Cas no 1065184-21-5 (2-Bromo-5-(ethoxymethyl)thiophene)

2-Bromo-5-(ethoxymethyl)thiophene is a brominated thiophene derivative featuring an ethoxymethyl substituent at the 5-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of functionalized heterocycles and conjugated materials. The bromine atom at the 2-position enables efficient cross-coupling reactions, such as Suzuki or Stille couplings, facilitating the construction of complex molecular architectures. The ethoxymethyl group enhances solubility and offers a handle for further functionalization. Its well-defined reactivity and stability make it suitable for applications in pharmaceuticals, agrochemicals, and materials science, particularly in the development of optoelectronic materials. The compound is typically handled under inert conditions to preserve its reactivity.
2-Bromo-5-(ethoxymethyl)thiophene structure
1065184-21-5 structure
Product Name:2-Bromo-5-(ethoxymethyl)thiophene
CAS No:1065184-21-5
MF:C7H9BrOS
MW:221.114760160446
MDL:MFCD16094454
CID:5074121
PubChem ID:59332739
Update Time:2026-03-01

2-Bromo-5-(ethoxymethyl)thiophene Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-5-(ethoxymethyl)thiophene
    • Thiophene, 2-bromo-5-(ethoxymethyl)-
    • 2-Bromo-5-(ethoxymethyl)thiophene
    • MDL: MFCD16094454
    • Inchi: 1S/C7H9BrOS/c1-2-9-5-6-3-4-7(8)10-6/h3-4H,2,5H2,1H3
    • InChI Key: AKCZPTUAEIAAFC-UHFFFAOYSA-N
    • SMILES: BrC1=CC=C(COCC)S1

Computed Properties

  • Exact Mass: 219.95575g/mol
  • Monoisotopic Mass: 219.95575g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 3
  • Complexity: 99.6
  • 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: 2.7
  • Topological Polar Surface Area: 37.5

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Additional information on 2-Bromo-5-(ethoxymethyl)thiophene

2-Bromo-5-(ethoxymethyl)thiophene (CAS 1065184-21-5): A Versatile Building Block in Organic Synthesis

2-Bromo-5-(ethoxymethyl)thiophene (CAS 1065184-21-5) is an important heterocyclic compound that has gained significant attention in recent years due to its versatile applications in organic synthesis, pharmaceutical intermediates, and material science. This brominated thiophene derivative features a unique molecular structure with both electrophilic and nucleophilic reactive sites, making it a valuable building block for various chemical transformations.

The compound's molecular formula is C7H9BrOS, with a molecular weight of 221.11 g/mol. Its structure combines a thiophene ring with a bromo substituent at the 2-position and an ethoxymethyl group at the 5-position. This particular arrangement of functional groups makes 2-Bromo-5-(ethoxymethyl)thiophene particularly useful in cross-coupling reactions, which are fundamental to modern organic chemistry and drug discovery processes.

In the field of medicinal chemistry, 2-Bromo-5-(ethoxymethyl)thiophene serves as a key intermediate for the synthesis of various biologically active compounds. Researchers have utilized this compound in the development of potential therapeutic agents targeting various diseases. The thiophene moiety is particularly valuable in drug design due to its metabolic stability and ability to participate in hydrogen bonding interactions.

Recent advancements in material science have highlighted the importance of 2-Bromo-5-(ethoxymethyl)thiophene in the development of organic electronic materials. The compound's ability to undergo various polymerization reactions makes it suitable for creating conductive polymers and organic semiconductors. These materials find applications in organic light-emitting diodes (OLEDs), organic photovoltaics, and flexible electronics - areas that are currently experiencing rapid growth due to increasing demand for sustainable energy solutions and wearable technologies.

The synthesis of 2-Bromo-5-(ethoxymethyl)thiophene typically involves electrophilic aromatic substitution reactions on the thiophene ring. Modern synthetic approaches focus on improving atom economy and reducing environmental impact, aligning with the principles of green chemistry. Many researchers are investigating catalytic methods and solvent-free conditions to produce this compound more efficiently, addressing current concerns about sustainable chemical production.

From a commercial perspective, the demand for 2-Bromo-5-(ethoxymethyl)thiophene has been steadily increasing, particularly from the pharmaceutical and electronics industries. Market analysis indicates growing interest in this compound as a specialty chemical, with manufacturers focusing on improving purity standards and developing reliable supply chains. The compound's stability and relatively long shelf life make it attractive for industrial applications.

Quality control of 2-Bromo-5-(ethoxymethyl)thiophene is crucial for its various applications. Analytical techniques such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) spectroscopy are commonly employed to verify the compound's purity and structural integrity. Recent advancements in analytical chemistry have enabled more precise characterization of this and similar heterocyclic compounds.

Storage and handling of 2-Bromo-5-(ethoxymethyl)thiophene require standard laboratory precautions. The compound should be kept in a cool, dry place, protected from light and moisture. While not classified as highly hazardous, proper personal protective equipment should be used when handling this chemical, in line with general laboratory safety protocols. Researchers are increasingly interested in developing safer alternatives and more sustainable versions of such synthetic intermediates.

The future outlook for 2-Bromo-5-(ethoxymethyl)thiophene appears promising, with ongoing research exploring its potential in catalysis, nanotechnology, and bioconjugation applications. As synthetic methodologies continue to advance, this compound is likely to find even broader utility in both academic and industrial settings. Its combination of reactivity and structural versatility ensures it will remain an important tool for chemists working across multiple disciplines.

For researchers interested in working with 2-Bromo-5-(ethoxymethyl)thiophene, it's important to consult recent literature for the latest synthetic protocols and applications. The compound's CAS number 1065184-21-5 serves as a unique identifier for sourcing and regulatory purposes. As with any chemical reagent, proper safety assessment should be conducted before use in any experimental procedure or industrial process.

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