This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
170.180 g/mol
XLogP3
1.500
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
170.074 Da
Monoisotopic Mass
170.074 Da
Topological Polar Surface Area
29.500 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
130.000
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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Recensioni
Recensioni dei clienti
Application Protocols
No assay or analytical application protocols are provided for this item in the Product Data.
General recommendations (literature/general):
Analytical characterization: 1H/13C NMR (look for benzylic CH2 ~4.5–5.0 ppm region depending on solvent; aromatic pattern influenced by F and OEt), 19F NMR for aryl F, IR (broad O–H ~3200–3600 cm−1), HRMS/GC–MS/LC–MS as applicable.
Handling at microscale: Prepare stock solutions in dry DMSO, MeCN, or DCM for reproducibility; record exact concentrations gravimetrically for kinetic or screening experiments.
For any specific protocols (e.g., oxidation, substitution), consult the Reaction Conditions tab and adapt to your substrate and scale.
Biological Roles
This product is supplied for research use only. No biological function or role is specified for this item.
From a general chemistry perspective (literature/general):
Aryl fluorides and aryl ethers are common motifs in bioactive molecules because fluorine can modulate lipophilicity, metabolic stability, and pKa of neighboring groups. However, such statements are class-level and do not imply activity for this specific compound.
Benzylic alcohols can undergo metabolic oxidation to aldehydes/acids in biological systems, but specific ADME/PK data for 3-ethoxy-5-fluorobenzyl alcohol are not provided.
No target, pathway, or biological activity data are available in the Product Data. Do not use for diagnostic or therapeutic purposes.
Buffer Applications
Not typically applicable. 3-Ethoxy-5-fluorobenzyl alcohol is an organic building block, not a buffering reagent.
Practical note (general): If used in biochemical assays or extractions, select compatible buffers that minimize partitioning issues (e.g., add co-solvent such as DMSO or EtOH at low percentages to aid dissolution). No buffer system is specifically associated with this compound.
Green Alternatives
This SKU is a functionalized building block, not a solvent. Green considerations pertain to the transformations you perform with it.
Greener choices by reaction class (literature/general)
Oxidation of benzylic alcohol → aldehyde/acid:
Greener options: TEMPO/bleach (NaOCl, aq., buffered), Oxone/TEMPO, air/O2 with nitroxyl catalysts, or electrochemical oxidation.
Less green to avoid when possible: Chromium(VI)-based (Jones/PCC/PDC), stoichiometric Dess–Martin on scale without recycling.
Activation/substitution at benzylic position:
Use sulfonyl carbonates or benign leaving groups; avoid large excesses of halogenating reagents. Consider catalytic dehydrative coupling (e.g., with phosphines under Mitsunobu alternatives like PMe3/DIAD recycling) or enzyme-catalyzed esterifications.
Solvents:
Prefer 2-MeTHF, CPME, EtOAc, or MeCN (where suitable) over chlorinated solvents. For chromatography, consider supercritical CO2 or minimal-solvent flash methods.
Comparison snapshot (illustrative)
TEMPO/NaOCl vs Jones: aqueous, catalytic nitroxyl, minimal heavy metals vs Cr(VI) hazardous waste.
2-MeTHF vs THF: bio-based source, higher boiling point, improved phase separations; watch peroxide control similarly to THF (general note).
Adopt process intensification (flow oxidation, electrochemistry) to reduce solvent and reagent use. Validate green options for selectivity with this substituted aromatic system.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation use is specified for this item. It is supplied strictly for research use only.
General chemistry context (non-clinical):
Fluorinated, ether-containing benzyl motifs appear in discovery chemistry libraries. This compound may serve as a synthetic intermediate to explore SAR around fluorinated aryl cores.
If used in pre-formulation research, anticipate limited aqueous solubility; co-solvents (PEG400, EtOH, propylene glycol) or nanosuspension approaches are typical for related aromatics. These are general strategies, not product claims.
No therapeutic indications or clinical applications should be inferred or stated.
Physical Properties
Item-specific specifications
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/computed (non-specification) properties for context
Approx. molecular formula (by name): C9H11FO2 (literature/computed)
Physical state/appearance: Likely colorless to pale liquid or low-melting solid for many benzylic alcohols with similar substitution (literature, general); actual item appearance not specified.
Acid-base: Primary alcohol; pKa of benzylic alcohols typically ~15–16 in water/MeOH (literature, general). Not a buffering agent.
Polarity/solubility (qualitative, literature): Expected low water solubility; good solubility in common organic solvents (EtOAc, DCM, THF, toluene, alcohols) due to aromatic core and polar OH/ether (literature, general).
LogP: Benzylic alcohols with one ether and one F are commonly in the moderate hydrophobic range (literature, qualitative). No item-specific value available.
Boiling/melting points, density, refractive index: Not found in primary literature databases for this exact substitution pattern at the time of writing; not specified for this item.
Always consult the product’s CoA/Spec Sheet for definitive physical specifications for the supplied lot.
Quality and Grades
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grades (general)
Research grade: Suitable for most synthetic and discovery workflows. If trace metals, residual solvents, or low-UV background are critical (e.g., for photophysics or analytical use), request the CoA and full specification sheet.
