2-(4-Methoxybenzyl)phenol - ≥97% , CAS No.37155-50-3

CAS: 37155-50-3 Cat. No.: M1067141 Formula: C₁₄H₁₄O₂ Peso molecolare: 214.260

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥97%

Nomi e identificatori

Sorrisi canonici

COC1=CC=C(C=C1)CC2=CC=CC=C2O

IUPAC Name

2-[(4-methoxyphenyl)methyl]phenol

InChIKey

ALZWVPLMSWPDQR-UHFFFAOYSA-N

INCHI

1S/C14H14O2/c1-16-13-8-6-11(7-9-13)10-12-4-2-3-5-14(12)15/h2-9,15H,10H2,1H3

Peso molecolare

214.260

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Diphenylmethanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylmethane - Phenoxy compound - Methoxybenzene - Phenol ether - Anisole - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Alkyl aryl ether - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 214.260 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 214.099 Da
• Monoisotopic Mass: 214.099 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 197.000
• 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

Application Protocols

Not applicable in the context of immunoassays or molecular biology kits. There are no WB/IHC/IF/FC protocols specific to this small-molecule substrate.

Practical handling protocols (general chemistry)

• Dissolution: Prepare stock solutions in DCM, MeCN, THF, or DMSO as required by the planned reaction or analysis.
• Analytical QC: Verify identity by 1H/13C NMR (look for benzylic CH2 singlet ~3.8–4.5 ppm and anisole OCH3 singlet ~3.7–3.9 ppm; ranges are solvent-dependent) and confirm purity by HPLC/GC/MS.
• Workup: Standard aqueous quench, extract into organic solvent, dry (Na2SO4/MgSO4), concentrate under reduced pressure.

Biological Roles

Applicability note: This compound is intended for research use only and is not a biological reagent per se. No clinical/therapeutic claims are made.

General biochemical context (literature)

• Phenolic moieties can participate in hydrogen bonding and radical-scavenging chemistry; they are common in natural products and can modulate redox behavior in model studies.
• The para‑methoxybenzyl (PMB) fragment is prevalent in protecting-group chemistry; compounds bearing PMB groups are used as model substrates for studying oxidative deprotection mechanisms (e.g., single-electron transfer to benzylic cations), which can inform understanding of oxidative pathways in biochemistry.
• Lipophilicity: With an estimated logP ~3, such structures can interact with hydrophobic protein pockets in binding studies, though 2-(4-methoxybenzyl)phenol is not known as a specific biological ligand.
• Metabolism (general): Benzylic oxidation to alcohols/aldehydes and O‑demethylation of anisoles are common Phase I transformations in microsomal systems; conjugation (glucuronidation/sulfation) is typical for phenolic OH groups.

Note: Any biological assays using this compound should be designed and interpreted within a laboratory research context only.

Buffer Applications

Not typically applicable. 2-(4-Methoxybenzyl)phenol is a hydrophobic aromatic substrate, not a buffering agent. It has no defined buffering range, and its low aqueous solubility limits use in aqueous buffers.

Practical note

• If introduced into aqueous systems for biochemical assays, dissolve first in a compatible co-solvent (e.g., DMSO or ethanol) and keep final organic content low (commonly ≤1–2% v/v), verifying assay tolerance.

Green Alternatives

Context: While 2-(4-methoxybenzyl)phenol is a substrate/reagent rather than a process solvent, greener choices can be made in the solvents and reagents used with it.

Greener solvent options (literature guidance)

• Replace chlorinated solvents (e.g., DCM, CHCl3) with:
  • 2-Methyltetrahydrofuran (2-MeTHF): bio-based, good for O‑alkylations and extractions; forms azeotropes for drying.
  • Cyclopentyl methyl ether (CPME): low peroxide formation, wide liquid range, suited for radical halogenations and oxidations.
  • Ethyl acetate or toluene: less hazardous alternatives for many workups and chromatographies.

Reagent choices and conditions

• Benzylic oxidation:
  • Prefer catalytic systems (e.g., TEMPO/NaOCl in biphasic setups, or IBX/DMSO under controlled conditions) over stoichiometric chromium oxidants.
• O‑Alkylation/acylation:
  • Use K2CO3 in MeCN/acetone or aqueous-organic phase-transfer conditions to reduce need for strong bases/cryogenic temperatures.
• Workup/waste minimization:
  • Apply solvent recycling, silica minimization, and higher-loading chromatography or crystallization where feasible.

