4'-Methoxy-3-(4-methylphenyl)propiophenone - ≥95% , CAS No.106511-65-3

CAS: 106511-65-3 Cat. No.: M970640 Formula: C₁₇H₁₈O₂ Molecular Weight: 254.329 PubChem CID: 12263036

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

CC1=CC=C(C=C1)CCC(=O)C2=CC=C(C=C2)OC

IUPAC Name

1-(4-methoxyphenyl)-3-(4-methylphenyl)propan-1-one

InChIKey

PILCQTXJJGELQA-UHFFFAOYSA-N

INCHI

1S/C17H18O2/c1-13-3-5-14(6-4-13)7-12-17(18)15-8-10-16(19-2)11-9-15/h3-6,8-11H,7,12H2,1-2H3

Isomeric SMILES

CC1=CC=C(C=C1)CCC(=O)C2=CC=C(C=C2)OC

PubChem CID

12263036

Molecular Weight

254.329

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: Retro-dihydrochalcones
• Alternative Parents: Alkyl-phenylketones Butyrophenones Phenoxy compounds Methoxybenzenes Benzoyl derivatives Aryl alkyl ketones Anisoles Toluenes Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Retro-dihydrochalcone - Alkyl-phenylketone - Butyrophenone - Phenylketone - Anisole - Benzoyl - Phenol ether - Phenoxy compound - Aryl ketone - Aryl alkyl ketone - Methoxybenzene - Toluene - Alkyl aryl ether - Monocyclic benzene moiety - Benzenoid - Ketone - Ether - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
• 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

Chemical and Physical Properties

• Molecular Weight: 254.320 g/mol
• XLogP3: 3.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 254.131 Da
• Monoisotopic Mass: 254.131 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 271.000
• 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 as an assay‑validated biological reagent. No WB/IHC/IF/FC or similar protocol data are associated with this small‑molecule building block.

Practical handling protocol (general)

• Analytical standard prep: Accurately weigh material, dissolve in acetonitrile or methanol to prepare a 1–10 mg/mL stock. Filter (0.22 μm PTFE) for LC work. Store aliquots tightly capped.
• Reaction setup: Dry glassware; dissolve substrate in chosen solvent; add reagents under inert gas as needed; monitor by TLC/HPLC.

Biological Roles

This product is provided strictly for research use and is not intended for biological administration. No item‑specific biochemical data are provided.

• General context (literature/general)

  • Aryl ketones with anisole and tolyl substituents are hydrophobic, aromatic scaffolds frequently explored in medicinal chemistry as cores for SAR studies due to their tunable electronics (methoxy and methyl donors) and metabolic handles (O‑demethylation, benzylic oxidation).
  • The ketone group can engage in reversible interactions (e.g., as a hydrogen‑bond acceptor) and is a common bioisostere explored in probe molecules; however, biological activity is highly substituent‑ and target‑dependent.

• Metabolic considerations (general)

  • Likely metabolic soft spots (in vivo, literature patterns): O‑demethylation to phenols, benzylic oxidation of the p‑tolyl group, and carbonyl reduction to secondary alcohols. These points inform design of metabolite standards and analytical methods.

No target specificity or biological function is claimed for this catalog item. For any use in biochemical assays, validate solubility and stability in the intended buffer system and follow institutional safety protocols.

Buffer Applications

Not typically applicable. This compound is a hydrophobic aryl ketone building block and does not serve as a buffering agent.

Practical note: If preparing assay stocks, dissolve first in DMSO, acetonitrile, or ethanol to make a concentrated organic stock, then dilute into the aqueous buffer with vigorous mixing to avoid precipitation. Determine the DMSO content tolerance of your system in advance.

Green Alternatives

While the compound itself is a target building block, its preparation, handling, and downstream transformations can incorporate greener choices. The following are literature‑based suggestions to reduce environmental impact without compromising performance.

