Cas no 1112209-24-1 (3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde)

3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is a versatile boronic ester derivative widely used in Suzuki-Miyaura cross-coupling reactions. Its key advantages include high stability under ambient conditions, making it suitable for storage and handling. The presence of the fluoro substituent enhances its reactivity and selectivity in palladium-catalyzed transformations, while the aldehyde group offers additional functionalization potential. This compound is particularly valuable in pharmaceutical and materials science research for constructing complex aryl-aryl bonds. Its compatibility with a broad range of reaction conditions and substrates makes it a reliable intermediate in synthetic organic chemistry. The dioxaborolane moiety ensures efficient transmetalation, contributing to high yields in coupling reactions.
3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde structure
1112209-24-1 structure
Product Name:3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
CAS No:1112209-24-1
MF:C13H16BFO3
MW:250.073747634888
MDL:MFCD16996301
CID:2606916
PubChem ID:56776723
Update Time:2025-06-13

3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
    • BENZALDEHYDE,3-FLUORO-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL);3-FLUORO-5-FORMYLBENZENEBORONIC ACID PINACOL ESTER;3-FLUORO-5-FORMYLPHENYLBORONIC ACID PINACOL ESTER;
    • DTXSID501160169
    • CS-0177824
    • 1112209-24-1
    • 3-Fluoro-1-formylbenzene-5-boronic Acid Pinacol Ester
    • 3-FLUORO-5-FORMYLPHENYLBORONIC ACID PINACOL ESTER
    • DB-183395
    • (3-FLUORO-5-FORMYLPHENYL)BORONIC ACID PINACOL ESTER
    • BS-30103
    • EN300-6746864
    • MFCD16996301
    • MB20441
    • 3-fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
    • AKOS025293596
    • 896-838-7
    • MDL: MFCD16996301
    • Inchi: 1S/C13H16BFO3/c1-12(2)13(3,4)18-14(17-12)10-5-9(8-16)6-11(15)7-10/h5-8H,1-4H3
    • InChI Key: WENPYTYJEVDZDV-UHFFFAOYSA-N
    • SMILES: FC1C=C(C=O)C=C(B2OC(C)(C)C(C)(C)O2)C=1

Computed Properties

  • Exact Mass: 250.11800
  • Monoisotopic Mass: 250.1176527g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 2
  • Complexity: 316
  • 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: 35.5?2

Experimental Properties

  • PSA: 35.53000
  • LogP: 1.93740

3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde Pricemore >>

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Additional information on 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

Professional Introduction to Compound with CAS No. 1112209-24-1 and Product Name: 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

The compound with the CAS number 1112209-24-1 and the product name 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde represents a significant advancement in the field of pharmaceutical chemistry. This compound has garnered considerable attention due to its unique structural properties and its potential applications in the development of novel therapeutic agents. The presence of a fluoro-substituent and a tetramethyl-substituted boronic ester moiety makes it a particularly intriguing molecule for further investigation.

In recent years, the pharmaceutical industry has witnessed a surge in the use of fluorinated compounds due to their enhanced metabolic stability and improved binding affinity to biological targets. The fluoro-substituent in this compound is strategically positioned at the 3-position of the benzaldehyde ring, which is known to modulate the electronic properties of the molecule. This modification can significantly influence the compound's interactions with biological receptors, making it a valuable candidate for drug discovery.

The other notable feature of this compound is the 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group attached to the 5-position of the benzaldehyde ring. This boronic ester moiety is particularly useful in cross-coupling reactions, which are fundamental to modern synthetic organic chemistry. The stability and reactivity of this boronic ester make it an excellent tool for constructing more complex molecular architectures. This property has been leveraged in various synthetic pathways to develop intricate pharmacophores.

Recent advancements in synthetic methodologies have enabled the efficient preparation of this compound using palladium-catalyzed cross-coupling reactions. These reactions are highly versatile and allow for the introduction of diverse functional groups into organic molecules. The use of tetramethyl-substituted boronic esters has been particularly advantageous due to their enhanced stability under various reaction conditions. This stability ensures higher yields and better reproducibility in synthetic protocols.

The applications of 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde extend beyond its role as a building block in drug synthesis. It has been explored as a key intermediate in the preparation of fluorinated heterocycles, which are known for their broad spectrum of biological activities. These heterocycles have shown promise in treating various diseases, including cancer and infectious disorders. The ability to introduce fluorine atoms into these heterocycles can fine-tune their pharmacological properties, leading to more effective therapeutic agents.

One of the most exciting areas where this compound has been applied is in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in many cellular processes and are often targeted by therapeutic agents. The presence of both a fluoro-substituent and a boronic ester allows for precise modulation of kinase activity. This dual functionality has been exploited to design inhibitors that exhibit high selectivity and potency against specific kinases involved in diseases such as cancer.

Furthermore, the structural features of this compound have made it an attractive candidate for studying structure-activity relationships (SAR). By systematically varying different parts of the molecule while keeping others constant, researchers can gain insights into how specific structural elements influence biological activity. This information is invaluable for designing next-generation drugs with improved efficacy and reduced side effects.

The synthesis of 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde also highlights the importance of green chemistry principles in modern pharmaceutical research. The use of catalytic amounts of palladium and mild reaction conditions minimizes waste and reduces energy consumption. These sustainable practices are essential for ensuring that drug development processes are environmentally friendly and economically viable.

In conclusion,3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde represents a significant contribution to the field of pharmaceutical chemistry. Its unique structural features make it a versatile tool for drug discovery and synthesis. The strategic use of fluorine and boronic ester functionalities allows for precise modulation of biological activity and improved synthetic efficiency. As research continues to uncover new applications for this compound,its importance is likely to grow further, driving innovation in therapeutic development.

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