This compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Sensibilidad
light sensitive;Moisture sensitive
Peso molecular
204.200 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
204.059 Da
Monoisotopic Mass
204.059 Da
Topological Polar Surface Area
29.500 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
182.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Application Protocols
No assay-validated biological or analytical protocols are provided for this item.
General lab usage suggestions (non-validated, for reference):
Stock solutions: Prepare 10–100 mM stocks in dry DMSO or acetonitrile; store aliquots under argon at 2–8 °C, protected from light.
Handling solids: Minimize exposure to air and light; quickly recap under argon. If static/dusting occurs, wet spatula with solvent.
Analytical QC: Confirm identity/purity by 1H/13C NMR and LC-MS upon receipt for critical applications; phenolic OH may appear broad and solvent-dependent.
Reaction setup: Dry glassware and solvents; for base-mediated O-functionalization, add base to solution at 0–5 °C to control exotherm.
For any application requiring specific conditions or performance guarantees, consult the product’s CoA/SDS and perform fit-for-purpose method development.
Biological Roles
Item-specific biological data are not provided for this product. The following are general, literature-based considerations for small aromatic phenolic compounds and are not medical/clinical claims:
Phenolic functionality
Phenols can engage in hydrogen bonding (donor/acceptor), π–π interactions, and can act as weak acids (pKa typically ~9–10), potentially affecting binding to proteins or synthetic receptors in chemical biology studies.
The phenoxy linkage donates electron density into the ring, modulating redox behavior and acidity compared with unsubstituted phenol.
Aryl fluoride influence
Fluorine substitution can alter lipophilicity, dipole moment, and metabolic stability of analogous scaffolds (general medicinal chemistry principle). The strong C–F bond is typically metabolically robust.
Use contexts in research
May serve as a model compound for studying phenolic oxidation, radical coupling, or enzyme-mimetic transformations (peroxidase-like systems) in vitro.
Structural motif for host–guest recognition studies due to its rigid, planar diaryl ether core and H-bonding phenol.
No biochemical targets, pathways, or activities are specified for this catalog item. For any biological testing, handle strictly as a research chemical and follow institutional safety and compliance requirements.
Buffer Applications
This product is not a buffering reagent and is not typically used to prepare aqueous buffer systems.
The phenolic pKa (~9–10, literature range for para-substituted phenols) lies outside the common biological buffer window and the compound is poorly water soluble at neutral pH.
For experiments requiring buffered conditions, prepare buffers separately (e.g., phosphate, HEPES, Tris) and dissolve this compound in a compatible co-solvent (DMSO or ethanol) before dilution, ensuring final organic content remains compatible with the system.
Refer to the Solvent Selection and Application Protocols sections for practical dissolution and stock solution advice.
Green Alternatives
As a solid aryl building block, 4-(4-fluorophenoxy)phenol itself is not replaced by a “green alternative.” However, its use frequently involves solvents and reagents with varying environmental and safety footprints. Consider the following greener choices when designing methods:
Solvent substitution (general guidance)
Replace DMF/NMP with safer polar aprotics where feasible: Cyrene, DMSO, propylene carbonate, or sulfolane (depending on base/coupling chemistry).
Replace chlorinated solvents (DCM, chloroform) with ethyl acetate, 2-MeTHF, CPME, or toluene for extractions and reactions when compatible.
Base and reagent choices
Favor carbonate bases (K2CO3, Cs2CO3) over NaH where kinetics permit to reduce pyrophoric hazards.
For esterifications, use green coupling agents (e.g., CDI for carbonate/urethane formation) or catalytic acyl transfers instead of stoichiometric acid chlorides, when applicable.
Energy and process efficiency
Use microwave or flow chemistry to reduce reaction times and solvent volumes.
Employ crystallization-driven purifications to avoid large silica waste.
Comparison (illustrative; literature/general):
DMF vs DMSO: Similar solvency; DMSO avoids DMF’s reproductive toxicity classification but has higher boiling point (removal tradeoff).
DCM vs 2-MeTHF: 2-MeTHF offers lower toxicity and renewable sourcing; however, it has water content challenges and can form peroxides—monitor and dry appropriately.
Always validate solvent changes with small-scale trials to confirm reactivity, selectivity, and impurity profiles.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; it is supplied strictly for research use.
General, non-clinical context (literature/industry practice):
As a substituted phenolic diaryl ether, this scaffold may be used as a synthetic intermediate in discovery chemistry to explore SAR, modulate lipophilicity, and probe H-bonding interactions.
