≥95% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Room temperature Spedizione Normal. Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
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
315.800 g/mol
XLogP3
3.400
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
315.103 Da
Monoisotopic Mass
315.103 Da
Topological Polar Surface Area
29.500 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
370.000
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
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Recensioni
Recensioni dei clienti
Application Protocols
No manufacturer-verified biological assay protocols or analytical methods are specified for this item.
General workflow examples (literature; adapt to your system):
Photo-crosslinking of a ligand–protein complex:
Prepare ligand bearing/containing this benzophenone scaffold in buffer (pH 6–7.4) with ≤10–20% MeCN or DMSO cosolvent.
Incubate with protein/cell lysate at 0–4 °C or room temperature to allow binding.
Irradiate at 350–365 nm for 5–20 min while keeping the sample cool and oxygen-controlled as needed.
Quench, denature, and analyze by SDS-PAGE/western blot or LC–MS/MS after enrichment.
Pd-catalyzed diversification (Suzuki example):
Combine aryl boronic acid (1.2–1.5 equiv), this aryl chloride (1.0 equiv), Pd catalyst/ligand, and K3PO4 (3 equiv) in 2-MeTHF/H2O (3:1).
Heat to 90 °C for 8–12 h under inert atmosphere.
Work up with EtOAc/brine, dry, and purify by silica gel chromatography (protect from strong UV).
Always validate conditions at small scale; this product is for research use only.
Biological Roles
Item-specific biological roles are not specified for this reagent; it is supplied for research use only.
Literature/general context:
Benzophenone motifs are widely used as photoaffinity tags because their triplet state can abstract hydrogen from C–H bonds in biomolecules, forming covalent adducts upon UV irradiation. This property is exploited in proteomics for target capture and mapping binding sites.
The morpholine substituent can enhance aqueous compatibility and modulate basicity, facilitating conjugation to biomolecules (e.g., via activated esters or click-ready linkers attached elsewhere in the molecule) and improving probe handling in buffered media.
No known endogenous metabolic role is associated with this specific synthetic benzophenone derivative. Biotransformation, if any, would likely involve N-oxidation/dealkylation of morpholine and reduction/photochemical transformations of the benzophenone core (literature precedence for related structures).
Caution: Do not infer biological safety, efficacy, or selectivity from these general statements. This material is not intended for diagnostic, therapeutic, or in vivo use.
Buffer Applications
This compound is not a conventional buffering agent. It lacks a defined acid/base pair with a narrow pKa window suitable for precise pH control in typical biological buffers.
Practical note (literature/general):
The morpholine nitrogen can be protonated (morpholine pKaH typically ~8.2–8.5), so the compound may be dissolved in mildly acidic buffers (e.g., acetate or citrate, pH 4–6) as its protonated form for photolabeling workflows. However, the buffer capacity is provided by the buffer system itself, not by this reagent.
For buffer recipes and pH control, select established systems (phosphate, HEPES, MOPS, acetate) appropriate to your biological assay; use this reagent as a solute within that buffer if needed.
Green Alternatives
Solvent and process choices often dominate the environmental footprint. For chemistry involving this benzophenone derivative, consider the following greener substitutions (literature/general guidance):
Comparison (use-case vs option)
Photocrosslinking medium:
Conventional: DCM, CHCl3.
Greener: EtOAc, MeCN, 2-MeTHF, or aqueous buffer with ≤20% MeCN/EtOH when protonated; trade-off: may reduce substrate solubility or change photochemical quantum yields.
Cross-coupling solvent:
Conventional: DMF, dioxane, toluene.
Greener: 2-MeTHF, cyclopentyl methyl ether (CPME), propylene carbonate, or Me-THF/water biphasic Suzuki; trade-off: base/catalyst solubility and rate can vary; screen ligands accordingly.
Base selection:
Conventional: Cs2CO3, NaOtBu.
Greener: K3PO4 or K2CO3 (lower toxicity, cost); trade-off: may require higher temperature or catalyst loading.
Workup:
Replace chlorinated solvent partitions with EtOAc/MTBE and brine; use solid-supported scavengers to minimize aqueous waste.
