Cas no 1747-80-4 (2-Fluoro-N-phenyl-benzamide)

2-Fluoro-N-phenyl-benzamide is a fluorinated aromatic amide compound with potential applications in pharmaceutical and agrochemical research. Its structure features a benzamide core substituted with a fluorine atom at the 2-position and an N-phenyl group, enhancing its reactivity and binding properties. The fluorine substitution improves metabolic stability and bioavailability, making it a valuable intermediate in drug discovery. This compound is particularly useful in the synthesis of bioactive molecules due to its ability to modulate electronic and steric effects. High purity and consistent quality ensure reliable performance in synthetic applications. Its well-defined chemical properties facilitate its use in structure-activity relationship (SAR) studies and medicinal chemistry optimization.
2-Fluoro-N-phenyl-benzamide structure
2-Fluoro-N-phenyl-benzamide structure
Product Name:2-Fluoro-N-phenyl-benzamide
CAS No:1747-80-4
MF:C13H10FNO
MW:215.223006725311
CID:186712
PubChem ID:242890
Update Time:2025-05-24

2-Fluoro-N-phenyl-benzamide Chemical and Physical Properties

Names and Identifiers

    • Benzamide,2-fluoro-N-phenyl-
    • 2-Fluoro-N-phenylbenzamide
    • 2-FLUOROBENZANILIDE
    • Benzanilide, 2-fluoro-
    • N-(2-fluorophenyl)benzamide
    • NSC 51889
    • Benzamide, 2-fluoro-N-phenyl-
    • DTXSID70938548
    • J-509517
    • 2-Fluoro-N-phenylbenzene-1-carboximidic acid
    • NSC51889
    • CHEMBL2046764
    • SCHEMBL4363732
    • AKOS000796678
    • CS-0304788
    • Z27782663
    • 1747-80-4
    • 2-FLUORO-N-PHENYL-BENZAMIDE
    • AH-034/01370042
    • 2-Fluoro-N-phenylbenzaMide, 97%
    • STK325488
    • 2-Fluoro-N-phenyl-benzamide
    • MDL: MFCD00454563
    • Inchi: 1S/C13H10FNO/c14-12-9-5-4-8-11(12)13(16)15-10-6-2-1-3-7-10/h1-9H,(H,15,16)
    • InChI Key: LFYRRNCQLJGEGP-UHFFFAOYSA-N
    • SMILES: FC1C=CC=CC=1C(NC1C=CC=CC=1)=O

Computed Properties

  • Exact Mass: 215.0747
  • Monoisotopic Mass: 215.075
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 238
  • 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: 3.2
  • Topological Polar Surface Area: 29.1A^2

Experimental Properties

  • Density: 1.2±0.1 g/cm3
  • Boiling Point: 256.9±23.0 °C at 760 mmHg
  • Flash Point: 109.2±22.6 °C
  • Refractive Index: 1.622
  • PSA: 29.1
  • Vapor Pressure: 0.0±0.5 mmHg at 25°C

2-Fluoro-N-phenyl-benzamide Security Information

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Additional information on 2-Fluoro-N-phenyl-benzamide

Professional Introduction to 2-Fluoro-N-phenyl-benzamide (CAS No. 1747-80-4)

2-Fluoro-N-phenyl-benzamide (CAS No. 1747-80-4) is a fluorinated benzamide derivative that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology due to its unique structural properties and potential biological activities. This compound belongs to a class of molecules that have been extensively studied for their pharmacological significance, particularly in the development of novel therapeutic agents.

The structural motif of 2-Fluoro-N-phenyl-benzamide consists of a benzamide core substituted with a fluorine atom at the 2-position and a phenyl group attached to the nitrogen atom of the amide moiety. The presence of the fluorine atom is particularly noteworthy, as fluorine substitution can significantly influence the electronic properties, metabolic stability, and binding affinity of a molecule. In pharmaceutical applications, fluorinated compounds often exhibit enhanced bioavailability, improved metabolic resistance, and increased binding affinity to biological targets.

Recent research in the field of drug discovery has highlighted the importance of fluorinated benzamides as scaffolds for developing small-molecule inhibitors. Specifically, studies have demonstrated that the fluorine atom in 2-Fluoro-N-phenyl-benzamide can modulate the interactions between the compound and its biological target, leading to more potent and selective inhibition. For instance, researchers have explored its potential as an inhibitor of enzymes involved in inflammatory pathways, such as cyclooxygenase (COX) and lipoxygenase (LOX). The electron-withdrawing nature of the fluorine atom can enhance the electrophilicity of key functional groups in the molecule, thereby improving its binding affinity to these enzymes.

In addition to its role as an enzyme inhibitor, 2-Fluoro-N-phenyl-benzamide has also been investigated for its potential anticancer properties. Preclinical studies have shown that this compound can induce apoptosis in certain cancer cell lines by modulating intracellular signaling pathways. The fluorine atom's ability to influence molecular interactions has been found to enhance the compound's ability to disrupt critical cellular processes involved in cancer progression. Furthermore, the phenyl group attached to the nitrogen atom provides a hydrophobic surface that can interact favorably with hydrophobic pockets on biological targets, further enhancing binding affinity.

The synthesis of 2-Fluoro-N-phenyl-benzamide involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include nucleophilic aromatic substitution reactions followed by amide bond formation. The introduction of the fluorine atom at the 2-position of the benzene ring typically involves halogen exchange or direct fluorination techniques. These synthetic strategies must be carefully designed to minimize side reactions and maximize the formation of the desired product.

The pharmacokinetic properties of 2-Fluoro-N-phenyl-benzamide are also an area of active investigation. Studies have shown that fluorinated benzamides generally exhibit good oral bioavailability due to their favorable solubility and metabolic stability. The presence of the fluorine atom can slow down metabolic degradation by enzymes such as cytochrome P450 (CYP450), thereby extending the half-life of the compound in vivo. This characteristic makes it an attractive candidate for chronic therapeutic applications where long-lasting effects are desired.

Efforts are ongoing to explore new derivatives of 2-Fluoro-N-phenyl-benzamide that may exhibit even greater pharmacological activity or improved pharmacokinetic profiles. Structural modifications such as varying substituents on the phenyl ring or introducing additional functional groups can lead to compounds with enhanced potency or selectivity. Computational methods, including molecular docking and quantum mechanical calculations, are being employed to predict how different structural modifications will affect the biological activity of these compounds.

The development of novel therapeutic agents relies heavily on understanding how structural features influence biological activity. In this context, 2-Fluoro-N-phenyl-benzamide serves as an important model compound for studying structure-activity relationships (SAR) in fluorinated benzamides. By analyzing how changes in its structure affect its biological properties, researchers can gain insights into general principles that may apply to other fluorinated compounds, accelerating the discovery process for new drugs.

The use of high-throughput screening (HTS) technologies has also played a crucial role in identifying new applications for 2-Fluoro-N-phenyl-benzamide. HTS allows researchers to rapidly test thousands of compounds against various biological targets simultaneously, enabling the identification of promising candidates for further development. This approach has been instrumental in uncovering novel therapeutic uses for existing compounds like benzamides and their derivatives.

In conclusion, 2-Fluoro-N-phenyl-benzamide (CAS No. 1747-80-4) is a versatile compound with significant potential in pharmaceutical research and drug development. Its unique structural features make it an attractive scaffold for designing novel therapeutic agents with improved pharmacological properties. Ongoing research continues to explore its applications in treating various diseases, including cancer and inflammatory disorders. As our understanding of structure-activity relationships improves, compounds like this are expected to play an increasingly important role in developing next-generation pharmaceuticals.

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