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
295.400 g/mol
XLogP3
3.300
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
295.157 Da
Monoisotopic Mass
295.157 Da
Topological Polar Surface Area
29.500 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
348.000
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 vendor-validated protocols are provided in the Product Data for this item. General, non-validated starting points are offered for research use:
Photo-crosslinking of proteins (general):
Prepare a 10–50 mM stock in acetonitrile or DMSO; protect from light.
Dilute into protein solution (e.g., HEPES or PBS, pH 7.4) to 25–200 µM final; keep co-solvent ≤2% v/v to maintain protein integrity.
Degas gently if compatible; place samples on ice to limit thermal effects.
Irradiate at 350–365 nm for 1–10 min at a measured irradiance (e.g., 5–20 mW cm−2). Include dark and solvent controls.
Quench and analyze by SDS-PAGE/MS.
UV-curing of (meth)acrylates (general):
Add 0.1–1.0 wt% initiator to monomer/oligomer blend; mix under yellow light.
Apply film; purge with N2 if possible.
Cure under 365–385 nm LEDs to target dose; assess tack-free time, gel fraction, and conversion (FTIR, DSC).
These are literature-style guidelines only. Validate and optimize for your system. Always consult the item’s SDS and CoA.
Biological Roles
This compound is a synthetic benzophenone bearing a tertiary morpholinomethyl substituent; it has no known natural biological role. However, benzophenone photochemistry is widely exploited in biochemistry as a non-specific photo-crosslinking handle.
Photoaffinity labeling (literature/general): upon 350–365 nm irradiation, triplet benzophenone can abstract hydrogen from aliphatic C–H bonds, forming diradical intermediates that recombine to yield covalent adducts to proteins, lipids, and nucleic acids. The reaction is relatively non-selective but tolerates aqueous environments and does not require specific chromophore alignment.
Utility of morpholine: the tertiary amine can be protonated to form water-soluble ammonium salts, improving compatibility with aqueous buffers during probe delivery or conjugation workflows (e.g., forming hydrochloride salts). Morpholine is common in medicinal chemistry scaffolds due to balanced basicity and polarity; here it primarily serves as an intramolecular donor and solubility/derivatization handle.
Caution: while useful for biochemical capture experiments, benzophenone-derived adducts are non-native modifications. Do not infer biological function or therapeutic utility from the presence of this group; use strictly for research workflows.
For specific biological performance (e.g., crosslinking efficiency in a given buffer or with a particular protein), empirical optimization of light dose, wavelength, and concentration is required; consult photolysis literature for guidance on actinic dose and quenching controls.
Buffer Applications
This product is not a buffering agent and does not form defined pH buffer systems by itself. In biochemical photo-crosslinking workflows, it may be dissolved in an organic co-solvent (e.g., acetonitrile, DMSO, ethanol) and then diluted into an aqueous buffer suitable for the biomolecule of interest (PBS, Tris, HEPES).
Practical notes (general):
Protonation: adding a stoichiometric acid (e.g., HCl) can form a water-soluble ammonium salt, improving compatibility with aqueous buffers; verify that acidity does not denature your target biomolecule.
Light control: minimize ambient UV during setup; irradiate with a defined wavelength (often 350–365 nm) to trigger benzophenone activation.
Quenching/controls: include dark controls and radical quenchers (e.g., TEMPO) when assessing specificity of crosslinking.
For precise buffer recipes or pH ranges: Not applicable to this compound; refer instead to your biomolecule’s stability profile and the SDS/CoA for solubility limits.
Green Alternatives
Greener choices center on solvent selection, energy input, and initiator design.
Solvent greening:
Replace chlorinated solvents (DCM, chloroform) with ethyl acetate, 2-MeTHF, propylene carbonate, or acetonitrile where compatible with your photochemistry.
For stock solutions used in bio-crosslinking, prefer ethanol or acetonitrile over DMF when feasible.
Energy efficiency:
Employ LED sources (e.g., 365–385 nm) rather than mercury lamps to cut energy use and heat load; tune emission to the benzophenone n→π* tail. LED setups also reduce hazardous waste from lamp disposal.
Acylphosphine oxides (e.g., TPO, BAPO) absorb further into visible light, enabling deeper cure with lower irradiance and potentially fewer amine-derived odors. However, they introduce phosphorus-containing residues and may be costlier.
