Cas no 425378-68-3 (2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a boronic ester derivative widely used as an intermediate in Suzuki-Miyaura cross-coupling reactions. Its key advantages include high stability under ambient conditions, facilitating handling and storage, and its compatibility with diverse reaction conditions. The fluorine and nitro substituents enhance its reactivity and selectivity in forming biaryl compounds, making it valuable for pharmaceutical and materials science applications. The tetramethyl dioxaborolane moiety ensures efficient transmetalation, improving yields in palladium-catalyzed couplings. This compound is particularly useful for constructing complex aromatic systems with precise functionalization.
2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane structure
425378-68-3 structure
Product Name:2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS No:425378-68-3
MF:C12H15BFNO4
MW:267.061207056046
MDL:MFCD06409955
CID:326777
PubChem ID:3833297
Update Time:2025-08-05

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical and Physical Properties

Names and Identifiers

    • 2-Fluoro-5-nitrophenylboronic acid pinacol ester
    • 1,3,2-Dioxaborolane,2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-
    • 2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
    • 2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 2-Fluoro-5-nitrophenylboronic acid
    • AKOS015920071
    • 2-(2-FLUORO-5-NITROPHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLANE
    • 2-(2-Fluoro-5-nitrophenyl)-4,4,5,5,-tetramethyl-[1,3,2]dioxaborolane
    • 2-(2-fluoro-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Fluoro-5-nitrophenylboronic Acid Pinacol Ester
    • A825926
    • SY024027
    • 2-Fluoro-5-nitrophenylboronic acid, pinacol ester
    • SCHEMBL2649866
    • 2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl- [1,3,2]dioxaborolane
    • FT-0644601
    • J-505619
    • DS-1163
    • MFCD06409955
    • AKOS025243917
    • 425378-68-3
    • AB23832
    • FXEVKZIXXGDLFW-UHFFFAOYSA-N
    • 2-FLUORO-5-NITROBENZENEBORONIC ACID, PINACOL ESTER
    • 2-(2-Fluoro-5-nitrophenyl)-4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolane
    • 2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, AldrichCPR
    • CS-0037855
    • EN300-7364517
    • (2-FLUORO-5-NITROPHENYL)BORONIC ACID PINACOL ESTER
    • DTXSID20397065
    • 2-(2-fluoro-5-nitro-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
    • MDL: MFCD06409955
    • Inchi: 1S/C12H15BFNO4/c1-11(2)12(3,4)19-13(18-11)9-7-8(15(16)17)5-6-10(9)14/h5-7H,1-4H3
    • InChI Key: FXEVKZIXXGDLFW-UHFFFAOYSA-N
    • SMILES: FC1=CC=C(C=C1B1OC(C)(C)C(C)(C)O1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 267.10800
  • Monoisotopic Mass: 267.108
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 2
  • Complexity: 355
  • 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: 64.3A^2

Experimental Properties

  • PSA: 64.28000
  • LogP: 2.55630

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Security Information

  • Hazard Statement: Irritant
  • Hazardous Material Identification: Xi

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Customs Data

  • HS CODE:2931900090
  • Customs Data:

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Pricemore >>

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2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Production Method

Additional information on 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane: A Key Compound in Modern Pharmaceutical Research

2-(2-Fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, with the CAS No. 425378-68-3, represents a pivotal molecule in the field of biomedical chemistry. This compound, characterized by its unique 1,3,2-dioxaborolane framework and 2-fluoro-5-nitrophenyl substituent, has garnered significant attention for its potential applications in drug discovery and targeted therapy. Recent studies highlight its role in enhancing the efficacy of therapeutic agents through its ability to modulate molecular interactions.

The 1,3,2-dioxaborolane core of this compound is a versatile platform for chemical modification and functionalization. This structural feature allows for the incorporation of diverse functional groups, making it a valuable scaffold in the development of antibody-drug conjugates (ADCs) and small molecule inhibitors. Researchers have demonstrated that the 2-fluoro-5-nitrophenyl group significantly influences the compound's bioavailability and metabolic stability, which are critical factors in pharmaceutical formulations.

Recent advancements in synthetic chemistry have enabled the efficient synthesis of 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane through transition-metal-catalyzed coupling reactions. These methods, such as Suzuki-Miyaura cross-coupling and Stille coupling, have been optimized to achieve high yields and purity, which are essential for preclinical studies and clinical trials. The use of organocatalysts and green chemistry principles further enhances the sustainability of its production.

Studies published in 2023 have shown that this compound exhibits promising antitumor activity against multidrug-resistant cancer cells. The nitrophenyl moiety is believed to interact with specific proteins involved in cell proliferation, thereby inhibiting mitotic processes. Additionally, its fluorinated substituent may contribute to metabolic stability, reducing the risk of drug metabolism in vivo.

The 4,4,5,5-tetramethyl groups in the 1,3,2-dioxaborolane ring provide steric bulk, which is crucial for enantioselective synthesis and stereospecific reactions. This structural feature allows for the precise control of molecular orientation, which is vital in the development of highly selective drugs. Researchers are exploring its potential in targeted drug delivery systems, where the compound's hydrophobic properties may facilitate cell membrane penetration.

Recent in vitro studies have demonstrated the compound's ability to modulate signal transduction pathways associated with apoptosis and cell cycle arrest. These findings suggest its potential as a chemotherapeutic agent or a targeted therapy for oncology applications. The nitrophenyl group's interaction with kinase enzymes is a focal point of current research, aiming to elucidate its mechanism of action.

Advances in computational chemistry have enabled the prediction of molecular dynamics and binding affinities for this compound. Machine learning models trained on large-scale datasets have identified potential binding sites on target proteins, which could accelerate the drug development process. These models are also being used to optimize synthetic pathways and reaction conditions for large-scale production.

The 1,3,2-dioxaborolane framework of this compound is also being explored for biodegradable materials and drug delivery systems. Its hydrolytic stability under physiological conditions makes it a suitable candidate for controlled release formulations. Researchers are investigating its potential in nanoparticle-based delivery systems, where the compound's solubility and compatibility with biomaterials are critical factors.

Current preclinical trials are focusing on the pharmacokinetics and pharmacodynamics of this compound in various animal models. These studies are crucial for understanding its toxicity profile and therapeutic window. The results of these trials will inform the design of clinical trials and the eventual regulatory approval process.

Moreover, the fluorinated substituent in this compound may offer advantages in imaging applications, such as positron emission tomography (PET) and magnetic resonance imaging (MRI). The fluorine atom's electronegativity and low molecular weight make it an ideal contrast agent, enhancing the resolution and accuracy of diagnostic imaging.

Collaborative efforts between pharmaceutical companies and academic institutions are driving the development of new therapeutic strategies involving this compound. These partnerships are leveraging high-throughput screening and automated synthesis techniques to expedite the drug discovery process. The integration of artificial intelligence in drug design is also playing a significant role in optimizing the chemical structure and functional properties of this compound.

As research continues, the potential applications of 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane are expanding beyond traditional pharmacological uses. Its unique chemical properties are being explored for biotechnology and nanotechnology applications, including biocompatible materials and smart drug delivery systems. These innovations underscore the importance of continued research and development in the field of biomedical chemistry.

In conclusion, the compound 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a promising candidate for novel therapeutic applications. Its unique structural features and chemical properties make it a valuable tool in the drug discovery and development process. Continued research and innovation in this area will undoubtedly lead to breakthroughs in biomedical science and clinical medicine.

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