Cas no 51285-60-0 (4,4'-Dibromo-2,2'-bithiophene)

4,4'-Dibromo-2,2'-bithiophene is a brominated bithiophene derivative widely used as a key intermediate in organic synthesis and materials science. Its rigid, conjugated structure and reactive bromine substituents make it valuable for cross-coupling reactions, particularly in the preparation of conjugated polymers and small molecules for optoelectronic applications. The compound’s high purity and well-defined reactivity facilitate precise molecular design in the development of organic semiconductors, OLEDs, and photovoltaic materials. Its stability under standard conditions ensures reliable handling and storage. Researchers favor 4,4'-Dibromo-2,2'-bithiophene for its consistent performance in Suzuki, Stille, and other palladium-catalyzed coupling reactions, enabling efficient synthesis of advanced functional materials.
4,4'-Dibromo-2,2'-bithiophene structure
4,4'-Dibromo-2,2'-bithiophene structure
Product Name:4,4'-Dibromo-2,2'-bithiophene
CAS No:51285-60-0
MF:C8H4Br2S2
MW:324.055357933044
MDL:MFCD00508561
CID:872262
PubChem ID:253659727
Update Time:2025-05-23

4,4'-Dibromo-2,2'-bithiophene Chemical and Physical Properties

Names and Identifiers

    • 4,4''-dibromo-2,2''-bithiophene
    • 4,4'-Dibromo-2,2'-bithiophene
    • 4-bromo-2-(4-bromothiophen-2-yl)thiophene
    • 2,2'-Bithiophene,4,4'-dibromo
    • 3,3'-dibromo-2,2'-bithiophene
    • 4,4’-dibromo-2,2’-bithiophene
    • 4,4'-Dibrom-2,2'-dithienyl
    • 4,4'-Dibromo-[2,2']bithiophenyl
    • 4,4'dibromo-2,2'-bithiophene
    • 4,4'-dibromo-2,2'-dithiophene
    • 4-bromo-2-(4-bromo(2-thienyl))thiophene
    • BAS 00529273
    • 4,4'-dibromo bithiophene
    • 2,2'-Bithiophene, 4,4'-dibromo-
    • ST024591
    • D4181
    • AS-59869
    • SCHEMBL771882
    • AKOS000664077
    • DTXSID40351982
    • MFCD00508561
    • 4 pound not4 inverted exclamation mark -dibromo-2 pound not2 inverted exclamation mark -bithiophene
    • T70985
    • 51285-60-0
    • MDL: MFCD00508561
    • Inchi: 1S/C8H4Br2S2/c9-5-1-7(11-3-5)8-2-6(10)4-12-8/h1-4H
    • InChI Key: KITUXFRDWJKACE-UHFFFAOYSA-N
    • SMILES: BrC1=CSC(=C1)C1=CC(=CS1)Br

Computed Properties

  • Exact Mass: 321.81200
  • Monoisotopic Mass: 321.81212g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 147
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 56.5
  • XLogP3: 4.4

Experimental Properties

  • Density: 2.0±0.1 g/cm3
  • Melting Point: 132.0 to 136.0 deg-C
  • Boiling Point: 324.8±37.0 °C at 760 mmHg
  • Flash Point: 150.3±26.5 °C
  • PSA: 56.48000
  • LogP: 5.00160
  • Vapor Pressure: 0.0±0.7 mmHg at 25°C

4,4'-Dibromo-2,2'-bithiophene Security Information

4,4'-Dibromo-2,2'-bithiophene Pricemore >>

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Additional information on 4,4'-Dibromo-2,2'-bithiophene

Professional Introduction to 4,4'-Dibromo-2,2'-bithiophene (CAS No. 51285-60-0)

4,4'-Dibromo-2,2'-bithiophene is a significant compound in the field of organic electronics and materials science, widely recognized for its unique structural and electronic properties. This bithiophene derivative, characterized by its brominated aromatic rings, has garnered considerable attention due to its potential applications in the development of advanced optoelectronic devices. The compound's molecular structure, featuring a conjugated system of sulfur-rich aromatic units, makes it an attractive candidate for various chemical and pharmaceutical research endeavors.

The chemical formula of 4,4'-Dibromo-2,2'-bithiophene is C8H4B2S2, and its CAS number, 51285-60-0, serves as a unique identifier in scientific literature and databases. This compound belongs to the class of bithiophene derivatives, which are known for their electron-deficient properties and ability to form stable π-conjugated systems. Such characteristics are highly valuable in the design of organic semiconductors, organic light-emitting diodes (OLEDs), and organic photovoltaic cells.

In recent years, research on bithiophene-based materials has seen substantial growth, driven by the increasing demand for lightweight, flexible, and cost-effective electronic components. The bromination of bithiophene at the 4-position enhances its reactivity, making it a versatile intermediate in synthetic chemistry. This reactivity has been leveraged in the development of novel polymers and small-molecule organic semiconductors that exhibit superior charge transport properties.

One of the most compelling aspects of 4,4'-Dibromo-2,2'-bithiophene is its role as a building block in the synthesis of more complex oligomers and polymers. These derivatives often exhibit improved thermal stability and solubility, which are critical factors for their application in industrial-scale manufacturing processes. For instance, researchers have utilized this compound to develop high-performance polythiophenes that demonstrate excellent performance in organic field-effect transistors (OFETs). The bromine atoms provide sites for further functionalization via cross-coupling reactions such as Suzuki or Stille couplings, enabling the creation of tailored materials with specific electronic characteristics.

The electronic properties of 4,4'-Dibromo-2,2'-bithiophene have been extensively studied in the context of molecular electronics. Its ability to undergo efficient charge transport makes it an ideal candidate for use in flexible electronics and wearable devices. Recent advancements in this area have shown that incorporating this bithiophene derivative into thin-film transistors can lead to devices with higher mobility and longer operational lifetimes. These findings are particularly relevant as the electronics industry moves towards more sustainable and energy-efficient technologies.

In addition to its applications in electronics, 4,4'-Dibromo-2,2'-bithiophene has shown promise in the field of photovoltaics. The compound's ability to absorb light across a broad spectrum and its efficient charge separation capabilities make it a valuable component in organic solar cells. Researchers have reported significant improvements in power conversion efficiencies by incorporating this bithiophene derivative into bulk heterojunction solar cell architectures. These developments highlight the potential of bithiophene-based materials to contribute to renewable energy solutions.

The synthesis of 4,4'-Dibromo-2,2'-bithiophene typically involves bromination reactions on a precursor bithiophene molecule. Advances in synthetic methodologies have enabled more efficient and scalable production processes for this compound. For example, electrochemical bromination techniques have been developed that offer higher selectivity and yield compared to traditional chemical bromination methods. Such improvements are crucial for reducing production costs and minimizing waste generation.

The impact of 4,4'-Dibromo-2,2'-bithiophene on academic research cannot be overstated. It has served as a catalyst for numerous studies exploring the fundamental principles of molecular electronics and materials science. By providing a platform for investigating charge transport mechanisms and molecular design strategies, this compound has fostered innovation across multiple disciplines. The findings from these studies not only enhance our understanding of bithiophene derivatives but also pave the way for new applications in technology and medicine.

, the future prospects for 4,4''-

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