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
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
238.320 g/mol
XLogP3
4.200
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
4
Exact Mass
238.136 Da
Monoisotopic Mass
238.136 Da
Topological Polar Surface Area
17.100 Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
255.000
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
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No validated bioassay protocols are provided for this item. As a small-molecule reagent, typical protocols are synthetic or analytical in nature.
General lab protocols (contextual, not product-specific):
Analytical characterization: Record 1H/13C NMR, IR (identify C=O), HRMS/LC–MS, and HPLC purity. Calibrate UV detection around 254 nm for chromatography.
Stock solution preparation: Dissolve in a suitable dry organic solvent (e.g., DMSO, acetonitrile, THF) to a convenient concentration (e.g., 10–100 mM), filter through 0.2 µm PTFE if needed, and store in sealed vials protected from light.
Reaction setup: For moisture-sensitive steps (e.g., organometallic additions), oven-dry glassware, use inert gas (N2/Ar), and titrate reagents.
For any application-specific instructions, consult the primary literature and adapt based on scale, equipment, and regulatory requirements. This product is for research use only.
Biological Roles
This compound is a synthetic aryl–alkyl ketone used primarily as a chemical intermediate. It does not have a recognized intrinsic biological role like metabolites, cofactors, or signaling molecules.
General considerations for aryl ketones (literature context; not product-specific):
Interaction motifs: Aromatic ketones can engage in hydrophobic and π–π interactions with biomolecules; the carbonyl provides a hydrogen-bond acceptor site.
Photobiology: Some aryl ketones are photosensitizers capable of triplet-state formation, which can generate reactive oxygen species under UV. Any such effects are highly structure- and condition-dependent.
ADME surrogacy: Propiophenone-like scaffolds are often used in medicinal chemistry as lipophilic fragments to tune permeability and metabolic stability in small-molecule libraries; however, this product is supplied strictly for research use and not for administration.
No clinical or therapeutic claims are made. Use is limited to laboratory research.
Buffer Applications
Not typically applicable. 3-(3,5-Dimethylphenyl)propiophenone is a hydrophobic organic ketone and is not used as a buffering agent or pH stabilizer in aqueous systems.
Practical note:
If aqueous handling is required (e.g., bioconjugation studies or photophysical measurements), employ water-miscible cosolvents such as acetonitrile, ethanol, or DMSO to prepare stock solutions, then dilute into the desired buffer while monitoring for precipitation. Validate that the organic content is compatible with your biological assay.
Green Alternatives
Opportunities to improve sustainability when working with aryl ketones (general guidance):
Solvent choices:
Prefer greener solvents when feasible (e.g., ethyl acetate, 2-MeTHF, CPME, propylene carbonate, Me-THF/water biphasic) over chlorinated solvents.
For reductions, aqueous ethanol or 2-propanol with transfer hydrogenation catalysts can replace metal hydrides.
Oxidation strategies:
Baeyer–Villiger oxidations: H2O2 with organocatalysts or biocatalysts (Baeyer–Villiger monooxygenases) can reduce waste vs peracids like mCPBA.
Photoredox catalysis under visible light can enable milder alpha-functionalizations.
Energy efficiency:
Conduct reactions at ambient temperature/pressure where possible; use continuous flow for enhanced heat/mass transfer and safer handling of oxidants/reductants.
Workup and purification:
Minimize solvent use with telescoped steps; employ crystallization-induced purifications when the product is a solid.
Illustrative comparison (general, not product-specific):
DCM vs Ethyl acetate: EtOAc offers lower toxicity and better environmental profile; often equivalent performance for extractions and some oxidations.
THF vs 2-MeTHF: 2-MeTHF is bio-based, forms fewer peroxides, and enables easier phase separation with water; drying demands are similar for organometallics.
Note: Select alternatives consistent with reaction compatibility and target specifications; verify on small scale.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; refer to CoA/Spec Sheet if applicable. This material is supplied for research use only and is not intended for human or veterinary use.
General context (non-clinical, formulation/manufacturing perspective):
Aryl–alkyl ketones such as substituted propiophenones are commonly encountered as synthetic intermediates during API route development, enabling downstream transformations (reductions to alcohols, oxidations, rearrangements) to access diverse scaffolds.
