13090-49-8

Basic information

• Product Name: Dithieno(3,4-b:3,4-d)thiophene
• Synonyms: Bisthieno[3,4-b:3',4'-d]thiophene
• CAS NO: 13090-49-8
• Molecular Formula: C₈H₄S₃
• Molecular Weight: 196.318
• Mol File: 13090-49-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 364.1 °C at 760 mmHg
• Flash Point: 129.8 °C
• Density: 1.556 g/cm³
• CAS DataBase Reference: Dithieno(3,4-b:3,4-d)thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: Dithieno(3,4-b:3,4-d)thiophene(13090-49-8)
• EPA Substance Registry System: Dithieno(3,4-b:3,4-d)thiophene(13090-49-8)

Safety Data

• Hazardous Substances Data: 13090-49-8(Hazardous Substances Data)

Usage

General Description

Dithieno(3,4-b:3,4-d)thiophene is a chemical compound that belongs to the family of thiophene derivatives. It is a heterocyclic compound with a unique structure, consisting of two thiophene rings fused together in a "b:d" orientation. Dithieno(3,4-b:3,4-d)thiophene has interesting electronic and optical properties, making it useful in organic electronic and optoelectronic devices. Dithieno(3,4-b:3,4-d)thiophene has been studied for its potential applications in organic semiconductors, organic thin-film transistors, and organic photovoltaic devices. Its synthesis and chemical properties make it a promising candidate for various technological applications in the field of organic electronics.

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Relevant articles and documents

The efficient synthesis of dithieno [3,4-b:3',4'-d] thiophene

The efficient synthesis of dithieno[3,4-b:3',4'-d]thiophene was improved by the introduction of TMS groups in four synthetic steps including TMS protection, sulfidation, intramolecular cyclization, and TMS removal. The total yield is 55-63% with 3,4-dibro

Asymmetric b thiopheneglyoxylic and fragrant heterocyclic the synthetic method of the compound of

The invention discloses a synthesis method of asymmetrical beta-bromodithieno heteroaromatic compounds, which comprises the following steps: reacting 4,4'-dibromo-3,3'-bithiophene used as a raw material and n-butyl lithium in anhydrous ethyl ether; then performing cyclization reaction under the action of different cyclization reagents (bis(benzenesulfonyl)thioether, N,N-dimethylformyl chloride and dimethyl dichlorosilane); and finally, performing water quenching to generate the asymmetrical beta-bromodithieno heteroaromatic compounds and symmetrical dithieno heteroaromatic compounds, wherein the asymmetrical beta-bromodithieno heteroaromatic compounds and a small amount of symmetrical dithieno heteroaromatic compounds are selectively obtained at a high yield in the presence of the n-butyl lithium; the asymmetrical beta-bromodithieno heteroaromatic compounds include 3-bromo-dithieno[2,3-b:3',4'-d]thiophene, 3-bromo-7H-cyclopentano[1,2-b:3,4-c']dithiophene-7-one and 3-bromo-7,7-dimethyl-7H-dithieno[2,3-b:3',4'-d]silole; and the symmetrical dithieno heteroaromatic compounds include dithieno[3,4-b:3',4'-d]thiophene, 7H-cyclopentano[1,2-c:3,4-c']dithiophene-7-one and 4,4-dimethyl-4H-dithieno[3,4-b:3',4'-d]silole. The synthesis process disclosed by the invention is operable, and the reaction condition is involved with a water-free, oxygen-free and low-temperature condition, thus ensuring that the invention is suitable for laboratory-scale preparation.

New syntheses of tricyclic thiophenes and cyclic tetrathiophenes using transition-metal-catalyzed cyclization

New synthetic methods for polycyclic thiophenes were developed. Thus, dithienothiophenes, cyclopentadithiophene, silacyclopentadithiophenes, and cyclooctatetrathiophenes were synthesized in moderate to good yields by using the CuCl2-mediated cyclization of organocopper(I) and organozinc intermediates prepared from dilithio-derivatives with CuCN or ZnCl2, respectively. A direct cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) also gave dithienothiophenes, cyclopenta-dithiophenes, and silacyclopentadithiophenes in good yields.