oxidation of 2-thiazolines and 2-oxazolines without requiring substituents at the C4 and C5 positions. DDQ plays an important role as the oxidant in this transformation and metal is unnecessary. This general procedure shows good functional group tolerance and provides a wide variety of 2-thiazoles and 2-oxazoles in moderate to excellent yields.

NOVEL ARTIFICIAL FLUORESCENT BASES

The present invention relates to novel unnatural fluorescent nucleic acid bases, that is, a purine base, a 2-deazapurine base, and a 2,7-deazapurine base each having a functional group which consists of two or more heterocyclic moieties linked together, at the 6-position thereof (the 6-position of purine ring). The present invention also relates to a compound containing the unnatural base, a derivative thereof, and a nucleic acid containing a nucleotide having the unnatural base. The present invention also relates to a method of preparing the nucleic acid. The unnatural base of the present invention has excellent fluorescence characteristics and also has excellent properties as a universal base.

Cyclometalated platinum polymers: Synthesis, photophysical properties, and photovoltaic performance

The synthesis and characterization of platinum-containing conjugated polymers in which the platinum atom is attached to the conjugated backbone via a CN ligand is presented. The newly designed platinum-containing monomer can be polymerized under both Stil

PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE AS SEMICONDUCTORS

The present invention relates to compounds of the formula (I) wherein the substituents are as defined in claim 1, and their use as organic semiconductor in organic devices, like diodes, organic field effect transistors and/or solar cells. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).

Preparation of 2- and 5-aryl substituted thiazoles via palladium-catalyzed Negishi cross-coupling

2-Aryl substituted thiazoles 3a-k were prepared by oxidative insertion of zinc into 2-bromothiazole (1) followed by palladium(0)-catalyzed Negishi cross-coupling in a one-pot procedure. 5-Aryl substituted thiazoles 6a-i were prepared by regioselective C-5 lithiation of 2-(trimethylsilyl)thiazole (4) followed by transmetalation with zinc chloride and palladium(0)-catalyzed Negishi cross-coupling in a one-pot procedure. The synthetic sequences were combined to give 2,5-diaryl substituted thiazoles 8a,b and 10 via stepwise C-2 and C-5 arylation and vice versa.

Photoactivated miticidal and insecticidal ethynylthiazoles

Pesticidal 2- or 5-ethenyl substituted thiazoles, compositions thereof and use thereof as insecticides and miticides are disclosed and exemplified.