• Solvent selection (greener options)

  • Replace chlorinated solvents (e.g., DCM) with ethyl acetate, 2‑MeTHF, CPME, or toluene where feasible. For extractions, ethyl acetate/MTBE often substitutes dichloromethane.
  • For enolate chemistry, 2‑MeTHF can substitute THF in many LDA/NaHMDS protocols, offering higher boiling point and biorenewable sourcing.

• Reductions/oxidations

  • Prefer catalytic hydrogenation (H2/Pd, H2/Raney Ni) over stoichiometric metal hydrides when selectivity permits. For selective ketone reduction, aqueous NaBH4 in EtOH/H2O minimizes hazardous solvents.
  • For Baeyer–Villiger, consider H2O2/organocatalyst systems or urea–hydrogen peroxide adducts instead of peracids.

• Workup and purification

  • Minimize silica usage via crystallization‑based purifications or catch‑and‑release techniques (e.g., reversible bisulfite adducts for carbonyls when appropriate).
  • Use normal‑phase greener eluents (heptane/EtOAc) and recycle solvent streams.

• Energy and safety

  • Apply flow chemistry for exothermic steps (e.g., halogenations, metalations) to improve heat transfer and reduce solvent inventory.

Trade‑offs: Greener solvents may alter reaction rates/selectivities; small‑scale scouting is recommended to maintain chemoselectivity around the electron‑rich anisole/tolyl rings and the benzylic carbonyl.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item. It is offered for research use only.

• General context (literature/general)
  • Diaryl aryl‑ketone motifs are common in discovery chemistry as intermediates or reference standards; they can serve as precursors to ethers, phenols (via O‑demethylation), or secondary alcohols (via reduction) for lead optimization.
  • Formulation considerations for in vitro testing: prepare DMSO or MeCN stock solutions; use co‑solvents or cyclodextrins for aqueous formulations if absolutely necessary (method development only). Avoid any clinical or therapeutic application.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are general, literature-style expectations for aryl aliphatic ketones of this class; verify with CoA/SDS for this exact item.

• Item-specific values

  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Typical properties for diaryl‑substituted propiophenones (literature/general)

  • Physical state: often low‑melting solids or high‑boiling oils depending on substitution; para‑methoxy and para‑methyl groups commonly raise melting points modestly relative to unsubstituted analogs.
  • Polarity: moderately nonpolar with a polarizable carbonyl; exhibits strong UV absorption in the near‑UV due to aryl–carbonyl conjugation (useful for detection by UV/Vis and HPLC‑UV).
  • Solubility: generally sparingly soluble in water, but readily soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, acetone, acetonitrile, toluene, THF, alcohols). Solubility in nonpolar hexanes may be moderate; aromatic solvents often enhance solubility.
  • Partitioning: expected high logP (literature: aryl ketones with two substituted rings commonly show logP >3), enabling normal‑phase chromatography or reverse‑phase HPLC with high organic content.
  • Spectroscopy: strong IR C=O stretch typically ~1680–1710 cm−1 (literature); 1H NMR shows benzylic CH2 next to carbonyl (2–3 ppm) and anisole OCH3 (~3.7–3.9 ppm) (literature). These are qualitative guides.

Always consult the item’s CoA for definitive physical constants and acceptance criteria.

Quality & Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades for research use (general context)

  • Research/technical grade: Suitable for most synthetic applications; typical specifications include identity (NMR/IR/HRMS), assay (%), and limits for residual solvents/heavy metals. UV impurities are less tightly controlled unless designated for chromatographic use.
  • High‑purity or ≥98–99% assay: Preferred when downstream spectroscopic characterization or structure–activity work requires minimal background. Often paired with HPLC/GC purity traces.
  • Stabilizers: Not typically required for simple aryl ketones; however, some suppliers add antioxidants for light‑sensitive ketones. If present, stabilizer identity and level should be disclosed on the CoA.
  • Water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. Do not assume trace‑level specifications without documentation.