HPLC/LC–MS grade solvents/reagents: Feature extremely low non-volatile residue and low UV absorbance; not stated for this item.
Purity metrics: Reported as assay (%), typically by GC or HPLC for organic liquids/low-melting solids, and may include limits for related substances, water (KF), and residual solvents. None are specified here for this SKU.
Lot-specific documentation
For applications sensitive to impurities (e.g., catalytic cross-couplings, photoredox, or medicinal chemistry SAR), request the latest CoA for: assay method and result, identity confirmation (1H/13C NMR, HRMS), moisture (KF), and if applicable residual metals/halides.
Note: In absence of item-specific grade or stabilizer info, treat the material as research-use only (as stated) and perform a quick identity/assay check (e.g., 1H NMR) upon receipt when project-critical.
Reaction and Applications
As a 3-ethoxy-5-fluoro-substituted benzyl alcohol, this compound is a versatile building block for aryl–alkyl frameworks and for late-stage diversification.
Transformation families (literature/general)
Oxidation: Benzylic alcohol → aldehyde (Dess–Martin, Swern, TEMPO/BAIB, TEMPO/NaOCl) or → acid (TEMPO/bleach with NaClO2, Jones/Pinnick). Aldehyde enables further reductive amination or Wittig/olefination.
Activation of –CH2OH: Convert to benzylic halides (PBr3, SOCl2), sulfonates (MsCl/TsCl) or carbonates, enabling SN1/SN2 substitutions, azidation, or cross-coupling via subsequent transformations.
Ether/ester formation: Mitsunobu (DEAD/DIAD, PPh3) to invert configuration at a secondary center is not applicable here (primary center), but Mitsunobu still serves to generate benzylic ethers/esters efficiently under mild conditions.
Protection/deprotection: As benzyl alcohol can be protected as TBDMS, TBS, TIPS silyl ethers or as benzyl carbonate; choose base and solvent to avoid competitive substitution.
Aryl chemistry: The ethoxy substituent is activating and ortho/para-directing; the fluoro substituent is deactivating and ortho/para-directing by resonance but strongly –I. This substitution pattern can modulate regioselectivity in electrophilic substitution and affect rates in metalation.
C–F activation (advanced): Under specific catalytic conditions, aryl–F can undergo borylation or defluoro-functionalization, though generally more challenging than C–Cl/Br.
Use cases
Synthesis of fluorinated aromatic scaffolds for materials or probe molecules.
Intermediate toward 3-ethoxy-5-fluorobenzaldehyde/acid/amines via oxidation and subsequent derivatizations.
Note: No manufacturer application notes were provided; guidance above reflects general synthetic utility.
Reaction Conditions
The following are general literature-level guidelines; optimize per your system.
Oxidation to aldehyde:
TEMPO/NaOCl (pH 8.6–9.5, NaHCO3/Na2CO3 buffer), 0–25 °C, DCM/H2O or EtOAc/H2O, 0.05–0.1 equiv TEMPO, catalytic NaBr. Typical conversions in 0.5–3 h with good selectivity to aldehyde when temperature controlled (literature/general).
Dess–Martin periodinane in DCM, 0–25 °C, 1.3–1.5 equiv, 0.5–2 h; quench with Na2S2O3/NaHCO3.
MsCl or TsCl, Et3N or pyridine, DCM, 0–25 °C; then SN2 with nucleophile in DMF/MeCN.
PBr3 (1.1–1.5 equiv), Et2O or DCM, 0–25 °C → benzyl bromide; avoid prolonged exposure to bases to limit elimination.
Ester/ether formation:
Steglich esterification (DCC/DMAP) in DCM at 0–25 °C; or catalytic DMAP with acid chloride under basic conditions.
Protective silylation:
TBSCl, imidazole, DMF or DCM, 0–25 °C; deprotect with TBAF in THF.
Notes
The ethoxy group is generally stable under above conditions, but avoid strong Lewis acids (e.g., BBr3) and harsh acidic media if aryl-ether cleavage is a concern.
Fluoro substitution can lower SEAr rates; metalation ortho to ethoxy may require strong bases (e.g., s-BuLi) at cryogenic temperatures in directed ortholithiation strategies (advanced).
Safety and Handling
Item-specific hazard information
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety guidance for benzylic alcohols and aryl ethers (literature/general)
Hazards: Many benzyl alcohol derivatives can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid aerosol formation.
PPE: Use lab coat, safety glasses or chemical splash goggles, and suitable gloves (e.g., nitrile). Employ in a fume hood to minimize inhalation exposure.
First aid (overview):
Inhalation: Move to fresh air; seek medical advice if symptoms persist.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if easy to do; continue rinsing.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities: Strong oxidizing agents (risk of exothermic reaction/oxidation). For alcohols: may react with acid chlorides/anhydrides and strong dehydrating agents. Avoid strong bases in the presence of air/heat if elimination/side reactions are undesirable.
Fire safety: Treat as combustible organic. Use CO2, dry chemical, or alcohol-resistant foam. Vapors from heated material may form explosive mixtures with air.
