2-Fluorophenyl 2-Nitrophenyl Ether: Properties & Applications
2-Fluorophenyl 2-Nitrophenyl Ether: Properties & Applications
2-Fluorophenyl 2-nitrophenyl ether is a difunctionalized diaryl ether reagent bearing both a fluorine substituent and a nitro group on separate phenyl rings, making it a versatile building block for nucleophilic aromatic substitution chemistry and the synthesis of complex heterocyclic or pharmaceutical intermediates.
- Chemical Name
- 2-Fluorophenyl 2-nitrophenyl ether
- SKU / Catalog Number
- F354345
- Santa Cruz Reference
- sc-254251
- Compound Class
- Diaryl ether (fluoronitro-substituted)
- Key Functional Groups
- Aryl fluoride, aryl nitro group, diaryl ether linkage
- Primary Use
- Synthetic intermediate in SNAr reactions and pharmaceutical research
Chemical Identity and Structure
2-Fluorophenyl 2-nitrophenyl ether is an aromatic ether in which a 2-fluorophenyl group and a 2-nitrophenyl group are connected through an oxygen bridge. The presence of an electron-withdrawing fluorine atom at the ortho position of one phenyl ring and an electron-withdrawing nitro group at the ortho position of the second phenyl ring imparts distinctive reactivity to this molecule.
The diaryl ether scaffold is a recurring motif in biologically active compounds and materials science applications. The ortho-fluorine substituent activates the aromatic ring toward nucleophilic aromatic substitution (SNAr), while the ortho-nitro group on the complementary ring further modulates electron density across the oxygen bridge, influencing reactivity and selectivity in downstream transformations.
This compound is catalogued at Aladdin Scientific under SKU F354345 and is cross-referenced with Santa Cruz catalog number sc-254251.
Physicochemical Properties
As a member of the diaryl ether family bearing two strong electron-withdrawing substituents, 2-Fluorophenyl 2-nitrophenyl ether is expected to be a solid or low-melting solid at ambient temperature, though researchers should consult the certificate of analysis supplied with each lot for confirmed physical state, melting point, and purity data.
The compound is anticipated to be sparingly soluble in water but readily soluble in common organic solvents such as dichloromethane, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ethyl acetate, and tetrahydrofuran (THF). Its lipophilicity, conferred by the two aromatic rings and the ether oxygen, makes it compatible with a broad range of reaction media used in synthetic organic chemistry.
The nitro group absorbs strongly in the UV region, facilitating detection and monitoring by UV-Vis spectroscopy and TLC with UV visualization. Researchers should verify exact melting point, molecular weight, and purity specifications from the product's certificate of analysis.
Synthetic Applications and Reactivity
The principal synthetic utility of 2-Fluorophenyl 2-nitrophenyl ether lies in its dual electrophilic activation. Aryl fluorides with ortho or para electron-withdrawing groups are classical substrates for nucleophilic aromatic substitution (SNAr), where nucleophiles such as amines, thiols, or alkoxides displace the fluoride ion to furnish new diaryl ethers, diarylamines, or thioethers.
Consequently, this compound can serve as a precursor to more complex molecules in medicinal chemistry programs, particularly in the construction of benzoxazole, phenoxazine, or acridine frameworks accessible through cyclization of appropriately substituted diaryl ether intermediates. The nitro group also provides a handle for further functionalization: it can be reduced to an aniline for subsequent acylation, diazotization, or heterocycle formation.
Palladium-catalyzed cross-coupling reactions and Ullmann-type ether synthesis are additional routes through which diaryl ethers bearing these functional groups can be elaborated. Researchers in agrochemical and materials science disciplines similarly exploit the electron-deficient aromatic ring system for the synthesis of functional dyes or polymer precursors.
Safe Handling, Storage, and Regulatory Considerations
As with all nitroaromatic and fluoroaromatic compounds, appropriate laboratory safety precautions must be observed when working with 2-Fluorophenyl 2-nitrophenyl ether. Personnel should wear appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a lab coat. Operations generating dust or aerosols should be conducted inside a certified fume hood.
The compound should be stored in a cool, dry, well-ventilated location away from strong oxidizers, acids, bases, and ignition sources. Researchers must consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for authoritative hazard classification, first-aid measures, disposal guidelines, and regulatory information specific to their jurisdiction before handling this reagent.
Waste disposal should comply with all applicable local, national, and institutional regulations governing halogenated and nitro-containing organic waste streams.
Frequently asked questions
What is the catalog number for 2-Fluorophenyl 2-nitrophenyl ether at Aladdin Scientific?
The catalog number (SKU) for 2-Fluorophenyl 2-nitrophenyl ether at Aladdin Scientific is F354345. It is also cross-referenced with Santa Cruz catalog number sc-254251.
What types of chemical reactions is 2-Fluorophenyl 2-nitrophenyl ether commonly used for?
This compound is most commonly employed as a substrate or intermediate in nucleophilic aromatic substitution (SNAr) reactions, where the activated aryl fluoride is displaced by nitrogen, oxygen, or sulfur nucleophiles. It can also serve as a precursor for heterocycle synthesis after reduction of the nitro group to an amine, and may be further elaborated via palladium-catalyzed cross-coupling strategies.
In which solvents is 2-Fluorophenyl 2-nitrophenyl ether soluble?
Based on its structure as a lipophilic diaryl ether, the compound is expected to dissolve readily in polar aprotic solvents such as DMF, DMSO, and THF, as well as chlorinated solvents like dichloromethane. It is anticipated to have very limited solubility in water. Researchers should conduct preliminary solubility tests and refer to the SDS and certificate of analysis for confirmed data.
How should 2-Fluorophenyl 2-nitrophenyl ether be stored to maintain stability?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from heat sources, strong oxidizers, and incompatible reagents. Always consult the Aladdin Scientific Safety Data Sheet for specific storage temperature recommendations and shelf-life information.
References
- Santa Cruz Biotechnology product reference sc-254251, cross-listed with Aladdin Scientific F354345.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for SNAr reactions involving activated aryl fluorides.)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry. Oxford University Press. (General reference for diaryl ether synthesis and nucleophilic aromatic substitution.)
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