151361-87-4 | 1-ETHYNYL-3 5-DIFLUOROBENZENE 97

CAS:151361-87-4 | 1-ETHYNYL-3 5-DIFLUOROBENZENE 97,Description

1-Ethynyl-3,5-difluorobenzene is a compound that is part of a broader class of ethynylbenzene derivatives. These compounds are characterized by the presence of an ethynyl group (-C≡CH) attached to a benzene ring that may also contain other substituents, such as fluorine atoms. The specific placement of the ethynyl group and the difluorine atoms at positions 3 and 5 on the benzene ring defines the compound's unique chemical identity and influences its reactivity and physical properties.

Synthesis Analysis

The synthesis of ethynylbenzene derivatives can vary depending on the desired substituents on the benzene ring. For instance, the synthesis of oligonucleotides containing a nucleotide analog with an ethynylfluorobenzene as a nucleobase surrogate involves the preparation of a 5'-protected 3'-phosphoramidite of 1-(2'-deoxy-β-d-ribofuranosyl)-2-ethynyl-4-fluorobenzene, which is then employed in the synthesis of oligonucleotides. This indicates that the synthesis of such compounds can be complex and may involve multiple steps, including protection and deprotection of functional groups, to achieve the desired molecular structure.

Molecular Structure Analysis

The molecular structure of ethynylbenzene derivatives can exhibit a significant diversity even with subtle changes in the molecular structure, such as the length of alkoxy chains. For example, the structures of three homologous dialkoxy ethynylnitrobenzenes, which differ only in the length of the alkoxy chain, show great diversity in their crystal structures. This suggests that the molecular structure of 1-Ethynyl-3,5-difluorobenzene would also be influenced by its substituents, potentially affecting its crystalline form and the interactions it can form with other molecules.

Chemical Reactions Analysis

Physical and Chemical Properties Analysis

The physical and chemical properties of ethynylbenzene derivatives are determined by their molecular structure. For instance, the melting points of oligonucleotide duplexes containing ethynylfluorobenzene nucleotide analogs are reported to be higher than those containing difluorotoluene moieties. This indicates that the introduction of the ethynyl group and fluorine atoms can significantly influence the stability and melting behavior of these compounds. The specific physical and chemical properties of 1-Ethynyl-3,5-difluorobenzene would depend on its molecular structure, which could include factors such as polarity, boiling point, solubility, and reactivity.

Scientific Research Applications

1. Ion-Pi Interactions

1-Ethynyl-3,5-difluorobenzene has been studied for its role in ion-pi interactions, specifically in 1,3,5-triethynylbenzene systems. The ethynyl group acts as an electron-withdrawing group, favoring anion-pi interaction but showing little influence on cation-pi interaction. This behavior was examined through geometrical and energetic features of the complexes, AIM, and charge analyses, and by partitioning the interaction energy (Lucas, Quiñonero, Frontera, & Deyà, 2009).

2. Inclusion in Oligonucleotides

Research on 1-Ethynyl-3,5-difluorobenzene includes its use in oligonucleotide synthesis. A study incorporated a 1-ethynyl-3,5-difluorobenzene analog into oligonucleotides, showing that it melts higher than a duplex containing a difluorotoluene moiety, indicating its potential for unique nucleotide interactions (Griesang & Richert, 2002).

3. Host-Guest Interactions

The compound is also noted for its role in unexpected host-guest interactions in crystalline states. For example, coupling 1-ethynyl-3-hydroxybenzene with 1,2-diiodobenzene led to a screw-type arrangement with tetrahedral cavities filled with water molecules, forming an unexpected host-guest complex (Schmittel, Morbach, Engelen, & Panthöfer, 2001).

4. Improved π-π Stacking Affinity

Another important application is in the study of π-π stacking affinity. The ethynyl substituent in 1,3,5-triethynylbenzene, a related compound, was found to improve stacking affinity compared to benzene and 1,3,5-trifluorobenzene. This indicates potential applications in molecular assembly and nanostructure design (Lucas, Quiñonero, Frontera, & Deyà, 2011).

5. Synthesis of Novel Molecules

The compound is also utilized in the synthesis of novel molecules. For instance, its use in the cyclocarbonylation of 1-ethynyl-2-allenylbenzenes to produce 1H-cyclopenta[a]inden-2-ones underlines its versatility in synthetic chemistry (Datta & Liu, 2005).

Safety And Hazards

1-Ethynyl-3,5-difluorobenzene is classified as a flammable liquid and vapor. It can cause skin irritation, serious eye irritation, and may cause respiratory irritation. It is recommended to avoid contact with skin and eyes, avoid inhalation of vapor or mist, and keep away from sources of ignition.

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