This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
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.
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Application Protocols
Not applicable. No validated bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance on handling and transformations.
Biological Roles
This compound is a synthetic, non-natural, substituted benzophenone intended for laboratory research and synthesis. It is not a biological buffer, enzyme substrate, or biomolecule.
General notes (literature-based; not item-specific)
Benzophenone chromophores can act as photo-crosslinkers in chemical biology when suitably positioned, exploiting triplet-state hydrogen abstraction; however, this requires specific probe designs and is beyond routine use of this item as a building block.
No known endogenous metabolic role or pathway participation is associated with 3-carboethoxy-2′-methoxybenzophenone.
For biological testing or probe development, users typically derivatize the scaffold (e.g., installing linkers, reactive handles). Any biological experiments should be designed and interpreted within research-only frameworks and appropriate institutional approvals.
Buffer Applications
Not typically applicable. 3-Carboethoxy-2′-methoxybenzophenone is a neutral, hydrophobic organic small molecule and is not used to prepare aqueous biological buffers or pH standards. For work involving this compound, focus on organic solvent selection, photostability, and purification strategies as outlined in the Solvent Selection and Reaction & Applications sections.
Green Alternatives
While this product is a solid building block rather than a solvent, greener choices can be applied to its handling and the reactions it undergoes.
Greener solvent choices for typical operations (general guidance)
Dissolution/workup: prefer ethyl acetate or 2‑MeTHF over dichloromethane or chloroform when solubility allows; replace hexanes with cyclopentyl methyl ether (CPME) or heptane isomers.
Reductions: use catalytic hydrogenation (H2, Pd/C) in ethanol or isopropanol where compatible, instead of stoichiometric metal hydrides.
Amidations/esterifications: employ carbodiimide or uronium couplings in green solvents (MeCN, EtOAc, 2‑MeTHF) and consider catalytic coupling strategies to reduce waste.
Photochemistry considerations
If using the benzophenone chromophore for triplet sensitization, operate in ethanol, acetonitrile, or water–miscible greener co-solvents when feasible, and adopt LED sources to reduce energy consumption and heat load.
Comparison snapshot (general; not item-specific)
DCM vs EtOAc: EtOAc has lower toxicity and environmental persistence; DCM often provides higher solubility and faster kinetics.
THF vs 2‑MeTHF: 2‑MeTHF is bio-based, less peroxide-prone, and often allows easier phase separations; THF remains more polar and sometimes affords better reactivity/solubility.
Waste minimization
Plan telescoped sequences (e.g., saponification → coupling without full isolation) to reduce solvent use and chromatography. Recycle mother liquors where crystallization-based purifications are viable.
Pharmaceutical Uses
Compendial/excipient status: None specified for this item; it is supplied for research use only.
Context in development chemistry (general)
Substituted benzophenones may serve as intermediates in discovery chemistry for small-molecule leads or UV-absorbing materials. When used in pre-formulation research, they are typically handled as synthetic intermediates, not as excipients or APIs.
The presence of an aryl ketone and an ester offers handles for late-stage diversification (e.g., conversion of the ester to acids/amides, or ketone to alcohols), aiding SAR exploration.
Regulatory note
No pharmacopoeial monograph is indicated. Any use in drug development requires internal qualification of identity, purity, residual solvents, and solid-state form according to project-specific and regulatory guidelines.
Reminder
Research Use Only. No medical, diagnostic, or therapeutic use is intended or implied.
Physical Properties
Item-specific properties from Product Data
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage Conditions: Room temperature (per Product Data)
Shipping: Shipped under normal conditions (per Product Data)
Computed/literature values (reference only; not item specifications)
Molecular formula: C17H16O4 (computed from structure-based interpretation of the name)
Molecular weight: ~284.31 g/mol (computed from formula)
Functional group profile: aromatic ketone, aryl ester, aryl ether; moderately polarizable, largely non-ionic across neutral pH.
Expected phase: aromatic benzophenone derivatives are typically crystalline solids at ambient conditions; specific melting/boiling points for this exact structure were not located.
