[4-(3-Methylphenoxy)phenyl]methanol , CAS No.53818-56-7

CAS: 53818-56-7 Cat. No.: M963151 Summenformel: C₁₄H₁₄O₂ Molekulargewicht: 214.27 PubChem CID: 28946093

Storage

Room temperature

Specifications

Storage

Room temperature

Namen und Kennungen

Kanonisches Lächeln

CC1=CC(=CC=C1)OC2=CC=C(C=C2)CO

IUPAC Name

[4-(3-methylphenoxy)phenyl]methanol

InChIKey

QHBCPJQVVMEFOR-UHFFFAOYSA-N

INCHI

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

Isomere SMILES

CC1=CC(=CC=C1)OC2=CC=C(C=C2)CO

PubChem CID

28946093

Molekulargewicht

214.27

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Diphenylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Diphenylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylethers
• Alternative Parents: Diarylethers Phenoxy compounds Phenol ethers Benzyl alcohols Toluenes Primary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylether - Diaryl ether - Phenoxy compound - Phenol ether - Benzyl alcohol - Toluene - Ether - Organic oxygen compound - Hydrocarbon derivative - Aromatic alcohol - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Beschreibung: 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

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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 214.260 g/mol
• XLogP3: 3.300
• 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

No assay-specific or bioanalytical application protocols are provided for this item.

General laboratory usage examples (non-binding, for context only):

• Stock solution preparation for screening: Dissolve to 10–50 mM in dry DMSO; vortex and sonicate if needed. Filter (0.2 µm PTFE) before use for LC/HPLC compatibility.
• Oxidation to the aldehyde (example workflow): Dissolve substrate in DCM, cool to 0 C, add Dess–Martin, stir and monitor by TLC; quench with aqueous NaHCO3 and extract; purify by silica chromatography using heptane/EtOAc.
• Formation of benzyl bromide (example): Treat with PBr3 at 0 C in DCM; warm to rt; quench cautiously with ice-water; extract and purify.

These are illustrative literature-style procedures and not product-validated protocols. For validated, item-specific protocols, refer to the CoA/Spec Sheet or develop methods under your laboratory’s SOPs.

Biological Roles

This compound is a synthetic aryl ether bearing a benzylic alcohol and is not known as a natural metabolite or biogenic molecule.

• General context (literature):
  • Aryl ether scaffolds occur in lignin and various natural products, but the specific 4-(3-methylphenoxy) substitution pattern is not a common endogenous motif.
  • The benzylic alcohol can engage in hydrogen bonding, which may be leveraged in structure–activity relationship (SAR) studies as a polar handle without conferring high aqueous solubility.
• Research use only:
  • Employed as a building block in medicinal chemistry campaigns to modulate lipophilicity and aromatic spacing without introducing heteroaromatic nitrogens.
  • Useful in probe design where benzylic functionality enables late-stage diversification (e.g., formation of esters, carbamates) for target engagement studies.

No specific biological pathways, receptors, or enzymatic roles are attributed to this exact compound in standard biochemical references. Any biological testing should be accompanied by appropriate controls, and handling must follow institutional safety protocols. For mechanistic or ADME studies, consider matched pairs (aldehyde, acid, ester) to explore oxidation state effects on permeability and stability. All uses are for research and laboratory investigation only; no clinical or diagnostic use is intended or implied.

Buffer Applications

Not typically applicable. [4-(3-Methylphenoxy)phenyl]methanol is a hydrophobic small-molecule intermediate and is not used to prepare aqueous buffer systems.

Practical notes for laboratory handling:

• If aqueous assays are required, dissolve first in a water-miscible co-solvent (e.g., DMSO, acetonitrile, or ethanol) to make a concentrated stock, then dilute into the buffer with vigorous mixing to avoid precipitation. Typical final organic content is kept ≤1–2% v/v to minimize effects on biological systems.
• For pH-sensitive experiments, note that the compound lacks ionizable groups in the physiological range; apparent solubility will not be strongly pH-dependent, but salts of derived esters/carbamates may show different behavior.