Process considerations: Choice of crystallization solvent system and control of polymorphism (if solid) may be relevant for impurity rejection during intermediate isolations. Residual solvent and impurity specifications should be defined per ICH Q3A/Q3C for any GMP-related development; this listing does not claim GMP compliance unless explicitly stated on the CoA.
No therapeutic claims are made, and no finished-dosage formulation guidance is implied.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for aryl–alkyl ketones of this class (for context only, not product specs):
State: Typically low-melting solids or high-boiling oils due to dual aryl substitution and a single carbonyl.
Solubility: Generally sparingly soluble in water; freely soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, toluene, THF, acetonitrile, alcohols). Increased aromatic content and two methyl groups raise hydrophobicity relative to unsubstituted propiophenone.
Volatility: Lower volatility compared with acetophenone/propiophenone; suitable for column chromatography under normal lab conditions.
UV–vis: Conjugated aryl ketones typically show strong π→π* absorption in the near-UV (~240–280 nm) and weaker n→π* transitions at longer wavelengths; exact maxima are structure-dependent (literature trends).
NMR: Diagnostic carbonyl at ~δC 195–200 ppm (13C); benzylic methylene of the ethyl group typically at ~δH 2.9–3.1 ppm (1H NMR) and ~δC 30–40 ppm; aromatic methyls at ~δH 2.2–2.4 ppm.
IR: Strong C=O stretch for aryl ketones typically ~1680–1710 cm⁻¹; aromatic C–H stretches ~3030 cm⁻¹; methyl C–H ~2950–2850 cm⁻¹.
Note: For any numerical values (bp, mp, density, refractive index, logP/pKa), consult the CoA/SDS and primary references; they are not specified here.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general information for context):
Research or laboratory grade materials are typically suitable for synthesis, method development, and analytical standards after appropriate verification. Absence of a specified HPLC/GC assay, water content, or trace metal limits means users should verify suitability for sensitive applications (e.g., photophysical studies, catalysis, or trace analysis) by in-house QC.
If provided on the CoA, an assay by GC/HPLC can indicate bulk purity; NMR assessment (1H/13C) often clarifies organic impurities (e.g., residual solvents, regioisomers). For aryl ketones, peroxides are generally not a concern (unlike ethers), but oxidized or reduced analogs (e.g., benzhydrols, alcohols) can appear as impurities.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Most aryl ketones do not require stabilizers; if present, it should be disclosed.
Recommendations:
For photochemical or analytical applications, confirm UV cutoff/absorbance baseline and impurity profile with your instrument.
For air/moisture-sensitive downstream chemistry (e.g., organometallic additions), consider pre-drying over molecular sieves and confirming absence of protic contaminants by Karl Fischer or NMR, as applicable.
Reaction and Applications
Use profile (general for aryl–alkyl ketones; expand as relevant to this scaffold):
Carbonyl transformations:
Nucleophilic additions to the ketone (Grignard, organolithium, organozinc) to afford tertiary alcohols bearing a biaryl framework; control temperature (−78 to 0 °C common) to limit side reactions.
Reductions to the corresponding secondary alcohol (NaBH4, catalytic hydrogenation with Raney Ni, Pd/C) or complete deoxygenation (e.g., Wolff–Kishner, Clemmensen) to yield biaryl ethylbenzenes.
Oxime/hydrazone formation enabling subsequent Beckmann or Wolff–Kishner-type transformations.
Oxidation chemistry:
Baeyer–Villiger oxidation to aryl esters; selectivity can be influenced by the migratory aptitude of aryl vs alkyl groups—aryl migration is often favored, potentially giving biaryl benzoates.
Alpha-functionalization:
Enolization/enolate trapping (LDA, NaHMDS) to introduce alpha-heteroatom or carbon substituents; halogenation (NBS/NCS), aldol condensations, or Claisen-type couplings.
Cross-coupling pathways:
If the biaryl substitution is orthogonally functionalized, subsequent C–C bond formations (Suzuki, Negishi) may be leveraged; the current substance serves as a protected carbonyl-bearing handle.
