248-70-4

Basic information

• Product Name: Benzo[b]benzo[4,5]thieno[2,3-d]thiophene
• Synonyms: Benzo[b]benzo[4,5]thieno[2,3-d]thiophene;benzthieno[3,2-b]benzothiophene;[1]benzothiolo[3,2-b][1]benzothiole
• CAS NO: 248-70-4
• Molecular Formula: C₁₄H₈S₂
• Molecular Weight: 240.34332
• EINECS: -0
• Mol File: 248-70-4.mol

Chemical Properties

• Melting Point: 218.0 to 222.0 °C
• Boiling Point: 432.3°C at 760 mmHg
• Flash Point: 162.1°C
• Appearance: /
• Density: 1.407g/cm³
• Vapor Pressure: 2.83E-07mmHg at 25°C
• Refractive Index: 1.854
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: Benzo[b]benzo[4,5]thieno[2,3-d]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[b]benzo[4,5]thieno[2,3-d]thiophene(248-70-4)
• EPA Substance Registry System: Benzo[b]benzo[4,5]thieno[2,3-d]thiophene(248-70-4)

Safety Data

• Hazardous Substances Data: 248-70-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzo[b]benzo[4,5]thieno[2,3-d]thiophene serves as a key building block in the creation of complex organic molecules, such as polymers, pharmaceuticals, and dyes. Its structural and functional attributes make it a versatile component in the development of new materials with tailored properties.
Used in Organic Electronics:
Due to its electronic properties, Benzo[b]benzo[4,5]thieno[2,3-d]thiophene is utilized in the field of organic electronics, where it contributes to the performance of devices such as organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). Its ability to modulate charge transport and its compatibility with other organic materials make it a promising candidate for enhancing device efficiency and stability.
Used in Optoelectronics:
Benzo[b]benzo[4,5]thieno[2,3-d]thiophene is also employed in optoelectronic applications, capitalizing on its optical characteristics to improve the performance of devices like solar cells and photodetectors. Its light absorption and emission properties are harnessed to optimize energy conversion and sensing capabilities.
Used in Organic Semiconductors:
Benzo[b]benzo[4,5]thieno[2,3-d]thiophene is being explored for its potential in organic semiconductors, where it could play a role in enhancing the performance of thin-film transistors and other semiconductor devices by improving charge mobility and stability.
Used in Organic Photovoltaics:
Benzo[b]benzo[4,5]thieno[2,3-d]thiophene is under investigation for its applications in organic photovoltaics, where it could contribute to the development of more efficient and cost-effective solar energy conversion technologies. Its light-absorbing properties and compatibility with other photovoltaic materials make it a candidate for improving the power conversion efficiency of organic solar cells.

InChI:InChI=1/C14H8S2/c1-3-7-11-9(5-1)13-14(15-11)10-6-2-4-8-12(10)16-13/h1-8H

Upstream product

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Downstream Products

• 1781261-95-7 C₂₈H₂₈S₂ 
• 1781261-91-3 C₂₄H₂₀S₂ 

Relevant articles and documents

Synthesis of [1]benzothiopheno[2,3-b][1]benzothiophene derivatives through iodine-mediated sulfuration reaction of 1,1-diarylethylenes

Acceleration of the reaction for the synthesis of [1]benzothiopheno[2,3-b][1]benzothiophenes (BTBTs) from 1,1-diarylethylenes was accomplished by the addition of molecular iodine. Postulated intermediates 3-arylbenzo[b]thiophenes were also selectively prepared by simply changing the amount of iodine and the reaction time.

Facile synthesis of [1]benzothieno[3,2-b]benzothiophene from o-dihalostilbenes

A convenient one-pot synthesis of [1]benzothieno[3,2-b]benzothiophene from readily available o-dihalostilbenes using combined reagents of sodium sulfide nonahydrate (Na2S·9H2O) or sodium hydrosulfide hydrate (NaSH·nH2O) and sulfur is described along with plausible reaction paths in this intriguing reaction.

Thiones as reactive intermediates in condensations of diketones with aromatics mediated by tetraphosphorus decasulfide

Phenanthrene-9,10-quinone and P4S10 react with phenols on being heated to give oxathiins, e.g., 9 the dioxin 22, ethers, e.g., 14 arylphenanthrenols, e.g., 10 and furanols, e.g., 17 in addition to sulfides, e.g., 26 and disulfides, e

A ONE-POT SYNTHESIS OF SUBSTITUTED THIENOTHIOPHENES AND SELENOLOSELENOPHENES

Heating a mixture of 2,5-dimethyl-3-hexyne-2,5-diol (3a) with elemental sulfur in benzene at 190-200 deg C in an autoclave affords 3,6-dimethylthienothiophene (5a) in 26percent yield.The reaction provides a practical one-pot synthesis of several gr

HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXII. THERMAL TRANSFORMATIONS OF EXO-CHLORINE-SUBSTITUTED TOLUENES

The gas-phase pyrolysis of exo-chlorine-substituted toluenes in an atmosphere of nitrogen or hydrogen sulfide was investigated.Hydrogen sulfide stimulates the thermolysis of benzyl chloride, accelerating the formation of toluene and stilbene at 430 deg C.The other reaction products are anthracene and bibenzyl.Similar compounds and also phenanthrene are formed during the pyrolysis of benzylidene chloride in an atmosphere of nitrogen or hydrogen sulfide (500 deg C).Benzotrichloride is distinguished by its high stability; its pyrolysis mainly with the formation of 1,2-dichloro-1,2-diphenylethylene is realized at temperatures above 550 deg C.With hydrogen sulfide it reacts at 400 deg C to form bibenzyl, stilbene, anthracene, phenanthrene, and thianaphtenothianaphthene.The latter is the main product in a recirculation-type system.

1,1'2,2'-Tetrathiafulvalenes, III. - Syhthesis, Properties, and Reactions of 3,3'-Bi(3H-1,2-dithiolylidenes)(1,1',2,2'-Tetrathiafulvalenes)

1,1',2,2'-tetrathiafulvalenes 1 can be prepared by different methods from the cations of 1,2-dithiolylium salts 4 which are either unsubstituted or appropriate substituted in 3-position (instead of 3-Cl also H or SCH3).The structure of 1 is substantiated by chemical arguments.IR and 13C-NMR spectra support the absence of thioxo groups. - Like the 1,1',3,3'-isomers 2 the 1,1',2,2'-tetrathiafulvalenes are disposed to stepwise donation of electrons with formation of the radical cation and dication salts 25 or 11, respectively, as well as to the formation of charge transfer complexes with tetracyanoethylene, tetracyanoquinodimethane, and 2,3-dichloro-5,6-dicyanobenzoquinone.Tris(triphenylphosphine)rhodium(I) chloride and tetrakis(triphenylphosphine)platinum(O) yield complexes with 1a. - Thermolysis of 1 produces thienothiophenes 6.Partial desulfuration of 1a, for example, is also feasible with oxidizing agents like lead(IV) acetate.Selenium dioxide, however, gives the corresponding thienofuran 41.The reaction with trialkyl phosphites yields a disulfide - probably the 2,2'-bi(2H-thietylidene) 38 - the thermolysis of which gives the thienothiophene 6a. - Compounds 1a and 1c do not react with dimethyl acetylenedicarboxylate, isothiocyanate, several 1,3-dipoles (azides), and also not with elementary sulfur, however, 1e forms with sulfur the 3H-1,2-dithiol-3-thione 5e (X = S).