Cas no 66952-36-1 (1-Bromo-3-(prop-1-yn-1-yl)benzene)

1-Bromo-3-(prop-1-yn-1-yl)benzene is a halogenated aromatic compound featuring a bromine substituent at the 1-position and a propynyl group at the 3-position of the benzene ring. This structure makes it a valuable intermediate in organic synthesis, particularly for cross-coupling reactions such as Sonogashira, Suzuki, and Heck couplings. The presence of both bromine and alkyne functionalities enhances its reactivity, enabling selective modifications for constructing complex molecular architectures. Its stability under standard conditions and compatibility with various reaction conditions further contribute to its utility in pharmaceutical and materials science research. The compound is typically handled under inert atmospheres to preserve its integrity.
1-Bromo-3-(prop-1-yn-1-yl)benzene structure
66952-36-1 structure
Product Name:1-Bromo-3-(prop-1-yn-1-yl)benzene
CAS No:66952-36-1
MF:C9H7Br
MW:195.055881738663
MDL:MFCD17677178
CID:395527
PubChem ID:69181882
Update Time:2025-06-08

1-Bromo-3-(prop-1-yn-1-yl)benzene Chemical and Physical Properties

Names and Identifiers

    • 1-Bromo-3-(prop-1-yn-1-yl)benzene
    • 1-bromo-3-(prop-1-ynyl)benzene
    • 1-bromo-3-prop-1-ynylbenzene
    • Benzene, 1-bromo-3-(1-propynyl)-
    • Y10633
    • AKOS022186371
    • A867358
    • A1-08123
    • SCHEMBL4769651
    • SB13083
    • DXYPQRPGSNUBFO-UHFFFAOYSA-N
    • 3-bromo-1-propynylbenzene
    • 1-Bromo-3-(1-propynyl)benzene
    • MFCD17677178
    • 66952-36-1
    • DTXSID40739968
    • BS-24643
    • DB-311929
    • MDL: MFCD17677178
    • Inchi: 1S/C9H7Br/c1-2-4-8-5-3-6-9(10)7-8/h3,5-7H,1H3
    • InChI Key: DXYPQRPGSNUBFO-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC(C#CC)=C1

Computed Properties

  • Exact Mass: 193.97311
  • Monoisotopic Mass: 193.97311g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 160
  • 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: 3.4
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0

1-Bromo-3-(prop-1-yn-1-yl)benzene Pricemore >>

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Additional information on 1-Bromo-3-(prop-1-yn-1-yl)benzene

Professional Introduction to 1-Bromo-3-(prop-1-yn-1-yl)benzene (CAS No. 66952-36-1)

1-Bromo-3-(prop-1-yn-1-yl)benzene, with the chemical formula C?H?Br, is a versatile organic compound that has garnered significant attention in the field of synthetic chemistry and pharmaceutical research. This compound serves as a crucial intermediate in the synthesis of various biologically active molecules, making it a subject of extensive study and application. Its unique structure, featuring both a bromine substituent and an alkyne moiety, imparts distinct reactivity that facilitates diverse chemical transformations.

The bromine atom in 1-Bromo-3-(prop-1-yn-1-yl)benzene acts as a handle for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings. These reactions are pivotal in constructing complex molecular architectures, particularly in the development of novel pharmaceuticals and agrochemicals. The propyne group, on the other hand, introduces a reactive triple bond that can undergo addition reactions or serve as a precursor for more elaborate functionalization strategies.

In recent years, the demand for efficient synthetic routes to 1-Bromo-3-(prop-1-yn-1-yl)benzene has been driven by its utility in drug discovery. Researchers have explored various synthetic methodologies to optimize yield and purity, ensuring that it meets the stringent requirements of pharmaceutical applications. Advances in catalytic systems and green chemistry principles have further enhanced the accessibility of this compound, making it more sustainable and scalable for industrial use.

One of the most compelling applications of 1-Bromo-3-(prop-1-yn-1-yl)benzene lies in its role as a precursor for bioactive heterocycles. Heterocyclic compounds are ubiquitous in medicinal chemistry due to their broad spectrum of biological activities. The bromine and alkyne functionalities provide multiple points of intervention for medicinal chemists to modify and tailor these structures. For instance, recent studies have demonstrated its use in synthesizing substituted benzothiophenes, which exhibit promising antimicrobial and anti-inflammatory properties.

The synthetic flexibility of 1-Bromo-3-(prop-1-yn-1-yl)benzene has also been leveraged in the development of materials science applications. Its ability to undergo polymerization or form covalent networks makes it a valuable building block for advanced materials. Researchers are exploring its potential in creating conductive polymers or stimuli-responsive materials, which could find applications in electronics and nanotechnology.

From a mechanistic standpoint, the reactivity of 1-Bromo-3-(prop-1-yn-1-yb)benzene has been extensively studied to understand its role in various chemical transformations. The interplay between the bromine atom and the propyne group often dictates the outcome of reactions, allowing chemists to predict and control product formation with high precision. This understanding has led to innovative synthetic strategies that enhance efficiency and selectivity.

The pharmaceutical industry has been particularly keen on exploring derivatives of 1-Bromo-3-(prop-ylnl-benzen) due to their potential therapeutic benefits. For example, researchers have synthesized analogs that mimic natural products known for their pharmacological activity. These derivatives have shown promise in preclinical studies, highlighting the importance of this compound as a scaffold for drug development.

Moreover, the growing interest in bioconjugation techniques has expanded the utility of 1-Bromo--(prop--yn--ytl-benzen) as a linker molecule. By incorporating this compound into biomolecules such as peptides or proteins, scientists can enhance stability or target specificity for therapeutic purposes. This approach is particularly relevant in antibody-drug conjugates (ADCs), where precise molecular design is critical for efficacy.

The environmental impact of synthesizing and handling 1-Bromo--(proplnyl-benzen) has also been a focus area. Efforts have been made to develop greener synthetic routes that minimize waste and energy consumption. These initiatives align with broader trends in sustainable chemistry, ensuring that industrial processes remain environmentally responsible while maintaining high-quality output.

In conclusion, 1-Bromo--(proplnyl-benzen) (CAS No. 66952--36--l) is a multifaceted compound with significant implications across multiple scientific disciplines. Its unique structural features make it an invaluable tool for synthetic chemists working on pharmaceuticals, materials science, and beyond. As research continues to uncover new applications and methodologies, 66952--36--l will undoubtedly remain at the forefront of scientific innovation.

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