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.
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
353.400 g/mol
XLogP3
2.900
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
7
Exact Mass
353.163 Da
Monoisotopic Mass
353.163 Da
Topological Polar Surface Area
55.800 Ų
Heavy Atom Count
26
Formal Charge
0
Complexity
467.000
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
No validated biological assay protocols, analytical methods, or kit-style applications are provided for this item in the Product Data.
General laboratory guidance (literature-based, for similar scaffolds):
Preparation of stock solutions: Dissolve in dry DMSO or DMF to 10–50 mM; store aliquots protected from light at room temperature or 4 °C per solubility/stability tests.
Photolabeling (conceptual): Incubate probe (containing this scaffold) with target mixture, irradiate at 350–365 nm for 5–20 min on ice or at room temperature, then analyze by SDS-PAGE/LC-MS. Include dark controls.
Analytical QC: Monitor purity by HPLC (UV 254–280 nm) and identity by LC-MS ([M+H]+ expected near m/z ~354, literature-based estimate).
For any specific, fit-for-purpose protocol, develop and qualify conditions empirically with appropriate controls. Always consult the SDS and CoA for handling and characterization details.
Biological Roles
This product is a synthetic organic research intermediate rather than a native metabolite or biomolecule.
Applicability: No intrinsic biological role is specified for this item. The content below reflects general, literature-based context for related scaffolds and is not a property of this specific lot.
Literature context for similar moieties:
Benzophenone chromophores are widely used in photoaffinity labeling to covalently capture protein–ligand interactions upon UV irradiation (350–365 nm), exploiting the benzophenone triplet’s hydrogen-abstraction capability.
Morpholine is a common tertiary amine motif in medicinal chemistry, valued for imparting water compatibility and modulating basicity (conjugate acid pKa typically ~8–9). Its presence can improve solubility of conjugates under acidic conditions and influence lysosomotropic behavior when embedded in drug-like molecules.
The ester handle allows installation of biomolecular conjugation handles (e.g., conversion to acids followed by amide coupling to peptides or reporter tags) to construct probes.
Important caveat: Any discussion of interactions with biological macromolecules pertains to designed probes derived from this scaffold. This product itself is supplied for research use only and is not intended for diagnostic, therapeutic, or in vivo applications. Performance in biological systems will depend on derivatization, formulation, and experimental design.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare defined pH buffer systems.
Practical note: When used in biochemical experiments as part of photoaffinity probes or conjugates, dissolution is usually achieved in organic cosolvents (e.g., DMSO) followed by dilution into assay buffer. Protonation of the morpholine nitrogen (e.g., with 0.1% HCl) can improve apparent aqueous compatibility for stock solutions of the salt.
For actual buffer preparation, select established buffering systems (e.g., phosphate, HEPES, Tris) appropriate to the target pH range and compatible with UV irradiation if photochemistry is involved (some buffers and additives absorb in the near-UV).
Green Alternatives
Context: The compound is a benzophenone-based photoreactive intermediate. Green chemistry considerations center on solvent choice, energy input for photolysis, and selection of alternative photophores when lifecycle impacts warrant.
Solvent choices (greener preferences):
Prefer ethyl acetate, 2-MeTHF, or MeCN over chlorinated solvents when solubility and reactivity permit.
Replace DMF/NMP with safer polar aprotics (e.g., propylene carbonate, Cyrene, or dimethyl carbonate) for certain couplings; verify compatibility with amide coupling reagents.
Photochemistry energy footprint:
Use LED sources at 350–365 nm to reduce energy consumption and heat compared to medium-pressure Hg lamps; LEDs also minimize hazardous Hg waste.
Alternative photophores (literature comparison, general):
Photophore | Pros | Cons
--- | --- | ---
Benzophenone (this scaffold) | Broad C–H insertion; long triplet lifetime; λex ~350–365 nm; robust | Can cause off-target labeling; requires longer irradiation; UV exposure
Diazirine (e.g., trifluoromethyl-aryl diazirines) | Short irradiation; more selective carbene insertion; compact | Less stable in some contexts; specialized synthesis; λex often ~350–370 nm
Aryl azides | Accessible; N2 extrusion | Potentially hazardous; side reactions; higher-energy UV often required
Workup/waste:
Implement solvent recovery (rotary evaporation + redistillation for EtOAc/2-MeTHF) and segregate chlorinated waste to reduce incineration burden.
All recommendations are general; validate green substitutions with small-scale trials.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulated pharmaceutical use is specified for this item; it is supplied for research use only.
