This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
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
299.160 g/mol
XLogP3
2.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
7
Exact Mass
298.02 Da
Monoisotopic Mass
298.02 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
265.000
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
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Recensioni
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Application Protocols
Not applicable. No bioassay or immunoassay protocols pertain to this small-molecule building block. For synthetic transformations, see the Reaction Conditions and Reaction & Applications sections for practical guidance.
Biological Roles
This product is a synthetic organic building block and is not a biomolecule. It has no intrinsic biological role specified for this item.
General context (for chemists planning bio-oriented synthesis):
The scaffold contains an aryl ketone and an ethyl ester, motifs that are frequently transformed en route to bioactive small molecules (e.g., amides, alcohols, alkenes). However, any biological activity would derive from the final designed molecules, not this intermediate.
The aryl bromide is a strategic handle for late-stage diversification via cross-coupling, enabling rapid generation of analog libraries for structure–activity relationship (SAR) studies.
No claims are made regarding biological activity, pharmacology, or clinical applicability of this item. For all laboratory uses involving biological systems, ensure appropriate controls and assess cytotoxicity or off-target effects of your final compounds independently.
Buffer Applications
Not typically applicable. Ethyl 5-(3-bromophenyl)-5-oxovalerate is a neutral, hydrophobic organic building block and is not used to prepare aqueous buffer systems. If your workflow involves biochemistry, focus on the Synthetic Utility and Reaction & Applications sections for guidance on transforming this compound into target molecules before introducing them into buffered media.
Green Alternatives
Sustainable choices often center on solvent and reagent selection; the substrate itself is a specialty building block. Consider the following greener options during synthesis, workup, and purification (general guidance):
Preferred solvents for routine operations:
Replace DCM/CHCl3 with EtOAc or 2-MeTHF where feasible (comparable solubility, reduced toxicity, and improved environmental metrics).
Use ethanol or isopropanol for recrystallization or as co-solvents when compatible.
Coupling chemistry:
Employ aqueous micellar catalysis (e.g., nonionic surfactant systems) for Suzuki couplings to minimize organic solvent use (literature reports show high efficiency for aryl bromides).
Choose ligand/catalyst systems effective at ppm Pd loadings to reduce precious metal consumption.
Bases and additives:
Favor inorganic carbonates/phosphates over strong alkoxides when compatible, reducing hazards and waste.
Workup and purification:
Opt for heptane/EtOAc gradients in flash chromatography over hexanes/DCM.
Consider crystallization-induced purification if solid derivatives are accessible, minimizing silica usage.
Illustrative comparison (general):
DCM vs EtOAc: EtOAc offers lower chronic toxicity, biodegradability, and easier waste handling, while maintaining good solvency for aryl ketone/ester substrates.
THF vs 2-MeTHF: 2-MeTHF derives from renewable resources, exhibits reduced peroxide formation tendency relative to THF, and simplifies phase separations; boiling point is higher, which can aid or hinder removal depending on process.
Assess green metrics (E-factor, PMI) at the route level; the orthogonal reactivity of this substrate can reduce step count by enabling convergent couplings.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. This material is supplied strictly for research and laboratory synthesis.
General formulation context (non-clinical):
As a synthetic intermediate, it may be used in discovery chemistry to access amides, alcohols, alkenes, or coupled aryl derivatives which, after further optimization and full qualification, could be evaluated in preclinical studies. The compound itself is not intended for administration.
If material from this intermediate must be handled in formulation laboratories (e.g., for in vitro assays), dissolve in appropriate organic co-solvents (DMSO, ethanol) before dilution, recognizing its limited aqueous solubility.
No therapeutic or clinical uses are claimed or implied. Refer to your institution’s regulations for handling research compounds and ensure all downstream candidates meet the necessary purity and documentation standards before any regulated studies.
Physical Properties
Item-specific physical specifications are not provided in the Product Data for SKU E947611. Do not treat the following as product specifications; they are literature/computed reference values for this structure and should be verified experimentally.