Comparison (illustrative)

• DCM vs 2-MeTHF: similar solvating power for aromatic substrates; 2-MeTHF offers lower toxicity and renewable sourcing but can be less effective for very polar reagents.
• NBS radical halogenation in CCl4 vs CPME/toluene: CPME/toluene avoid persistent pollutants with comparable outcomes under photochemical initiation.

Pharmaceutical Uses

Not a pharmacopeial excipient and not used as an API. For research use only.

Relevant laboratory/pharmaceutical-adjacent contexts (literature/practice)

• Analytical reference or impurity/degradation model: The benzylic/aromatic framework can serve as a reference compound for method development (HPLC/GC/MS) involving phenolic/anisolic analytes.
• Synthetic intermediate: May be used to construct diarylmethane or benzofuran scaffolds that are later elaborated into candidate molecules; however, this product itself is not formulated for therapeutic use.
• Preformulation studies: If used in discovery settings, solubility enhancement strategies (cosolvents, cyclodextrins) may be explored purely for analytical/sample-prep purposes.

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.

Literature/computed values (for reference only; not item specifications)

• Molecular formula: C14H14O2 (literature)
• Molecular weight: 214.26 g/mol (calculated)
• State at ambient conditions: typically a low-melting solid or viscous oil depending on purity and form (literature/general observation for analogous benzylic phenols).
• Aqueous solubility: expected very low; phenolic/aromatic, better solubility in organic solvents (literature expectation).
• Organic solubility: commonly soluble in dichloromethane, ethyl acetate, THF, toluene, acetone, acetonitrile, alcohols (literature expectation for similar structures).
• Partitioning: logP generally reported around 2.8–3.2 for closely related PMB–phenol frameworks (literature/computational estimates).
• Acid–base behavior: phenolic pKa typically ~9.5–10.5 for substituted phenols; methoxy and benzylic ortho substitution can slightly modulate acidity (literature range).

Notes

• Where precise specifications are required (mp, bp, density, refractive index, UV cutoff, water/peroxide/metal limits), consult the item’s CoA/Spec Sheet. This section provides general literature context only.

Quality and Grades

Item-specific (from Product Data)

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on quality expectations (literature/practice)

• Typical analytical controls for this class of compound include: identity by 1H/13C NMR, purity by HPLC/GC, and residual solvents by GC. Water content by Karl Fischer may be reported when relevant (though low water uptake is expected for hydrophobic aromatics).
• UV characteristics: Aromatic systems with phenol/anisole typically show strong UV absorbance; if intended for chromatographic uses, low-UV-absorbance solvent residues and clean baselines are desirable.
• Stabilizers: None are typically required; however, protection from strong oxidants is prudent. If any stabilizer is added for a specific lot, it will be disclosed on the CoA.
• What to check on receipt: appearance versus CoA, purity assay, and consistency of NMR with expected substitution pattern (phenolic OH, benzylic CH2 singlet, anisole OCH3 singlet).

Reaction and Applications

General applications (literature/practice)

• Phenolic derivatization: The phenol can be deprotonated (e.g., with K2CO3, NaH, or t-BuOK) and converted to ethers (Williamson O‑alkylation), esters (acyl chlorides/anhydrides), or carbonates/carbamates—useful for protecting groups or for downstream diversification.
• Benzylic functionalization: The PMB-linked benzylic CH2 is activated toward radical or ionic transformations.
  • Benzylic halogenation: NBS or NCS under radical initiation to give benzyl halides for further SN1/SN2 chemistry.
  • Benzylic oxidation: DDQ, MnO2, or TEMPO/bleach systems to yield the corresponding aldehyde or ketone (depending on substitution), enabling further elaboration (e.g., Wittig/aldol).
• Electrophilic aromatic substitution:
  • Anisole ring (para‑methoxyphenyl) is activated; conditions favor substitution ortho/para to methoxy (with para already occupied). Nitration, sulfonation, and Friedel–Crafts acylation/alkylation are feasible with control.
  • Phenol ring is also activated; directing effects of –OH and the ortho‑benzylic substituent can be leveraged for selective halogenation or acylation at the remaining activated positions.
• Cyclizations: Intramolecular Friedel–Crafts or oxidative cyclizations can forge benzofuran or diarylmethane-derived frameworks from benzylic-oxidized intermediates.
• Cross-coupling handles: While the parent compound lacks halogens/boron, installation (e.g., via selective bromination/iodination) enables Suzuki, Buchwald–Hartwig (after conversion to aryl triflates from the phenol), or Kumada couplings.