Typical solvent compatibility (general guidance)
Likely solubility: good in moderately polar organic solvents (e.g., dichloromethane, chloroform, THF, acetone, ethyl acetate) and in aromatic hydrocarbons; limited solubility in water. Actual solubility should be verified experimentally.
UV properties: benzophenone chromophore exhibits strong UV absorption (literature); substituents shift λmax. Use UV-protective handling if photochemical stability is a concern.
Not available for this specific item; consult CoA/Spec Sheet
Melting point, boiling point, density, refractive index, logP, pKa, water content, residual metals, stabilizers, and chromatographic purity: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades (general guidance)
Research-grade: suitable for most synthetic and method-development work. Purity typically ≥95% (varies by supplier/specification).
HPLC grade (when applicable to solvents or UV-sensitive analytes): low UV background and particulate; relevant if compound is used as a standard or analytical reference.
≥98–99% purity: beneficial for structure–activity studies or photophysical measurements where trace impurities affect data.
Stabilizers/inhibitors
None specified for this item; refer to CoA/Spec Sheet. Benzophenone derivatives generally do not require polymerization inhibitors, but light protection can be prudent due to photosensitivity.
What to check on the CoA/Spec Sheet for this compound type
Assay/purity method (HPLC, GC, NMR qNMR), residual solvents, identity confirmation (1H/13C NMR, MS), and if relevant, water content (KF) and UV–Vis profile due to the benzophenone chromophore.
Batch-to-batch considerations
Substituted benzophenones may display polymorphism; if crystallinity impacts your process (e.g., filtration, crystallization), confirm melting behavior and XRPD if critical to your application.
Reaction and Applications
As a functionalized benzophenone, 3-carboethoxy-2′-methoxybenzophenone is a versatile intermediate for constructing densely substituted diaryl frameworks and triarylmethanol derivatives.
Transformations at the benzophenone carbonyl (general literature)
Nucleophilic additions: Grignard/organolithium reagents add to the diaryl ketone to form tertiary alcohols (triarylcarbinols after dehydration where applicable). Use dry ethereal solvents (THF/Et2O), 0 to −78 °C, followed by aqueous workup.
Reductions: NaBH4 (mild) often insufficient for diaryl ketones; stronger hydrides (LiAlH4, Red‑Al) or catalytic hydrogenation (Pd/C, H2) reduce to the corresponding benzhydrol. Selectivity must consider the intact ethyl ester.
Photochemistry: benzophenones undergo Norrish Type I/II pathways or triplet-sensitized reactions under UV; substituents modulate triplet energies and reactivity.
Transformations at the ester (general literature)
Hydrolysis to the carboxylic acid (saponification, aq. NaOH/MeOH, rt–reflux), followed by coupling to amides (EDC/HOBt, HATU) or alcohols (Fischer or Steglich esterification) to diversify the ring.
Reduction: DIBAL‑H at low temperature to the aldehyde; LiAlH4 to the benzyl alcohol derivative, leaving the aryl ketone sensitive—conditions should be optimized to avoid over-reduction.
Aryl ether behavior
Methoxy is a para/ortho-directing, electron-donating group facilitating EAS on that ring; however, the ketone deactivates the opposite ring. Demethylation to phenol (BBr3, AlCl3/thiols) opens access to further derivatization (sulfonates, ether libraries).
Use cases (manufacturer text expansion)
Suitable as a building block for photophysical probes, UV-absorbing motifs, or as a masked benzoic acid equivalent in stepwise synthesis of benzophenone-derived ligands and materials. Research use only.
Reaction Conditions
General literature guidance for transformations relevant to 3-carboethoxy-2′-methoxybenzophenone (reference-only; optimize per lab):
Grignard addition to the benzophenone carbonyl
Typical: RMgBr (1.2–2.0 equiv) in dry THF or Et2O, 0 °C → rt, 1–4 h; quench with saturated NH4Cl. Tertiary alcohols form cleanly with aryl/alkyl Grignards. Protect or avoid conditions that transesterify the ethyl ester.