The phenolic OH enables rapid access to prodrug-like esters and carbonates for structure diversification in screening libraries.
Fluorination is a common strategy to tune metabolic and physicochemical properties in analog design; this compound can serve as a fluorinated phenoxyphenol synthon for parallel synthesis.
Manufacturing/formulation notes (general):
If used as a reference or process intermediate, control solid-state form and residual solvents to meet internal R&D specifications.
Ensure thorough documentation (NMR, LC purity, water content as needed) for regulated environments; consult the item’s CoA for lot-specific details.
No therapeutic claims or clinical uses are associated with this catalog product.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for reference; not item specifications):
Molecular formula (literature): C12H9FO2
Molecular weight (literature): ~204.20 g/mol
Physical state: Typically a crystalline aromatic solid (literature/general observation for para–para diaryl ether phenols).
Acidity: Phenolic pKa for para-substituted phenols commonly ~9–10 in water (literature, general range); the ether linkage and para-F may slightly modulate acidity.
Solubility profile (general):
Low solubility in water (phenolic, hydrophobic polyaromatic core).
Good solubility in polar aprotic organics (DMF, DMSO, NMP) and moderate in less polar organics (EtOAc, acetone, toluene, CH2Cl2).
Partitioning: Expected logP in the 2–3 range for diaryl ether phenols (literature, class-based expectation).
Notes for practitioners:
For analytical preparation, dissolve in dry DMSO or acetonitrile for stock solutions, or in acetone/EtOAc for workups. If precise constants (mp, solubility, refractive index) are required for method development, consult the item-specific CoA/SDS or measure under your lab conditions.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvents, metal content, and other release criteria.
Context and expectations (general guidance):
Research-grade aromatic building blocks are typically released against identity (1H NMR/13C NMR and/or HRMS), purity by HPLC/GC, and appearance. Trace water, residual solvent, or stabilizers are reported when relevant to stability or performance.
For chromatography-driven workflows (e.g., medicinal chemistry libraries), higher-purity material can reduce purification burden and baseline noise. If UV cutoff or HPLC background is critical, request our HPLC trace or low-UV grade when available.
Stabilizers: None are indicated in the Product Data. If a stabilizer is present in a particular lot, it will be disclosed on the CoA; phenolic solids are generally shipped without stabilizers but may benefit from inert-gas headspace and light protection.
Trace metals/halides: Not specified for this item; refer to CoA/Spec Sheet. If using in cross-coupling, you may wish to pre-screen by ICP-MS depending on sensitivity.
Lot-to-lot consistency: For scale-up or regulated workflows, request the same lot or a retained sample for bridging studies and ensure internal specs align with your method performance.
Reaction and Applications
This compound is a versatile bifunctional aryl building block combining a phenolic OH (nucleophilic after deprotonation) and a para-fluorinated aryl ether ring. Typical uses include:
Phenolic derivatization
O-alkylation: Williamson ether synthesis using alkyl halides or sulfonates with K2CO3/Cs2CO3 in DMF/acetone to generate anisole-type derivatives.
O-acylation/carbamate formation: Acyl chlorides, anhydrides, or chloroformates in pyridine/Et3N or DMAP catalysis to access esters, carbonates, or carbamates.
Mitsunobu reactions: Inversion-enabled etherifications with primary alcohols under DEAD/DIAD–PPh3 conditions to form aryl ethers.
Protecting groups: Silylation (TBS/TBDPS–Imidazole, DMF) or benzylation to mask the phenol for downstream chemistry.
Aromatic substitution and functionalization
Electrophilic substitution on the anisyl-like ring (para-F ring is inductively deactivated; the phenoxy-bearing ring is activated by the ether oxygen): nitration, halogenation, or Friedel–Crafts acylation under controlled conditions.
Directed metalation: Ortho-lithiation adjacent to the phenoxy group can be feasible using strong bases (s-BuLi/TMEDA) at low temperature, followed by quench with electrophiles (literature precedence for diaryl ethers).
Cross-coupling considerations
Aryl C–F activation is challenging; direct Pd/Ni-catalyzed coupling of aryl fluorides generally requires specialized catalysts and harsh conditions. The substrate is therefore more often used as a coupling partner through transformations at the phenolic oxygen (e.g., conversion to aryl triflate from the phenol, then Suzuki/Negishi/Stille at the aryl C–OTf position).
Materials and supramolecular chemistry
Phenolic H-bonding and the rigid diaryl ether scaffold support applications in crystal engineering and as a motif in liquid crystals or polymer additives.