Thioxanthone derivatives show strong visible absorption and can be paired with amine co-initiators; some exhibit better performance in pigmented systems but may require hydrogen donors.
2,4,6-Trimethylbenzophenone (TMB) is a simpler benzophenone initiator; requires external amine synergists, providing formulation flexibility but losing the intramolecular donor advantage.
Comparison (general):
This product: built-in amine donor; efficient Type II initiation; UV-A activation.
Acylphosphine oxides: visible-light activation; fast cure; different byproducts.
Thioxanthones: visible activation; often need co-initiator; colored.
Select based on wavelength availability, curing depth, extractables, and regulatory constraints for your end-use.
Pharmaceutical Uses
No pharmacopeial monograph or excipient grade is specified for this item. It is not an approved drug substance or excipient within this listing.
As a benzophenone-based photoreactive moiety, derivatives of this compound are sometimes incorporated into research tools (e.g., photoaffinity probes, crosslinkable polymers) for analytical discovery and materials development. Such uses are strictly for non-clinical, research applications.
The tertiary amine can be converted to salts (e.g., HCl) to modulate solubility in formulation studies; confirm stability under light and oxygen before storage.
Extractables/leachables: if used in curing resins or coatings for device R&D, evaluate residual monomer/initiator levels and photolysis byproducts via GC/MS or LC/MS.
Statement of use: For research use only (per Product Data). Not for human or veterinary use, clinical diagnostics, or as a drug/excipient without appropriate regulatory qualification.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
Melting point, boiling point, density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (for context; not product specifications):
Empirical formula (computed from structure): C19H22NO2
Formula weight (computed): ~296.38 g/mol
Polarity/partitioning: expected moderately lipophilic due to benzophenone core; tertiary amine and morpholine oxygen impart some polarity (estimated logP in the 3–4 range; literature/est.).
UV–Vis: benzophenone chromophore with strong absorption in UV-B/UV-A; typical π→π* band near ~250–260 nm and n→π* tailing into 330–365 nm region (literature; chromophore behavior).
Solubility (qualitative, literature): soluble in common organic solvents (DCM, chloroform, THF, acetone, acetonitrile, toluene, ethyl acetate); limited solubility in water due to hydrophobic aryl core despite tertiary amine.
Notes for users:
Photoreactive ketones can isomerize or initiate reactions under strong UV; handle under subdued light when purity is critical.
Verify exact performance-relevant properties (e.g., UV absorbance profile, purity) on the item’s CoA/SDS for your lot.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. Without a stated grade (e.g., AR, HPLC, or photoinitiator grade), users should confirm by CoA that impurity profiles, UV absorbance baselines, and residual solvents meet their application needs (e.g., polymerization vs. photoaffinity labeling).
How grade impacts use (general guidance):
Analytical Reagent (AR)/≥98–99% purity: suitable for synthetic method development and photochemical screening; fewer baseline interferences in UV–Vis and HPLC.
HPLC/UV-grade: minimized UV-absorbing impurities—important when quantifying photolysis kinetics or doing analytical photometry.
Photoinitiator grade: often specifies absorbance coefficients, photobleaching profiles, and impurity classes relevant to radical polymerization.
Stabilizers and additives:
None specified for this item; refer to CoA/Spec Sheet. For photoreactive ketones, suppliers sometimes pack under amber light or include trace stabilizers; verify presence/absence if your process is inhibitor-sensitive.
Lot release and documentation:
Request CoA for each lot to confirm identification (NMR/FTIR/MS), assay/purity, residual solvents, and moisture.
If used in polymerization, consider supplier data on photoinitiation efficiency, E-value (molar absorptivity), and cure depth (if available) to compare lots.
Reaction and Applications
This molecule is a built-in donor–acceptor photoinitiator: a benzophenone (acceptor/triplet sensitizer) tethered to a tertiary amine (electron/H-donor). It supports both synthetic photochemistry and materials applications.
Photochemistry and materials:
Type II photoinitiation: upon UV-A/near-UV (ca. 320–380 nm), the benzophenone triplet abstracts a hydrogen or accepts an electron from the tethered morpholine, generating radicals that initiate (meth)acrylate polymerization. Intramolecular donor proximity can improve quantum efficiency versus simple benzophenone/amine mixtures (literature).
Photo-crosslinking tag: benzophenone inserts into C–H bonds in proteins/lipids under 350–365 nm irradiation, enabling covalent capture of interactors (photoaffinity labeling). The morpholine nitrogen offers a handle for salt formation or further derivatization.