State/appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not broadly tabulated for this exact structure; analogous aryl-benzoyl butanoate esters are typically high-boiling oils (literature, >300 °C at ambient pressure) and are commonly purified by column chromatography rather than distillation.
Melting point: Not specified; many close analogs are liquids or low-melting solids (literature).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Water: very low solubility (hydrophobic aryl core and neutral carbonyls)
Organic: soluble in chlorinated solvents (DCM, CHCl3), aromatic hydrocarbons (toluene), ethers (THF, MTBE), and esters (EtOAc)
Partitioning (qualitative, literature): high logP expected due to aryl bromide and neutral carbonyls.
UV absorption (qualitative, literature): aromatic ketone chromophore absorbs in near-UV; useful for TLC visualization under 254 nm.
For method development (e.g., HPLC), determine exact retention and UV response empirically under your conditions.
Quality and Grades
Grade/Purity: Not specified in the Product Data for SKU E947611; refer to the CoA/Spec Sheet for actual assay, impurity profile, and any stabilizers.
Interpretation guidance (general):
If provided as “research grade,” the material is intended for laboratory R&D only and may not conform to pharmacopeial monographs. Typical quality controls may include NMR identity, LC/HPLC purity, and water content by Karl Fischer.
If a specific purity (e.g., ≥98%) is listed on your lot’s CoA, this commonly reflects area% by HPLC or GC unless otherwise noted. Confirm the method when purity is critical (e.g., quantitative synthesis or analytical calibration).
UV cutoffs, metal content, residual solvents, and stabilizers are item-specific. In the absence of provided values, assume none are certified and verify analytically if these parameters affect your application (e.g., cross-coupling sensitivity to residual sulfur or water).
What to check on receipt (best practice):
Inspect physical form and color; verify against CoA.
Acquire a quick 1H NMR to confirm identity (diagnostic signals: ethyl ester quartet/triplet, benzylic CH2 next to the benzoyl carbonyl, aliphatic CH2 next to the ester carbonyl, aromatic multiplets; a distinct aryl ketone 13C resonance ~195–200 ppm, literature).
Confirm water content and residual solvents if moisture-sensitive downstream chemistry is planned.
Reaction and Applications
Ethyl 5-(3-bromophenyl)-5-oxovalerate is a versatile, bifunctional synthon. Its aryl bromide, aryl ketone, and ethyl ester enable orthogonal diversification.
Cross-coupling (aryl Br):
Suzuki–Miyaura: installation of aryl, heteroaryl, or vinyl partners under Pd(0/II) catalysis. Typical bases: K2CO3, K3PO4, Cs2CO3; solvents: dioxane/H2O, toluene/H2O, or MeOH/H2O.
Sonogashira: coupling with terminal alkynes (Pd/Cu co-catalysis) followed by downstream cyclizations or hydrofunctionalizations.
Buchwald–Hartwig amination: formation of anilines that remain tethered to the benzoyl–butanoate fragment.
Carbonyl chemistry (benzoyl ketone):
Reductions to secondary benzylic alcohols (NaBH4, CBS, or catalytic hydrogenation); subsequent ester manipulations enable bifunctional scaffolds.
Formation of oximes/hydrazones (NH2OH, hydrazines) as handles for Beckmann or Wolff–Kishner strategies (literature).
Olefination (Wittig/HWE) at the aryl ketone to access aryl enones or styrenyl derivatives tethered to the ester.
Ester transformations:
Saponification to the corresponding acid for amide coupling (EDC/HATU/T3P) or intramolecular cyclization strategies.
Transesterification to tune leaving group properties or introduce isotopic labels.
Orthogonal elaboration:
Sequence coupling first, then reduce/functionalize the ketone; or vice versa, leveraging the robustness of the ethyl ester.
Late-stage functionalization on the ring post-coupling (electrophilic substitutions directed by installed groups).
Applications (general in synthesis): fragments for preparing arylated aliphatic scaffolds, precursors to benzocycloalkanones via ring-forming strategies, and modular handles in medicinal chemistry SAR campaigns. Always optimize order of operations to preserve sensitive motifs.
Reaction Conditions
The following are general, literature-informed conditions for the functional groups present; they are not product specifications. Optimize for your substrate and scale.