Literature/general context (non-clinical):
Benzophenone-containing building blocks are sometimes used in discovery chemistry to build photoreactive probes for target identification and SAR exploration.
The morpholine motif is common in drug discovery for modulating solubility and pKa; in this scaffold it can aid handling and conjugation chemistry.
If incorporated into screening libraries, solid handling can benefit from preparation of well-characterized salts (e.g., HCl) to improve weighing and dissolution repeatability.
For analytical support, LC-MS compatible diluents (MeCN/H2O + 0.1% formic acid) are typically suitable for tertiary amine-containing compounds.
No therapeutic, diagnostic, or clinical claims are made or implied.
Physical Properties
Item-specific (from Product Data):
Appearance: 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.
Literature/computed values (context only; not product specifications):
Estimated molecular formula: ~C21H23NO4; MW ~353.4 g/mol (computed from name; see Structure & Identity).
Physical state: many benzophenone derivatives of comparable size are crystalline solids or viscous oils at ambient temperature; specific state for this item is not established in the provided data.
Solubility (qualitative, literature expectation for benzophenone derivatives):
Organic: generally soluble in chlorinated solvents (DCM, chloroform), THF, acetone, ethyl acetate; often moderately soluble in MeOH/EtOH; good in polar aprotics (DMF/DMSO).
Aqueous: typically low water solubility due to aromatic core; protonation of the morpholine nitrogen under acidic conditions can enhance apparent aqueous solubility.
LogP: benzophenone scaffold is hydrophobic; tertiary amine can reduce effective logP upon protonation. No experimental value located for this exact structure.
pKa: morpholine conjugate acid typically pKa ~8.3–8.6 (literature, for morpholine); tertiary amine here is embedded and benzylic—actual pKa may be similar though slightly perturbed.
Refractive index, density, UV cutoff, melting/boiling point: Not located in literature for this exact compound.
Always consult the product CoA/Spec Sheet for definitive item-specific properties.
Quality and Grades
Item-specific (from Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grade (general guidance):
When specified, synthetic intermediate grade typically emphasizes identity and assay suitable for R&D synthesis; HPLC or LC-MS trace profiling may accompany higher research grades.
If labeled “>98%” or similar on the CoA, assay indicates purity by a specified method (often HPLC or GC). Absence of stabilizers would be indicated explicitly if relevant; none are specified here.
For photoactive benzophenones, low UV-absorbing impurities are beneficial in photolabeling workflows; HPLC-grade solvents and clean glassware minimize background.
Practical QC notes for this scaffold (general/literature):
Identity confirmation: 1H/13C NMR should show benzylic –CH2– (approx. 3.5–4.5 ppm depending on solvent/protonation), morpholine methylenes (two sets ~2.4–3.8 ppm), aromatic resonances (6.8–8.0 ppm), ester ethyl quartet/triplet, and a carbonyl at ~195–200 ppm (ketone) and ~165–173 ppm (ester) in 13C.
MS (ESI+): expected [M+H]+ around m/z ~354 (literature expectation from computed MW).
Chromatography: Usually elutes at moderate polarity on silica; amine protonation (1–2% Et3N in eluents) can suppress tailing.
Always defer to the item’s CoA/Spec Sheet for the definitive assay method, acceptance criteria, and impurities profile.
Reaction and Applications
Role of the scaffold (literature/general):
Benzophenone is a classical photoreactive chromophore that, upon n→π* excitation (typically 350–365 nm), can form a triplet state capable of abstracting hydrogen and inserting into C–H, N–H, or other bonds—useful for photoaffinity labeling.
The para-morpholinomethyl group increases basicity and water compatibility (upon protonation), aiding conjugation to biological ligands or improving probe handling.
The ortho ethyl ester provides a handle for further derivatization (hydrolysis to acid, amide coupling, or conversion to other esters/activated intermediates).
Typical applications:
Photoaffinity probe intermediate: install ligand on the morpholine nitrogen (quaternization/alkylation) or on the benzyl position; use benzophenone for covalent capture after UV irradiation.
Crosslinker development: leverage benzophenone’s broad reactivity and long-lived triplet to crosslink to C–H rich environments.
Synthetic intermediate: transform the ester to the acid and couple to amines (HATU/EDC) to append tags (biotin/fluorophores) while retaining the benzophenone photophore.
Practical tips:
Minimize unintended photolysis during synthesis/handling by working under subdued light or amber glass.