• What to look for on the CoA

  • Identity confirmation: 1H/13C NMR, IR (C=O band), MS/HRMS, and, if solid, melting range.
  • Purity method: HPLC/GC area % method parameters, and residual solvent profile.
  • Storage statement: This item is listed for room‑temperature storage; verify any light protection or desiccation recommendations on the CoA/SDS before long‑term storage.

Reaction & Applications

As a diaryl‑substituted propiophenone, this molecule serves as a versatile synthon in aryl‑ketone chemistry and SAR programs.

• Transformations of the carbonyl (literature/general)

  • Reductions: NaBH4 or catalytic hydrogenation to the corresponding secondary alcohol; Luche reduction (CeCl3/NaBH4) to enhance 1,2‑selectivity. Further hydrogenation can access saturated alcohols.
  • Oxime/hydrazone formation: reaction with hydroxylamine or hydrazines enables derivatization, crystallinity enhancement, and subsequent Beckmann rearrangement or Wolff–Kishner reductions.
  • Baeyer–Villiger oxidation: conversion to the aryl acetate/benzoate ester, providing access to diaryl esters.
  • Acyl activation: formation of imidazolides or mixed anhydrides for subsequent coupling.

• Alpha‑functionalization (enolate chemistry)

  • LDA/NaHMDS generates the kinetic enolate in dry THF at low temperature for alkylation, aldol, or Michael additions. Thermodynamic enolates via weaker bases/higher temperature in toluene or THF.
  • Halogenation (α‑bromination/chlorination) and subsequent substitution open routes to heteroatom incorporation.

• Aryl‑ring derivatization

  • Electrophilic aromatic substitution is directed/activated by the para‑methoxy and para‑methyl groups, enabling selective halogenation, nitration (mild), or Friedel–Crafts alkylation on the appropriate ring (observe chemoselectivity vs carbonyl).
  • Demethylation of the anisole (BBr3, AlCl3/thiols) affords the corresponding phenol for further diversification (etherification, esterification).

• Utility in method development

  • Strong UV chromophore facilitates LC method development and in‑process control.
  • The combination of electron‑donating substituents and a benzylic carbonyl provides a tunable platform for photochemistry, radical bromination at benzylic positions, and late‑stage diversification.

Reaction Conditions

The following literature‑style conditions are common for aryl‑ketone derivatives of this class; optimize for the specific substrate.

• Reduction to secondary alcohol

  • Typical: NaBH4 (1.2–2.0 eq) in MeOH or EtOH at 0–25 °C, 0.5–2 h. Quench with aqueous NH4Cl. Alternative: catalytic hydrogenation (H2, 1–3 bar) with Pd/C in EtOH at rt–40 °C.

• Baeyer–Villiger oxidation

  • mCPBA (1.2–1.5 eq) in DCM at 0–25 °C, 2–16 h; or H2O2 (30%) with a Lewis/Brønsted acid catalyst in MeCN or AcOH. Monitor for over‑oxidation on activated rings.

• Oxime formation

  • Hydroxylamine·HCl (1.2–2.0 eq), pyridine or NaOAc, EtOH/H2O, 25–60 °C, 2–12 h; isolate oxime for characterization or downstream Beckmann rearrangement.

• Enolate alkylation

  • LDA (1.1–1.5 eq) from n‑BuLi/diisopropylamine in dry THF, −78 to −20 °C; add alkyl halide slowly. Typical total time 1–3 h. Quench with NH4Cl and extract with EtOAc.

• Benzylic bromination (p‑tolyl ring)

  • NBS (1.1 eq), AIBN (cat.), CCl4 or toluene, reflux with light or thermal initiation, 2–6 h. Greener variants use ethyl acetate or acetonitrile under LED irradiation.

