7-Phenoxy-1-tetralone - ≥95% , CAS No.151453-21-3

CAS: 151453-21-3 Cat. No.: P1007356 Formula: C₁₆H₁₄O₂ Peso molecolare: 238.280 Numero EC: 621-128-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1CC2=C(C=C(C=C2)OC3=CC=CC=C3)C(=O)C1
• IUPAC Name: 7-phenoxy-3,4-dihydro-2H-naphthalen-1-one
• InChIKey: ZFOLQUQHELUVNU-UHFFFAOYSA-N
• INCHI: 1S/C16H14O2/c17-16-8-4-5-12-9-10-14(11-15(12)16)18-13-6-2-1-3-7-13/h1-3,6-7,9-11H,4-5,8H2
• Peso molecolare: 238.280

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Diarylethers
• Alternative Parents: Tetralins Phenoxy compounds Phenol ethers Aryl alkyl ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Diaryl ether - Tetralin - Phenoxy compound - Aryl alkyl ketone - Aryl ketone - Phenol ether - Benzenoid - Monocyclic benzene moiety - Ketone - Organic oxide - Hydrocarbon derivative - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl 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: 238.280 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 238.099 Da
• Monoisotopic Mass: 238.099 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 293.000
• 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 application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For synthetic use, follow the Reaction Conditions and Synthetic Utility sections. For biochemical assays, prepare concentrated DMSO stocks (e.g., 10–50 mM), then dilute into assay media with appropriate cosolvent limits (commonly ≤1–2% v/v DMSO), verifying solubility and avoiding precipitation.

Biological Roles

This product is a synthetic organic building block and does not have a recognized endogenous biological role.

• General considerations (for researchers exploring bioactive analogs):
  • The tetralone core is a common motif in discovery chemistry; derivatization at the alpha-position and on the phenoxy ring is frequently used to tune physicochemical properties (lipophilicity, aromatic stacking potential, H-bond acceptors/donors via further substitution).
  • The parent compound itself is neutral, lacks ionizable groups under physiological pH, and is expected to be hydrophobic; it may partition into membranes, but no specific biological function is established.

No medical, therapeutic, or diagnostic claims are made for this material. For biological testing, ensure appropriate formulation (e.g., DMSO stock solutions diluted into assay buffers with surfactants) and conduct standard controls for aggregation and nonspecific binding typical of hydrophobic aromatics.

Buffer Applications

Not typically applicable. 7-Phenoxy-1-tetralone is a neutral, hydrophobic organic small molecule and does not function as a buffering agent. For laboratory use involving this compound, select buffers based on the biological assay needs and dissolve the compound first in a compatible cosolvent (e.g., DMSO) before dilution into aqueous buffers.

Green Alternatives

Where feasible, select greener solvents and conditions without compromising reaction performance on this hydrophobic aryl ketone/ether.

• Preferred solvent substitutions (general guidance):
  • Replace dichloromethane/chloroform with ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or toluene, depending on solubility/selectivity.
  • Use bio-based 2-MeTHF instead of THF for enolate and reduction chemistry; it offers improved phase separation and often similar outcomes.
  • Favor ethanol/iPrOH as hydrogenation media over higher-toxicity solvents when compatible with catalyst and substrate.

Comparison (general):

• THF vs 2-MeTHF:
  • Sustainability: 2-MeTHF (renewable feedstocks) > THF.
  • Peroxide tendency: Both form peroxides; 2-MeTHF often slower—still test and manage.
  • Performance: Often comparable for enolizations and hydride reductions; check solubility.
• DCM vs EtOAc:
  • Environmental/health: EtOAc preferred (lower toxicity/halogen-free).
  • Solvency: DCM dissolves more hydrophobic substrates; EtOAc may require heat or higher volumes.

Additional considerations:

• Avoid stoichiometric heavy metals; use catalytic hydrogenation or organocatalysis where possible.
• Employ energy-efficient conditions (microwave, flow) to reduce time and solvent usage when appropriate.

Always validate greener swaps at small scale to confirm reaction fidelity and product quality.

Pharmaceutical Uses

This material is supplied for research use only.

