Cas no 519059-03-1 (3-(Difluoromethoxy)phenylacetylene)

3-(Difluoromethoxy)phenylacetylene is a fluorinated aromatic acetylene compound characterized by the presence of a difluoromethoxy group (–OCF?H) attached to a phenyl ring. This structural feature enhances its utility as a versatile building block in organic synthesis, particularly in cross-coupling reactions such as Sonogashira, Heck, and Suzuki couplings. The difluoromethoxy group imparts unique electronic and steric properties, making it valuable for modifying pharmaceuticals, agrochemicals, and advanced materials. Its stability and reactivity under mild conditions allow for efficient functionalization, while the fluorine atoms contribute to improved metabolic stability and lipophilicity in derived compounds. This compound is particularly useful in medicinal chemistry for the development of bioactive molecules.
3-(Difluoromethoxy)phenylacetylene structure
519059-03-1 structure
Product Name:3-(Difluoromethoxy)phenylacetylene
CAS No:519059-03-1
MF:C9H6F2O
MW:168.140149593353
MDL:MFCD03094334
CID:2624887
PubChem ID:2778495
Update Time:2025-06-08

3-(Difluoromethoxy)phenylacetylene Chemical and Physical Properties

Names and Identifiers

    • 1-(Difluoromethoxy)-3-ethynylbenzene
    • 3-(DIFLUOROMETHOXY)PHENYLACETYLEN
    • 3-(Difluoromethoxy)phenylacetylene
    • SCHEMBL3456218
    • 519059-03-1
    • DB-182833
    • DTXSID20380977
    • EN300-1933931
    • 961-716-5
    • MFCD03094334
    • 3-(difluoromethoxy)phenylacetylene, AldrichCPR
    • PS-6744
    • CS-0212376
    • AKOS026675561
    • alpha,alpha-Difluoro-3-ethynylanisole, 1-(Difluoromethoxy)-3-ethynylbenzene, Difluoromethyl 3-ethynylphenyl ether
    • UVA05903
    • G29990
    • MDL: MFCD03094334
    • Inchi: 1S/C9H6F2O/c1-2-7-4-3-5-8(6-7)12-9(10)11/h1,3-6,9H
    • InChI Key: UGUOBKVALAVDFR-UHFFFAOYSA-N
    • SMILES: FC(OC1C=CC=C(C#C)C=1)F

Computed Properties

  • Exact Mass: 168.03867113Da
  • Monoisotopic Mass: 168.03867113Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 182
  • 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: 3.1
  • Topological Polar Surface Area: 9.2?2

3-(Difluoromethoxy)phenylacetylene Pricemore >>

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Additional information on 3-(Difluoromethoxy)phenylacetylene

3-(Difluoromethoxy)phenylacetylene (CAS No. 519059-03-1): A Comprehensive Overview

3-(Difluoromethoxy)phenylacetylene (CAS No. 519059-03-1) is a versatile organic compound that has garnered significant attention in recent years due to its unique chemical properties and potential applications in various fields, including pharmaceuticals, materials science, and chemical synthesis. This compound is characterized by its difluoromethoxy substituent and acetylene moiety, which contribute to its reactivity and functional versatility.

The molecular formula of 3-(Difluoromethoxy)phenylacetyyne is C9H6F2O, and its molecular weight is approximately 164.14 g/mol. The compound's structure consists of a phenyl ring with a difluoromethoxy group at the 3-position and an acetylene group attached to the phenyl ring. This unique combination of functional groups imparts distinct chemical properties that make it a valuable intermediate in organic synthesis.

In the realm of pharmaceutical research, 3-(Difluoromethoxy)phenylacetylene has shown promise as a building block for the synthesis of bioactive molecules. The difluoromethoxy group is known to enhance the lipophilicity and metabolic stability of drug candidates, which can improve their pharmacokinetic profiles. Additionally, the acetylene moiety can be readily functionalized through various chemical reactions, such as copper-catalyzed azide-alkyne cycloaddition (CuAAC), making it a useful handle for click chemistry applications.

Recent studies have explored the use of 3-(Difluoromethoxy)phenylacetylene in the development of novel therapeutic agents. For instance, researchers at the University of California, San Francisco, have utilized this compound as a key intermediate in the synthesis of a new class of anti-inflammatory drugs. These compounds have demonstrated potent anti-inflammatory activity in preclinical models, suggesting their potential for treating inflammatory diseases such as rheumatoid arthritis and Crohn's disease.

Beyond pharmaceutical applications, 3-(Difluoromethoxy)phenylacetylene has also found utility in materials science. Its unique electronic properties make it an attractive candidate for the development of advanced materials with tailored optical and electronic characteristics. For example, researchers at the Massachusetts Institute of Technology (MIT) have incorporated this compound into polymer matrices to create materials with enhanced photoluminescence properties. These materials have potential applications in optoelectronic devices, such as organic light-emitting diodes (OLEDs) and solar cells.

The synthetic accessibility of 3-(Difluoromethoxy)phenylacetylene further enhances its appeal as a versatile building block. Several efficient synthetic routes have been developed to prepare this compound on both laboratory and industrial scales. One common method involves the reaction of 3-hydroxybenzaldehyde with difluoroiodomethane followed by a Sonogashira coupling reaction with terminal alkynes. This multi-step process yields high-purity 3-(Difluoromethoxy)phenylacetylene, which can be readily used in subsequent synthetic transformations.

In addition to its synthetic utility, 3-(Difluoromethoxy)phenylacetylene has been studied for its potential as a probe molecule in chemical biology research. The difluoromethoxy group can serve as a bioisostere for hydroxyl or methoxy groups, allowing researchers to explore the effects of these substitutions on biological activity. For example, studies have shown that replacing hydroxyl groups with difluoromethoxy groups can lead to improved metabolic stability and reduced toxicity in certain drug candidates.

The environmental impact of 3-(Difluoromethoxy)phenylacetylene is another important consideration. While this compound is not classified as hazardous or toxic under current regulations, it is essential to handle it with care and follow standard laboratory safety protocols. Proper disposal methods should be employed to minimize any potential environmental impact.

In conclusion, 3-(Difluoromethoxy)phenylacetylene (CAS No. 519059-03-1) is a multifunctional compound with a wide range of applications in pharmaceuticals, materials science, and chemical synthesis. Its unique combination of functional groups makes it an attractive building block for the development of novel therapeutic agents and advanced materials. Ongoing research continues to uncover new possibilities for this versatile compound, solidifying its importance in modern chemistry and related fields.

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