Reduction of the diaryl ketone
Catalytic hydrogenation: H2 (1–5 bar), Pd/C (5–10 wt%), EtOH or EtOAc, rt–50 °C, 2–12 h → benzhydrol. Monitor to avoid over-reduction of the ester (typically stable under mild conditions).
Hydride: LiAlH4 (1–2 equiv) in THF, 0 °C → reflux, 1–3 h; quenched carefully. Risk of ester reduction; DIBAL‑H at −78 to −20 °C can modulate selectivity.
Ester transformations
Saponification: NaOH (2–5 equiv) in MeOH/H2O (4:1), rt–reflux, 2–6 h → carboxylic acid; acidify to precipitate product.
Amidation (via acid): HATU or EDCI (1.1–1.5 equiv), DIPEA (2–3 equiv), DMF/MeCN, 0 °C → rt, 2–16 h.
Reduction: DIBAL‑H (1.5–2.0 equiv), toluene or DCM, −78 °C to −20 °C, 1–3 h → aldehyde; warmer/stronger conditions reduce further to alcohol.
Demethylation of aryl methoxy
BBr3 (1–3 equiv), DCM, −78 °C → 0 °C then rt, 2–6 h → phenol; quench with MeOH/H2O cautiously.
Photochemistry
UV irradiation (e.g., 300–365 nm) in acetonitrile or ethanol, oxygen-free for triplet-sensitized reactions. Use amberware to avoid unintended photolysis during storage/handling.
Yields and exact conditions depend on substrate substitution; conduct pilot trials and analytical monitoring (TLC/HPLC/NMR).
Safety and Handling
GHS classification and hazard statements: Not specified for this item; refer to the SDS for authoritative information.
General hazards (literature-based for benzophenone derivatives; not item-specific)
May cause skin/eye irritation upon contact; avoid inhalation of dust if solid. Aromatic ketones can act as photosensitizers; minimize direct UV exposure to reduce risk of photoinduced reactions.
Combustible organic solid; keep away from ignition sources and strong oxidants.
Recommended PPE and engineering controls
Wear safety glasses, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to prevent inhalation and to control solvent vapors during dissolution.
Incompatibilities (general)
Strong oxidizing agents; strong bases and strong acids may promote transesterification/hydrolysis of the carboethoxy group or cleavage of the methoxy substituent under forcing conditions.
First-aid overview (general guidance; defer to SDS)
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin/eyes: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Special risks/handling notes
Light sensitivity: benzophenone chromophores absorb UV; store in amber container if long-term light exposure is anticipated.
Waste disposal: Collect organic waste according to institutional and local regulations; avoid release to environment.
Solvent Selection
This product is a substituted benzophenone (aromatic ketone with ester and methoxy substituents) and is typically handled as a neutral organic solid.
Polarity and miscibility (general)
Polarity class: moderately polar aromatic compound; non-ionizable under neutral conditions.
Expected solubility: good in chlorinated solvents (DCM, CHCl3), ethyl acetate, acetone, THF, and aromatic hydrocarbons (toluene); limited in aliphatic hexanes; negligible in water. Verify experimentally.
When to choose specific solvents
Purification by chromatography: ethyl acetate/hexanes or DCM/MeOH gradients commonly separate benzophenone derivatives; adjust polarity to resolve ester/methoxy substituted aromatics.
Photochemical work: use UV-transparent solvents (e.g., acetonitrile, ethanol) if monitoring or inducing photoreactions; protect from light otherwise.
NMR analysis: CDCl3 typically affords well-resolved spectra for benzophenones; DMSO‑d6 for limited solubility cases.
Comparison to alternatives (general guidance)
DCM vs. ethyl acetate: DCM offers higher solubility and faster evaporation; EtOAc is a greener, less chlorinated choice but may offer lower solubility.
THF vs. toluene: THF enhances solubility and supports polar reactions; toluene preferred for higher-boiling operations or when avoiding ethers.