Synthetic transformations (using the ketone):
Reductions to the corresponding benzhydrol (e.g., NaBH4, catalytic hydrogenation) enable subsequent functionalization.
Nucleophilic additions (e.g., organometallics) to the carbonyl provide tertiary alcohols; intramolecular interactions with the amine are minimal under standard conditions.
Mannich/benzyl chemistry: the benzylic –CH2–N(morpholine) can undergo quaternization (alkyl halides) to form ammonium salts; oxidative dealkylation or N-oxide formation is also possible.
Practical tips:
Degas solutions (N2/Ar) for polymerization studies; oxygen quenches benzophenone triplets.
Use amber glassware and calibrate light intensity (actinometry) for reproducible photolysis.
Add co-initiators (alcohols, tertiary amines, thiols) deliberately if faster cure is desired, noting the molecule already contains an intramolecular donor.
Reaction Conditions
General photochemical conditions (literature guidance; optimize per system):
Wavelength: 320–365 nm (benzophenone n→π* absorption tail). 365 nm LEDs are commonly used; verify overlap with your lamp spectrum.
Atmosphere: deoxygenate solutions (N2 or Ar sparge 15–30 min) to minimize triplet quenching and radical scavenging by O2.
Solvent: acetonitrile, acetone, ethyl acetate, MEK, or toluene depending on monomer/substrate solubility; avoid strong H-donors unless intended as co-initiators.
Concentration: 0.01–1 wt% relative to monomer for radical polymerization; 10–200 µM for photo-crosslinking of biomolecules. Start low and titrate based on cure/labeling efficiency.
Light dose: tens to hundreds of mJ cm−2 at 365 nm often sufficient for thin films; biomolecule crosslinking can require 1–30 minutes depending on intensity and path length.
Temperature: ambient; manage heat from lamps to maintain reproducibility.
Reductions: NaBH4 or catalytic hydrogenation (Pd/C) in MeOH/EtOH/DCM at 0–25 °C to give benzhydrols in good yields.
Organometallic additions: RMgX/RLi in THF or ether at −78 to 0 °C; standard workups with NH4Cl.
Benzylic functionalization: NBS-mediated bromination (AIBN, CCl4 or greener solvents like EtOAc under photolysis) to install benzyl bromide, followed by SN2 with nucleophiles.
Notes:
Monitor by HPLC/GC or NMR; protect samples from ambient UV during analysis.
For polymer curing, oxygen inhibition layers may require inerting or amine co-initiators; here, the intramolecular amine already assists initiation.
Safety and Handling
Item-specific hazard data (GHS) for this SKU:
Signal Word: Not specified for this item; refer to SDS.
Hazard Statements (H-Statements): Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/analog-based; not a substitute for SDS):
Likely hazards: aromatic ketones and tertiary amines can cause skin/eye irritation; amines may be harmful if swallowed or inhaled. Avoid dust/aerosol formation.
Light sensitivity: benzophenone chromophore is photoreactive; minimize exposure to UV sources. Use amber glassware or foil wrap for long experiments.
PPE: lab coat, nitrile gloves, safety glasses; use chemical splash goggles and face shield for scale-up or where splashes are possible.
Engineering controls: handle in a fume hood; ensure good ventilation, especially during UV irradiation or thermal processing.
Skin/eye: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: move to fresh air; monitor breathing; seek medical advice.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Spill/fire response: contain with inert absorbent; for fires use CO2, dry chemical, or foam. Combustion may produce NOx and COx.
Always consult the lot-specific SDS for authoritative hazard, exposure limits, and emergency procedures.
Solvent Selection
This compound is an organic, moderately lipophilic benzophenone bearing a tertiary amine. It dissolves readily in many aprotic organic solvents and some polar protic ones.
Polarity class (general): mid-polar, aromatic ketone with tertiary amine; favors aprotic media.
Miscibility/solubility (literature/experience-based): good in DCM, chloroform, THF, acetone, acetonitrile, toluene, ethyl acetate; limited in hexanes; poor in water.
UV-related work: for photochemistry, choose solvents with low UV cutoffs and minimal triplet quenching (e.g., acetonitrile, acetone, ethyl acetate). Alcohols and amines can act as H-donors/cosensitizers—use intentionally.