Solvent: 1,4-dioxane/H2O (4:1) or toluene/H2O, 80–100 °C, 2–8 h.
Typical isolated yields for aryl–aryl couplings: 70–95% (literature ranges).
Buchwald–Hartwig amination:
Pd2(dba)3 (1 mol%) + BrettPhos/XPhos (2–3 mol%), NaOtBu or K3PO4, toluene or tBuOH, 80–110 °C.
Sonogashira coupling:
Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), Et3N or iPr2NH, THF or DMF, rt–60 °C.
Selective ketone reduction (ester tolerant):
NaBH4 (1.2–2.0 equiv) in MeOH/EtOH, 0–25 °C, 0.5–2 h → secondary benzylic alcohol; ester remains intact (literature selectivity).
Alternatively, catalytic hydrogenation (Pd/C, 1–3 bar H2) reduces the ketone; monitor to avoid ring hydrogenation if sensitive substituents are present.
Oxime formation:
NH2OH·HCl (1.5–2.0 equiv), pyridine or NaOAc, EtOH or MeOH, reflux 2–6 h.
Ester hydrolysis (saponification):
NaOH or KOH (1–3 equiv) in MeOH/H2O or THF/H2O, rt–50 °C, 1–6 h → corresponding acid; acidify and extract.
Chromatography: Start with hexanes/EtOAc 7:3 to 5:5; adjust based on TLC (UV 254 nm active due to aryl ketone).
Safety and Handling
Item-specific GHS hazard classification and statements are not provided in the Product Data. Always consult the SDS for SKU E947611 for authoritative safety guidance.
General laboratory safety considerations for aryl bromide-containing aryl–aliphatic carbonyls (literature/practice):
Likely hazards: may cause skin/eye irritation and respiratory tract irritation. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
PPE: lab coat, nitrile gloves, splash goggles; handle in a fume hood. Use secondary containment to prevent spills.
First aid (general):
Skin: wash with soap and water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
Inhalation: move to fresh air; seek medical attention if symptoms develop.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities (general): strong oxidizing agents; strong bases and strong acids can promote hydrolysis or undesired side reactions. Avoid prolonged contact with reactive metals during Pd-catalyzed workups.
Thermal stability: aromatic ketones/esters are generally thermally stable; avoid overheating and open flames. Use heat-resistant gloves if warming for dissolution.
Waste: collect organic residues/solvents in halogenated or non-halogenated waste streams as appropriate per your site EHS rules.
Signal word, H-statements, pictograms, and exact GHS classification: Not specified for this item; refer to SDS/CoA.
Solvent Selection
This compound is a moderately lipophilic aryl–aliphatic carbonyl ester. Solvent choices are driven by solubility, reactivity, and downstream processing.
Polarity/miscibility (general):
Highly soluble in DCM, CHCl3, EtOAc, THF, toluene, and MeCN; sparingly soluble in hexanes depending on temperature.
Practically insoluble in water.
Typical use scenarios:
Synthesis and transformations: DCM or THF for carbonyl chemistry (acylations, reductions, oxime formation); toluene or dioxane for Pd cross-couplings on the aryl bromide; MeCN or DMF for base-mediated steps (e.g., saponification of the ester or nucleophilic substitutions on coupled derivatives).
Purification: flash chromatography with hexanes/EtOAc gradients exploits the moderate polarity from the diketone/ester motif.
Small comparison (general guidance):
DCM vs EtOAc: DCM offers faster chromatography and higher solubility; EtOAc is greener and suitable when chlorinated solvents are restricted.
THF vs 2-MeTHF: both dissolve well; 2-MeTHF provides better separations from aqueous layers and improved sustainability.
DMF/DMSO: powerful solvents for coupling chemistry but challenging to remove; reserve for steps requiring high polarity.
Drying/handling tips:
For base- or moisture-sensitive steps, dry solvents (molecular sieves or solvent purification systems). Although the substrate is not especially moisture sensitive, water promotes ester hydrolysis under basic/acidic conditions.