Drying/deoxygenation
For moisture-sensitive transformations on the ester (e.g., amidation via activated intermediates) or organometallic additions to the ketone, dry solvents (molecular sieves or distillation) and inert atmosphere improve reproducibility.
Storage and Reconstitution
Storage (item-specific)
Store at room temperature (per Product Data). Keep container tightly closed in a dry place. Protect from prolonged exposure to light due to the benzophenone chromophore.
Shipped under normal conditions.
Reconstitution and handling (general guidance)
Dissolution: Start with chlorinated solvents (DCM, CHCl3) or moderately polar organics (THF, acetone, ethyl acetate). If needed, gentle warming and sonication aid dissolution. Verify solubility before scale-up.
Solution stability: Prepare fresh solutions for moisture/air-sensitive reactions. For longer-term stock solutions, store in amber vials under inert gas at 2–8 °C when compatible with the solvent.
Solid handling: Minimize dust generation. If hygroscopic behavior is observed (not expected but possible with finely powdered solids), store with desiccant.
Freeze–thaw guidance
Not applicable to the neat solid. If prepared as a solution, avoid repeated freeze–thaw cycles; aliquot solutions when possible.
Research Use Only
For research and laboratory use only. Not for human or animal therapeutic, diagnostic, or clinical use.
Structure and Identity
3-Carboethoxy-2'-methoxybenzophenone is a substituted benzophenone scaffold bearing one methoxy substituent and one ethyl ester (carboethoxy) substituent on the aromatic rings.
Item-specific identifiers (from Product Data)
SKU: C1253156
CAS: 746652-01-7
CID: 22365788
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity (for reference; not item specifications)
Expected molecular formula (based on name): C17H16O4 (computed from benzophenone core + OMe + CO2Et)
Structural features: diaryl ketone (benzophenone) core; one ring carries a 2′-methoxy substituent (anisole-type ether), the other ring carries a meta (3-) carboethoxy substituent (ethyl benzoate-type ester). Overall the molecule contains one ketone carbonyl and one aryl ester functional group plus one aryl methoxy ether.
2D description: Two phenyl rings connected via a central carbonyl (Ph–C(=O)–Ph). On ring A (prime ring) the 2′-position relative to the carbonyl linkage is methoxy (–OCH3). On ring B the 3-position relative to the carbonyl linkage is an ethyl ester substituent (–C(=O)OCH2CH3) attached directly to the aromatic carbon.
Stereochemistry: None (achiral, no stereocenters).
Synthetic Utility
Functional handles and reactivity
Diaryl ketone (benzophenone) center: platform for nucleophilic additions (RMgX/RLi → tertiary alcohols), reductive transformations (benzhydrols), imine/enamine formation (with amines under dehydrating conditions), and photochemical triplet-sensitized processes.
Ethyl ester (meta to the carbonyl on the second ring): convertible to acid (saponification), amide (coupling), aldehyde (DIBAL‑H), or alcohol (LiAlH4). It also modulates ring electronics (meta EWG), influencing EAS and cross-coupling reactivity of any future halogen handles introduced.
Methoxy (2′-OMe): electron-donating/ortho–para directing; demethylation to phenol enables further diversification (ether libraries, carbonate/urethane formation, Mitsunobu inversions after phenol derivatization).
Retrosynthetic value
Accessible via Friedel–Crafts acylation routes or cross-coupling strategies from anisole- and ethyl benzoate-derived fragments. The orthogonal handles (ester vs ketone vs methoxy) allow stepwise, chemoselective modifications.
Applications in materials/photochemistry (general)
The benzophenone chromophore is useful as a photoreactive tag or UV-absorbing unit in polymers and probes; substitution pattern tunes absorption/emission and triplet energies. This molecule can serve as a precursor to such motifs after functional group interconversions.
Practical notes
Maintain anhydrous conditions for organometallic additions; protect from strong base/acid when preserving the ester; consider light protection during long operations to mitigate photoreactions.
Target Specificity
Not applicable. This product is a small-molecule organic reagent and is not an antibody, enzyme, or targeted biological agent. No antigen/epitope, species reactivity, clone, or isotype information applies.
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