For benzylic functionalization, mild conditions (e.g., reductive amination, SN1/SN2 variants under activation) can be employed; avoid over-alkylation unless a quaternary ammonium is desired.
During photocrosslinking, purge oxygen when possible (oxygen can quench triplet states) and irradiate at 350–365 nm using quartzware; monitor by LC-MS.
Limitations:
Benzophenone can undergo side photoreactions and dimerizations; diazirines may offer higher selectivity in some systems (see Green Alternatives).
Reaction Conditions
The following are literature-based general conditions for transformations relevant to this scaffold; they are not product-specific specifications.
Ester hydrolysis (to acid):
Conditions: NaOH (1–2 equiv) in MeOH/H2O (3:1 to 9:1), 0–25 °C, 1–12 h; acidify to pH ~2 and extract. Yields commonly high for unhindered ethyl esters.
Amide coupling (from acid):
Reagents: HATU or EDC·HCl with HOBt/HOAt (or OxymaPure), DIPEA or NMM base, DMF or MeCN solvent, 0–25 °C, 1–6 h. Typical isolated yields 60–90% depending on partner sterics.
Benzylic functionalization of –CH2–N(morpholine):
Quaternization: Alkyl halide (e.g., MeI, BnBr), acetonitrile or acetone, 20–50 °C, 2–24 h. Monitor to avoid overalkylation at benzylic sites if undesired.
Acylation of morpholine N: Acyl chloride (1.1 equiv), DCM, 0 °C to rt, Et3N (2 equiv). Rapid, typically high yielding.
Photocrosslinking (benzophenone triplet):
Irradiation: 350–365 nm LEDs, quartz vials, 0–25 °C, 5–60 min under air or argon (better under inert atmosphere to minimize quenching). Employ concentrations 0.01–1 mM in assay media. Confirm adducts by LC-MS/MS.
Reductive amination at the benzophenone carbonyl (if pursued):
Amine partner (1.2–2 equiv), NaBH(OAc)3 in DCE or MeOH, 0–25 °C; or NaBH3CN in MeOH/pH 5–6 acetate buffer. Benzophenone cores can be less reactive; longer times or Lewis acid activation may be needed.
Note: Conditions may require optimization given steric/electronic effects of the ortho ester and para morpholinomethyl substituents.
Safety and Handling
Item-specific (from Product Data):
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements / Pictograms: Not specified for this item; refer to SDS.
Storage Conditions: Room temperature.
General safety considerations for benzophenone-based, tertiary-amine, ester-containing organics (literature/general guidance; not a substitute for SDS):
Hazards: Aromatic ketones may cause skin/eye irritation; tertiary amines can be irritants and may emit amine-like odors. Avoid inhalation of dust/aerosols and skin contact.
Light sensitivity: Benzophenone chromophore absorbs near-UV; minimize prolonged exposure to strong UV to avoid unwanted photoreactions during handling.
Incompatibilities: Strong oxidizers (risk of exotherm/oxidation); strong acids or bases may hydrolyze the ester; strong acids will protonate the amine and can alter solubility; strong bases may induce elimination or transesterification.
PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, safety glasses or goggles; handle in a fume hood to avoid inhalation of vapors or dust.
First aid (overview):
Skin/eye: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill/Disposal: Absorb small spills with inert material; dispose of waste according to institutional and local regulations.
Refer to the product’s SDS for authoritative hazard classification and response measures.
Solvent Selection
Applicability: This compound is a moderately lipophilic aromatic ketone bearing a tertiary amine (morpholine) and an ester; solvent selection impacts solubility and reaction outcomes.
General miscibility/solubility profile (literature expectations):
Moderate: methanol, ethanol, isopropanol (often improved by slight acidification to protonate the amine).
Poor: water at neutral pH; aqueous solubility increases in acidic media (e.g., 0.1–0.5% HCl) via salt formation.
Polarity considerations:
Neutral/base form prefers mid-polar aprotic or chlorinated solvents.
As an amine salt (e.g., HCl salt formed in situ), better compatibility with aqueous-organic systems and reverse-phase methods.
When to choose what:
Spectroscopy/NMR: CDCl3 or DMSO-d6; add a drop of TFA-d for sharper amine signals if needed.
Couplings/derivatizations: DMF, DCM, THF are common; include base scavengers or acid additives depending on the transformation (see Reaction Conditions).
