932-93-4

Usage

Uses

Used in Pharmaceutical Industry:
Thiophene-2,4-dicarbaldehyde is utilized as a key intermediate in the synthesis of pharmaceutical compounds due to its ability to form a wide range of functionalized thiophene derivatives. These derivatives exhibit various biological activities, making them essential in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, thiophene-2,4-dicarbaldehyde serves as a precursor for the synthesis of various agrochemicals, including pesticides and herbicides. Its unique structure allows for the creation of compounds with specific target pest or weed control properties, contributing to more effective and environmentally friendly agricultural practices.
Used in Materials Science:
Thiophene-2,4-dicarbaldehyde is employed as a building block in the development of advanced materials with unique electronic, optical, and structural properties. Its electron-rich nature and aromatic structure make it suitable for the synthesis of conductive polymers, organic semiconductors, and other materials with potential applications in electronic devices, sensors, and energy storage systems.
Used in Organic Synthesis:
As a versatile chemical, thiophene-2,4-dicarbaldehyde is used as a starting material in organic synthesis for the preparation of a variety of functionalized thiophene derivatives. These derivatives find applications in various fields, including pharmaceuticals, agrochemicals, and materials science, showcasing the compound's broad utility in chemical research and development.

Upstream product

• 19259-06-4 diiodo-2,4 thiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 3140-92-9 2,4-dibromothiophene 
• 1487-22-5 4-bromo-2-thiophenecarboxaldehyde diethyl acetal 

Downstream Products

• 638-00-6 2,4-dimethylthiophene 
• 1431984-42-7 2,4-bis{(E)-2-[4-(tert-butylsulfanyl)phenyl]ethenyl}thiophene 

Relevant academic research and scientific papers

Exchange interactions between two nitronyl nitroxide or iminyl nitroxide radicals attached to thiophene and 2,2′-bithienyl rings

Eight bis(nitronyl nitroxide) and bis(iminyl nitroxide) diradicals having thiophene (2,4NT, 2,5NT, 2,4IT, and 2,5IT) and 2,2′-bithienyl units (4,4′NB, 3,3′NB, 4,5′IB, and 5,5′IB) as couplers were prepared. Both 2,5NT and 4,4′NB crystallized in monoclinic space group P21/n with a = 12.430(2) ?, b = 13.968(4) ?, c = 12.470(2) ?, β = 107.26(1)°, and Z = 4 and with a = 10.766(7) ?, b = 10.186(3) ?, c = 11.625(4) ?, β= 1199(3)°, and Z = 2. The dihedral angles between the imidazoline and thiophene rings were only 6 and 10° in 2,5NT and 21° in 4,4′NB. The 2,2′-bithienyl chromophore assumed a planar anti-conformation. A dimer structure with the oxygen atom in one molecule and the nearest nitrogen atom in the other at a distance of 3.9 ? stacks linearly along the b axis in 2,5NT. Each nitronyl nitroxide group at both ends of the 4,4′B molecule is in close contact with that of the neighboring molecule to make a one-dimensional chain. EPR spectra of all the diradicals in frozen toluene solutions showed typical fine structures due to triplet states with hyperfine splitting with nitrogen as well as the signals due to Δms = 2 transitions. The zero-field splitting constants were determined as |D/hc| = 0.0071, 0.0085, 0.0066, 0.0108, and 0.0149 cm-1 for 2,4NT, 2,5NT, 2,4IT, 2,5IT, and 3,3′NB, respectively. Temperature dependence of the EPR triplet signal intensities in the monothiophene derivatives suggested that the triplets would be ground states in the 2,4-isomers and that they are excited states lying above singlet ground states by ΔEST (= 2J) = -218 kB and -52 kB K in 2,5NT and 2,5IT, respectively. The couplings for 2,4NT and 2,4IT were determined to be Jintra/kB = 40 and 16 K (H = -2JintraS1S2 for an S-T model), respectively, by SQUID measurements. Similar data were analyzed in terms of a linear four-spin model (H = -2Jintra(S1S2+S3S 4)-2JinterS2S3) for 2,5NT and an S-T model for 2,5IT to give Jintra/kB = -114.6, Jinter/kB = -34, and θ/S(S+ 1) = -0.8 K and Jintra/kB = -29.7 and θ/S(S + 1) = -2.5 K, respectively. In the four bithienyl derivatives, the interaction was weak with |Jintra/kB| values being less than 10 K. The signs were barely judged to be positive for 4,5′IB and negative for 3,3′NB and 5,5′IB. Manganese(II) bis(hexafluoroacetylacetonate) formed a microcrystalline complex with 2,4NT which underwent the transition to a ferrimagnet at 11 K, demonstrating the potentiality of 2,4NT as a multi(monodentate) triplet diradical coupler.

Oxidative Transformation of a Tetrathia S-Confused Isophlorin into Porphyrin Cation

The synthesis and redox properties of first generation S-confused isophlorins are described. Despite structural resemblance to a confused porphyrin, spectroscopic and computational studies reveal weak paratropic ring current effects in these 20π macrocycles. They display redox properties atypical of parent tetrathia isophlorins. Experimental evidence supports the oxidation of an unstable 19π neutral radical, as a transient intermediate, for the formation of a unique 18π aromatic monocationic species. Spectroscopic and structural characterization revealed the substituent dependent macrocycle oxidation unfamiliar to the chemistry of antiaromatic isophlorinoids.

The synthesis of π-electron molecular rods with a thiophene or thieno[3,2-b]thiophene core unit and sulfur alligator clips

A series of short oligo(p-phenylene-ethynylene)- and oligo(p- phenylenevinylene)-type molecular rods with an electronically rich thiophene or thieno[3,2-b]thiophene core unit and sulfur anchoring groups (AcS-, t-BuS-) at the termini have been synthesised