For buffer formulation details, refer instead to standard buffering agents (phosphate, HEPES, Tris, MOPS) as this compound does not serve as a buffering component.

Green Alternatives

Although [4-(3-Methylphenoxy)phenyl]methanol is a target molecule rather than a solvent, greener choices can be made in its preparation and downstream transformations.

• Greener solvents for workup and reaction (literature guidance):
  • Replace chlorinated solvents (DCM, chloroform) with ethyl acetate, 2-MeTHF, CPME, or anisole where feasible.
  • For extractions, consider EtOAc or MTBE over DCM; for chromatography, heptane/EtOAc over hexane/DCM.
• Oxidations to the aldehyde/acid:
  • Use catalytic TEMPO/NaOCl in biphasic water/EtOAc systems or Oxone in aqueous media instead of Cr(VI) reagents. Tradeoff: careful pH control and phase-transfer catalyst may be required.
• Esterifications:
  • Employ catalytic DMAP with greener coupling reagents (e.g., CDI or EDC·HCl in 2-MeTHF) rather than DCC in DCM. Tradeoff: urea byproducts differ; filtration ease varies.
• Benzylic activation:
  • Appel alternatives include PPh3/CBr4-free protocols (e.g., triphenylphosphine with NBS in greener solvents) or direct Mitsunobu substitutions to avoid halide waste; tradeoff: stereochemical considerations are minimal here, but waste streams still need management.

Comparison snapshot (literature-based):

• 2-MeTHF vs THF: similar polarity; 2-MeTHF offers partially renewable sourcing and easier phase separation but sometimes slower rates.
• CPME vs toluene/DCM: broad solubility window and low peroxide formation; higher bp can complicate solvent removal.

Adopt LCA-aware choices for protection/deprotection and minimize chromatography by crystallization when feasible.

Pharmaceutical Uses

No excipient or compendial roles are specified for this item.

• Item-specific status:
  • Pharmaceutical/compendial grade: Not specified for this item; refer to CoA/Spec Sheet.
  • Research Use Note: For research use only.

General context (literature):

• As a benzyl alcohol–bearing aryl ether, this structure type appears in medicinal chemistry as a scaffold or intermediate. The benzylic OH allows rapid generation of prodrug-like esters/carbamates to tune permeability and clearance during lead optimization.
• Not intended for human or veterinary use. No claims are made regarding safety, efficacy, or therapeutic application.

Formulation/processing considerations (for research):

• Solubilization for screening: DMSO stock solutions (e.g., 10–50 mM) are commonly used; verify stability over time and avoid freeze–thaw cycling.
• Solid-form screening: If crystalline, polymorph/solvate formation may influence dissolution rate; characterize as needed by PXRD/DSC for preformulation studies in a research context.

All pharmaceutical-related work with this compound should be confined to nonclinical, exploratory research environments.

Physical Properties

Item-specific properties:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Storage conditions: Room temperature (per Product Data).

Literature/computed (reference, not product specifications):

• Expected phase at ambient: organic solid or high-boiling liquid, depending on purity and crystal habit (aryl ethers with MW ~214 often crystallize).
• Solubility (qualitative, literature expectation):
  • Water: very low solubility due to hydrophobic aryl ether scaffold.
  • Organic: soluble in common organics (EtOAc, dichloromethane, toluene, THF, acetone, acetonitrile, alcohols) typical for aryl ethers/benzyl alcohols.
• Lipophilicity: benzylic alcohol moderates, but aryl ether + aryl methyl suggest moderate-to-high logP (literature expectation for C14 aryl ether alcohol ~2–3.5). Exact logP not specified for this item.
• Boiling/melting points, density, refractive index, pKa: Not specified for this item; refer to CoA/Spec Sheet. If needed, consult primary literature or measure under your laboratory conditions.