Storage and Reconstitution
Storage (from Product Data): Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Good laboratory practice (general):
Keep the container tightly closed under an inert gas blanket (nitrogen or argon) if storing for extended periods, to minimize oxidative degradation and moisture ingress (which can promote ester hydrolysis under adventitious acidic/basic conditions).
Store away from strong acids/bases and oxidizers. Protect from prolonged light and heat.
If the material is an oil, consider aliquoting to minimize headspace and repeated exposure during use.
Reconstitution/solubility:
Readily dissolves in common organic solvents (DCM, THF, EtOAc, toluene, MeCN). For analytical stock solutions, DMSO or MeCN at 10–100 mM are typical; filter through PTFE (0.2 µm) if particulate is observed.
Aqueous reconstitution is not recommended due to low water solubility; use water-miscible cosolvents (MeCN, ethanol) if aqueous dilutions are required for method development.
Shelf-life and specifications such as water content, peroxide content, or inhibitor levels: Not specified for this item; refer to the lot-specific CoA/Spec Sheet. Research use only.
Structure and Identity
Ethyl 5-(3-bromophenyl)-5-oxovalerate (also describable as ethyl 4-(3-bromobenzoyl)butanoate) is a bifunctional aryl–aliphatic carbonyl building block bearing an aryl bromide, an aryl ketone, and an ethyl ester in a single molecule.
Item-specific identifiers from Product Data:
SKU: E947611
CAS: 898792-69-3
InChIKey: 85684 (as provided)
Storage condition: Room temperature
Computed/literature structural information (for reference; not item-specific specifications):
Representative formula (literature/computed): C12H13BrO3
Connectivity description (2D): a 3-bromophenyl ring attached via a benzoyl carbonyl to a three-carbon aliphatic spacer terminating in an ethyl ester (Ar–C(=O)–CH2–CH2–C(=O)OEt). No stereocenters.
Structural features relevant to reactivity (general chemistry):
The aryl bromide enables Pd-catalyzed cross-couplings (e.g., Suzuki, Heck, Sonogashira).
The benzylic ketone supports classic carbonyl transformations (reduction, oxime/hydrazone formation, Wittig/olefination on the ketone).
The terminal ethyl ester enables hydrolysis, amidation, and ester exchange.
Note: Where exact identifiers (full InChI, verified formula, precise MW) are needed for regulatory or analytical purposes, consult the CoA/Spec Sheet for this specific lot.
Synthetic Utility
This substrate combines three orthogonal handles, enabling diverse retrosynthetic disconnections and convergent assembly:
Aryl bromide (meta-bromophenyl):
Disconnection to boronic acids/esters (Suzuki), stannanes (Stille), alkynes (Sonogashira), or amines (Buchwald–Hartwig). This handle allows late-stage diversification without perturbing the aliphatic carbonyl chain.
Aryl ketone (benzoyl):
Carbonyl umpolung via hydrazone anions; Wittig/HWE olefinations to install alkenes; NaBH4/CBS reductions to secondary alcohols amenable to further activation (e.g., Mitsunobu or sulfonate formation).
Formation of enones (via selective oxidation of the secondary alcohol) creating Michael acceptors tethered to the ester.
Ethyl ester terminus:
Hydrolysis → carboxylic acid for amide coupling or intramolecular cyclizations.
Alcoholysis/transesterification to introduce chiral or functionalized alcohols.
Activation as acid chloride (after hydrolysis) for Friedel–Crafts acylation to build polycyclic frameworks.
Strategic notes:
Order of operations: perform Pd-catalyzed coupling first if strongly basic nucleophiles are planned later; alternatively, reduce/functionalize the ketone before base-sensitive couplings if β-hydride elimination from coupled partners is a concern.
Chemoselectivity: the benzylic ketone is generally more reactive than the ester toward nucleophilic additions and reductions; conditions can be tuned (e.g., NaBH4 in MeOH reduces the ketone selectively, leaving the ester intact, literature).
Protecting-group economy: the neutral, non-chelating ester often survives many coupling and electrophilic substitution conditions.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope or isotype information applies.
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