Purification: Silica gel with EtOAc/hexane plus 0.5–2% Et3N to prevent amine tailing; reverse-phase prep-HPLC with acetonitrile/water + 0.1% formic acid as an alternative.
Small comparison (literature-based):
DCM vs. EtOAc: DCM typically affords higher solubility and faster chromatography; EtOAc is a greener choice but may give broader bands.
DMF/DMSO vs. MeCN: DMF/DMSO dissolve more but are harder to remove; MeCN is easier to evaporate but may limit concentration.
Storage and Reconstitution
Item-specific (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice; not item specification):
Light protection: Store in amber containers or away from strong UV sources to mitigate unintended photoreactions of the benzophenone chromophore.
Atmosphere: Normal laboratory atmosphere is typically acceptable; for long-term storage of amines/esters, keeping containers tightly closed with desiccant can reduce hydrolysis/oxidation.
Reconstitution/dissolution: If supplied as a solid or viscous oil, dissolve in dry DMSO, DMF, THF, acetone, EtOAc, or DCM as appropriate. For aqueous work, prepare an acidified aqueous-organic mixture (e.g., 10–50% MeCN or MeOH with 0.1% HCl) to form a soluble amine salt.
Working solutions: Prepare fresh before use when possible. If aliquoting, minimize headspace and avoid repeated opening to limit moisture uptake and photolysis.
Freeze–thaw: Not typically required at room-temperature storage; if cold storage is used for formulated solutions, avoid repeated freeze–thaw cycles which can lead to precipitation or degradation.
Always consult the product’s CoA and SDS for definitive storage, shelf-life, and handling instructions. Research use only.
Structure and Identity
A benzophenone-derived photoreactive building block bearing an ortho ethyl ester (carboethoxy) and a para-morpholinomethyl substituent across the two phenyl rings.
Structural features: diphenyl ketone (benzophenone) core; one ring carries an ortho ethyl ester (–CO2Et, i.e., carboethoxy) substituent relative to the carbonyl; the other ring bears a para –CH2–N(morpholine) substituent (tertiary amine embedded in a morpholine ring).
Central carbonyl (C=O) linked to two phenyl rings (Ph–CO–Ph').
On the “benzoyl” ring, the position ortho to the carbonyl is substituted with an ethyl ester group (–C(=O)OCH2CH3).
On the opposite ring (Ph'), the para position carries a benzylic methylene (–CH2–) connecting to an N-substituted morpholine ring [–N–(CH2CH2–O–CH2CH2)–].
Stereochemistry: none (as drawn, no stereogenic centers expected).
Synthetic Utility
Functional handles and their reactivity (literature/general):
Ester (–CO2Et, ortho to benzophenone carbonyl): convertible to acid via saponification (NaOH, MeOH/H2O) or to amides via activation (HATU/EDC/DIC) after hydrolysis; can also undergo transesterification (ROH, acid/base catalysis).
Benzylic morpholinomethyl (–CH2–N–morpholine): reactive toward quaternization (alkyl halides), acylation at nitrogen (acid chlorides/anhydrides), and can be oxidized at benzylic position under certain conditions (careful to avoid overoxidation of benzophenone core).
Benzophenone carbonyl: amenable to typical ketone chemistry (e.g., reductive amination, though deactivation by conjugation and sterics should be considered); forms imines/oximes/hydrazones; engages in photochemical hydrogen abstraction.
Retrosynthetic value:
The scaffold can be disconnected to an ortho-ester-substituted benzoyl chloride (or acid) and a para-morpholinomethyl phenyl nucleophile, or assembled via benzoin/benzophenone-forming acylation followed by late-stage benzylic amination.
Benzylic introduction of morpholine: via chloromethylation/bromomethylation of the para ring, followed by substitution with morpholine; or via reductive amination from the corresponding 4′-formyl derivative.
Derivatization pathways:
Convert ester to acid then couple to affinity tags (biotin, fluorophores) to build photoaffinity probes.
Quaternize morpholine to generate permanent cationic handles for ion-exchange or cellular uptake studies (note altered physicochemical profile).
Install isotopic labels at benzylic or carbonyl positions for mechanistic studies.
Target Specificity
Not applicable. This product is a small-molecule research intermediate, not a biological targeting reagent, antibody, or enzyme inhibitor with defined target specificity in the catalog entry.
If used as part of a photoaffinity probe, any “specificity” arises from the conjugated ligand, not from the benzophenone scaffold itself. The benzophenone moiety reacts broadly with proximal C–H/N–H sites upon UV activation.
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