4-Methoxy-4'-morpholinomethyl benzophenone , CAS No.898769-72-7

CAS: 898769-72-7 Cat. No.: M974936 Formula: C₁₉H₂₁NO₃ Peso molecolare: 311.381 PubChem CID: 24724221

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: COC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)CN3CCOCC3
• IUPAC Name: (4-methoxyphenyl)-[4-(morpholin-4-ylmethyl)phenyl]methanone
• InChIKey: FWYBMCXYENKRML-UHFFFAOYSA-N
• INCHI: 1S/C19H21NO3/c1-22-18-8-6-17(7-9-18)19(21)16-4-2-15(3-5-16)14-20-10-12-23-13-11-20/h2-9H,10-14H2,1H3
• Isomeri SMILES: COC1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)CN3CCOCC3
• PubChem CID: 24724221
• Peso molecolare: 311.381

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzophenones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Diphenylmethanes Aryl-phenylketones Phenylmethylamines Phenoxy compounds Anisoles Methoxybenzenes Benzylamines Benzoyl derivatives Alkyl aryl ethers Aralkylamines Morpholines Trialkylamines Oxacyclic compounds Dialkyl ethers Azacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzophenone - Diphenylmethane - Aryl-phenylketone - Anisole - Benzoyl - Benzylamine - Phenoxy compound - Phenol ether - Phenylmethylamine - Aryl ketone - Methoxybenzene - Alkyl aryl ether - Aralkylamine - Oxazinane - Morpholine - Tertiary aliphatic amine - Tertiary amine - Ketone - Oxacycle - Azacycle - Dialkyl ether - Organoheterocyclic compound - Ether - Organic oxide - Amine - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
• Descrizione: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 311.400 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 311.152 Da
• Monoisotopic Mass: 311.152 Da
• Topological Polar Surface Area: 38.800 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 365.000
• 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

Application Protocols

No assay protocols are specified for this item; refer to CoA/Spec Sheet. For general photopolymer use (literature/general):

• Prepare a resin with 0.5–1.0 wt% initiator in the monomer/oligomer matrix.
• Degas by N2 sparging for 5–10 min if oxygen inhibition is problematic.
• Coat a thin film (50–200 µm) and irradiate at 365–405 nm at 5–20 mW/cm² for 5–60 s; adjust based on film thickness and opacity.
• Assess cure via FTIR or tack test; post-cure as needed under inert atmosphere.

These general steps must be optimized for the specific formulation and light source. For synthetic applications, follow standard protocols for benzophenone derivatives with appropriate controls.

Biological Roles

This compound is a synthetic benzophenone-based photoinitiator/building block and is not known to have intrinsic biological roles.

• Biochemical interaction potential (literature/general): Aromatic ketones can photosensitize and generate reactive species under UV; tertiary amines can be protonated near physiological pH (pKaH typical for morpholines ~7–8.5), potentially affecting membrane association in model systems.
• Use context: Suitable for materials science, polymer chemistry, photopatterning of biomaterials, and surface modification. Any use involving biological matrices should consider cytocompatibility and extractables testing, as radicals and residuals may be deleterious to cells.
• No metabolic or pathway relevance is ascribed; it is provided strictly for research use in chemical and materials experiments.

Buffer Applications

Not typically applicable. This is not a buffering reagent and has no defined acid/base pair suitable for preparing standard biological buffers. For work in aqueous systems (e.g., photografting to hydrogels), choose a compatible buffer (PBS, HEPES) separately, and evaluate solubilization strategies (co-solvent or emulsification) as needed.

Green Alternatives

Selection of photoinitiators and solvents can be optimized for greener performance without sacrificing cure speed.

• Photoinitiator choices (literature/general):
  • Tethered benzophenone–amine systems (this compound) reduce migration versus separate amine synergists, potentially lowering extractables.
  • Alternatives: acetophenone or hydroxyalkyl ketone PIs (e.g., 1-hydroxycyclohexyl phenyl ketone), acylphosphine oxides (e.g., TPO, BAPO) with improved absorption at longer wavelengths for LED curing; thioxanthones for visible-light initiation. Trade-offs include cost, yellowing, migration, and toxicity profiles.

Comparison snapshot (literature/general):

• Benzophenone-amine (this item):

  • Pros: good efficiency, lower oxygen sensitivity, reduced amine migration.
  • Cons: UV-A requirement; potential odor/color; limited water compatibility.

• Acylphosphine oxides:

  • Pros: strong LED (365–405 nm) absorption; deep cure.
  • Cons: potential phosphate residues; cost.

• Hydroxyalkyl ketones:

  • Pros: lower odor, often better EHS profile.
  • Cons: shallower penetration at 365 nm; sometimes slower.

• Greener solvents for processing (literature/general): Prefer ethyl acetate, 2-MeTHF, dimethyl carbonate, or propylene carbonate over chlorinated solvents where feasible. Validate solubility and cure kinetics before scale-up.

Pharmaceutical Uses

No pharmacopeial excipient status is indicated. Not specified for this item; refer to CoA/Spec Sheet.

