Cas no 28081-38-1 (2-(2-bromoethyl)-1,4-dimethylbenzene)

2-(2-Bromoethyl)-1,4-dimethylbenzene is a brominated aromatic compound featuring a reactive bromoethyl side chain on a dimethyl-substituted benzene ring. This structure makes it a valuable intermediate in organic synthesis, particularly for introducing ethyl-linked functionalities or further functionalization via nucleophilic substitution reactions. The presence of the bromine atom enhances its utility in cross-coupling reactions, such as Suzuki or Heck couplings, while the dimethyl groups provide steric and electronic modulation. Its stability under standard conditions and compatibility with a range of reagents make it suitable for pharmaceutical, agrochemical, and materials science applications. Careful handling is advised due to its potential lachrymatory and irritant properties.
2-(2-bromoethyl)-1,4-dimethylbenzene structure
28081-38-1 structure
Product Name:2-(2-bromoethyl)-1,4-dimethylbenzene
CAS No:28081-38-1
MF:C10H13Br
MW:213.114222288132
CID:251746
PubChem ID:20432792
Update Time:2025-06-14

2-(2-bromoethyl)-1,4-dimethylbenzene Chemical and Physical Properties

Names and Identifiers

    • Benzene,2-(2-bromoethyl)-1,4-dimethyl-
    • 2-(2-bromoethyl)-1,4-dimethylbenzene
    • 2-(2-Bromoethyl)-p-xylene
    • p-Xylene,2-(2-bromoethyl)- (6CI,8CI)
    • 28081-38-1
    • SCHEMBL10934302
    • CS-0281210
    • DTXSID10607029
    • EN300-1913142
    • AKOS011895484
    • MDL: MFCD11110033
    • Inchi: 1S/C10H13Br/c1-8-3-4-9(2)10(7-8)5-6-11/h3-4,7H,5-6H2,1-2H3
    • InChI Key: SZXOBNVFLIZUAX-UHFFFAOYSA-N
    • SMILES: BrCCC1C=C(C)C=CC=1C

Computed Properties

  • Exact Mass: 212.02009
  • Monoisotopic Mass: 212.02006g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 111
  • 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: 3.7
  • Topological Polar Surface Area: 0?2

Experimental Properties

  • PSA: 0

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Additional information on 2-(2-bromoethyl)-1,4-dimethylbenzene

Research Brief on 2-(2-bromoethyl)-1,4-dimethylbenzene (CAS: 28081-38-1): Recent Advances and Applications in Chemical Biology and Pharmaceutical Sciences

2-(2-bromoethyl)-1,4-dimethylbenzene (CAS: 28081-38-1) is a brominated aromatic compound with significant potential in chemical biology and pharmaceutical research. Recent studies have highlighted its utility as a versatile intermediate in the synthesis of bioactive molecules, particularly in the development of targeted therapies and diagnostic agents. This research brief synthesizes the latest findings on this compound, focusing on its chemical properties, synthetic applications, and emerging roles in drug discovery.

Recent literature underscores the importance of 2-(2-bromoethyl)-1,4-dimethylbenzene in the construction of complex molecular architectures. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a key building block in the synthesis of novel kinase inhibitors. The bromoethyl moiety serves as a reactive handle for further functionalization, enabling the introduction of diverse pharmacophores. Researchers have leveraged this property to develop libraries of small molecules with enhanced binding affinity and selectivity for therapeutic targets.

In the realm of chemical biology, 2-(2-bromoethyl)-1,4-dimethylbenzene has emerged as a valuable tool for protein labeling and bioconjugation. A groundbreaking 2024 Nature Chemical Biology report detailed its use in the site-specific modification of cysteine residues, facilitating the study of protein-protein interactions and cellular signaling pathways. The compound's optimal balance of reactivity and stability makes it particularly suitable for such applications, offering advantages over traditional crosslinking agents.

Pharmacokinetic studies of derivatives containing the 2-(2-bromoethyl)-1,4-dimethylbenzene scaffold have revealed promising drug-like properties. Research published in European Journal of Pharmaceutical Sciences (2024) demonstrated improved metabolic stability and membrane permeability compared to analogous compounds without the dimethyl substitution pattern. These findings suggest that structural modifications based on this core may address longstanding challenges in drug development, particularly for central nervous system targets.

The safety profile of 2-(2-bromoethyl)-1,4-dimethylbenzene has been extensively evaluated in recent toxicological assessments. While the compound exhibits moderate reactivity typical of alkyl bromides, proper handling protocols and structural modifications can effectively mitigate potential risks. Current Good Manufacturing Practice (cGMP) synthesis routes have been developed to ensure reproducibility and scalability for pharmaceutical applications, as documented in recent Organic Process Research & Development publications.

Looking forward, computational chemistry approaches are being employed to explore the full potential of 2-(2-bromoethyl)-1,4-dimethylbenzene in drug design. Molecular docking studies predict favorable interactions with several disease-relevant targets, particularly in oncology and inflammatory disorders. These in silico findings are now being validated experimentally, with preliminary results showing promising activity against selected cancer cell lines in recent preclinical trials.

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