Cas no 76557-94-3 (1-(2-bromoethenyl)-4-methylbenzene)

1-(2-Bromoethenyl)-4-methylbenzene is a brominated aromatic compound featuring a vinyl bromide substituent on a toluene backbone. This structure imparts reactivity suitable for cross-coupling reactions, such as Suzuki or Heck couplings, making it valuable in synthetic organic chemistry. The electron-withdrawing bromoethenyl group enhances its utility in nucleophilic substitution and polymerization processes. Its crystalline solid form ensures stability under standard conditions, while the methyl group offers additional functionalization potential. The compound is particularly useful in pharmaceutical intermediates and advanced material synthesis due to its balanced reactivity and structural versatility. Proper handling is required due to its sensitivity to light and moisture.
1-(2-bromoethenyl)-4-methylbenzene structure
76557-94-3 structure
Product Name:1-(2-bromoethenyl)-4-methylbenzene
CAS No:76557-94-3
MF:C9H9Br
MW:197.071761846542
CID:537588
PubChem ID:11446920
Update Time:2025-10-18

1-(2-bromoethenyl)-4-methylbenzene Chemical and Physical Properties

Names and Identifiers

    • Benzene, 1-[(1E)-2-bromoethenyl]-4-methyl-
    • 1-(2-bromoethenyl)-4-methylbenzene
    • EN300-125200
    • (E)-1-(2-bromovinyl)-4-methylbenzene
    • 76557-94-3
    • SCHEMBL8447454
    • Inchi: 1S/C9H9Br/c1-8-2-4-9(5-3-8)6-7-10/h2-7H,1H3/b7-6+
    • InChI Key: VDQOXWRCEPPGRE-VOTSOKGWSA-N
    • SMILES: Br/C=C/C1C=CC(C)=CC=1

Computed Properties

  • Exact Mass: 195.98877
  • Monoisotopic Mass: 195.98876g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 110
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 3.5
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0

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1-(2-bromoethenyl)-4-methylbenzene Related Literature

Additional information on 1-(2-bromoethenyl)-4-methylbenzene

Introduction to 1-(2-bromoethenyl)-4-methylbenzene (CAS No. 76557-94-3)

1-(2-bromoethenyl)-4-methylbenzene, identified by its Chemical Abstracts Service (CAS) number 76557-94-3, is a significant organic compound that has garnered attention in the field of pharmaceutical and agrochemical research. This compound, featuring a brominated vinyl group attached to a methyl-substituted benzene ring, exhibits unique chemical properties that make it a valuable intermediate in synthetic chemistry. Its molecular structure, characterized by a combination of aromatic and alkenyl functionalities, positions it as a versatile building block for the development of novel bioactive molecules.

The structural motif of 1-(2-bromoethenyl)-4-methylbenzene consists of a benzene ring substituted at the 4-position with a methyl group and at the 2-position with a vinyl group that is further brominated. This specific arrangement imparts distinct reactivity patterns, making it particularly useful in cross-coupling reactions such as Suzuki-Miyaura and Heck couplings, which are pivotal in constructing complex molecular architectures. The presence of the bromine atom enhances the electrophilicity of the vinyl group, facilitating its participation in various synthetic transformations.

In recent years, 1-(2-bromoethenyl)-4-methylbenzene has been explored in the context of drug discovery and development. Its ability to serve as a precursor for more complex scaffolds has been leveraged in the synthesis of potential therapeutic agents. For instance, derivatives of this compound have been investigated for their pharmacological properties, including antimicrobial and anti-inflammatory activities. The benzene ring core is a common structural feature in many drugs, and modifications at specific positions can lead to significant changes in biological activity.

One of the most compelling aspects of 1-(2-bromoethenyl)-4-methylbenzene is its role in the synthesis of heterocyclic compounds. Heterocycles are essential components of numerous pharmaceuticals due to their ability to mimic natural products and interact with biological targets. By incorporating this compound into synthetic pathways, researchers can efficiently generate substituted heterocycles that may exhibit improved efficacy or reduced toxicity compared to existing treatments. The bromine substituent also allows for further functionalization via palladium-catalyzed reactions, enabling the introduction of diverse functional groups.

The applications of 1-(2-bromoethenyl)-4-methylbenzene extend beyond pharmaceuticals into the realm of materials science. Its unique electronic properties make it a candidate for use in organic electronics, such as OLEDs (organic light-emitting diodes) and semiconductors. The conjugated system provided by the vinyl group can contribute to charge transport properties, making it an attractive candidate for developing novel optoelectronic materials. Additionally, its aromatic nature suggests potential utility in polymer chemistry, where aromatic compounds are often employed to enhance material stability and mechanical strength.

Recent advancements in synthetic methodologies have further expanded the utility of 1-(2-bromoethenyl)-4-methylbenzene. Transition-metal-catalyzed reactions, particularly those involving palladium and copper catalysts, have enabled efficient transformations of this compound into more complex structures. These methods have been instrumental in accessing novel derivatives with tailored biological activities. For example, functionalization at the vinyl or methyl positions can yield compounds with enhanced binding affinity to biological targets, making them promising candidates for drug development.

The environmental impact and sustainability considerations are also important when evaluating compounds like 1-(2-bromoethenyl)-4-methylbenzene. Efforts have been made to develop greener synthetic routes that minimize waste and reduce energy consumption. Catalytic processes that utilize recyclable catalysts or operate under mild conditions are particularly desirable in modern chemical synthesis. Such approaches align with broader sustainability goals within the pharmaceutical industry and contribute to reducing the ecological footprint of chemical manufacturing.

In conclusion,1-(2-bromoethenyl)-4-methylbenzene (CAS No. 76557-94-3) is a multifaceted compound with significant potential in pharmaceutical research, materials science, and synthetic chemistry. Its unique structural features enable diverse applications, from drug development to advanced materials fabrication. As research continues to uncover new methodologies for utilizing this compound, its importance is likely to grow further, driving innovation across multiple scientific disciplines.

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