• Relevant formulation context (literature/general): Benzophenone-derived photoinitiators are used in UV-curable coatings/adhesives and research-grade photopolymer systems. For any contact with biomedical prototypes (e.g., dental resins, tissue-engineering scaffolds), comprehensive leachables/cytotoxicity testing is required. This product is supplied strictly for research and development use, not for human or animal administration.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting/boiling points: Not specified for this item; refer to CoA/Spec Sheet. For related para-disubstituted benzophenones, melting points often fall in the ~80–150 °C range (literature, compound-specific data required).
• Density/refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/general):
  • Expected to be soluble in common organic solvents (e.g., dichloromethane, THF, acetonitrile, ethyl acetate, toluene) due to aromatic core and tertiary amine; limited water solubility.
  • The morpholine moiety may enhance solubility in polar organics (MeCN, acetone, alcohols) vs. unsubstituted benzophenone.
• LogP (qualitative, literature expectation): Moderate hydrophobicity mitigated by one tertiary amine and one ether oxygen; exact value not established here.
• pKa (literature/general): Tertiary amine of morpholine typically pKaH ~7–8.5 (literature for N-substituted morpholines); exact value for this compound not specified.
• UV–vis (literature/general): Benzophenone chromophore shows n→π* absorption in near-UV (ca. 250–365 nm); the para-methoxy donor typically red-shifts/strengthens π→π* bands. Exact λmax and ε are not specified for this item.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting grades (general guidance):
  • Research grade materials are suitable for R&D, synthesis method development, and photopolymerization screening.
  • If offered as HPLC grade/low-UV (not specified here), such designation indicates tight control of UV-absorbing impurities critical for photophysical studies or chromatographic baselines.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Some photoinitiators are shipped with trace stabilizers to control premature radical formation; if present, this will be declared on the CoA.
• Batch documentation: For identity and purity verification, consult the lot-specific CoA for NMR, HPLC/GC purity, residual solvents, and water/peroxide/metal limits. When values are not stated here, they are: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Benzophenone chromophores are classic Type II photoinitiators. The para-morpholinomethyl substituent serves as a built-in amine donor, facilitating intramolecular hydrogen/electron transfer upon triplet excitation.

• Photoinitiation (literature/general):
  • Upon UV (≈ 320–380 nm) excitation, the n→π* triplet state of benzophenone abstracts a hydrogen from the benzylic or amine environment, generating radicals that initiate polymerization (e.g., acrylates, methacrylates, styrenics).
  • Tethering the amine (morpholine) can enhance initiation efficiency and reduce oxygen inhibition versus non-tethered benzophenone/amine blends.
• Applications:
  • UV-curing of inks, coatings, 3D printing resins, and adhesives; photoinduced grafting/modification of surfaces; initiating thiol–ene and acrylate homopolymerizations (literature).
  • Photoredox and photosensitization roles where benzophenone acts as a triplet sensitizer.
• Synthetic transformations (non-photochemical, literature/general):
  • Carbonyl chemistry: reduction to benzhydrols (e.g., NaBH4), Grignard additions to form tertiary carbinols.
  • Benzylic functionalization at the morpholinomethyl position (e.g., oxidation to iminium followed by nucleophile trapping; reductive aminations).
  • Demethylation of the anisole to para-phenol (e.g., BBr3) for further diversification.
• Practical tips: Work under subdued light for non-photochemical steps; deoxygenate resin formulations to minimize inhibition; verify cure via FTIR (C=C conversion) or photo-DSC.

Reaction Conditions

• Photoinitiated polymerization (literature/general):

  • Wavelength: 320–405 nm (UV-A/near-UV LEDs); benzophenone absorbs more strongly ≤365 nm; para-methoxy can modestly red-shift.
  • Loading: 0.1–2.0 wt% relative to monomer/oligomer; optimize for formulation opacity and thickness.
  • Atmosphere: Reduced oxygen improves surface cure; use N2 purge, inert blankets, or amine synergists (tethered here) to mitigate inhibition.
  • Solvents/medium: Neat acrylates/methacrylates, or polar aprotic solvents (MeCN, EtOAc, propylene carbonate) when needed.
  • Monitoring: FTIR (C=C band decay), photo-DSC, gel fraction, tack-free time.

• Representative non-photochemical operations (literature/general):

  • Carbonyl reduction: NaBH4 or BH3·THF, 0–25 °C, protic quench; typical high conversions for benzophenone derivatives.
  • Demethylation: BBr3 in DCM, −78 to 0 °C, 1–6 h to give para-phenol; moisture exclusion required.
  • Quaternization: Alkyl halide in MeCN or acetone, 20–60 °C, 2–24 h to form morpholinium salts; isolate as halide or exchange anion.

All parameters are general literature guidance; verify on small scale for this specific compound.