• Typical roles in R&D (general):
  • Synthetic intermediate/scaffold in medicinal chemistry for structure–activity relationship (SAR) exploration.
  • Precursor to libraries via alpha-functionalization of the tetralone or electrophilic substitution on the phenoxy ring.
• Excipients/compendial status: No pharmacopeial excipient role is indicated for this item. Not specified for this item; refer to CoA/Spec Sheet.
• Process chemistry notes (general):
  • The aryl ether is stable to many base-mediated steps, enabling telescoped sequences without protection.
  • Hydrophobicity supports crystallization-driven purifications from alcohol/ester solvent systems when derivatives are formed.

No claims are made regarding therapeutic use, efficacy, or safety in humans or animals.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following notes distinguish between unspecified catalog specs and general literature expectations.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet. Literature/calculated MW for C16H14O2 ≈ 238.28 g/mol.
• Melting point (item-specific): Not specified for this item; refer to CoA/Spec Sheet. (No authoritative literature value cited here.)
• Boiling point (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Density (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general/literature expectations):
  • Expected to be soluble in common organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, acetone, THF) and sparingly soluble in alcohols; poor water solubility is anticipated for this hydrophobic aryl ketone/ether scaffold.
• LogP, pKa (general/computed expectations):
  • The structure is neutral (no readily ionizable groups); pKa not applicable for the parent compound.
  • cLogP expected to be moderate-to-high due to two aromatic rings and limited heteroatom content; specific value not provided here.

For experimentally controlled values (mp, residual solvents, water content, purity, etc.), consult the lot-specific CoA/SDS.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoffs, trace metals, water/peroxides, stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Context for professional users:

• Research use designation: Supplied for research and laboratory use only (per Product Data). Not for human or veterinary use, clinical diagnostics, or household applications.
• Interpreting common grades (general guidance):
  • “Analytical/AR” grade targets low inorganic/organic impurities for analytical work.
  • “Synthesis” grade is appropriate for routine preparative chemistry where trace UV/metal content is less critical.
  • “HPLC” grade (for solvents) emphasizes low UV background and particulate; typically not applicable to solid building blocks.
• Quality control suggestions (practical):
  • Verify identity by 1H/13C NMR and HRMS; aryl ether protons (phenoxy) and tetralone methylene signals should be diagnostic.
  • Purity assessment by HPLC/UPLC with diode array detection at multiple wavelengths (e.g., 210–280 nm) to capture aromatic chromophores.
  • If chromatography is needed, normal-phase silica with gradient hexanes/EtOAc or toluene/EtOAc typically resolves aromatic ketone/ether impurities.

For lot-specific assay, residual solvents, and impurity profile, consult the Certificate of Analysis.

Reaction and Applications

As a substituted tetralone, 7-phenoxy-1-tetralone is a versatile building block in synthesis, especially in the construction and diversification of polycyclic aromatic/benzylic frameworks.

• Enolate chemistry:
  • Alpha-functionalization: LDA/NaHMDS enolization enables alkylation, acylation, and aldol-type additions to install side chains at C-2. Silyl enol ether formation (TMSCl/Et3N) provides handles for Mukaiyama aldol reactions.
  • Michael donor: The enol/enolate participates in conjugate additions to activated Michael acceptors under soft base catalysis (e.g., DBU).
• Reductive transformations:
  • Carbonyl reduction to secondary alcohols (NaBH4, DIBAL, catalytic hydrogenation). Further dehydration/hydrogenation can yield tetralin derivatives.
  • Carbonyl deoxygenation (Wolff–Kishner, Clemmensen) affords the corresponding 1-methylene or tetralin cores.
• Aromatic modifications:
  • Electrophilic aromatic substitution on the phenyl of the phenoxy group (e.g., nitration, halogenation) guided by the ether’s ortho/para-directing influence, enabling late-stage diversification.
  • Cross-coupling on pre-functionalized derivatives (e.g., install halogen on the phenoxy ring, then perform Suzuki/Negishi) to elaborate the pendant aryl.
• Cyclizations and annulations:
  • Intramolecular Friedel–Crafts or radical annulations from suitably derivatized side chains enable access to tricyclic motifs common in materials and discovery chemistry.

The phenoxy ether generally tolerates bases/reductants but may cleave under strong Lewis/Brønsted acids at elevated temperatures—plan protection strategies accordingly.