Acid/base considerations: in acidic media the tertiary amine will be protonated (enhanced water solubility, reduced nucleophilicity); in basic media, free base is maintained (higher organic solubility).
When to choose vs alternatives:
For photo-crosslinking in biochemical settings, acetonitrile or DMSO (co-solvent) are typical to prepare stock solutions; then dilute into aqueous buffers with minimal precipitation by adjusting pH (protonation improves aqueous tolerance).
For radical photopolymerization, low-oxygen, low-water solvents give more reproducible rates; use dry acetonitrile, MEK, or ethyl acetate depending on monomer compatibility.
Light: As a benzophenone-containing compound, protect from prolonged UV exposure. Store in amber containers or within secondary light-protective packaging for best stability (general guidance).
Atmosphere: Store tightly closed under dry conditions. Desiccation and inert headspace are prudent for long-term storage (general guidance).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and handling (general, not item-specific specs):
Stock solutions: prepare in acetonitrile, DMSO, ethanol, THF, or DCM at 10–100 mM depending on intended use; filter if particulates are present. Label with preparation date and solvent.
Aqueous use: to increase aqueous compatibility, form a protonated salt (e.g., add HCl in ethanol to generate the hydrochloride) or use minimal DMSO/MeCN co-solvent upon dilution into buffer.
Freeze–thaw: if making aliquots of solutions, avoid repeated freeze–thaw cycles; store at −20 to 4 °C depending on solvent and project needs. Allow to equilibrate to room temperature before opening to prevent moisture ingress.
Always refer to the lot-specific CoA and SDS for confirmed storage and stability details. Research use only (Product Data).
Structure and Identity
A benzophenone-derived, bifunctional photoreactive amine featuring a para-methyl group on one ring and a para-morpholinomethyl group on the other. The carbonyl of the benzophenone core is conjugated with both phenyl rings; the morpholinomethyl substituent is a benzyl–tertiary amine linkage.
Core: benzophenone (diphenyl ketone, Ar–CO–Ar′) with two para substituents on opposite rings.
Substituents: one ring bears a 4-methyl (–CH3) group; the other bears a 4′-morpholinomethyl (–CH2–N(–CH2CH2–O–CH2CH2–)–) group, making the nitrogen tertiary.
Functional groups: conjugated aryl ketone (photochemically active triplet), tertiary amine (electron donor), cyclic ether within morpholine (heterocycle).
2D description: two phenyl rings flanking a carbonyl; para to the carbonyl bond on ring A is –CH3; para on ring B is –CH2–N(morpholine). No stereocenters; molecule is achiral.
Synthetic Utility
Functional group set and reactivity enable multiple synthetic entry points:
Photochemical handle: the benzophenone carbonyl undergoes efficient intersystem crossing to a reactive triplet; intramolecular electron transfer from the morpholine accelerates radical generation. Use to initiate radical polymerizations or to graft onto C–H-rich substrates under UV-A.
Carbonyl chemistry:
Reduction to the corresponding benzhydrol provides an intermediate for further alkylation, esterification (via chloroformate formation), or activation as a leaving group.
Nucleophilic additions (RMgX/RLi) deliver tertiary carbinols with defined aryl substitution, valuable in building densely arylated alcohols.
Imine/enamine chemistry is limited by tertiary amine presence; however, the ketone can still undergo oxime/hydrazone formation.
Benzylic amine chemistry:
Quaternization at nitrogen (alkyl halides) affords ammonium salts that can act as phase-transfer catalysts or ionic handles for purification.
Oxidation to the amine N-oxide (m-CPBA) modulates electron donation and can direct subsequent rearrangements or eliminations (literature strategy).
Benzyl deprotonation adjacent to nitrogen is feasible under strong base to enable substitution on the benzylic position (careful control required).
Conjugation strategies: the tertiary amine can be acylated to amides only after prior dealkylation; alternatively, linkers can be installed at benzylic carbon via halogenation (e.g., NBS) followed by nucleophilic substitution, yielding benzophenone-containing probes/polymers.
This combination of a photoreactive aryl ketone and a tunable tertiary amine makes the molecule a versatile platform for photoresponsive materials and probe synthesis.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological affinity reagent or antibody. No antigen, epitope, or species reactivity applies. For biochemical photo-crosslinking, benzophenone insertion is broadly non-selective toward C–H bonds (literature generality), and specificity must be engineered via the scaffold to which this chromophore is attached.
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