Safety and Handling

• GHS classification, pictograms, H-statements: Not specified for this item; refer to SDS for authoritative safety information.
• Signal word: Not specified for this item; refer to SDS.
• General hazards (literature/general for benzophenone photoinitiators): May cause skin/eye irritation; harmful if swallowed; photosensitizing behavior under UV can generate radicals. Avoid UV exposure to bulk material outside intended experimental use.
• PPE: Laboratory coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure to dust or solvent vapors.
• Handling notes:
  • Avoid direct sunlight/UV during weighing and solution prep to prevent unintended photochemical reactions.
  • Prevent aerosol/dust formation; wash hands and exposed skin thoroughly after handling.
• Incompatibilities (general): Strong oxidizers, strong acids may protonate the tertiary amine; strong bases may promote side reactions at the benzylic position.
• First aid (overview; defer to SDS):
  • Eye/skin contact: Rinse cautiously with water for several minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Spill/Disposal: Collect solids by gentle sweeping; absorb solutions with inert material. Dispose according to local regulations and SDS guidance.

Solvent Selection

This aromatic ketone with a tethered tertiary amine dissolves readily in many organic solvents used for photochemistry and synthesis.

• Polarity/miscibility (literature/general):
  • Good solubility expected in DCM, chloroform, THF, acetone, acetonitrile, DMF/DMSO, ethyl acetate, toluene, and alcohols; poor in water.
  • The morpholine increases affinity for polar organics relative to unsubstituted benzophenone.
• Use-case guidance:
  • For photopolymer formulations: choose low-volatility solvents (e.g., acetonitrile, propylene carbonate) or use neat/oligomeric monomers to minimize solvent residues.
  • For synthesis/derivatization: DCM or THF are convenient for acyl and reductive transformations; MeOH/EtOH for quaternization or salt formation with acids.
• Comparison (literature/general):
  • Versus highly nonpolar PIs, this compound is more compatible with acrylate/urethane oligomers of moderate polarity.
  • Versus strongly protic media, neutral/polar aprotic solvents better preserve the tertiary amine basicity and maximize photoinitiation efficiency.
• If a chromatography solvent system is needed, start with hexane/EtOAc or toluene/EtOAc gradients; adjust with 0.5–1% Et3N to suppress amine tailing.

Storage and Reconstitution

• Storage conditions (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.
• Light sensitivity (literature/general): Store in amber container or protect from light to prevent unintended photoreactions.
• Moisture/air: Keep container tightly closed in a dry, well-ventilated place. For long-term stability studies, consult CoA for any stabilizers.
• Reconstitution: If supplied as a solid, prepare stock solutions in dry organic solvents (e.g., acetonitrile, DCM, THF, DMSO) at convenient concentrations (e.g., 10–100 mg/mL). Filter if particulates are present using PTFE syringe filters.
• Freeze–thaw guidance: Not typically required; if preparing DMSO or MeCN stocks for repeated use, aliquot to minimize light/air exposure.
• Research use note: For research use only (per Product Data).

Structure and Identity

A para-disubstituted benzophenone bearing a para-methoxy group on one ring and a para-morpholinomethyl substituent on the other. The benzophenone carbonyl links two phenyl rings; one ring is anisyl (–OCH3 at para), the other bears a –CH2–N(–CH2CH2–O–CH2CH2–) morpholine substituent at the para position.

• Product name: 4-Methoxy-4'-morpholinomethyl benzophenone
• CAS: 898769-72-7
• PubChem CID: 24724221
• InChIKey: 94375 (as provided; atypical length—consult CoA/SDS for verified identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C19H21NO3 (literature/computed from name)
• Molecular weight: ~311.38 g/mol (literature/computed)

Structural features (descriptive):

• Functional groups: aromatic ketone (benzophenone), anisole ether (–OCH3), tertiary amine within a morpholine ring tethered via a benzylic –CH2–.
• Substitution pattern: para–para disubstitution minimizes steric clash and increases conjugation; the methoxy is an electron donor, and the benzophenone carbonyl is an acceptor.
• Stereochemistry: none (achiral, no stereocenters).

Synthetic Utility

Functional group set enables multiple diversification vectors:

• Aromatic ketone (benzophenone):
  • Reductions to benzhydrols (NaBH4, hydrosilanes, catalytic hydrogenation) and further transformations to ethers/esters.
  • Nucleophilic additions (Grignard/organolithium) to form tertiary alcohols; potential for subsequent dehydrations or rearrangements (literature/general).
  • Photochemical triplet sensitizer for energy/electron transfer.
• Para-methoxy (anisole):
  • Demethylation to phenol (BBr3, AlCl3/thiols) unlocking cross-coupling via aryl triflates or Mitsunobu-type derivatizations (literature/general).
  • Direct electrophilic aromatic substitution is deactivated by the carbonyl across the scaffold; regioselectivity governed by para substitution.
• Morpholinomethyl (tertiary amine):
  • Quaternization (e.g., MeI, benzyl halides) to generate ammonium salts; salt formation with acids for altered solubility.
  • Benzylic oxidation to iminium followed by nucleophile capture (Mannich-like elaborations); reductive transformations at the benzylic position (e.g., catalytic hydrogenation) as handles for linker chemistry.

Collectively, this scaffold serves as a modular photoreactive handle with orthogonal reactivity at the carbonyl, ether, and tertiary amine.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent or antibody. No antigen/epitope, clone, isotype, or species reactivity information applies.