Reaction Conditions

General literature-style guidance for common transformations on tetralone scaffolds (adjust to your system via small-scale trials):

• Alpha-alkylation (enolate route):
  • Base: LDA (1.1–1.5 equiv) in dry THF or 2-MeTHF at −78 to −20 °C.
  • Electrophile: Primary alkyl halides or Michael acceptors (1.2–2.0 equiv).
  • Workup: Quench with NH4Cl; typical reaction times 0.5–3 h. Yields vary widely (40–85%, literature) depending on sterics and electrophile.
• Mukaiyama aldol (silyl enol ether):
  • Generate TMS enol ether (TMSCl/Et3N or TMSOTf/2,6-lutidine), then couple with aldehyde under Lewis acid (TiCl4, BF3·OEt2) at −78 to 0 °C. Often provides higher diastereocontrol than direct aldol.
• Carbonyl reduction:
  • NaBH4 in MeOH/EtOH at 0–25 °C affords the secondary alcohol (minutes to hours). DIBAL-H in toluene/THF at −78 to 0 °C provides complementary selectivity. Catalytic hydrogenation (Pd/C, 1–5 bar H2) reduces the carbonyl and may partially hydrogenate the ring depending on conditions.
• Deoxygenation:
  • Wolff–Kishner (NH2NH2, KOH, high-boiling solvent, 120–200 °C) or Clemmensen (Zn(Hg), HCl, reflux) convert the ketone to methylene; compatibility with the phenoxy ether should be assessed (acidic conditions can promote ether cleavage).
• Aromatic functionalization:
  • Electrophilic substitution on the phenoxy ring under standard conditions (e.g., nitration with HNO3/Ac2O at low temperature; halogenation with NBS/NCS under photolysis) followed by cross-coupling on the installed halide using Pd catalysis.

All conditions above are general literature guidance; optimize for scale, safety, and selectivity.

Safety and Handling

GHS classification and pictograms are not provided in the Product Data for this item. Always consult the SDS for authoritative hazard and precautionary statements.

• Expected hazards (general for aryl ketones/aryl ethers; not a substitute for SDS):
  • May cause skin/eye irritation and respiratory irritation upon dust or vapor exposure.
  • Combustible organic solid/liquid depending on physical form; avoid ignition sources.
• Special risks/compatibilities:
  • Avoid strong oxidizing agents (risk of exothermic reaction/oxidation).
  • Strong bases form enolates; handle under inert atmosphere if performing base-mediated reactions.
  • Lewis/Brønsted acids can catalyze side reactions (e.g., ether cleavage under forcing conditions).
• Handling recommendations:
  • Use in a fume hood. Wear appropriate PPE: lab coat, safety glasses, and compatible gloves (e.g., nitrile). Avoid inhalation of dust/fumes and contact with skin/eyes.
  • Use inert atmosphere (N2/Ar) for moisture/air-sensitive transformations on the ketone enolate.
• First-aid overview (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice as needed.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/fire response (general):
  • Small spill: Absorb with inert material, collect for disposal.
  • Fire: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and irritant fumes.

Defer to the SDS and institutional protocols for definitive guidance.

Solvent Selection

7-Phenoxy-1-tetralone is a hydrophobic, neutral aryl ketone/ether. Solvent choice is governed by its low polarity and aromaticity.

• Polarity/miscibility (general expectations):
  • Poorly soluble in water; good solubility anticipated in chlorinated solvents (DCM, CHCl3), ethyl acetate, acetone/MEK, THF/2-MeTHF, and moderately in acetonitrile; variable in alcohols depending on temperature.
• Typical use scenarios:
  • Reaction medium for enolate chemistry: dry THF, 2-MeTHF, or toluene with strong bases (LDA, NaHMDS).
  • Reductions and hydrogenations: ethanol, isopropanol, or ethyl acetate with catalytic hydrogenation; or THF/toluene for hydride reductions.
  • Purification: normal-phase silica using hexanes/EtOAc or heptane/EtOAc; DCM/MeOH blends if needed.
• Choosing among options (practical comparison):
  • DCM vs EtOAc: DCM offers higher solubility and fast evaporation; EtOAc is a greener alternative with higher polarity—useful for crystallizations and extractions.
  • THF vs 2-MeTHF: 2-MeTHF provides comparable solvating power with improved sustainability and water separations; THF offers broader literature precedent.
  • Toluene vs acetonitrile: Toluene enhances selectivity in some enolizations; MeCN can aid polar transition states but may under-dissolve very hydrophobic substrates.

