Cas no 79757-98-5 (4-Bromo-2-(bromomethyl)thiophene)

4-Bromo-2-(bromomethyl)thiophene structure
79757-98-5 structure
Product Name:4-Bromo-2-(bromomethyl)thiophene
CAS No:79757-98-5
MF:C5H4Br2S
MW:255.958258628845
MDL:MFCD09909587
CID:1036305
PubChem ID:15386015
Update Time:2025-10-29

4-Bromo-2-(bromomethyl)thiophene Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-2-(bromomethyl)thiophene
    • 2-bromomethyl-4-bromothiophene
    • SCHEMBL506596
    • DTXSID20572254
    • NANALAOSHGYIEJ-UHFFFAOYSA-N
    • AKOS009308056
    • EN300-79151
    • 4-bromo-2-bromomethylthiophene
    • 79757-98-5
    • DB-106620
    • MDL: MFCD09909587
    • Inchi: 1S/C5H4Br2S/c6-2-5-1-4(7)3-8-5/h1,3H,2H2
    • InChI Key: NANALAOSHGYIEJ-UHFFFAOYSA-N
    • SMILES: BrCC1=CC(=CS1)Br

Computed Properties

  • Exact Mass: 255.83800g/mol
  • Monoisotopic Mass: 253.84005g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 1
  • Complexity: 76.8
  • 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: 2.9
  • Topological Polar Surface Area: 28.2?2

Experimental Properties

  • Density: 2.1±0.1 g/cm3
  • Boiling Point: 258.7±25.0 °C at 760 mmHg
  • Flash Point: 110.3±23.2 °C
  • Vapor Pressure: 0.0±0.5 mmHg at 25°C

4-Bromo-2-(bromomethyl)thiophene Security Information

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Additional information on 4-Bromo-2-(bromomethyl)thiophene

4-Bromo-2-(bromomethyl)thiophene (CAS No. 79757-98-5): A Versatile Building Block in Organic Synthesis

4-Bromo-2-(bromomethyl)thiophene (CAS No. 79757-98-5) is a highly valuable brominated thiophene derivative that has gained significant attention in recent years due to its versatile applications in organic synthesis, pharmaceutical intermediates, and material science. This compound, with its unique bromine substitution pattern, serves as a crucial building block for the development of various advanced materials and bioactive molecules.

The molecular structure of 4-Bromo-2-(bromomethyl)thiophene features a thiophene ring with two strategically positioned bromine atoms - one at the 4-position and another as a bromomethyl group at the 2-position. This specific arrangement makes it an ideal substrate for cross-coupling reactions, particularly in palladium-catalyzed reactions such as Suzuki, Stille, and Negishi couplings. Recent studies have highlighted its importance in the synthesis of π-conjugated systems, which are essential for organic electronics applications.

In the pharmaceutical industry, 4-Bromo-2-(bromomethyl)thiophene has emerged as a key intermediate for the development of thiophene-containing drugs. Many researchers are exploring its potential in creating novel antimicrobial agents and anti-inflammatory compounds, especially in light of the growing concern about antibiotic resistance. The compound's ability to undergo various nucleophilic substitutions makes it particularly valuable for structure-activity relationship studies in drug discovery programs.

The material science applications of 4-Bromo-2-(bromomethyl)thiophene are equally impressive. It serves as a precursor for conducting polymers and organic semiconductors, which are critical components in flexible electronics and organic photovoltaic devices. With the increasing demand for sustainable energy solutions, researchers are particularly interested in how this compound can contribute to the development of more efficient organic solar cells and light-emitting diodes (OLEDs).

From a synthetic chemistry perspective, 4-Bromo-2-(bromomethyl)thiophene offers multiple reactive sites that can be selectively modified. The bromomethyl group is particularly reactive towards nucleophiles, allowing for the introduction of various functional groups. This characteristic has made it a popular choice for creating molecular libraries in combinatorial chemistry approaches. Recent publications have demonstrated its utility in click chemistry applications and the construction of complex heterocyclic systems.

The stability and storage requirements of 4-Bromo-2-(bromomethyl)thiophene are important considerations for researchers. While the compound is generally stable under recommended storage conditions (typically at 2-8°C in a dry environment), proper handling procedures should always be followed. Many laboratories are now focusing on developing greener synthetic routes for such brominated compounds to align with the principles of green chemistry and sustainable synthesis.

Analytical characterization of 4-Bromo-2-(bromomethyl)thiophene typically involves a combination of techniques including NMR spectroscopy (both 1H and 13C), mass spectrometry, and HPLC analysis for purity determination. The compound's distinct spectral signatures make it relatively easy to identify and quantify in reaction mixtures. Recent advances in analytical chemistry have enabled more precise monitoring of its transformations in complex reaction systems.

In terms of commercial availability, 4-Bromo-2-(bromomethyl)thiophene is supplied by several specialty chemical manufacturers worldwide. The global market for such fine chemicals has been growing steadily, driven by increasing demand from both academic and industrial research sectors. Quality control parameters typically include specifications for purity grade (often ≥95% or ≥98%), moisture content, and residual solvent levels.

Future research directions for 4-Bromo-2-(bromomethyl)thiophene are likely to focus on its applications in bioconjugation chemistry and the development of smart materials. With the rapid advancement of nanotechnology, there is growing interest in how this compound can be incorporated into functional nanomaterials with tailored properties. Additionally, its potential in medicinal chemistry continues to be explored, particularly in the design of targeted therapeutics and diagnostic agents.

For researchers working with 4-Bromo-2-(bromomethyl)thiophene, it's important to stay updated with the latest literature and patent developments. Many recent innovations have focused on improving the atom economy of reactions involving this compound and developing more efficient catalytic systems for its transformations. The compound's versatility ensures that it will remain an important tool in the synthetic chemist's arsenal for years to come.

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