Use contexts

• Building block for lignan-/diarylmethane-like scaffolds.
• Model substrate for studying benzylic oxidation or radical chain functionalizations in method-development.
• Precursor to O‑protected derivatives (carbonate/carbamate) for orthogonal deprotection studies.

Reaction Conditions

General, literature-reported conditions (guidance only; optimize per substrate and scale)

• O‑Alkylation of the phenol (Williamson):
  • Base: K2CO3 (1.5–3.0 equiv) or NaH (1.1–1.5 equiv).
  • Solvent: acetone, MeCN, DMF, or THF (anhydrous).
  • Electrophile: primary alkyl halides/sulfonates (1.2–1.5 equiv).
  • Temperature/time: rt to reflux, 1–16 h.
  • Notes: Avoid strong bases with secondary/tertiary halides (elimination). Work under N2/Ar when using NaH.
• Benzylic bromination (radical):
  • Reagents: NBS (1.1–1.3 equiv), AIBN or light initiation.
  • Solvent: CCl4 (legacy), toluene or CPME (greener options).
  • Temperature/time: reflux or hv, 2–6 h.
  • Notes: Control equivalents to minimize overbromination; monitor by TLC/GC.
• Benzylic oxidation to aldehyde:
  • Reagents: MnO2 (excess) in DCM/toluene; or DDQ (1.2–2.0 equiv) in DCM; or TEMPO/NaOCl (catalytic TEMPO) in biphasic toluene/aqueous buffer with phase-transfer catalyst.
  • Temperature: 0 °C to rt; time: 1–12 h.
  • Notes: Protect phenol if over-oxidation or ether cleavage is a concern; buffer pH for TEMPO systems to ~9–10.
• Electrophilic aromatic substitution (EAS) on anisole ring:
  • Iodination: NIS (1.1–1.2 equiv) in HFIP or MeCN with acid catalyst; rt, 1–3 h.
  • Friedel–Crafts acylation: acid chloride (1.1–1.5 equiv), AlCl3 (cat.–stoich), DCM or nitrobenzene; 0 °C to rt, 1–6 h.

Yields: Dependent on substitution and conditions; literature reports for analogous substrates commonly range 60–90% for well-optimized steps. Always consult primary literature and run small-scale pilots.

Safety and Handling

Item-specific (from Product Data)

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature.

General safety guidance (literature/practice; defer to SDS for authoritative data)

• Likely hazards: Aromatic phenols can cause skin/eye irritation; avoid inhalation/ingestion. Anisole-containing benzylic compounds may be harmful if swallowed. Handle as a combustible organic.
• PPE: Use lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize vapor/aerosol exposure.
• Incompatibilities: Strong oxidizing agents (risk of exothermic reaction/oxidation, especially at the benzylic position); strong bases form phenoxide (reactive toward alkylation/acylation); strong acids may promote electrophilic substitution or dehydration in complex mixtures.
• First aid (overview):
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spills: Absorb with inert material (vermiculite, sand), collect in suitable container for disposal. Prevent entry to drains.
• Stability notes: Avoid prolonged exposure to air/strong light in the presence of oxidants; benzylic positions can oxidize under harsh conditions. Always consult the product SDS for definitive hazard and response information.

Solvent Selection

Applicability note: This product is a small-molecule aromatic phenol (solid/liquid substrate), not a solvent. The following guidance addresses solvent choice for handling and reactions involving 2-(4-methoxybenzyl)phenol.