Energy and light source:
Prefer LED sources at 365 nm over mercury lamps; improved energy efficiency and reduced hazardous waste.
Safety/environmental note:
Avoid unnecessary photoinitiator additives; the benzophenone core is intrinsically photoactive. Optimize concentration to minimize unreacted residues and downstream purification.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is supplied for research use only.
Literature/general context:
Benzophenone-based photoaffinity handles are occasionally incorporated into discovery-stage tool compounds for target identification. Such use is confined to research workflows (e.g., chemical biology, proteomics) and not to formulated drug products.
The morpholine motif is common in medicinal chemistry for tuning basicity and solubility; in this reagent, it primarily serves as a polarity-modulating and derivatization handle rather than a defined pharmaceutical excipient.
Manufacturing/process note:
If employed in process development as a synthetic intermediate, standard impurity profiles, residual solvent limits, and purge studies should be conducted. Any discussion of GMP applicability would require item-specific grade documentation, which is not provided here (refer to CoA/Spec Sheet).
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for this scaffold (not item specifications):
Phase at ambient conditions: typically a solid or high-boiling viscous liquid for benzophenone derivatives with tertiary amine side chains (literature, general observation).
UV–Vis (benzophenone chromophore, literature): strong absorption in the near-UV; π→π* band ≈ 250–260 nm; n→π* band ≈ 330–365 nm depending on substitution and solvent polarity.
Photochemical behavior (literature): efficient intersystem crossing to the triplet state; capable of hydrogen abstraction from C–H donors under UV irradiation.
Solubility profile (literature, qualitative): expected high solubility in common organic solvents (DCM, THF, EtOAc, MeCN, toluene); limited aqueous solubility at neutral pH; increased aqueous miscibility under acidic conditions (protonation of morpholine nitrogen).
Acid–base character (literature): morpholine pKaH typically ~8.2–8.5, implying protonation under mildly acidic conditions; exact value depends on benzylic attachment and ring electronics.
LogP/logD (literature, qualitative): overall amphiphilic; diaryl ketone increases lipophilicity, morpholine increases polarity; logP likely in the moderate-to-high range relative to benzophenone; exact value not established for this specific derivative.
Note: All numerical values are not specified for this item; consult CoA/SDS for measured properties.
Quality and Grades
Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance):
If provided as “research grade,” it is intended for laboratory R&D use; not for human or veterinary use, food, or household applications.
If purity (e.g., >95%) is provided on the CoA, it typically reflects HPLC/GC or NMR assay; impurities may include regioisomers, residual solvents, or inorganic residues from synthesis and workup.
Stabilizers/additives: None specified for this item; if present, they will be listed on the CoA. Benzophenone derivatives generally do not require inhibitors, but light protection can improve shelf-life.
Documentation: Each lot’s CoA will indicate analytical method(s), assay, and key impurity thresholds. For sensitive photochemical studies, request data on UV cut-off/absorbance profile if critical to your application.
Research Use Note: For research use only.
Reaction and Applications
Functional platform (general/literature):
Benzophenone core: robust photoreactive chromophore; upon UV irradiation, forms a triplet biradical capable of hydrogen abstraction, enabling covalent attachment to C–H containing substrates (photo-crosslinking, photoaffinity labeling).
Aryl chloride handle (2-chloro): participates in Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) to diversify the aryl ring.
Benzylic morpholinomethyl: provides basicity and aqueous compatibility; can be further derivatized (e.g., quaternization to form water-soluble salts, acylation/carbamoylation at nitrogen).
Photoaffinity probes: attachment of the morpholine-bearing benzophenone to ligands to enable UV-triggered protein capture.
Polymer surface modification: UV-induced grafting to hydrocarbon polymers for improved wettability/adhesion; morpholine enhances adhesion to polar substrates.
Building block for medicinal chemistry libraries: orthogonal handles (aryl–Cl and tertiary amine) allow late-stage diversification.
Practical tips:
Photocrosslinking: 350–365 nm irradiation is commonly used for benzophenone; purge oxygen if radical pathways are quenched; monitor by UV–Vis or LC–MS.
