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Application Protocols
No antibody- or assay-specific application protocols apply to this small-molecule building block. For synthetic use, see the Reaction Conditions, Synthetic Utility, and Reaction & Applications sections for general guidance. Item-specific tested applications/dilutions: Not specified for this item; refer to CoA/Spec Sheet.
Biological Roles
No item-specific biological data are provided. The following is general background on phenolic and fluorinated aromatic motifs; it is not a statement of biological activity for this product and must not be used for clinical interpretation.
Phenolic functionality (general biochemistry): Phenols can engage in hydrogen bonding and π–π interactions with proteins and nucleic acids. Their acidity enables phenoxide formation at physiological/basic pH, altering membrane permeability and binding.
Fluorination effects (general): Aryl fluorides modulate lipophilicity, metabolic stability, and pKa. Strategic difluoro substitution is widely used in medicinal chemistry to tune electron density and block oxidative metabolism on aromatic rings.
Enzymatic interactions: Phenols are substrates/inhibitors in oxidative pathways (e.g., peroxidases, cytochrome P450s) in general; fluorination can reduce rates of aromatic hydroxylation.
Analytical/probe relevance: Difluorinated phenols offer distinct 19F NMR handles for studying binding or microenvironments due to sensitive 19F chemical shifts; incorporation into probes or polymers enables 19F-based assays.
Important: This product is supplied strictly for research use in chemical/biochemical laboratories. No claims are made regarding biological efficacy, safety, or pharmacology. For any biological testing, follow institutional biosafety procedures and consult the SDS.
Buffer Applications
Not typically applicable. 2,5-Difluorophenol is a small organic building block, not a conventional buffering agent. While phenols have measurable pKa values, they are generally unsuitable as laboratory buffers over biologically relevant pH ranges due to limited aqueous solubility and poor buffering capacity around physiological pH. For aqueous work, dissolve the compound in a water-miscible cosolvent (e.g., DMSO, acetonitrile) and add to pre-made buffers if needed for assays.
Green Alternatives
While 2,5-difluorophenol itself is the intended building block, greener choices concern how you process and transform it.
Safer solvent choices (general):
Prefer 2-MeTHF, CPME, or EtOAc over chlorinated solvents for extractions and some reactions, when compatible.
Use acetonitrile or MeOH/EtOH in place of DMF/DMSO when feasible to improve work-up and reduce energy for solvent removal.
Energy and waste minimization:
Conduct O-alkylations at ambient temperature with carbonate bases in MeCN or acetone to reduce cryogenic cooling and pyrophoric reagents.
Apply catalytic esterifications (e.g., acid catalysts with azeotropic water removal) instead of stoichiometric coupling reagents when selectivity allows.
Activation/cross-coupling route selection:
Phenol-to-triflate activation is effective but generates sulfonyl fluoride waste; consider direct C–O activation protocols (e.g., Ni-catalyzed coupling of aryl pivalates/carbonates) by first converting OH to a carbonate/pivalate, which can be milder in waste profile.
Work-up and purification:
Favor crystallization or trituration of protected intermediates instead of silica chromatography; recycle solvents.
Comparison snapshot (general)
Triflation (Tf2O, DCM) vs carbonate activation (Boc2O or pivaloyl chloride, greener solvent): latter avoids perfluorosulfonyl reagents but may require tailored catalysts.
Always cross-check with process safety/green metrics (E-factor, PMI) and your reaction’s compatibility before switching.
Pharmaceutical Uses
No item-specific pharmacopeial status, grade, or formulation role is provided.
General context (non-clinical, no therapeutic claims): Fluorinated phenols can serve as synthetic intermediates toward APIs, agrochemicals, and materials. The phenolic OH provides a handle for prodrug/ester formation or for conversion to aryl electrophiles (e.g., triflates) enabling rapid diversification.
Excipient role: Phenolic small molecules like 2,5-difluorophenol are not used as pharmaceutical excipients due to reactivity, potential toxicity, odor, and color-forming tendencies.
Manufacturing relevance: In process R&D, such building blocks are evaluated for step economy and robustness (e.g., O-protection, activation, cross-coupling). When used, they are typically upgraded to higher purity and controlled for residual solvents and metal content according to internal specifications.
