267-65-2

Basic information

• Product Name: Benzo[1,2-b:4,5-b']dithiophene
• Synonyms: Benzo[1,2-b:4,5-b']dithiophene;Benzo[1,2-b:4,5-b']dithiophene;IN1601, Benzo[1,2-b:4,5-b']dithiophene;Benzo[1,2-b:4,5-b']dithioph;thieno[2,3-f][1]benzothiole;1,5-Dithia-s-indacene
• CAS NO: 267-65-2
• Molecular Formula: C₁₀H₆S₂
• Molecular Weight: 190.29
• Mol File: 267-65-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 196.0 to 200.0 °C
• Boiling Point: 344.4±15.0 °C(Predicted)
• Appearance: /
• Density: 1.392±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: Benzo[1,2-b:4,5-b']dithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[1,2-b:4,5-b']dithiophene(267-65-2)
• EPA Substance Registry System: Benzo[1,2-b:4,5-b']dithiophene(267-65-2)

Safety Data

• Hazardous Substances Data: 267-65-2(Hazardous Substances Data)

Usage

Description

Benzo[1,2-b:4,5-b']dithiophene is a heterocyclic organic compound characterized by the fusion of two thiophene rings with a benzene ring. This unique structure endows it with specific chemical and electronic properties, making it a valuable component in various applications within the fields of organic electronics and materials science.

Uses

Used in Organic Electronics Industry:
Benzo[1,2-b:4,5-b']dithiophene serves as a reagent in the synthesis of high-crystalline medium-band-gap polymers, which are crucial for the development of organic photovoltaic cells. These polymers contribute to the efficiency and performance of solar cells by optimizing the absorption of light and charge transport.
Additionally, Benzo[1,2-b:4,5-b']dithiophene acts as a precursor in the preparation of benzodithiophene derivatives. These derivatives possess versatile applications within the realm of organic electroluminescence devices. They can be utilized as hole injection materials, enhancing the efficiency of charge injection at the anode interface. Furthermore, they can function as hole transport materials, facilitating the movement of holes within the device and improving overall performance. Lastly, they can also be employed as fluorescent materials, contributing to the emission of light in electroluminescent applications.

Upstream product

• 116598-74-4 4,8-dichloro-benzo[1,2-b;4,5-b']dithiophene 
• 105-05-5 1,4-diethylbenzene 
• 478190-79-3 1,4-dibromo-2,5-bis-(trimethylsilylethynyl)benzene 
• 100130-93-6 2,5,2',5'-tetrachloro-4,4'-disulfanediyl-bis-benzenesulfonyl chloride 
• 109402-24-6 1,4-dichloro-2,5-bis-(2,2-dimethoxy-ethylsulfanyl)-benzene 
• 100606-87-9 2,5-dichloro-benzene-1,4-dithiol 
• 182952-34-7 Benzo[1,2-b;4,5-b']dithiophene-4,8-dicarboxylic acid diethyl ester 
• 63262-06-6 1,4-dibromo-2,5-diiodobenzene 
• 872513-79-6 2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']dithiophene 
• 35991-68-5 4,8-benzo<1,2-b:4,5-b'>dithiophenedicarboxylic acid 
• 72771-52-9 2-(3-Thienylmethyl)-3-thiophenecarboxaldehyde 

Downstream Products

• 32281-36-0 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione 
• 1448449-14-6 2,6-di(2-(pyridine-2-yl)-phenyl)benzo[1,2-b;4,5-b']dithiophene 
• 861398-06-3 2,6-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzo[1,2-b:4,5-b′]dithiophene 

Relevant articles and documents

Facile synthesis, structure, and properties of benzo[1,2-b:4,5-b′] dichalcogenophenes

A general and convenient synthesis of benzo[1,2-b:4,5-b′]- dichalcogenophenes including the thiophene (BDT, 1), selenophene (BDS, 2), and tellurophene (BDTe, 3) homologues is developed. Thus synthesized heterocycles are structurally characterized by single-crystal X-ray analysis, and all three homologues are isostructural with one another. They all have completely planar molecular structures packed in a herringbone arrangement. Their physicochemical properties were also elucidated by means of cyclic voltammetry (CV) and UV-vis spectra.

One-pot synthesis of benzo[b]thiophenes and benzo[b]selenophenes from o-halo-substituted ethynylbenzenes: convenient approach to mono-, bis-, and tris-chalcogenophene-annulated benzenes

A convenient one-pot procedure for the synthesis of benzo[b]thiophenes and selenophenes from readily available o-halo-ethynylbenzene precursors is described. Regardless of the substituent on the acetylene terminus or the number of cyclization moieties on the precursors, various benzo[b]thiophenes and selenophenes, including not only the parent, alkyl-, and phenyl-substituted derivatives but also benzo[1,2-b:4,5-b']dithiophenes and diselenophenes and benzo[1,2-b:3,4-b':5,6-b'']trithiophenes and triselenophenes can be prepared in good to high yields.

CATALYTIC SYNTHESIS OF BENZOTHIOPHENE AND BENZODITHIOPHENES

A heterocyclization reaction, namely, the interaction of H2S and ethylbenzene with the formation of benzothiophene on an effective catalyst has been studied in a flowing bed system under atmospheric pressure at temperatures from 525 to 625 deg C, a liquid ethylbenzene space velocity, νwt., from 0.3 to 1.3 h-1 and a 2:9.0 H2S/ethylbenzene molar ratio.On the basis of the kinetic data obtained, it is suggested that the heterocyclization reaction proceeds via dehydrogenation of ethylbenzene to styrene.Two isomeric benzodithiophenes have been prepared from H2S and p-diethylbenzene using the same catalyst.