Always dry aprotic solvents rigorously for base- or moisture-sensitive transformations.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Protect from light and moisture. Keep container tightly closed.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Stability notes (general):
  • Aryl ketones/ethers are typically stable under ambient conditions. Avoid prolonged exposure to strong light/UV to minimize potential photochemical changes.
  • For long-term storage, consider desiccation (dry cabinet or desiccant pouch) to prevent moisture uptake that can complicate weighing and reactions.
• Reconstitution/dissolution (general guidance):
  • Prepare stock solutions in dry organic solvents such as DMSO, DMF, acetone, acetonitrile, THF, ethyl acetate, or dichloromethane, depending on intended use.
  • For biological testing, dissolve in DMSO to make a concentrated stock (e.g., 10–50 mM), then dilute into buffer with vigorous mixing; monitor for precipitation and keep final DMSO within assay tolerance.
  • For synthetic applications, dry solvents prior to base-mediated steps and, if necessary, degas for air-sensitive reactions.

Always refer to the SDS and lot-specific CoA for definitive handling, stability, and storage information.

Structure and Identity

7-Phenoxy-1-tetralone is an aryl ether–substituted tetralone scaffold combining a benzopyran-like ether motif with a cyclic aryl ketone.

• Product identifiers (item-specific):
  • CAS: 151453-21-3
  • PubChem CID: 4318753
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Empirical composition (literature/structure-derived):
  • Molecular formula (literature): C16H14O2
  • Molecular weight (literature, calculated from formula): 238.28 g/mol
• Structural features (general description based on name):
  • Core: 1-tetralone (1,2,3,4-tetrahydronaphthalen-1-one) ring system bearing a ketone at C-1.
  • Substitution: A phenoxy group (–O–C6H5) at the 7-position of the tetralone aromatic ring.
  • Functional groups: Aryl ether (phenoxy), aryl ketone (conjugated to a partially saturated ring).
  • Stereochemistry: None (achiral as named; no stereogenic centers).
• 2D structure (verbal): A bicyclic framework composed of a benzene ring fused to a partially saturated cyclohexanone; the benzene ring carries an –O–Ph substituent para to the ring fusion (position 7), and the carbonyl resides on the adjacent saturated ring at position 1.

Synthetic Utility

Key reactivity arises from the conjugated aryl ketone and the appended phenoxy aryl ether.

• Transformations at the carbonyl/alpha-position:
  • Enolate formation (LDA, NaHMDS, KHMDS) for alkylation, acylation, and aldol reactions; soft enolization (silyl enol ethers) for Mukaiyama aldol variants.
  • Reduction to alcohols (NaBH4, DIBAL-H, catalytic hydrogenation); subsequent functionalization (e.g., Mitsunobu, acylation) diversifies the scaffold.
  • Deoxygenation (Wolff–Kishner, Clemmensen) to afford tetralin frameworks common in materials and discovery chemistry.
• Modifications on the aromatic domains:
  • Phenoxy ring: Electrophilic substitutions (e.g., halogenation, nitration) directed by the ether; subsequent cross-couplings (Suzuki, Buchwald–Hartwig on preinstalled aryl halides) enable rapid analog buildup.
  • Tetralone aryl ring: Friedel–Crafts and directed ortho-metalation become accessible after appropriate directing group installation.
• Strategic value:
  • The phenoxy substituent increases solubility in organic media and can act as a temporary directing/modulating group; under forcing conditions it may be transformed (e.g., ether cleavage or rearrangement) to tune electronics.
  • The scaffold’s rigidity plus benzylic positions provides handles for late-stage C–H functionalization (radical bromination at benzylic positions, followed by substitution).

Overall, 7-phenoxy-1-tetralone serves as a robust entry point for multi-directional diversification in complex-molecule synthesis.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or biological ligand with defined target specificity. No antigen/epitope, isotype, or species reactivity is associated with this item.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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

The CAS Number is 151453-21-3, the molecular formula is C16H14O2, and the molecular weight is 238.280 g/mol. InChIKey ZFOLQUQHELUVNU-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.