Photochemistry:
Aryl ketones can act as triplet sensitizers or participate in Norrish/Yang reactions under UV; steric and substitution patterns dictate feasibility.
Applications:
Intermediate for advanced biaryl scaffolds in materials, ligands, and discovery chemistry.
Model substrate for studying migratory aptitude and selectivity in Baeyer–Villiger or radical hydrogen atom transfer processes.
Manufacturer Applications: Not specified beyond research use; the above reflects typical literature uses for this structural class.
Reaction Conditions
General, literature-based guidance for typical transformations of aryl–alkyl ketones (not product specifications):
Grignard/organolithium additions:
Solvent: Dry THF or diethyl ether; rigorously anhydrous, inert atmosphere.
Temperature: −78 to 0 °C for selectivity; quench at 0–25 °C.
Workup: Saturated NH4Cl or aqueous acid to decompose adducts; monitor by TLC/HPLC.
NaBH4 reduction to secondary alcohol:
Solvent: MeOH, EtOH, or THF/alcohol mixtures.
Temperature/time: 0–25 °C, 0.5–2 h typical; monitor disappearance of carbonyl IR band.
Catalytic hydrogenation (C=O to alcohol or deoxygenation with modifiers):
Catalyst: Pd/C, Pt/C, or Raney Ni; solvent iPrOH/EtOH/EtOAc.
Conditions: 1–5 bar H2, 20–50 °C; watch for unwanted aromatic hydrogenation (rare at mild conditions).
Baeyer–Villiger oxidation:
Oxidants: mCPBA in DCM or H2O2 with catalysts (Sn-beta, polyoxometalates, organocatalysts) in MeCN/EtOAc.
Temperature: 0–25 °C; control exotherm; buffering may be required to limit acid-promoted side reactions.
Alpha-halogenation/functionalization:
Base: LDA/NaHMDS in THF at −78 to −20 °C; electrophiles added slowly.
Expected yields are substrate- and method-dependent; consult primary literature for specific procedures on biaryl propiophenone analogs before scale-up.
Safety and Handling
Item-specific hazard classification: Not specified for this item; refer to SDS for authoritative information. Signal word, H-statements, GHS class, and pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl ketones (literature/practice; not product-specific):
Likely hazards: Many aromatic ketones are combustible liquids/solids and may cause skin/eye irritation. Avoid inhalation of vapors and dust. Use in a fume hood.
PPE: Safety glasses or goggles, lab coat, appropriate chemically resistant gloves (e.g., nitrile), and closed-toe shoes. Consider splash protection for scaling.
Storage incompatibilities: Separate from strong oxidizers, strong bases (which may promote aldol/self-condensation under forcing conditions), and strong reducing agents (which may reduce the carbonyl). Keep away from ignition sources.
Handling: Minimize exposure; use local exhaust ventilation. Prevent release to the environment.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; seek medical attention if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
Firefighting: Use dry chemical, CO2, or alcohol-resistant foam. Combustion may yield CO/CO2 and irritant smoke. Firefighters should wear self-contained breathing apparatus.
Research Use Note: For research use only.
Solvent Selection
Applicability: This product is itself an organic compound (aryl–alkyl ketone), not a general laboratory solvent. However, its handling and reactions benefit from judicious solvent choice.
General solvent compatibility and selection (literature/practice):
Polarity class: Moderately polar aprotic solute; dissolves well in mid-polarity organic solvents (e.g., dichloromethane, THF, ethyl acetate, toluene, acetonitrile) and in alcohols. Poorly soluble in water.
Chromatography: Normal-phase silica gel with hexanes/ethyl acetate or toluene/ethyl acetate systems commonly provide good separations. Aromatic content often leads to strong UV detection at ~254 nm.
Reaction media:
Nucleophilic additions (e.g., Grignard, organolithium): Dry ethereal solvents (THF, Et2O) or toluene with cosolvent; rigorously anhydrous conditions are recommended.
Baeyer–Villiger oxidations: DCM, chloroform, or acetonitrile often used; greener solvents such as ethyl acetate or MeCN/water biphasic systems are alternatives with peracids or H2O2 catalysts.