Practical handling notes (general):

• Drying: can be dried under vacuum at ambient to 40–50 C to remove residual solvents; avoid prolonged heating to prevent discoloration.
• Spectral ID: benzylic OH typically shows broad 1H NMR signal ~1.5–2.5 ppm (exchangeable), benzylic CH2 singlet ~4.5–4.8 ppm; IR OH stretch ~3200–3500 cm−1; strong aromatic C–O–C stretch ~1200–1270 cm−1 (literature characteristics).

Quality and Grades

Item-specific details:

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

General guidance (for interpretation of potential grades):

• Research-grade aryl alcohols are typically supplied at high purity suitable for synthetic chemistry and analytical characterization. If labeled as “>98%” or similar on the CoA, minor impurities often include residual solvents or oxidized benzylic species (e.g., traces of aldehyde/ester).
• HPLC-grade designation (if present) typically refers to low UV-absorbing impurities and suitability as a reference material; for solids/liquids like this, it may indicate rigorous purification and low baseline drift in UV.
• Metal content/trace analysis: Unless specified, metals are not typically controlled tightly for small-molecule intermediates; request elemental or ICP data if catalytic applications are metal-sensitive.
• Water/peroxide/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. Note that aryl ethers do not generally form peroxides under normal storage, unlike dialkyl ethers.

Practical QC suggestions:

• Verify identity and purity by 1H/13C NMR and HPLC/GC as appropriate. Benzylic OH can broaden; a D2O shake helps confirm. LC–MS with ESI typically shows [M+H]+ at m/z ~215 (literature expectation for C14H14O2).

Reaction and Applications

Use this benzylic alcohol–aryl ether as a versatile intermediate in synthesis and materials discovery.

• Transformation families centered on the benzylic alcohol:
  • Oxidation to aldehyde/acid: TEMPO/bleach, Dess–Martin, or Swern for aldehyde; Pinnick or further oxidation to acid (literature practice).
  • Esterification/carbonate/urethane formation: Steglich or acid chloride couplings to generate esters; triphosgene/Boc2O for carbonates; isocyanates to urethanes.
  • Mitsunobu inversion/substitution: Convert to diverse benzylic ethers/esters using DEAD/DIAD and PPh3; note aryl ether core is stable to these conditions.
  • Benzylic halogenation/activation: PBr3, SOCl2, Appel, or TMSCl/NaI give benzyl halides for subsequent SN1/SN2 or cross-coupling (e.g., Pd-catalyzed benzylation).
• Aryl ether scaffold utility:
  • The 4,3-disubstitution pattern modulates electronics; serves as a fragment for SAR in medicinal chemistry and agrochemicals.
  • Thermal/oxidative stability of aryl–O–aryl bonds supports use as a building block in photoactive materials and polymer side-chains.
• Application domains (research use only):
  • Preparation of libraries where benzylic substituent variation tunes potency and PK surrogates.
  • Installation into oligomers via ester/urethane linkages to probe rigidity and π–stacking.

Practical tips:

• Drying the substrate and solvent improves yields in carbodiimide couplings and halogenations.
• Monitor for minor oxidation to the aldehyde during prolonged storage; add antioxidant-free, dry conditions to minimize.

Reaction Conditions

General literature guidance for common transformations of [4-(3-Methylphenoxy)phenyl]methanol (conditions are examples; optimize per substrate):