For regulated applications, obtain full impurity profiles, residual solvent data, and elemental analysis; none are specified for this item—refer to CoA/Spec Sheet.
Physical Properties
Note: No item-specific specifications were provided. Values below are general literature/computed guidance and should not be used as product specifications.
Typical appearance (literature): colorless to pale liquid or low-melting solid depending on temperature; phenolic odor. Item-specific appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point (literature): reports typically in the ~160–180 °C range at 1 atm for difluorophenol isomers; consult primary data for the 2,5-isomer.
Melting point (literature): low melting; various reports place difluorophenols near or below ambient; specific value for 2,5-isomer varies by source.
Density (literature): expected slightly greater than water due to F substitution; specific value not consolidated across sources.
pKa (phenolic, literature): generally lower than phenol (phenol pKa ~9.9) due to –F inductive effects; difluoro substitution often yields pKa in the ~8–9.5 range depending on substitution pattern.
logP/logD (computed/literature): modest hydrophobicity (logP often ~1.5–2 for difluorophenols; method-dependent).
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general):
Water: limited (phenolic H-bonding vs hydrophobic ring; expect low-to-moderate solubility).
Organic solvents: miscible or highly soluble in polar aprotic solvents (DMF, DMSO, acetonitrile) and moderately polar/protic solvents (alcohols); soluble in chlorinated and aromatic solvents.
Always consult the product CoA/SDS for definitive physical data for this specific lot.
Quality & Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance for chemists):
If offered as “standard” lab grade without chromatographic designation, UV cutoffs, peroxide content, or metal limits are typically not controlled at ultra-trace levels. For sensitive catalysis (e.g., Pd-catalyzed cross-coupling after triflation) or trace analyses, request/specify the purity, water content, and any stabilizers.
Phenolic compounds are often shipped without stabilizers; if stabilizers are present (e.g., BHT), they can interfere in radical chemistry or polymerizations—confirm via CoA.
For synthesis workflows:
Spectroscopic grade (if available) emphasizes low UV impurities for photochemical or analytical use.
High-purity/reagent-grade material is preferred for metal-catalyzed steps following activation (e.g., aryl triflation → Suzuki). Residual water and bases/acids will influence deprotonation/derivatization steps.
What to check on receipt:
Confirm identity (1H/13C NMR in CDCl3/CD3CN; characteristic phenolic OH often broad and downfield; 19F NMR shows two aryl-F resonances) and purity (GC/LC).
Verify absence of polymeric tars or discoloration; slight coloration can appear over time due to trace oxidation—purify by distillation or column if required.
Reaction & Applications
2,5-Difluorophenol serves as a versatile aryl-phenol building block for synthesis of fluorinated aromatics, ligands, and materials precursors. Selected use cases (general literature guidance):
O-Functionalization
Williamson ether synthesis: deprotonation (e.g., NaH, Cs2CO3) followed by alkyl halide or sulfonate to access aryl ethers. Fluorine substituents modulate electronics but do not impede O-alkylation.
Esterification: acyl chlorides/anhydrides or Steglich conditions (DCC/DMAP) to make aryl esters; useful as protecting groups or intermediates.
Activation for cross-coupling
Triflation of the phenol (Tf2O + base) affords the corresponding aryl triflate, which undergoes Pd-catalyzed Suzuki–Miyaura, Stille, Negishi, or Buchwald–Hartwig amination to elaborate the ring while retaining/leveraging the remaining aryl–F substituents.
Directed ortho metalation (DoM)
Phenolic oxygen (often as O-protecting group or as phenoxide/amide) can direct lithiation ortho to OH, enabling regioselective introduction of electrophiles (D, 13C, 19F-containing groups, borylation via B(OMe)3 then oxidation, etc.).
Electrophilic aromatic substitution (EAS)
The –OH directs ortho/para, but the two –F substituents reduce overall ring reactivity; nitration/halogenation generally require stronger conditions and careful control to avoid overreaction or deactivation.
Materials/ligands
Fluorination patterns tune lipophilicity, H-bonding, and electronic properties—useful in designing fluorinated monomers, agrochemical motifs, and probes.
