Cas no 1598810-50-4 (1-(5-bromothiophen-3-yl)prop-2-en-1-one)

1-(5-Bromothiophen-3-yl)prop-2-en-1-one is a brominated thiophene derivative featuring an α,β-unsaturated ketone functional group. This compound serves as a versatile intermediate in organic synthesis, particularly in the construction of heterocyclic frameworks and pharmaceutical scaffolds. The presence of both the bromo substituent and the reactive enone moiety enables selective cross-coupling reactions, such as Suzuki or Heck couplings, as well as Michael additions. Its electron-deficient thiophene core enhances reactivity in nucleophilic aromatic substitutions. The compound is valued for its stability under standard conditions and its utility in generating complex molecular architectures for applications in medicinal chemistry and materials science.
1-(5-bromothiophen-3-yl)prop-2-en-1-one structure
1598810-50-4 structure
Product Name:1-(5-bromothiophen-3-yl)prop-2-en-1-one
CAS No:1598810-50-4
MF:C7H5BrOS
MW:217.082999944687
CID:5824816
PubChem ID:105110897
Update Time:2025-10-29

1-(5-bromothiophen-3-yl)prop-2-en-1-one Chemical and Physical Properties

Names and Identifiers

    • 1-(5-bromothiophen-3-yl)prop-2-en-1-one
    • EN300-1893988
    • 1598810-50-4
    • Inchi: 1S/C7H5BrOS/c1-2-6(9)5-3-7(8)10-4-5/h2-4H,1H2
    • InChI Key: JTYSRUBXAQJBOM-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C(C=C)=O)=CS1

Computed Properties

  • Exact Mass: 215.92445g/mol
  • Monoisotopic Mass: 215.92445g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 2
  • Complexity: 158
  • 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: 45.3?2

1-(5-bromothiophen-3-yl)prop-2-en-1-one Pricemore >>

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Additional information on 1-(5-bromothiophen-3-yl)prop-2-en-1-one

Professional Introduction to Compound with CAS No. 1598810-50-4 and Product Name: 1-(5-bromothiophen-3-yl)prop-2-en-1-one

The compound with the CAS number 1598810-50-4 and the product name 1-(5-bromothiophen-3-yl)prop-2-en-1-one represents a significant advancement in the field of pharmaceutical chemistry. This molecule, characterized by its unique structural framework, has garnered considerable attention due to its potential applications in medicinal chemistry and drug development. The presence of a bromothiophene moiety and an α,β-unsaturated ketone group makes it a versatile scaffold for further chemical modifications and biological evaluations.

Recent studies have highlighted the importance of heterocyclic compounds in the design of novel therapeutic agents. The bromothiophene ring, a sulfur-containing aromatic system, is known for its stability and reactivity, making it an ideal candidate for constructing complex molecular architectures. In particular, the 5-bromothiophen-3-yl substituent in this compound enhances its utility as a building block for synthesizing more intricate pharmacophores. This feature has been leveraged in several research endeavors to develop molecules with enhanced binding affinity and selectivity towards target enzymes and receptors.

The α,β-unsaturated ketone functionality, also known as an enone, is another critical feature of this compound. Enones are well-documented for their ability to participate in various chemical reactions, including Michael additions, aldol condensations, and cycloadditions. These reactions are pivotal in organic synthesis, enabling the construction of complex molecules with precise stereochemical control. In the context of drug discovery, enones have been utilized to develop molecules with desirable pharmacological properties, such as anti-inflammatory, antimicrobial, and anticancer activities.

One of the most compelling aspects of 1-(5-bromothiophen-3-yl)prop-2-en-1-one is its potential as a precursor for developing small-molecule inhibitors. The bromine atom on the thiophene ring provides a handle for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings. These transformations allow for the introduction of diverse aryl or heteroaryl groups, thereby expanding the chemical space available for drug discovery. Such modifications can be tailored to optimize interactions with biological targets, leading to improved drug efficacy and reduced side effects.

Moreover, the structural features of this compound make it an attractive candidate for exploring structure-activity relationships (SAR). By systematically varying substituents on the thiophene ring or the enone moiety, researchers can gain insights into how different structural elements influence biological activity. This approach has been instrumental in identifying lead compounds that exhibit promising pharmacological profiles. For instance, derivatives of this molecule have shown potential in inhibiting kinases and other enzymes implicated in cancer progression.

Recent advancements in computational chemistry have further enhanced the utility of 1-(5-bromothiophen-3-yl)prop-2-en-1-one in drug design. Molecular modeling techniques, such as molecular dynamics simulations and quantum mechanical calculations, have enabled researchers to predict how this compound interacts with biological targets at an atomic level. These predictions are crucial for guiding experimental efforts and reducing the time required to identify lead compounds. By integrating experimental data with computational insights, scientists can accelerate the development of novel therapeutics.

The pharmaceutical industry has increasingly recognized the value of heterocyclic compounds like bromothiophenes in drug development. Their unique electronic properties and biological activities make them ideal candidates for designing molecules with therapeutic potential. The enone group further enhances these properties by providing multiple sites for functionalization and interaction with biological targets. As a result, compounds like 1-(5-bromothiophen-3-yl)prop-2-en-1-one are being explored in various therapeutic areas, including oncology, neurology, and immunology.

In conclusion,1-(5-bromothiophen-3-yl)prop-2-en-1-one represents a promising scaffold for developing novel pharmaceuticals. Its unique structural features—combining a bromothiophene moiety with an α,β-unsaturated ketone—make it a versatile building block for synthetic chemistry and drug discovery. Recent research highlights its potential as a precursor for developing small-molecule inhibitors with applications across multiple therapeutic areas. As computational methods continue to evolve, the utility of this compound is expected to grow further, contributing to advancements in medicinal chemistry and therapeutic development.

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