• Oxidation to aldehyde:
  • Dess–Martin periodinane (1.2–1.5 equiv) in DCM, 0–25 C, 0.5–2 h; typical yields 80–95% for benzylic alcohols.
  • TEMPO (5–10 mol%), NaOCl (1.5 equiv active), KBr (cat.), pH ~9, biphasic EtOAc/H2O, 0–25 C; 1–3 h.
• Oxidation to acid:
  • Pinnick (NaClO2, NaH2PO4 buffer, 2-methyl-2-butene scavenger) from the aldehyde in tBuOH/H2O, 0–25 C; typically high yields.
• Esterification:
  • Steglich: Carboxylic acid (1.2 equiv), DCC (1.2 equiv), DMAP (0.1 equiv), DCM or 2-MeTHF, 0–25 C, 2–16 h.
  • Acid chloride method: RCOCl (1.2 equiv), base (2 equiv pyridine or Et3N), DCM, 0–25 C.
• Halide formation:
  • PBr3 (0.33–0.5 equiv), solvent-free or DCM, 0–25 C; 0.5–2 h gives benzyl bromide intermediates.
  • SOCl2 (2–3 equiv) with catalytic DMF, reflux in toluene or neat; monitor for overreaction.
• Mitsunobu substitutions:
  • DIAD/DEAD (1.1–1.5 equiv), PPh3 (1.2–1.5 equiv), nucleophile (1.5–2.0 equiv), THF or toluene, 0–25 C; 2–6 h.
• Protection of alcohol:
  • Silylation: TBSCl (1.2–1.5 equiv), imidazole (2 equiv), DMF, rt; or TBDPSCl for robustness.

Notes:

• The aryl ether linkage tolerates these conditions well. Avoid strong Brønsted acids at elevated temperatures that could risk ether cleavage.
• Typical monitoring by TLC/HPLC; benzylic derivatives show strong UV at 254 nm.

Safety and Handling

GHS and hazard information (item-specific):

• 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 aryl ether benzyl alcohols (literature/experience; not a substitute for the SDS):

• Likely hazards: May cause skin/eye irritation and respiratory irritation upon dust or vapor exposure; ingestion/inhalation harmful if misused. Avoid aerosolization.
• PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
• Handling: Avoid contact with strong oxidizers; the benzylic alcohol can undergo oxidation under harsh conditions. Keep containers tightly closed to prevent contamination and moisture uptake.
• Incompatibilities: Strong oxidizing agents; strong acids may promote aryl ether cleavage only under forcing conditions; bases generally compatible. Avoid reactive acylating/halogenating agents unless intended.
• First aid overview:
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; continue rinsing; seek medical attention.
  • 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. Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and phenolic/aryl ether decomposition products.
• Always consult the product-specific SDS for authoritative hazard, toxicology, and regulatory information.

Solvent Selection

This compound is an organic, moderately lipophilic aryl ether bearing a benzylic alcohol. It is not used as a solvent; the following guidance addresses dissolving it for reactions or analysis.

• Polarity/miscibility (literature expectations):
  • Limited water solubility; miscible/soluble in common organic solvents (DCM, chloroform, ethyl acetate, toluene, THF, acetone, acetonitrile, lower alcohols).
  • The OH group enhances solubility in polar aprotic/protic media relative to nonpolar aryl ethers.
• Selection by task:
  • Synthesis/transformations: Choose dry, oxygen-free solvents when performing oxidations or reactions sensitive to moisture (e.g., DCM, MeCN, toluene, THF). Alcoholic solvents can engage in H-bonding and may slow some nucleophilic substitutions at the benzylic position.
  • Purification: Elutes on silica with EtOAc/hexanes (or toluene) gradients; polar functional group aids chromatographic control.
  • Analytics: For HPLC, acetonitrile/water with small acid modifier or methanol/water systems are typical; ensure analyte solubility by pre-dissolution in ACN or MeOH. For GC, derivatization to the acetate or silyl ether can improve volatility and peak shape if needed.
• Comparison hints:
  • Versus nonfunctional diphenyl ethers, this material dissolves better in polar organic media due to the benzylic OH.
  • If aqueous handling is required, co-solvents (DMSO, ACN, MeOH) or cyclodextrin inclusion can be considered for stock solutions.

Storage and Reconstitution

Item-specific storage:

• Storage conditions: Room temperature (per Product Data). Store in a tightly sealed container.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General best practices (literature/experience):

• Protect from prolonged exposure to air and light to minimize slow benzylic oxidation or discoloration. Consider storing under inert gas (argon/nitrogen) if long-term storage is anticipated.
• Keep dry; while the benzylic alcohol is not highly hygroscopic, moisture can affect certain downstream reactions.
• If supplied as a solid, break up lumps under inert atmosphere; if as a liquid, use dry syringes/pipettes and recap promptly.

