Cas no 1881327-86-1 (4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol)

4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol is a fluorinated phenol derivative protected with a tert-butyldimethylsilyl (TBS) group, enhancing its stability and handling properties. The TBS group serves as a robust protecting moiety for the hydroxyl functionality, allowing selective deprotection under mild conditions. The presence of fluorine atoms at the 2- and 6-positions introduces electron-withdrawing effects, making this compound valuable in synthetic organic chemistry, particularly in the preparation of fluorinated intermediates for pharmaceuticals and agrochemicals. Its structural features enable precise reactivity control in cross-coupling and nucleophilic substitution reactions. The compound is typically used under inert conditions to preserve its integrity, ensuring consistent performance in complex synthetic pathways.
4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol structure
1881327-86-1 structure
Product Name:4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol
CAS No:1881327-86-1
MF:C12H18F2O2Si
MW:260.352431774139
CID:4626585
Update Time:2025-10-30

4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol Chemical and Physical Properties

Names and Identifiers

    • 4-[(TERT-BUTYLDIMETHYLSILYL)OXY]-2,6-DIFLUOROPHENOL
    • 4-[tert-butyl(dimethyl)silyl]oxy-2,6-difluorophenol
    • 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol
    • Inchi: 1S/C12H18F2O2Si/c1-12(2,3)17(4,5)16-8-6-9(13)11(15)10(14)7-8/h6-7,15H,1-5H3
    • InChI Key: GFUWGGBYTYXUSC-UHFFFAOYSA-N
    • SMILES: [Si](C)(C)(C(C)(C)C)OC1C=C(C(=C(C=1)F)O)F

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 17
  • Rotatable Bond Count: 3
  • Complexity: 254
  • Topological Polar Surface Area: 29.5

4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
A2B Chem LLC
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Additional information on 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol

Recent Advances in the Application of 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol (CAS: 1881327-86-1) in Chemical Biology and Pharmaceutical Research

The compound 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol (CAS: 1881327-86-1) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and versatile applications. This phenol derivative, protected by a tert-butyldimethylsilyl (TBS) group, serves as a key intermediate in the synthesis of various biologically active molecules, including fluorinated pharmaceuticals and agrochemicals. Recent studies have highlighted its role in facilitating selective reactions, enhancing compound stability, and enabling the development of novel therapeutic agents.

One of the most notable applications of 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol is its use in the synthesis of fluorinated aromatic compounds, which are increasingly important in drug discovery. Fluorination often improves the pharmacokinetic properties of drug candidates, such as metabolic stability and membrane permeability. Researchers have successfully employed this compound in palladium-catalyzed cross-coupling reactions to construct complex fluorinated scaffolds, which are prevalent in many FDA-approved drugs. The TBS-protecting group ensures the stability of the phenol moiety during these transformations, allowing for high-yield and regioselective reactions.

In addition to its synthetic utility, 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol has been investigated for its potential as a building block in the development of enzyme inhibitors. Recent studies have demonstrated its incorporation into inhibitors targeting tyrosine kinases and other key enzymes involved in cancer progression. The difluorophenol moiety, in particular, has been shown to enhance binding affinity and selectivity, making it a valuable structural motif in medicinal chemistry. Furthermore, the TBS group can be selectively removed under mild conditions, enabling further functionalization of the inhibitor scaffold.

Another emerging area of research involves the use of this compound in the design of prodrugs. Prodrug strategies are widely employed to improve the bioavailability and delivery of active pharmaceutical ingredients. The TBS-protected phenol can serve as a masked hydroxyl group, which can be enzymatically or chemically cleaved in vivo to release the active drug. Recent preclinical studies have reported promising results with prodrugs derived from 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol, particularly in the context of targeted therapies for inflammatory diseases and central nervous system disorders.

Despite its promising applications, challenges remain in the large-scale synthesis and purification of 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol. Recent advancements in flow chemistry and continuous manufacturing have shown potential in addressing these issues, offering more efficient and scalable production methods. Additionally, researchers are exploring greener alternatives to traditional silylation reagents to reduce the environmental impact of its synthesis.

In conclusion, 4-[(Tert-butyldimethylsilyl)oxy]-2,6-difluorophenol (CAS: 1881327-86-1) represents a versatile and valuable tool in modern chemical biology and pharmaceutical research. Its applications span from synthetic chemistry to drug development, highlighting its importance in the discovery of next-generation therapeutics. Ongoing research efforts are expected to further expand its utility and optimize its production, solidifying its role in the advancement of the field.

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