Cross-coupling on aryl–Cl: use Pd(0/II) catalysts with appropriate ligands (e.g., XPhos/BrettPhos for C–N; SPhos for Suzuki), bases such as K3PO4 or Cs2CO3, and temperatures 80–120 °C depending on system.
Salt formation: protonate with HCl/HBr or organic acids (e.g., TFA) to enhance aqueous solubility; isolate as crystalline salts for handling.
Reaction Conditions
Cross-coupling on aryl chloride (literature, representative):
Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%) with SPhos/XPhos (2–5 mol%), K3PO4 (2–3 equiv), 2-MeTHF or dioxane/H2O (3:1), 80–100 °C, 6–16 h; typical isolated yields for activated aryl chlorides 60–90% (ligand/coupling partner dependent).
Buchwald–Hartwig amination: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%) with BrettPhos or RuPhos, NaOtBu or Cs2CO3, toluene or dioxane, 90–110 °C, 8–18 h.
Sonogashira: Pd(PPh3)2Cl2/CuI, Et3N or iPr2NH, THF or MeCN, 50–80 °C, 4–12 h; avoid overexposure to air/moisture if Glaser coupling is undesired.
Photocrosslinking with benzophenone core (literature):
Irradiation: 350–365 nm LEDs or mercury lamp with appropriate bandpass; 0.1–1 mM reagent in solvent or buffer; 5–30 min typical exposure.
Atmosphere: O2 can quench radical processes; consider N2/Ar purge when necessary. Keep samples cool to avoid thermal side reactions.
Quenching/analysis: Add radical scavengers post-irradiation to stop secondary reactions; analyze by SDS-PAGE/LC–MS in bio-conjugation workflows.
Benzylic modifications (literature):
Oxidation: TEMPO/bleach or MnO2 in DCM/MeCN at rt–40 °C to aldehyde/ketone (depending on substitution).
Quaternization: alkyl halide (e.g., MeI) in MeCN, rt–50 °C, 2–24 h.
Notes: Conditions are general literature guidance for related scaffolds; optimize per substrate and catalyst system.
Safety and Handling
GHS/CLP (Product Data):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification and Pictograms: Not specified for this item; refer to SDS.
General hazards for benzophenone/morpholine derivatives (literature/general):
May cause skin/eye irritation; tertiary amines can be irritating and are harmful if swallowed or inhaled at sufficient doses. Avoid aerosol formation.
Benzophenone chromophore is UV-active; avoid unnecessary UV exposure of material and skin/eyes during photochemical work.
Handling recommendations (professional practice):
Use in a chemical fume hood with appropriate PPE: lab coat, safety glasses, and nitrile gloves. For weighing dusty solids, consider a balance enclosure.
Avoid contact with strong oxidizers and strong acids/bases unless intended; tertiary amine can be protonated by acids and oxidized by strong oxidants.
Prevent prolonged light exposure if photoreactivity is undesirable; wrap glassware in foil during storage or dark reactions.
First aid (summary; defer to SDS):
Skin/eye contact: Rinse with water for several 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 attention.
Spill/fire response (general):
Absorb small spills with inert material; for fire use dry chemical, CO2, or foam. Combustion may release CO/CO2, HCl-containing fumes.
Always consult the product-specific SDS for authoritative safety information.
Solvent Selection
Polarity and miscibility (literature/general for this scaffold):
Expected to dissolve well in polar aprotic solvents (DMF, DMSO, MeCN), halogenated solvents (DCM, CHCl3), ethers (THF, MTBE), and aromatics (toluene).
Limited solubility in water at neutral pH; solubility increases in acidic aqueous media by protonation of the morpholine nitrogen; decreases under strong base (free base form, more hydrophobic).
Practical selection by task:
Photochemistry and surface grafting: MeCN, isopropanol, or mixed aqueous buffers (pH < 6) with a small percentage of organic cosolvent to maintain solubility while enabling protonation.
Cross-coupling on the aryl chloride: toluene, dioxane, or DMF/MeCN with Pd catalysts; add base (e.g., K3PO4, Cs2CO3) as appropriate.
N-alkylation/quaternization of morpholine: polar aprotic media (MeCN, DMF) to enhance SN2 rates; control water content.
