3319-41-3

Usage

Uses

Used in Organic Synthesis:
2,3-Thiophenedicarboxylic acid, 4,5-diphenyl-, dimethyl ester is used as a building block for the synthesis of various organic compounds. Its unique structure allows it to be a key component in the creation of new molecules with different properties and applications.
Used in Materials Science:
In the field of materials science, 2,3-Thiophenedicarboxylic acid, 4,5-diphenyl-, dimethyl ester is used as a potential material for optoelectronic devices. Its properties make it a candidate for use in the development of advanced materials with applications in electronics and photonics.
Used in Pharmaceutical Research:
Although its specific pharmaceutical uses have not been widely explored, 2,3-Thiophenedicarboxylic acid, 4,5-diphenyl-, dimethyl ester has been investigated for its potential medicinal properties. It may serve as a starting point for the development of new drugs or therapeutic agents in the future.

Upstream product

• 501-65-5 diphenyl acetylene 
• 217084-64-5 3,4-bis(methoxycarbonyl)-1,2-dithiete 
• 217084-66-7 (Z,Z,Z,Z)-3,4,7,8,11,12,15,16-octakis(methoxycarbonyl)-1,2,5,6,9,10,13,14-octathiacyclohexadeca-3,7,11,15-tetraene 
• 86543-64-8 (η-cyclopentadienyl)(1,2-diphenyl-1,2-ethylenedithiolato)cobalt(III) 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 403520-39-8 S-α-(dimethyl(phenyl)silyl)benzyl thiobenzoate 

Relevant academic research and scientific papers

Reaction of 1,2-Dithiete with Alkenes and Alkynes: Experimental and Theoretical Study

Reactions of 3,4-bis(methoxycarbonyl)-1,2-dithiete (1) with various alkenes or alkynes formed 2,3-dihydro-1,4-dithiins or thiophenes, respectively. The reactions with alkenes were stereospecific, which indicates the concerted reaction between 1,2-bis(methoxycarbonyl)ethane-1,2-dithione (13), the valence isomer of the 1,2-dithiete, and the dienophiles. Theoretical study confirmed the reactions of 13 with alkenes and alkynes are of reverse electron demand hetero Diels-Alder type. The MO calculations showed the 1,2-dithiete 1 was 5.8 kcal mol-1 more stable than the corresponding ethane-1,2-dithione 13, and the tautomerization energy between the 1,2-dithiete and the ethane-1,2-dithione was also calculated to be 28.5 kcal mol-1 from the 1,2-dithiete, which suggests the tautomerization from 1,2-dithiete 1 to ethane-1,2-dithione 13 is possible at least at high temperature. Reaction of 3,4,7,8-tetrakis(methoxycarbonyl)-1,2,5,6-tetrathiocin (2) or (Z,Z,Z,Z)-3,4,7,8,11,12,15,16-octakis-(methoxycarbonyl)-1,2,5,6,9,10,13,14- octathiacyclohexadeca-3,7,11,15-tetraene (3) with ethyl vinyl ether also formed the 2,3-dihydro-1,4-dithiin derivative, which is the same compound obtained by the reaction of 1,2-dithiete 1 with the ether. 1,2,5,6-Tetrathiocin 2 and 16-membered cyclic compound 3 also reacted with diphenylacetylene to give the thiophene derivative.

A new simple method for the synthesis of thiophene derivatives - Generation of thiocarbonyl ylides from S-α-(dimethylphenylsilyl)benzyl acylates and their cycloaddition with acetylenic dipolarophilesn

The cycloaddition of S-α-(dimethylphenylsilyl)benzyl acylates (1) with acetylenic dipolarophiles via 1,4-silatropy proceeded readily to afford thiophene derivatives. The reaction of thioesters (1) with 1-diethylamino-1-propyne (A), an electron-rich acetylenic dipolarophile, gave 5-aryl-3-diethylamino-4-methyl-2-phenylthiophenes (3) and 4-aryl-2-diethylamino- 3-methyl-5-phenylthiophenes (4). When dimethyl acetylenedicarboxylate (DMAD), an electron-deficient alkyne, was used, the reaction of thioesters (1) afforded thiophene derivatives (4) exclusively.

REACTIONS OF ELEMENTAL SULFUR AND SELENIUM WITH SOME ACETYLENIC COMPOUNDS. FORMATION OF THIOPHENES AND SELENOPHENES

The reaction of 3-butyn-2-one with elemental sulfur at 205-215 deg C in benzene in a stainless autoclave afforded 2,4- and 2,5-diacetylthiophenes in 43percent and 22percent yields, respectively. Under similar conditions, the reaction with elemental selenium gave 2,4- and 2,5-diacetylselenophenes in 32percent and 29percent yields, respectively. Diphenylacetylene reacted with sulfur and selenium to produce tetraphenylthiophene (78percent) and tetraphenylselenophene (38percent), respectively. The reaction of di(2-thienyl)acetylene with sulfur provided tetra(2-thienyl)thiophene in 57percent yield. The reactionof dimethyl acetylenedicarboxylate with sulfur in the presence of diphenylacetylene afforded 2,3-bis(methoxycarbonyl)-4,5-diphenylthiophene (29percent) and tetrakis(methoxycarbonyl)thiophene (15percent). On the basis of these results, the mechanism for the formation of thiophenes and selenophenes is discussed.