Cas no 1245252-62-3 (2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester)

2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic acid pinacol ester is a boronic acid derivative commonly employed in Suzuki-Miyaura cross-coupling reactions due to its stability and reactivity. The pinacol ester group enhances shelf life and handling by protecting the boronic acid moiety from protodeboronation. The fluorine substituent and phenoxycarbonylamino group introduce steric and electronic effects, making it a versatile intermediate in pharmaceutical and agrochemical synthesis. Its compatibility with various reaction conditions and functional group tolerance allow for selective C-C bond formation in complex molecular architectures. The compound is particularly useful in constructing biaryl systems, where controlled coupling efficiency is required. Proper storage under inert conditions is recommended to maintain stability.
2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester structure
1245252-62-3 structure
Product Name:2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester
CAS No:1245252-62-3
MF:C19H21BFNO4
MW:357.183748960495
CID:2127537
PubChem ID:66678788
Update Time:2025-05-19

2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester Chemical and Physical Properties

Names and Identifiers

    • phenyl 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate
    • KELNKADYNHJFRO-UHFFFAOYSA-N
    • phenyl (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate
    • phenyl(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate
    • 2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic acid pinacol ester
    • DA-13710
    • SCHEMBL411985
    • phenyl N-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate
    • 1245252-62-3
    • 2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester
    • MDL: MFCD22419258
    • Inchi: 1S/C19H21BFNO4/c1-18(2)19(3,4)26-20(25-18)15-11-10-13(12-16(15)21)22-17(23)24-14-8-6-5-7-9-14/h5-12H,1-4H3,(H,22,23)
    • InChI Key: KELNKADYNHJFRO-UHFFFAOYSA-N
    • SMILES: FC1C=C(C=CC=1B1OC(C)(C)C(C)(C)O1)NC(=O)OC1C=CC=CC=1

Computed Properties

  • Exact Mass: 357.155
  • Monoisotopic Mass: 357.155
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 4
  • Complexity: 494
  • 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: 56.8

2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
TRC
F402048-10mg
2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester
1245252-62-3
10mg
$ 50.00 2022-06-05
TRC
F402048-50mg
2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester
1245252-62-3
50mg
$ 210.00 2022-06-05
TRC
F402048-100mg
2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester
1245252-62-3
100mg
$ 295.00 2022-06-05

Additional information on 2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester

2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester: A Comprehensive Overview

The compound with CAS No. 1245252-62-3, known as 2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester, is a highly specialized organic compound that has garnered significant attention in the fields of organic synthesis, medicinal chemistry, and materials science. This compound is a derivative of benzeneboronic acid, featuring a fluoro group at the 2-position and a phenoxycarbonylamino substituent at the 4-position. The pinacol ester functional group further enhances its reactivity and versatility in various chemical reactions.

The benzeneboronic acid core of this compound is a fundamental building block in modern organic chemistry, particularly in Suzuki-Miyaura coupling reactions. These reactions are pivotal in the construction of biaryl structures, which are widely used in drug discovery and materials synthesis. The presence of the fluoro group introduces electronic effects that can modulate the reactivity of the boronic acid moiety, making it an attractive substrate for cross-coupling reactions under mild conditions.

The phenoxycarbonylamino substituent adds another layer of complexity to this molecule. This group is known to enhance solubility and bioavailability, making it particularly relevant in pharmaceutical applications. Recent studies have explored the use of such substituents in improving the pharmacokinetic profiles of drug candidates, underscoring the potential of this compound in medicinal chemistry.

From a synthetic perspective, the preparation of 2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester involves a series of carefully orchestrated reactions. The synthesis typically begins with the fluorination of a suitable benzene derivative, followed by the introduction of the phenoxycarbonylamino group via nucleophilic aromatic substitution or other coupling methods. The final step involves the formation of the pinacol ester, which is achieved through boronate esterification using pinacol borane.

Recent advancements in catalytic methods have significantly streamlined the synthesis of such compounds. For instance, the use of palladium catalysts has enabled more efficient Suzuki couplings, reducing reaction times and improving yields. These developments have made compounds like 1245252-62-3 more accessible for large-scale applications in drug discovery and materials science.

In terms of applications, this compound is particularly valuable in the construction of heterocyclic frameworks. Its ability to undergo various cross-coupling reactions makes it an ideal precursor for synthesizing complex molecules with diverse functionalities. For example, researchers have utilized this compound to synthesize novel kinase inhibitors and GPCR modulators, demonstrating its potential in drug development.

The pinacol ester functionality also plays a critical role in enabling controlled release mechanisms in drug delivery systems. By incorporating this group into polymer backbones or nanoparticles, scientists can design systems that release therapeutic agents at specific rates and locations within the body. This has opened new avenues for targeted drug delivery and personalized medicine.

From an analytical standpoint, modern spectroscopic techniques such as NMR and mass spectrometry have been instrumental in confirming the structure and purity of this compound. These tools allow researchers to perform detailed characterization, ensuring that the compound meets rigorous quality standards required for both academic and industrial applications.

In conclusion, CAS No. 1245252-62-3, or 2-Fluoro-4-(phenoxycarbonylamino)benzeneboronic Acid Pinacol Ester, represents a cutting-edge compound with multifaceted applications across various scientific disciplines. Its unique combination of functional groups positions it as a valuable tool in modern organic synthesis and drug discovery. As research continues to uncover new synthetic pathways and applications for this compound, its significance in advancing chemical science will undoubtedly grow.

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