Cas no 1150114-60-5 (3,5-Difluoro-2-nitrophenylboronic acid)

3,5-Difluoro-2-nitrophenylboronic acid is a specialized boronic acid derivative featuring both nitro and fluorine substituents on the aromatic ring. This compound is particularly valuable in Suzuki-Miyaura cross-coupling reactions due to the electron-withdrawing effects of the nitro and fluorine groups, which enhance the reactivity of the boronic acid moiety. The presence of fluorine atoms also offers opportunities for further functionalization, making it a versatile intermediate in pharmaceutical and agrochemical synthesis. Its stability under typical reaction conditions and compatibility with various catalysts contribute to its utility in constructing complex heterocyclic and biaryl structures. The compound is supplied in high purity to ensure consistent performance in synthetic applications.
3,5-Difluoro-2-nitrophenylboronic acid structure
1150114-60-5 structure
Product Name:3,5-Difluoro-2-nitrophenylboronic acid
CAS No:1150114-60-5
MF:C6H4BF2NO4
MW:202.908068656921
MDL:MFCD12025971
CID:839966
PubChem ID:46739458
Update Time:2025-06-11

3,5-Difluoro-2-nitrophenylboronic acid Chemical and Physical Properties

Names and Identifiers

    • (3,5-Difluoro-2-nitrophenyl)boronic acid
    • 3,5-Difluoro-2-nitrophenylboronic acid
    • DTXSID30675063
    • AKOS015852920
    • EN300-7366289
    • (3,5-Difluoro-2-nitrophenyl)boronicacid
    • 1150114-60-5
    • BS-19334
    • E84342
    • MFCD12025971
    • CS-0175128
    • Boronic acid, B-(3,5-difluoro-2-nitrophenyl)-
    • MDL: MFCD12025971
    • Inchi: 1S/C6H4BF2NO4/c8-3-1-4(7(11)12)6(10(13)14)5(9)2-3/h1-2,11-12H
    • InChI Key: QSDKRMBLAFJYCE-UHFFFAOYSA-N
    • SMILES: FC1=CC(=CC(B(O)O)=C1[N+](=O)[O-])F

Computed Properties

  • Exact Mass: 203.02000
  • Monoisotopic Mass: 203.0201441g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 224
  • 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
  • Topological Polar Surface Area: 86.3?2

Experimental Properties

  • PSA: 86.28000
  • LogP: 0.07600

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Additional information on 3,5-Difluoro-2-nitrophenylboronic acid

Recent Advances in the Application of 3,5-Difluoro-2-nitrophenylboronic acid (CAS: 1150114-60-5) in Chemical Biology and Pharmaceutical Research

3,5-Difluoro-2-nitrophenylboronic acid (CAS: 1150114-60-5) has emerged as a versatile building block in chemical biology and pharmaceutical research due to its unique structural and electronic properties. This boronic acid derivative, characterized by the presence of two fluorine atoms and a nitro group on the phenyl ring, exhibits enhanced reactivity and selectivity in various chemical transformations. Recent studies have highlighted its potential in the development of novel therapeutics, diagnostic agents, and chemical probes for studying biological systems.

One of the key applications of 3,5-Difluoro-2-nitrophenylboronic acid is in the field of targeted drug delivery. Researchers have exploited its ability to form reversible covalent bonds with diols and other nucleophiles to design prodrugs and drug conjugates that can selectively release active compounds in specific physiological environments. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated the use of this compound in the development of glucose-responsive insulin delivery systems, where the boronic acid moiety facilitated the controlled release of insulin in response to varying glucose concentrations.

In addition to drug delivery, 3,5-Difluoro-2-nitrophenylboronic acid has found applications in the development of fluorescent probes for detecting reactive oxygen species (ROS) and other biologically relevant analytes. The electron-withdrawing effects of the fluorine and nitro groups enhance the sensitivity of these probes, enabling real-time monitoring of oxidative stress in cellular systems. A recent study in Analytical Chemistry reported the synthesis of a novel boronic acid-based probe that exhibited high selectivity for peroxynitrite, a key ROS involved in numerous pathological conditions.

The compound's utility extends to the field of protein labeling and modification. Researchers have utilized its boronic acid functionality to selectively modify proteins at serine, threonine, and tyrosine residues, enabling site-specific conjugation of payloads such as fluorophores, drugs, and affinity tags. A 2024 publication in Chemical Science detailed the use of 3,5-Difluoro-2-nitrophenylboronic acid in the development of a new class of protein-protein interaction inhibitors, where the boronic acid moiety served as a key pharmacophore for binding to target proteins.

Despite its promising applications, challenges remain in the optimization of 3,5-Difluoro-2-nitrophenylboronic acid-based compounds for clinical use. Issues such as stability, bioavailability, and off-target effects need to be addressed through further structural modifications and formulation strategies. Ongoing research efforts are focused on improving the pharmacokinetic properties of these compounds while maintaining their therapeutic efficacy and selectivity.

In conclusion, 3,5-Difluoro-2-nitrophenylboronic acid (CAS: 1150114-60-5) represents a valuable tool in chemical biology and pharmaceutical research, with diverse applications ranging from drug delivery to diagnostic imaging. Continued exploration of its chemical properties and biological interactions is expected to yield new insights and innovations in the development of next-generation therapeutics and research tools.

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