Comparison notes (literature):
DCM vs EtOAc: DCM offers higher solubility and faster evaporation; EtOAc is greener but may provide lower solubility.
DMF/DMSO maximize solubility but complicate workup; consider MeCN or 2-MeTHF when possible.
Drying/quality: For moisture-sensitive transformations (e.g., metal-catalyzed couplings), use anhydrous, degassed solvents. Filter through basic alumina to remove acid traces before base-sensitive steps.
Storage and Reconstitution
Storage (Product Data): Room temperature. Protect from prolonged light exposure to preserve the benzophenone chromophore; store tightly closed in a dry place. Shipped at ambient conditions (Normal).
Stability notes (general/literature):
Benzophenone derivatives are typically stable at ambient conditions when kept dry and dark. Tertiary amines can absorb CO2/H2O forming salts; keep container well sealed.
Reconstitution/dissolution (general guidance):
Readily dissolves in common organic solvents (e.g., DCM, THF, MeCN, DMSO, EtOH). For aqueous work, prepare stock solutions in DMSO or MeCN; alternatively, form an acid salt (e.g., HCl) to enhance water solubility.
Filter solutions (0.2 µm PTFE) for photochemical/bioconjugation experiments to remove particulates.
For long-term solution storage, keep aliquots at 2–8 °C, protected from light; verify no precipitation before use.
Shelf-life: Not specified for this item; refer to CoA/Spec Sheet.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
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 (general description from name; literature/interpretation)
Core scaffold: a benzophenone (diphenyl ketone, Ar–CO–Ar′) chromophore.
Substituents: one ring bears a chloro substituent at the 2-position; the other ring bears a benzylic morpholinomethyl (–CH2–O–(CH2)2–N–(CH2)2–O–) at the 2′-position.
Functional groups: aromatic chloride (aryl–Cl), tertiary amine within a morpholine ring (cyclic tertiary aminal/ether), and a diaryl ketone (benzophenone) capable of n→π* excitation.
Stereochemistry: none (achiral as named), but conformationally restricted around the carbonyl due to aryl–carbonyl conjugation.
2D description: two phenyl rings linked by a carbonyl; ortho to the carbonyl on one ring is Cl; ortho on the other ring is a –CH2–morpholine substituent extending out of the aromatic plane.
Synthetic Utility
Orthogonal handles:
Aryl chloride (2-position): enables Pd-catalyzed cross-coupling diversification (Suzuki–Miyaura for C–C, Buchwald–Hartwig for C–N, Sonogashira for C(sp)–C) and, under strong activation, nucleophilic aromatic substitution if the ring is sufficiently activated.
Tertiary amine (morpholine): amenable to salt formation (HCl, TFA) for purification; quaternization (e.g., with MeI, benzyl halides) to tune solubility and create phase-transfer-like properties.
Benzylic position (–CH2–Ar): susceptible to oxidation (e.g., to aldehyde/acid) or functionalization via radical or photoredox pathways (literature precedence for benzylic C–H activation).
Chromophore leverage:
The benzophenone carbonyl offers UV-induced triplet reactivity enabling covalent capture to C–H rich substrates; useful for immobilization or capture-and-release strategies (after reductive cleavage or linker incorporation).
Suzuki on aryl–Cl with boronic acids to introduce diverse aryl/heteroaryl groups, preserving the morpholine side chain.
Reductive amination on morpholine nitrogen is not applicable (tertiary amine), but acylation/carbamate formation with activated carbonyls provides handle protection or function.
Amide coupling at other positions requires prior introduction of linkers (e.g., via benzylic functionalization to carboxylate/amine).
Purification tips:
Free-base often streaks on silica; protonate to form salts for sharp bands. Protect from intense UV during chromatography to minimize on-column photoreactions.
Target Specificity
Not an antibody or biological targeting reagent. No target, epitope, species reactivity, clone, or isotype information applies to this product.
In chemical biology, benzophenone-based reagents can be used in untargeted photoaffinity labeling; any “specificity” derives from appended recognition elements introduced by the user, not from this scaffold itself.
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