Cas no 783342-33-6 (2-Fluoro-3,6-dimethoxybenzaldehyde)

2-Fluoro-3,6-dimethoxybenzaldehyde is a fluorinated and methoxy-substituted benzaldehyde derivative, primarily utilized as a versatile intermediate in organic synthesis and pharmaceutical research. The presence of both fluorine and methoxy groups enhances its reactivity, making it valuable for constructing complex molecular frameworks, particularly in medicinal chemistry and agrochemical applications. Its electron-withdrawing fluorine and electron-donating methoxy substituents influence its electrophilic properties, enabling selective functionalization. The compound's stability and well-defined structure facilitate its use in cross-coupling reactions, nucleophilic substitutions, and as a precursor for heterocyclic compounds. It is typically handled under controlled conditions due to its sensitivity to light and moisture.
2-Fluoro-3,6-dimethoxybenzaldehyde structure
783342-33-6 structure
Product Name:2-Fluoro-3,6-dimethoxybenzaldehyde
CAS No:783342-33-6
MF:C9H9FO3
MW:184.164366483688
MDL:MFCD19439911
CID:1040842
PubChem ID:10583615
Update Time:2025-05-19

2-Fluoro-3,6-dimethoxybenzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-Fluoro-3,6-dimethoxybenzaldehyde
    • NULL
    • AK103220
    • ANW-64997
    • Benzaldehyde, 2-fluoro-3,6-dimethoxy-
    • CTK2F9879
    • KB-230484
    • 3,6-Dimethoxy-2-fluorobenzaldehyde
    • E91855
    • SCHEMBL1478225
    • MFCD19439911
    • CS-0131632
    • 783342-33-6
    • LNPHQRXMWZSAHH-UHFFFAOYSA-N
    • DTXSID50442032
    • DB-330314
    • MDL: MFCD19439911
    • Inchi: 1S/C9H9FO3/c1-12-7-3-4-8(13-2)9(10)6(7)5-11/h3-5H,1-2H3
    • InChI Key: LNPHQRXMWZSAHH-UHFFFAOYSA-N
    • SMILES: FC1=C(C=CC(=C1C=O)OC)OC

Computed Properties

  • Exact Mass: 184.05357231g/mol
  • Monoisotopic Mass: 184.05357231g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 174
  • 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: 1.4
  • Topological Polar Surface Area: 35.5?2

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Additional information on 2-Fluoro-3,6-dimethoxybenzaldehyde

Introduction to 2-Fluoro-3,6-dimethoxybenzaldehyde (CAS No. 783342-33-6)

2-Fluoro-3,6-dimethoxybenzaldehyde, identified by its Chemical Abstracts Service (CAS) number 783342-33-6, is a fluorinated aromatic aldehyde that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to a class of molecules that exhibit a unique combination of structural features, making it a valuable intermediate in the synthesis of various bioactive agents. The presence of both fluoro and methoxy substituents on a benzaldehyde backbone imparts distinct electronic and steric properties, which are leveraged in drug design and development.

The structural motif of 2-fluoro-3,6-dimethoxybenzaldehyde is highly versatile, enabling its incorporation into diverse molecular frameworks. The fluorine atom, being electron-withdrawing, can modulate the reactivity of the benzene ring and the aldehyde group, while the methoxy groups enhance lipophilicity and metabolic stability. Such characteristics make this compound a promising candidate for further derivatization and exploration in medicinal chemistry.

In recent years, there has been a growing interest in fluorinated aromatic compounds due to their enhanced binding affinity and metabolic profiles compared to their non-fluorinated counterparts. For instance, studies have demonstrated that fluorine substitution can improve the pharmacokinetic properties of drug candidates by increasing their bioavailability and reducing susceptibility to enzymatic degradation. The introduction of fluorine at the 2-position of the benzaldehyde ring in 2-fluoro-3,6-dimethoxybenzaldehyde is particularly noteworthy, as it has been shown to enhance receptor binding in certain therapeutic targets.

One of the most compelling applications of 2-fluoro-3,6-dimethoxybenzaldehyde lies in its role as a key intermediate in the synthesis of kinase inhibitors. Kinases are enzymes that play critical roles in cellular signaling pathways and are frequently targeted in anticancer therapies. The aldehyde functionality of this compound allows for facile condensation reactions with various nitrogen-containing heterocycles, leading to the formation of Schiff bases and other bioactive molecules. These derivatives have shown promise in preclinical studies as inhibitors of aberrantly activated kinases associated with cancer.

Moreover, the methoxy groups in 2-fluoro-3,6-dimethoxybenzaldehyde contribute to its solubility and interaction with biological targets. This feature is particularly important in drug development, where poor solubility can hinder drug absorption and efficacy. Recent research has highlighted the use of this compound in designing small-molecule inhibitors for neurological disorders. The ability to fine-tune the electronic properties of the benzaldehyde core through fluorination and methoxylation has led to the discovery of novel compounds with improved pharmacological profiles.

The synthesis of 2-fluoro-3,6-dimethoxybenzaldehyde typically involves multi-step organic transformations starting from commercially available precursors. Advanced synthetic methodologies, such as palladium-catalyzed cross-coupling reactions and fluorochemical transformations, have been employed to achieve high yields and purity. These synthetic strategies not only facilitate large-scale production but also allow for structural modifications to tailor the compound's properties for specific applications.

In conclusion, 2-fluoro-3,6-dimethoxybenzaldehyde (CAS No. 783342-33-6) represents a significant advancement in pharmaceutical chemistry due to its versatile structural features and potential therapeutic applications. Its role as an intermediate in synthesizing kinase inhibitors and other bioactive agents underscores its importance in drug discovery efforts. As research continues to uncover new biological targets and synthetic methodologies, compounds like this will remain at the forefront of medicinal chemistry innovation.

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