• Demethylation of anisole

  • BBr3 (1–3 eq) in DCM at −78 to 0 °C, then warm to rt, 2–6 h; quench cautiously with MeOH/H2O. Alternative: AlCl3/thiols or TMSI for sensitive substrates.

Notes

• Maintain anhydrous, oxygen‑free conditions for strong‑base chemistry.
• Electron‑rich rings may undergo side EAS; temperature control and reagent stoichiometry are critical.
• Expected yields vary with substitution and conditions; run small‑scale scouts and monitor by TLC/HPLC (UV 254 nm).

Safety & Handling

No item-specific GHS classification or hazard statements were supplied. Handle as an organic aryl ketone with standard lab precautions and consult the SDS for authoritative guidance.

• Item-specific safety data

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word / H‑statements / pictograms: Not specified for this item; refer to SDS.

• General safety considerations for aryl aliphatic ketones (literature/general)

  • Hazards: May cause skin/eye irritation and respiratory irritation upon dust or vapor exposure. Combustible organic compound; keep away from ignition sources. Avoid inhalation of particulates and prolonged skin contact.
  • PPE: Use lab coat, safety glasses, and appropriate chemical‑resistant gloves (e.g., nitrile). Work in a fume hood to minimize exposure to vapors and dust.
  • Incompatibilities: Strong oxidizers (risk of exothermic reactions), strong bases (can promote enolate formation/side reactions), strong reducing agents (may reduce the ketone). Avoid prolonged exposure to strong UV light which can promote photochemical reactions in aryl ketones.
  • First aid (overview; see SDS): If on skin, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and remove contact lenses if present and easy to do. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention.
  • Fire response: Use CO2, dry chemical, or foam. Combustion can produce CO/CO2 and soot.

Dispose of waste following local regulations for halogen‑free organic residues unless process chemistry introduces other hazards.

Solvent Selection

This product is an aryl ketone building block, not a laboratory solvent. Solvent selection here refers to media for dissolution, handling, purification, and reactions involving the compound.

• Dissolution and handling (general guidance)

  • Readily dissolves in moderately polar organic solvents: dichloromethane (DCM), ethyl acetate, acetone, acetonitrile, THF, toluene, and alcohols. A small amount of heat or sonication may aid dissolution in less polar media (hexanes/heptane).
  • For analytical work: acetonitrile or methanol are common HPLC diluents; DMSO works well for stock solutions in bioassay screening (if applicable), followed by dilution with buffered aqueous media containing co‑solvent.

• Purification

  • Normal‑phase flash chromatography with hexanes/ethyl acetate or toluene/ethyl acetate gradients provides good resolution for aryl ketones with electron‑donating substituents.
  • Recrystallization solvents to evaluate: ethanol, isopropanol, toluene/hexanes, or ethyl acetate/hexanes (selection depends on the actual melting behavior).

• Reaction media considerations (literature/general)

  • Enolate chemistry: dry THF, toluene, or DME under inert atmosphere; polar aprotic solvents (DMF/DMSO) when using stronger bases or for SNAr on activated systems.
  • Reductions/oxidations: alcoholic solvents (MeOH/EtOH) for NaBH4 reductions; DCM or MeCN for chemoselective oxidations.

• Quick comparison (general)

  • DCM vs toluene: DCM maximizes solubility and fast workups; toluene offers higher boiling point and greener profile relative to chlorinated solvents.

Storage & Reconstitution

• Item-specific storage

  • Storage conditions: Room temperature (per Product Data). Store in a tightly closed container in a dry, well‑ventilated place. Keep away from strong oxidants and direct sunlight.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Stability (general for aryl ketones)

  • Typically stable at ambient conditions for extended periods. Protect from prolonged UV exposure to prevent potential photochemical alterations. Desiccation is recommended if hygroscopic excipients are present in the packaging (not typical for aryl ketones).