General conditions from literature/practice for phenolic difluoroarenes; optimize per substrate and scale. These are guidelines, not specifications for this item.
O-alkylation (Williamson ether synthesis)
Base: NaH (60% in mineral oil, 1.1–1.5 eq) or Cs2CO3/K2CO3 (2–3 eq).
Solvent: dry DMF, DMSO, or acetonitrile.
Temperature: 0–25 °C (NaH) or 50–80 °C (carbonate bases).
Cross-coupling of aryl triflate (to be prepared from this phenol)
Suzuki–Miyaura: Pd(dppf)Cl2 (1–3 mol%), base (K3PO4 or Cs2CO3, 2–3 eq), solvent (dioxane/H2O or toluene/EtOH/H2O), 50–90 °C, 2–12 h.
Buchwald–Hartwig amination: Pd2(dba)3 or Pd(OAc)2 (1–2 mol%), ligand (BINAP, XPhos), base (NaOtBu), toluene or dioxane, 80–110 °C.
Directed ortho metalation (DoM)
Typical: s-BuLi (1.1–1.5 eq) with TMEDA in THF, −78 to −50 °C, 0.5–2 h, then electrophile (CO2, I2, B(OMe)3 etc.). Protecting the phenol as an O-carbamate/silyl ether often enhances regioselectivity and stability.
Yields vary with substrate and conditions; consult primary literature for analogous difluorophenol substrates.
Safety & Handling
Item-specific hazard classification was not provided. The following are general safety considerations for phenolic/aromatic fluorinated compounds; defer to the SDS for definitive guidance.
GHS/SDS: GHS classification, pictograms, and H-statements: Not specified for this item; refer to CoA/Spec Sheet and SDS.
Likely hazards (general): phenols can be harmful if swallowed, inhaled, or absorbed through skin; cause skin/eye irritation or burns at higher concentrations; may have acute toxicity. Fluorinated aromatics can be irritating.
PPE (general best practice): lab coat, safety glasses or face shield, appropriate chemical-resistant gloves (e.g., nitrile), and use in a fume hood to avoid inhalation exposure.
First aid overview (general):
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical evaluation.
Inhalation: move to fresh air; monitor respiration; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Handling notes (general):
Avoid contact with bases or strong oxidants; phenols are reactive toward strong bases (deprotonation) and toward acylation/alkylation agents.
Prevent prolonged exposure to air and light which can promote slow oxidation/darkening in some phenols.
Avoid heating in confined systems; ensure adequate ventilation.
Incompatibilities (general): strong bases (forms phenoxide; can be exothermic), strong oxidizers, acid chlorides/anhydrides without control (rapid acylation), alkylating agents.
Always consult the SDS for this SKU before use.
Solvent Selection
This product is a reactive small-molecule building block rather than a working solvent. Solvent selection pertains to dissolving it for reactions or analyses.
Polarity/solubility profile (general):
High solubility in polar aprotic media (DMF, DMSO, acetonitrile) supports deprotonation/alkylation chemistry.
Good solubility in chlorinated (DCM, chloroform) and aromatic solvents (toluene) for electrophilic substitution or protection steps.
Moderate solubility in alcohols; limited in water due to hydrophobic ring despite H-bond donor ability.
Triflation (activation to aryl triflate): DCM or CH3CN with organic base (pyridine, DIPEA) at 0–25 °C.
Directed ortho metalation (DoM): THF or ether solvents at −78 to −40 °C (s-BuLi/TMEDA), then electrophile quench.
Purification: normal-phase silica with hexanes/EtOAc or toluene/EtOAc; monitor by 19F NMR/TLC.
Analytical:
NMR: CDCl3 commonly suitable; OH may exchange—add a drop of D2O to confirm assignment. 19F NMR diagnostic.
HPLC: reversed-phase with MeCN/H2O + modifier; phenols may tail—use acidic mobile phase or ion-pairing if needed.
Comparison note (general): Relative to non-fluorinated phenol, increased lipophilicity can improve solubility in less polar media; relative to polyfluorophenols, acidity is moderate, easing base handling.