Photochemistry: Acetonitrile or acetonitrile/water mixtures for triplet-sensitized processes; ensure oxygen control as needed.
Crystallization: If solid, typical systems include hexanes/toluene or hexanes/ethyl acetate; exact choice is structure- and impurity-dependent.
Note: Always verify solubility and chemical stability in the chosen medium on small scale before process application.
Storage and Reconstitution
Item-specific storage: Room temperature (as provided). Keep container tightly closed in a dry, well-ventilated place. Protect from strong light and heat sources. Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for aryl ketones (not product-specific):
Moisture/air: Typically stable under ambient atmosphere. Avoid prolonged exposure to strong light if photoreactivity is a concern; use amber glass for long-term storage.
Stability: Aryl ketones are generally robust; avoid contact with strong oxidizers/reductants during storage.
Reconstitution/preparation of solutions:
Choose a compatible solvent (e.g., acetonitrile, DMSO, THF, toluene, ethyl acetate). Ensure solvent quality (water and impurities) meets your application needs.
For stock solutions, purge headspace with inert gas if long-term storage is planned, cap tightly, and store at recommended temperature. Monitor for precipitation or discoloration over time.
Freeze–thaw: Typically not required for neat solids/liquids. If storing solutions, aliquot to minimize freeze–thaw cycles that can concentrate impurities or promote degradation.
Always refer to the product’s CoA and SDS for definitive storage, stability, and compatibility information.
Structure and Identity
Brief description: 3-(3,5-Dimethylphenyl)propiophenone is an aromatic aryl–alkyl ketone structurally related to propiophenone, bearing an additional 3,5-dimethylphenyl substituent.
Item-specific (Product Data):
SKU: D942841
Product Name: 3-(3,5-Dimethylphenyl)propiophenone
CAS: 854692-50-5
PubChem CID: 24726482
InChIKey: 145354 (as provided)
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.
Structural features (interpretation of chemical name; literature description, not a product specification):
Core motif: a propiophenone scaffold (benzoyl–ethyl, Ph–CO–CH2–CH3) with an additional aryl substituent at the 3-position of the benzoyl ring.
Substituent: a 3,5-dimethylphenyl ring (meta,meta-dimethyl), introducing increased hydrophobicity and steric bulk.
2D description: Two benzene rings connected through the ketone-bearing benzoyl ring (biaryl arrangement), with methyl groups at the 3 and 5 positions on the distal ring; carbonyl lies between the benzoyl ring and the ethyl side chain.
Stereochemistry: None (achiral as named).
Synthetic Utility
Functional group leverage:
Carbonyl chemistry: The ketone enables a broad menu of nucleophilic additions (RMgX, RLi, R2Zn), selective reductions (NaBH4 vs catalytic hydrogenation), and rearrangements (Baeyer–Villiger) to diversify the biaryl scaffold.
Alpha-functionalization: Enolate formation under strong base permits C–C bond construction (aldol, Mannich, Michael via enamine strategies) and C–X installation (alpha-halogenation). Subsequent substitutions enable further diversification.
Protecting-group–like behavior: The carbonyl can serve as a temporary handle for directing metalation on adjacent aromatic rings (e.g., ortho metalation when auxiliary groups are present), followed by carbonyl removal (Wolff–Kishner/Clemmensen) if desired.
Retrosynthetic value:
Readily accessible via Friedel–Crafts acylation of an appropriately substituted biaryl or through cross-coupling to assemble the biaryl followed by acylation/oxidation sequences.
Orthogonal diversification points: The alpha position (to the carbonyl) and both aromatic rings can be independently functionalized if leaving groups or directing groups are installed.
Purification/analytics:
Strong UV chromophore simplifies HPLC/UPLC monitoring; MS readily shows [M+H]+ and characteristic fragment for aryl ketones (loss of C2H4 or cleavage adjacent to carbonyl).
Impurities typically include over-reduced alcohols, starting aryl precursors, and acylation byproducts; tune chromatography solvent polarity and gradient to resolve closely eluting biaryls.
Target Specificity
Not applicable. This product is a small-molecule aryl ketone and is not an antibody, probe, or biologic. No antigen, epitope, clone, isotype, or species reactivity information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