• Reconstitution and solution handling

  • Prepare concentrated stocks in DCM, acetonitrile, methanol, ethanol, THF, or DMSO as appropriate. For long‑term solution storage, prefer amber vials at 2–8 °C and minimize headspace to reduce oxidative processes; validate stability by HPLC before use.
  • If crystals/oil form upon cooling, gently warm and sonicate to fully dissolve before use; avoid repeated heating–cooling cycles.

• Research use note

  • For research use only. Not for human or veterinary use. Always consult the product CoA and SDS for definitive storage and handling instructions.

Structure & Identity

A para‑methoxy, para‑methyl diaryl–propiophenone scaffold useful as an aryl‑ketone building block.

• Item-specific identifiers (from Product Data)

  • SKU: M970640
  • Product name: 4'-Methoxy-3-(4-methylphenyl)propiophenone
  • CAS: 106511-65-3
  • CID: 12263036
  • InChIKey: 278267 (as provided; format appears truncated)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general, literature-based description)

  • Core functionality: aryl aliphatic ketone (propiophenone) with an ethyl side chain at the carbonyl (–CO–CH2–CH3).
  • Aromatic substitution pattern implied by name: one ring bearing a 4′‑methoxy (–OCH3) substituent; the other ring described as a 4‑methylphenyl fragment appended at the 3‑position of the propiophenone framework, yielding a diaryl‑substituted ketone.
  • Functional groups: conjugated carbonyl (ketone), anisole ether (Ar–OCH3), and p‑tolyl (Ar–CH3); no heteroatoms beyond the single methoxy oxygen and the carbonyl oxygen.
  • Stereochemistry: none expected at the carbonyl carbon; the molecule is achiral in the absence of restricted rotation.

• 2D structure in words (literature-style depiction)

  • A benzoyl fragment (Ar–CO–) is extended by an ethyl unit (–CH2–CH3). The benzoyl ring carries a para‑methoxy substituent. The “3‑(4‑methylphenyl)” descriptor denotes a second aryl ring (p‑tolyl) attached to the propiophenone backbone, yielding a diaryl ketone with electron‑donating groups (–OCH3, –CH3) on each ring.

Note: Exact atom connectivity should be verified against the CoA/structure file due to limited item-specific identifiers provided.

Synthetic Utility

This diaryl‑substituted propiophenone is a flexible platform for diversification on three vectors: the carbonyl center/α‑position, the anisole ether, and the p‑tolyl ring.

• Carbonyl/α‑position

  • Enolate generation with LDA/NaHMDS enables α‑alkylation, aldol couplings, and Michael additions. Auxiliary formation (e.g., Evans oxazolidinones via acyl transfer from the ketone equivalents) can be considered via oxidative strategies.
  • Reductive routes to secondary alcohols enable further functional group interconversions (e.g., Mitsunobu inversion, carbonate/ester formation, or oxidation to rearranged frameworks).

• Anisole handle

  • Demethylation (BBr3) to phenol allows etherification (Williamson), carbonate/carbamate installation, or late‑stage sulfamates and phosphates.
  • Directed ortho‑metalation strategies adjacent to the anisole can introduce halogens or carbon substituents, guided by the methoxy director.

• p‑Tolyl ring

  • Benzylic bromination (NBS/AIBN) introduces a handle for substitution or cross‑coupling (via conversion to boronate/halide). Electrophilic substitution is facilitated by the methyl donor.

• Strategic value

  • The combination of electron donors on both rings stabilizes cationic and radical intermediates, broadening scope for photoredox, EAS, and oxidative couplings.
  • Strong UV chromophore simplifies reaction monitoring (TLC/HPLC) and quantitative assay development.

Target Specificity

Not applicable. This product is a small‑molecule aryl ketone and does not have antibody/biologic target specificity. No antigen, epitope, or isotype information applies.

Frequently Asked Questions

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 106511-65-3, the molecular formula is C17H18O2, and the molecular weight is 254.329 g/mol. InChIKey PILCQTXJJGELQA-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.