Reconstitution/solution stability:

• Prepare stock solutions in dry organic solvents (DMSO, acetonitrile, THF, ethanol). For biological assays, DMSO stocks are common.
• Suggested stock concentrations: 10–100 mM depending on solubility; filter through 0.2 µm PTFE for analytical uses.
• Stability of solutions is system-dependent; for DMSO/ACN solutions, use within days to weeks at 2–8 C or freeze at −20 C for longer-term, avoiding repeated freeze–thaw cycles.

Always consult the product-specific CoA/SDS for authoritative handling and storage details.

Structure and Identity

A bifunctional aryl ether–benzyl alcohol useful as a synthetic intermediate.

• Item-specific identifiers (from Product Data):
  • CAS: 53818-56-7
  • InChIKey: 296755 (as provided)
  • CID: 28946093
  • SMILES: 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 structural details (for reference only, not product specifications):
  • Representative SMILES (literature): OCc1ccc(Oc2cccc(c2)C)cc1
  • Putative molecular formula (literature): C14H14O2
  • Calculated molecular weight (literature): ~214.26 g/mol
• Structural features (general description):
  • Consists of two phenyl rings linked via an ether oxygen (aryl–O–aryl), with a benzyl alcohol (-CH2OH) at the para position of one ring and a meta-methyl substituent on the distal ring.
  • Functional groups: primary alcohol (benzylic), aryl ether, aryl methyl.
  • 2D description: a para-substituted phenyl bearing –CH2OH is connected through an oxygen to a second phenyl ring bearing a 3-methyl group; all centers are aromatic, no stereocenters present.
• Notes:
  • The aryl–O–aryl linkage confers stability toward many nucleophiles and mild bases; reactivity is focused at the benzylic alcohol for derivatization (oxidation, esterification, Mitsunobu).

Synthetic Utility

Functional handles and reactivity make this a flexible intermediate for multi-step synthesis.

• Benzylic alcohol chemistry:
  • Oxidation: Access the corresponding aldehyde or acid for further C–C bond formations (e.g., Wittig/olefination from aldehyde; HWE; reductive amination after oxidation-to-aldehyde).
  • Activation: Convert to halides (PBr3, SOCl2) or sulfonates (MsCl/TsCl) for SN2/SN1 reactions introducing heteroatoms or carbon nucleophiles.
  • Substitution via Mitsunobu: Install oxygen or nitrogen nucleophiles under inversion (stereochemistry not a concern at benzylic CH2).
• Aryl ether core:
  • Generally inert to many conditions, serving as a stable spacer. Under harsh Lewis acid conditions, demethylation-type pathways are irrelevant here; the O–aryl is robust, enabling late-stage modifications at the benzylic site without cleaving the ether.
• Orthogonal derivatization:
  • Para position occupied by CH2OH; remote ring bears a meta-methyl group. Directed metalation on the methyl-bearing ring (e.g., ortho to O) may be feasible with strong bases (s-BuLi/TMEDA) to introduce additional functionality (literature strategy, handle with care).
• Retrosynthetic value:
  • Retrosynthetically disconnects to a 4-hydroxymethylphenyl nucleophile and a 3-methylphenyl electrophile via nucleophilic aromatic substitution or Ullmann/Cu- or Buchwald–Hartwig-type O-arylation using 3-methyl aryl halides/triflates and 4-hydroxymethylphenol.

These features support its role in building polyaromatic materials, ligands, and SAR analogs.

Target Specificity

Not applicable. This product is a small-molecule chemical intermediate and not a biological targeting reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.

Häufig gestellte Fragen

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 53818-56-7, the molecular formula is C14H14O2, and the molecular weight is 214.27 g/mol. InChIKey QHBCPJQVVMEFOR-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.