Cas no 80395-30-8 (2,4-bis(difluoromethoxy)benzaldehyde)

2,4-Bis(difluoromethoxy)benzaldehyde is a fluorinated aromatic aldehyde characterized by the presence of two difluoromethoxy groups at the 2- and 4-positions of the benzene ring. This compound is of interest in synthetic organic chemistry due to its electron-withdrawing substituents, which enhance reactivity in nucleophilic aromatic substitution and cross-coupling reactions. The difluoromethoxy groups contribute to improved metabolic stability and lipophilicity, making it a valuable intermediate in pharmaceutical and agrochemical research. Its structural features also facilitate applications in materials science, particularly in the development of liquid crystals and specialty polymers. The compound is typically handled under controlled conditions due to its sensitivity to moisture and light.
2,4-bis(difluoromethoxy)benzaldehyde structure
80395-30-8 structure
Product Name:2,4-bis(difluoromethoxy)benzaldehyde
CAS No:80395-30-8
MF:C9H6F4O3
MW:238.135756969452
CID:3353312
PubChem ID:4218025
Update Time:2025-10-12

2,4-bis(difluoromethoxy)benzaldehyde Chemical and Physical Properties

Names and Identifiers

    • BENZALDEHYDE, 2,4-BIS(DIFLUOROMETHOXY)-
    • 2,4-bis(difluoromethoxy)benzaldehyde
    • G40718
    • AKOS000115391
    • Z55671899
    • 2,4-Bis-difluoromethoxy-benzaldehyde
    • VACUIYCDKQBXCB-UHFFFAOYSA-N
    • EN300-01088
    • 80395-30-8
    • 990-502-4
    • CS-0218470
    • SCHEMBL11260550
    • Inchi: 1S/C9H6F4O3/c10-8(11)15-6-2-1-5(4-14)7(3-6)16-9(12)13/h1-4,8-9H
    • InChI Key: VACUIYCDKQBXCB-UHFFFAOYSA-N
    • SMILES: C(=O)C1=CC=C(OC(F)F)C=C1OC(F)F

Computed Properties

  • Exact Mass: 238.025
  • Monoisotopic Mass: 238.025
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 5
  • Complexity: 225
  • 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: 35.5A^2
  • XLogP3: 3.2

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2,4-bis(difluoromethoxy)benzaldehyde Related Literature

Additional information on 2,4-bis(difluoromethoxy)benzaldehyde

Professional Introduction to 2,4-bis(difluoromethoxy)benzaldehyde (CAS No. 80395-30-8)

2,4-bis(difluoromethoxy)benzaldehyde, with the chemical formula C?H?F?O?, is a fluorinated aromatic aldehyde that has garnered significant attention in the field of pharmaceutical and agrochemical research due to its unique structural properties and potential biological activities. This compound, identified by its CAS number 80395-30-8, belongs to a class of molecules that exhibit promising characteristics for further development into novel therapeutic agents. The presence of both difluoromethoxy and aldehyde functional groups makes it a versatile intermediate in synthetic chemistry, particularly in the design of molecules targeting various biological pathways.

The significance of 2,4-bis(difluoromethoxy)benzaldehyde lies in its potential applications across multiple domains. In pharmaceutical research, the fluorine atoms and methoxy groups contribute to the compound's lipophilicity and metabolic stability, which are critical factors in drug design. The aldehyde group provides a reactive site for further functionalization, enabling the synthesis of more complex molecules with tailored properties. Recent studies have highlighted its role as a precursor in the development of inhibitors for enzymes involved in inflammatory and infectious diseases.

One of the most compelling aspects of 2,4-bis(difluoromethoxy)benzaldehyde is its structural similarity to naturally occurring bioactive compounds. This similarity suggests that it may interact with biological targets in a manner akin to known pharmacophores. For instance, researchers have explored its potential as a scaffold for developing kinase inhibitors, which are crucial in treating cancers and inflammatory disorders. The fluorine atoms, in particular, have been shown to enhance binding affinity and selectivity, making this compound an attractive candidate for medicinal chemistry.

In addition to its pharmaceutical applications, 2,4-bis(difluoromethoxy)benzaldehyde has shown promise in agrochemical research. The compound's ability to act as an intermediate in the synthesis of novel pesticides and herbicides is being actively investigated. Its structural features contribute to enhanced stability against environmental degradation, which is essential for effective agricultural use. Furthermore, the fluorinated aromatic ring can improve the bioavailability of agrochemicals, ensuring better absorption and efficacy in target plants.

The synthesis of 2,4-bis(difluoromethoxy)benzaldehyde involves multi-step organic reactions that highlight the compound's synthetic utility. Common synthetic routes include the condensation of 2,4-dihydroxybenzaldehyde with difluoromethylating agents under controlled conditions. Advances in catalytic methods have enabled more efficient and sustainable production processes, reducing waste and energy consumption. These improvements align with the growing emphasis on green chemistry principles in industrial applications.

The chemical properties of 2,4-bis(difluoromethoxy)benzaldehyde, such as its solubility and reactivity, make it a valuable tool for researchers exploring new synthetic pathways. Its high melting point and stability under various conditions enhance its suitability for laboratory-scale reactions as well as large-scale industrial processes. The compound's ability to participate in multiple types of organic reactions—such as condensation, oxidation, and reduction—further underscores its versatility.

In recent years, computational chemistry has played a pivotal role in understanding the behavior of 2,4-bis(difluoromethoxy)benzaldehyde. Molecular modeling studies have provided insights into its interactions with biological targets at an atomic level. These studies not only aid in predicting potential drug candidates but also help optimize synthetic routes by identifying key intermediates and reaction mechanisms. The integration of computational methods with experimental approaches has accelerated the discovery process significantly.

The future prospects for 2,4-bis(difluoromethoxy)benzaldehyde are vast and multifaceted. Ongoing research aims to expand its applications into new areas such as materials science and nanotechnology. Its unique electronic properties make it a candidate for developing advanced materials with specialized functions. Additionally, the compound's role in designing novel catalysts for organic transformations is being explored.

In conclusion, 2,4-bis(difluoromethoxy)benzaldehyde (CAS No. 80395-30-8) represents a significant advancement in synthetic chemistry with broad implications for pharmaceuticals and agrochemicals. Its structural features and reactivity make it a valuable intermediate for developing innovative molecules with therapeutic potential. As research continues to uncover new applications and synthetic methodologies, this compound is poised to play an increasingly important role in scientific innovation.

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