5556-13-8

Basic information

• Product Name: 4,4'-Dibromo-3,3'-bithiophene
• Synonyms: 4,4'-Dibromo-3,3'-bithiophene;4,4'-Dibromo-3,3'-dithienyl;4,4'-Dibrom-3,3'-bithiophen
• CAS NO: 5556-13-8
• Molecular Formula: C₈H₄Br₂S₂
• Molecular Weight: 324.05536
• Mol File: 5556-13-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 129℃ (ligroine )
• Boiling Point: 271.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.951±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4,4'-Dibromo-3,3'-bithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dibromo-3,3'-bithiophene(5556-13-8)
• EPA Substance Registry System: 4,4'-Dibromo-3,3'-bithiophene(5556-13-8)

Safety Data

• Hazardous Substances Data: 5556-13-8(Hazardous Substances Data)

Usage

General Description

4,4'-Dibromo-3,3'-bithiophene is a chemical compound consisting of two bromine atoms and two thiophene rings. It is commonly used in organic synthesis and material science, particularly in the field of organic electronics. The presence of bromine atoms in its structure makes it useful as a building block for the synthesis of functional materials such as conducting polymers and organic semiconductors. It has also been studied for its potential applications in the development of organic light-emitting diodes (OLEDs) and organic photovoltaic devices (OPVs) due to its favorable electronic and optical properties. Additionally, 4,4'-Dibromo-3,3'-bithiophene has been investigated for its potential as a corrosion inhibitor in metal surfaces and as a precursor for the synthesis of heterocyclic compounds with biological activity.

Upstream product

• 3141-26-2 3,4-dibromothiophene 
• 262858-24-2 bis(4-bromo-3-thienyl)dimethyltin 

Downstream Products

• 56598-43-7 cycloocta[1,2-c:3,4-c':5,6-c'':7,8-c''']tetrathiophene 
• 1032350-44-9 4,4'-bis(phenylethynyl)-3,3'-bithiophene 
• 3172-56-3 3,3'-bithiophene 
• 28686-96-6 4-bromo-3,3'-bithiophene 
• 13090-49-8 dithieno[3, 4-b:3',4'-d]thiophene 
• 1422259-89-9 3-bromodithieno[2,3-b,3′,4′-d]thiophene 
• 25796-78-5 7H-cyclopenta[1,2-c:3,4-c']dithiophene-7-one 
• 1422259-90-2 3-bromo-7H-cyclopenta[1,2-b:3,4-c']-dithiophen-7-one 

Relevant articles and documents

Rethinking Uncaging: A New Antiaromatic Photocage Driven by a Gain of Resonance Energy

Photoactivatable compounds for example photoswitches or photolabile protecting groups (PPGs, photocages) for spatiotemporal light control, play a crucial role in different areas of research. For each application, parameters such as the absorption spectrum, solubility in the respective media and/or photochemical quantum yields for several competing processes need to be optimized. The design of new photochemical tools therefore remains an important task. In this study, we exploited the concept of excited-state-aromaticity, first described by N. Colin Baird in 1971, to investigate a new class of photocages, based on cyclic, ground-state-antiaromatic systems. Several thio- and nitrogen-functionalized compounds were synthesized, photochemically characterized and further optimized, supported by quantum chemical calculations. After choosing the optimal scaffold, which shows an excellent uncaging quantum yield of 28 %, we achieved a bathochromic shift of over 100 nm, resulting in a robust, well accessible, visible light absorbing, compact new photocage with a clean photoreaction and a high quantum product (??Φ) of 893 M?1 cm?1 at 405 nm.

Efficient construction of biaryls and macrocyclic cyclophanes via electron-transfer oxidation of Lipshutz cuprates

An efficient method for the homocoupling of aryl halides by electron-transfer oxidation of Lipshutz cuprates (Ar2Cu(CN)Li 2) with organic electron acceptors is disclosed. Thus, various types of Lipshutz cuprates are prepared by successive treatment of aryl or heteroaryl bromides with tert-butyllithium and CuCN. The electron-transfer oxidation of Lipshutz cuprates with p-benzoquinones proceeds smoothly to afford the corresponding homocoupling products in moderate to good yields. Furthermore, it can be applied to the construction of either thiophene- or benzene-fused 10-membered ring cyclophanes. For the synthesis of 10-membered cyclophanes, the linear C-Cu-C structure of Lipshutz cuprates should be maintained in the dimetallacyclic intermediates, producing the large ring cyclophanes efficiently. The X-ray analysis of the cyclophanes reveals that the difference in the bridging atoms results in the different conformations of the macrocyclic rings. Thus, the silicon-bridged cyclophane 5a adopts a D2-symmetric structure with a twisted rhombic arrangement of four thiophene rings, whereas the methylene- and oxygen-bridged cyclophanes 5b and 5c possess C2h- and C2-symmetric structures with chair- and boatlike conformations, respectively. The 1H NMR spectrum of C2-symmetric 5c is temperature-dependent, and the activation energy (ΔG?) for the conformational change is 10.1 kcal/mol.

Helically annelated and cross-conjugated oligothiophenes: Asymmetric synthesis, resolution, and characterization of a carbon-sulfur [7]helicene

The synthesis and characterization of a novel oligothiophene, in which the thiophene rings are annelated into a [7]helicene with cross-conjugated π-system, are described. Such [7]helicenes may be viewed as fragments of the unprecedented carbon-sulfur (Cs