Cas no 5556-13-8 (4,4'-dibromo-3,3'-bithiophene)

4,4'-Dibromo-3,3'-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, such as Suzuki or Stille couplings, enabling the construction of extended π-conjugated systems. This compound is particularly useful in the development of organic semiconductors, conductive polymers, and optoelectronic materials due to its ability to facilitate precise molecular design and controlled polymerization. Its high purity and stability ensure reliable performance in demanding applications, including organic field-effect transistors (OFETs) and photovoltaic devices.
4,4'-dibromo-3,3'-bithiophene structure
4,4'-dibromo-3,3'-bithiophene structure
Product Name:4,4'-dibromo-3,3'-bithiophene
CAS No:5556-13-8
MF:C8H4Br2S2
MW:324.055357933044
MDL:MFCD17012206
CID:351542
PubChem ID:11438704
Update Time:2025-05-26

4,4'-dibromo-3,3'-bithiophene Chemical and Physical Properties

Names and Identifiers

    • 3,3'-Bithiophene, 4,4'-dibromo-
    • 3-bromo-4-(4-bromothiophen-3-yl)thiophene
    • 4,4'-DIBROMO-3,3'-BITHIOPHENE
    • 4,4'-Dibromo-3,3'-dithienyl
    • DTXSID60465954
    • CS-16747
    • 5556-13-8
    • AKOS025395144
    • SCHEMBL7253177
    • D5374
    • FT-0763096
    • 4,4'-dibrom-3,3'-bithiophen
    • MFCD17012206
    • F15698
    • CS-0102872
    • DB-083579
    • 4,4'-dibromo-3,3'-bithiophene
    • MDL: MFCD17012206
    • Inchi: 1S/C8H4Br2S2/c9-7-3-11-1-5(7)6-2-12-4-8(6)10/h1-4H
    • InChI Key: QAVREGJMFYCNKD-UHFFFAOYSA-N
    • SMILES: BrC1=CSC=C1C1=CSC=C1Br

Computed Properties

  • Exact Mass: 321.81212
  • 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
  • XLogP3: 4.3
  • Topological Polar Surface Area: 56.5?2

Experimental Properties

  • Density: 1.951±0.06 g/cm3 (20 oC 760 Torr),
  • Melting Point: 129 oC (ligroine )
  • Boiling Point: 271.4±35.0 oC (760 Torr),
  • Flash Point: 117.9±25.9 oC,
  • Solubility: Almost insoluble (0.013 g/l) (25 o C),
  • PSA: 0

4,4'-dibromo-3,3'-bithiophene Pricemore >>

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Additional information on 4,4'-dibromo-3,3'-bithiophene

Introduction to 4,4'-Dibromo-3,3'-Bithiophene (CAS No. 5556-13-8)

4,4'-Dibromo-3,3'-bithiophene, also known by its CAS registry number CAS No. 5556-13-8, is a versatile organic compound that has garnered significant attention in the fields of materials science and organic electronics. This compound belongs to the family of bithiophenes, which are extensively studied for their unique electronic properties and potential applications in advanced materials. The molecule consists of two thiophene rings connected through a sulfur atom at the 3-position, with bromine substituents at the 4-position of each ring. This structure imparts the compound with a combination of conjugation and halogen substitution, making it highly suitable for various chemical modifications and functionalization.

Recent advancements in synthetic methodologies have enabled researchers to explore novel routes for the synthesis of 4,4'-dibromo-3,3'-bithiophene. One such approach involves the coupling of bromothiophene derivatives under controlled conditions to form the bithiophene framework. These methods not only enhance the yield but also provide better control over the purity of the final product. The compound's ability to undergo further substitution reactions has made it a valuable precursor in the synthesis of more complex structures, such as oligothiophenes and polythiophenes.

The electronic properties of 4,4'-dibromo-3,3'-bithiophene have been extensively studied using computational chemistry techniques and experimental measurements. The presence of bromine atoms introduces electron-withdrawing effects, which modulate the compound's optical and electronic characteristics. These properties make it an attractive candidate for applications in organic semiconductors, light-emitting diodes (LEDs), and photovoltaic devices. Recent studies have demonstrated that incorporating this compound into polymer blends can significantly improve charge transport properties, paving the way for its use in next-generation electronic devices.

In terms of physical properties, 4,4'-dibromo-3,3'-bithiophene exhibits a high degree of thermal stability and good solubility in common organic solvents. These characteristics are advantageous for processing techniques such as spin-coating and inkjet printing, which are widely used in the fabrication of thin-film devices. Moreover, the compound's ability to form stable films has been leveraged in research aimed at developing flexible electronics and wearable devices.

The application of 4,4'-dibromo-3,3'-bithiophene extends beyond electronics into areas such as sensing and catalysis. For instance, recent research has explored its potential as a sensing material for detecting trace amounts of gases like oxygen and nitrogen dioxide. The compound's responsiveness to these gases is attributed to its ability to undergo reversible redox reactions upon exposure.

In conclusion, 4,4'-dibromo-3,3'-bithiophene (CAS No. 5556-13-8) stands out as a promising material with a wide range of applications across multiple disciplines. Its unique combination of structural features and electronic properties continues to drive innovative research efforts aimed at harnessing its full potential in modern technology.

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