Spill response: Contain and absorb with inert material (vermiculite, silica). Prevent entry into drains. Dispose according to local regulations.
Always consult the SDS for authoritative, product-specific safety and regulatory information.
Solvent Selection
This product is a functionalized benzyl alcohol (organic substrate), not a solvent. Solvent choice relates to its use in synthesis, purification, and analysis.
General solvent compatibility (literature/general)
Likely good solubility in: dichloromethane (DCM), chloroform, ethyl acetate, THF/2-MeTHF, acetone/MEK, acetonitrile, toluene, and alcoholic solvents (MeOH, EtOH, i-PrOH).
Limited solubility expected in water due to aromatic core and only one OH group.
Selection guidance by operation
Nucleophilic substitutions at benzylic position (via activated derivatives): polar aprotic solvents (DMF, DMSO, MeCN) often enhance rates; ensure dryness if using strong bases.
Oxidations to aldehyde/acid: DCM, EtOAc, MeCN, or biphasic systems (e.g., AcOEt/H2O with TEMPO–bleach) are common. Avoid basic alcohol solvents if over-oxidation or acetalization is problematic.
Protecting group chemistry (e.g., carbonate, silyl ethers): use dry DCM, THF, or toluene; add amine base (DIPEA, pyridine) as needed.
Cross-couplings on the aryl ring (if functionalized): mixed solvents (toluene/EtOH/H2O or dioxane/H2O) depending on catalyst and base.
Workup/purification notes
Benzylic alcohols often streak on silica; adding 1–2% Et3N or using buffered silica can improve chromatography. Gradient elution with hexanes/EtOAc or toluene/EtOAc is typical.
Always validate solubility and chromatographic behavior at small scale before scale-up.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (as provided in Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling for benzylic alcohols (literature/general)
Store tightly closed under inert atmosphere if long-term storage is anticipated to minimize slow oxidation to aldehyde/acid, especially if headspace oxygen and light are present.
Protect from strong oxidizers and prolonged UV exposure. Use amber bottles where feasible.
If solidifies on cold storage, allow to warm to ambient and homogenize before use. If needed, gently warm in a water bath (<40 °C) to fully dissolve and mix.
Reconstitution/dissolution
Readily prepared stock solutions in DCM, THF/2-MeTHF, EtOAc, MeCN, or alcohols. For aqueous applications, use co-solvents (e.g., 1–10% DMSO or EtOH) and verify compatibility with downstream steps.
Always follow the latest CoA/SDS for lot-specific storage and handling recommendations.
Functional groups: primary benzyl alcohol (–CH2OH), aryl ether (–O–CH2CH3, ethoxy substituent), aryl fluoride (–F on the ring).
Ring system: monosubstituted benzene bearing three substituents (1-benzyl alcohol, 3-ethoxy, 5-fluoro; relative to the –CH2OH as the reference position).
2D structural description (general)
The core is a phenyl ring. One ring carbon is benzylic and bears a –CH2OH group (primary alcohol). At the meta position relative to the –CH2OH (3-position) is an ethoxy substituent (–O–CH2–CH3). At the 5-position (para to the ethoxy and meta to the –CH2OH) is a fluorine atom. The ethoxy group is electron-donating (via resonance/induction), while the fluoro substituent is strongly inductively withdrawing and weakly donating by resonance. The benzylic alcohol provides a handle for oxidation, substitution, or protection chemistry.
Note: Where item-specific identifiers are missing in Product Data, values above are provided as literature/computed context only and are not product specifications.
Synthetic Utility
Functional group leverage (literature/general)
Benzylic alcohol (–CH2OH):
Oxidize to aldehyde/acid for further elaboration (Wittig, reductive amination, amide coupling via acid/acid chloride).
Convert to halide/sulfonate for nucleophilic substitution (to install N, O, S, or C substituents).
Form carbonates/carbamates as masked leaving groups or protecting strategies.
Aryl ether (ethoxy): Electron-donating, ortho/para-directing; modulates SEAr regioselectivity and oxidative stability. Can be demethylated analogously in some systems, but ethoxy is more resistant than methoxy; harsh conditions (e.g., BBr3) are generally ineffective for dealkylating ethoxy compared to methoxy.
Aryl fluoride: Useful for tuning electronics and, in advanced contexts, as a handle for SNAr if ring is sufficiently activated elsewhere, or for catalytic C–F borylation/defluorofunctionalization.
Retrosynthetic value
Accessible via alkylation of a 3-hydroxy-5-fluorobenzyl precursor (etherification) or via ethoxylation of the phenol followed by benzylic functionalization (literature strategies). Alternative routes include selective reduction of the corresponding aldehyde/ester.
Orthogonality
The benzylic alcohol can be manipulated independently of the aryl ether and C–F bond under many conditions, enabling stepwise diversification. Electronic interplay (ethoxy donating vs fluoro withdrawing) tunes reactivity of the ring toward electrophiles and bases.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological reagent such as an antibody or ligand with defined target specificity. No target, epitope, or binding data are provided in the Product Data.
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