General solvent behavior (literature/practice)

• Polarity: Moderately nonpolar, aromatic; favors medium-polarity organic solvents.
• Miscibility/solubility (literature expectations):
  • Good: dichloromethane, chloroform, ethyl acetate, acetone, THF, acetonitrile, toluene, ethyl ether, alcohols.
  • Poor: water and highly aqueous buffers.
• Selection tips:
  • For base-promoted O-alkylation/acylation: polar aprotic solvents (DMF, DMSO, MeCN) or THF; ensure anhydrous conditions when forming phenoxide.
  • For benzylic oxidations (e.g., DDQ, MnO2): DCM, toluene, or dioxane commonly used; choose based on oxidant solubility and temperature control.
  • For electrophilic substitutions on the anisole ring: use non-nucleophilic media (Ac2O, nitromethane, DCM) and suitable Lewis/Brønsted acid catalysts.
  • For chromatographic purification: hexanes/EtOAc or toluene/EtOAc gradients often give good resolution due to differential polarity of the phenolic vs anisole ring.
• Practical note: The phenolic OH can hydrogen-bond; modest solvent polarity aids dissolution but may also broaden NMR signals—add a drop of DMSO-d6 or CD3OD to sharpen OH signals if needed (analytical consideration).

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Best practices (general)

• Container: Store in a tightly closed, chemically compatible container. Use amber glass to minimize light exposure, as benzylic/aromatic systems can undergo slow photo-induced changes under harsh light.
• Atmosphere: Normal lab atmosphere is typically acceptable; for long-term storage, keep dry and avoid prolonged exposure to strong oxidants. Adding a small desiccant pack to the secondary container can help maintain dryness.
• Stability: Phenolic/aromatic compounds are generally stable at ambient conditions; avoid strong bases/acids and oxidants in storage areas.
• Reconstitution/dissolution: If supplied as a solid, dissolve in anhydrous organic solvent (e.g., DCM, THF, MeCN, ethanol) to the desired concentration immediately before use. If an oil, use volumetric addition or prepare a weighed stock solution.
• Freeze–thaw: Not typically required. If solutions are prepared for short-term use, store at 2–8 °C protected from light; equilibrate to room temperature before use and inspect for precipitation.

Research use note

• For research use only. Not for human or veterinary use.

Structure and Identity

Item-specific (from Product Data)

• Product name: 2-(4-Methoxybenzyl)phenol
• CAS: 37155-50-3
• CID: 258451
• InChIKey: 9012
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed (general identity and structural description)

• Typical molecular formula (literature): C14H14O2
• Typical molecular weight (literature): ~214.26 g/mol (calculated from C14H14O2)
• Structural features: two aromatic rings connected through a benzylic CH2 linker; one ring is a phenol (–OH), the other is a para‑methoxyphenyl (anisole) ring. The phenolic OH is ortho to the benzylic substituent (i.e., the benzyl group is at the 2-position of phenol).
• Functional groups: phenol (Ar–OH), anisole methoxy (Ar–O–CH3), benzylic methylene (Ar–CH2–Ar).
• 2D description in words: a phenol ring bearing an o‑benzyl substituent; the benzyl’s distal ring bears a para‑methoxy substituent. No stereocenters; overall a neutral, moderately lipophilic biaryl-ether motif joined via –CH2–.

Synthetic Utility

Key functional elements and their reactivity (literature)

• Phenolic OH: readily converted to ethers (Williamson), esters (acyl chlorides/anhydrides), carbonates/carbamates; transformed into aryl triflates to create a coupling handle (e.g., Pd-catalyzed cross-coupling to diversify the phenolic ring).
• Benzylic CH2 (between rings): activated toward radical halogenation (NBS/AIBN, photolysis), oxidation (DDQ, MnO2, TEMPO systems), and formation of benzyl cations under strongly acidic/oxidizing conditions leading to substitution or rearrangement chemistry.
• Anisole ring: strongly activating methoxy group directs EAS to ortho/para positions; with para occupied by CH2– linkage, the remaining ortho positions are most reactive. Friedel–Crafts acylations/alkylations and iodination/bromination are typical.

Strategic applications

• Diarylmethane diversification: Benzylic functionalization gives a versatile branch-point (e.g., benzyl halide → nucleophilic substitutions; benzyl alcohol/aldehyde → condensations/Wittig).
• Cyclization platforms: Benzylic oxidation to aldehyde followed by intramolecular electrophilic attack from the phenol can forge benzofurans under acid catalysis.
• Protecting-group orthogonality: Although the compound is not a PMB ether, the embedded PMB motif enables studies on selective oxidative activation without cleaving O‑protecting groups elsewhere in a molecule.

Target Specificity

Not applicable. This product is a small organic molecule, not an affinity reagent or biologic. No antigen/epitope specificity, species reactivity, clone, or isotype information applies.