Note: Choose conditions that respect the aryl–O–aryl bond integrity; avoid strong Lewis acids or high-temperature conditions that can promote C–O cleavage.
Reaction Conditions
General literature-guided conditions for common transformations of 4-(4-fluorophenoxy)phenol’s functional handles (not item specifications):
O-Alkylation (Williamson ether synthesis)
Conditions: Alkyl bromide/iodide (1.1–1.5 equiv), K2CO3 or Cs2CO3 (2–3 equiv), DMF or acetone, 25–60 °C, 2–16 h.
Notes: Exclude water; monitor by TLC/LC. For hindered electrophiles, use NaH (1.1–1.5 equiv) in THF/DMF at 0–25 °C.
O-Acylation/Carbonate formation
Conditions: Acyl chloride or chloroformate (1.1–1.5 equiv), pyridine or Et3N (2–3 equiv), catalytic DMAP (5–10 mol%), DCM/ACN, 0–25 °C, 0.5–4 h.
Notes: Quench with aqueous NH4Cl/NaHCO3; avoid strong Lewis acids that may cleave Ar–O–Ar at high T.
Triflation of phenol for cross-coupling
Conditions: Tf2O (1.2–1.5 equiv), pyridine or 2,6-lutidine, DCM, 0 °C to rt; then Pd-catalyzed Suzuki with boronic acids (Pd(PPh3)4 or Pd2(dba)3/XPhos), base (K3PO4, Cs2CO3), dioxane/H2O, 50–90 °C.
Electrophilic aromatic substitution on the activated ring
Nitration: AcOH or H2SO4/Ac2O media, low temperature (0–5 °C) to control regioselectivity; workup to regenerate phenol.
Halogenation: NBS/NCS with acid or Lewis acid promoters in DCM/AcOH at 0–25 °C.
Directed ortho-lithiation (DoL) adjacent to the phenoxy oxygen (literature precedent)
Conditions: s-BuLi (1.1–1.5 equiv) with TMEDA in THF/Et2O at −78 to −40 °C; trap with electrophiles (CO2 → salicylate-type acids; DMF → aldehydes).
Yields and selectivities depend on substituent effects and scale; optimize bases/ligands and temperature profiles experimentally.
Safety and Handling
Item-specific hazard classification: Not specified for this item; refer to SDS for authoritative GHS, pictograms, H/P statements, and exposure limits.
General handling guidance for phenolic diaryl ethers (literature/Best Practice):
Hazards: Phenols can be harmful if swallowed, cause skin/eye irritation, and may be harmful by inhalation. Aromatic powders may cause respiratory irritation.
PPE: Wear lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (nitrile recommended). Handle powders in a fume hood to avoid inhalation.
Storage (from Product Data):
Store at 2–8°C.
Protect from light.
Maintain under inert atmosphere (argon charged).
Shipped on wet ice.
Incompatibilities: Strong oxidizers; strong bases will deprotonate the phenol to form phenoxide (highly nucleophilic and air/moisture sensitive in some solvents). Avoid prolonged exposure to air and light to limit oxidation/discoloration.
First aid (overview; defer to SDS):
Skin/eye contact: Flush with water for at least 15 minutes; remove contaminated clothing; seek medical advice.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may release irritating fumes (e.g., HF is not expected under mild conditions but fluorinated aromatics can generate hydrogen fluoride under extreme combustion—use appropriate respiratory protection for fires).
Hygiene: Avoid dust formation; wash hands after handling; keep containers tightly closed under inert gas.
Solvent Selection
Solubility/miscibility (general behavior of phenolic diaryl ethers):
Water: Poorly soluble at neutral pH; solubility increases upon deprotonation (phenoxide formation) in basic aqueous media.
Polar aprotic: Freely soluble in DMSO, DMF, NMP, DMAc; good choice for stock solutions and reactions requiring high concentration.
Medium polarity: Soluble to moderately soluble in acetone, acetonitrile, ethyl acetate, THF, dioxane.
Nonpolar aromatics/chlorinated: Moderately soluble in toluene, chlorobenzene, dichloromethane; variable in hexanes.
Selection guidance:
Analytical stocks: Dry DMSO or acetonitrile give robust, stable solutions; filter (0.2 µm) for LC compatibility.
Nucleophilic O-derivatizations (acylation/alkylation): Choose polar aprotic media (DMF/ACN/acetone) with K2CO3, Cs2CO3, or NaH.
Electrophilic aromatic substitution on the activated ring: Use non-nucleophilic solvents (DCM, nitromethane, acetic acid) appropriate to the transformation.