Storage & Reconstitution
Storage conditions (from Product Data): Store at −80 °C.
Practical handling guidance (general best practice for phenols and temperature-sensitive reagents):
Upon receipt, keep sealed and cold; allow to equilibrate in a desiccator before opening to minimize condensation.
Store under inert gas (N2/Ar) in an amber vial to limit oxidation and photodegradation. Use septum-sealed vials for repeated access.
If solutions are prepared (e.g., in anhydrous DMSO, MeCN, or THF), store aliquots at ≤ −20 °C for short term; for longest stability, keep aliquots at −80 °C. Avoid repeated freeze–thaw cycles; dispense single-use aliquots.
Drying: If needed, dry over molecular sieves (3 Å) in an appropriate solvent. Avoid strong bases unless intended for immediate reaction (phenoxide formation).
Reconstitution: This is a neat small molecule; no aqueous reconstitution protocol applies. For stock solutions, prepare at known concentration in a compatible anhydrous solvent (e.g., 0.1–1.0 M in DMSO, MeCN, or THF), label with solvent and date, and store as above.
Always defer to the product’s label and SDS for storage limitations and stability information specific to this SKU.
Structure & Identity
Brief overview: 2,5-Difluorophenol is a difluorinated phenolic building block featuring an OH group para-/meta- to two fluorine substituents, useful for derivatization, directing-group chemistry, and cross-coupling after activation.
Item-specific identifiers (from Product Data)
CAS: 2713-31-7
PubChem CID: 94952
SKU: D660557
Research use: For research use only
Structure descriptors (literature/computed; not item-specific specs)
IUPAC name (literature): 2,5-difluorophenol
Molecular formula (literature): C6H4F2O
Molecular weight (literature): ~130.10 g/mol
SMILES (literature): OC1=CC(F)=CC=C1F
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general chemistry)
Aromatic ring bearing one phenolic hydroxyl (–OH) and two ring fluorides at the 2- and 5-positions relative to –OH.
Electron-withdrawing F substituents lower phenolic pKa and decrease ring electron density; –OH remains an o/p-directing, metalation-directing group.
Functional groups: phenol (acidic OH), aryl–F (strong C–F bonds, poor σ-leaving groups but strongly inductive). 2D description: a benzene ring with OH at position 1, F atoms at positions 2 (ortho) and 5 (meta) to the OH.
No stereogenic centers; planar aromatic core.
Synthetic Utility
Key reactivity features enabling diverse transformations (general literature guidance):
Phenolic handle as a gateway functionality
O-alkylation/acylation to tune electronics and sterics or to protect the phenol. Protecting groups include benzyl (hydrogenolysis removal), silyl (TBS/TIPS, fluoride removal), carbonate/pivalate (also act as cross-coupling electrophiles under Ni catalysis).
Conversion to aryl triflate enables Pd-catalyzed cross-couplings (Suzuki, Stille, Negishi) to install C–C bonds at the phenolic ipso position while retaining other ring positions for later elaboration.
Fluorine as a modulator
The 2,5-difluoro pattern deactivates EAS but enhances chemoselectivity, allowing transformations at activated sites (ipso after activation or ortho via DoM). Aryl–F is generally inert to oxidative addition under standard Pd conditions, supporting selective coupling elsewhere.
Directed ortho metalation (DoM)
Phenoxide or O-carbamates direct lithiation ortho to O; subsequent quench with electrophiles enables regio-defined halogenation, acylation, or borylation (→ Suzuki partners).
Late-stage diversification
Sequential strategy: (1) protect/activate OH, (2) install substituent via coupling, (3) deprotect and further elaborate via O-chemistry. 19F NMR simplifies tracking of each stage.
Retrosynthetic value
Serves as a convergent node: one can introduce functionality at the ipso position via C–O activation and at the remaining aryl positions through DoM or selective halogenation, giving rapid access to densely substituted, fluorinated scaffolds.
Target Specificity
Not applicable. This product is a small organic reagent, not a biological targeting reagent. No antigen/epitope, clone, isotype, or species reactivity information applies. Item-specific targeting data: Not specified for this item; refer to CoA/Spec Sheet.
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