Comparison snapshot (general):
DMSO vs DMF: DMSO offers higher solubility and is greener from a worker-exposure perspective; DMF can be easier to remove but has stricter hazard classifications.
Acetone/EtOAc: Easier workup and greener profiles but may limit solubility for highly conjugated solids.
Practical tip:
If precipitation occurs during aqueous workup (common for hydrophobic phenols), seed crystallization from EtOAc/hexanes or adjust pH to neutralize phenoxide prior to extraction.
Storage and Reconstitution
Storage (from Product Data)
Temperature: 2–8 °C.
Atmosphere: Store under inert gas (argon charged).
Light: Protect from light (amber vial or foil wrap recommended).
Shipping: Shipped on wet ice.
Container and handling
Keep tightly closed to limit moisture/oxygen ingress. Open/aliquot under inert atmosphere when practical, especially for long-term stability.
If transferring to a glovebox-free workflow, purge headspace with argon before recapping.
Reconstitution/Dissolution (general guidance)
Prepare concentrated stocks in dry DMSO, DMF, or acetonitrile (10–100 mM typical). For synthetic use, also soluble in THF, acetone, or ethyl acetate.
Filter sterilization is generally unnecessary for chemical synthesis; for bioassays, pass through 0.2 µm PTFE if particulate-free solutions are required.
For aqueous systems, pre-dissolve in a miscible organic co-solvent; add slowly to buffer under stirring to avoid precipitation. Target final organic content ≤1–2% v/v when biology requires.
Stability
Phenolic compounds can slowly oxidize/discolor upon light/air exposure; adhere to the recommended storage to maximize shelf life.
Freeze–thaw: Not typically applicable to solids; if storing solutions, aliquot to minimize freeze–thaw cycles.
Specifications
Appearance, assay, water, and impurity limits: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Overview: 4-(4-Fluorophenoxy)phenol is a para–para linked diaryl ether bearing a free phenolic OH and a para-fluoro substituent on the distal aryl ring.
Item-specific (from Product Data)
CAS: 1524-19-2
CID (PubChem): 12940624
InChIKey: 181163 (provided; appears truncated—complete standard InChIKey not specified for this item)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (for reference only; not item specifications)
Preferred IUPAC name (literature): 4-(4-fluorophenoxy)phenol
Molecular formula (literature): C12H9FO2
Molecular weight (literature): ~204.20 g/mol
Example SMILES (literature): Oc1ccc(Oc2ccc(F)cc2)cc1
Structural features (general chemistry description)
Two benzene rings connected by an ether oxygen (Ar–O–Ar), with the OH at the para position on one ring and F at the para position on the other ring.
2D description: One phenyl ring bears OH at C-1 and the ether at C-4; the second phenyl ring bears F at C-4 relative to the ether linkage. Overall a rigid, planar, conjugated system with p–p stacking propensity.
Stereochemistry: None (achiral, no stereocenters).
Synthetic Utility
Functional group handles and their value:
Phenolic OH
O-alkylation to access anisoles/benzyl ethers (Williamson conditions). Useful for masking acidity and modulating lipophilicity.
O-acylation and carbonate/urethane formation provide traceless protecting groups and pro-moieties.
Conversion to aryl sulfonates (triflate/mesylate) enables subsequent cross-couplings (Suzuki, Sonogashira, Buchwald–Hartwig) at the aryl carbon.
Aryl ether linkage (Ar–O–Ar)
Electron donation activates the phenolic ring toward electrophilic aromatic substitution; permits late-stage nitration/halogenation under controlled conditions.
Ortho-directing effects can be leveraged in lithiation–electrophile trapping sequences (e.g., s-BuLi/TMEDA, −78 °C, then CO2, DMF, halogens).
Aryl fluoride
Typically inert to SNAr unless strongly activated by additional electron-withdrawing groups; here it is a robust handle that can tune electronics without compromising stability.
Rare but possible metal-catalyzed C–F activation with specialized Ni/Pd catalysts under forcing conditions (literature niche).
Retrosynthetic perspective:
Serves as a convergent node: either from fluorophenol + 4-halophenyl derivatives via Ullmann/Buchwald–Hartwig diaryl ether formation, or from 4-fluorophenol and 4-hydroxyiodobenzene derivatives using copper or palladium catalysis.
Applications:
Library synthesis, materials monomers, and probes where a stable, planar, H-bond-capable aromatic core is desired.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not have antigen/epitope/clone attributes. No target specificity data are provided for this item.
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