2-Methoxy-3'-morpholinomethyl benzophenone - ≥95% , CAS No.898765-05-4

CAS: 898765-05-4 Cat. No.: M1253277 Formule: C₁₉H₂₁NO₃ Poids moléculaire: 311.381 PubChem CID: 24724671

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥95%

Noms et identifiants

Sourires canoniques

COC1=CC=CC=C1C(=O)C2=CC=CC(=C2)CN3CCOCC3

IUPAC Name

(2-methoxyphenyl)-[3-(morpholin-4-ylmethyl)phenyl]methanone

InChIKey

DNQLKRZGUNRODU-UHFFFAOYSA-N

INCHI

1S/C19H21NO3/c1-22-18-8-3-2-7-17(18)19(21)16-6-4-5-15(13-16)14-20-9-11-23-12-10-20/h2-8,13H,9-12,14H2,1H3

Isomères SMILES

COC1=CC=CC=C1C(=O)C2=CC=CC(=C2)CN3CCOCC3

PubChem CID

24724671

Poids moléculaire

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
• Description: 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

Propriétés chimiques et physiques

• Poids moléculaire: 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: 381.000
• 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 validated biological assay protocols are provided for this item. As a general laboratory reagent:

• Stock preparation (general): Dissolve in a suitable organic solvent (e.g., DMSO, acetonitrile, ethanol) to prepare a concentrated stock (e.g., 10–100 mM). Filter through 0.22 μm PTFE if particulate is present.
• Photochemical experiments (general): Prepare solutions in amber vials, degas if needed, irradiate at 350–365 nm with calibrated intensity, and analyze by HPLC/LC–MS.
• Purification (general): Silica gel chromatography using DCM/MeOH gradients; or reverse-phase preparative HPLC if strong adsorption occurs.

For any application, optimize conditions empirically. No item-specific dilutions or positive controls are provided.

Biological Roles

This product is a synthetic benzophenone derivative intended for research and chemical synthesis; it is not a natural metabolite.

General/literature context (no clinical claims)

• Benzophenone chromophores are widely used in chemical biology as photoaffinity labels: upon UV irradiation, the triplet state can abstract hydrogen to form a diradical that inserts into C–H/N–H bonds, creating covalent adducts. The presence of a tertiary amine (morpholine) can aid cellular uptake in probe designs and enables salt formation for improved aqueous handling.
• The methoxy substituent can modulate electronic properties of the aryl ketone, tuning absorption and reactivity (general effect observed for substituted benzophenones).

No endogenous biological role is assigned to this compound. Any use in biological experiments should be under appropriate research approvals, with conditions optimized empirically for the specific system.

Buffer Applications

Not typically applicable. 2-Methoxy-3'-morpholinomethyl benzophenone is a non-buffering organic small molecule. It does not constitute a defined buffer system.

Practical note (general)

• If used in aqueous biological assays, it may be dissolved as a stock in DMSO or ethanol and then diluted into a suitable buffer (e.g., phosphate, HEPES). Final organic solvent content should be minimized to avoid perturbing the system. These are general handling practices and not product specifications.

Green Alternatives

Greener considerations here focus on the solvents and operations commonly used with benzophenone derivatives; the compound itself is a specific research reagent without direct “green substitute.”

Greener solvent choices (literature/general)

• Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), or dimethyl carbonate (DMC) when reaction compatibility allows.
• For polar aprotic needs, consider propylene carbonate or Cyrene as alternatives to DMF/DMAc/DMSO in certain transformations.
• For extractions, ethyl acetate or MTBE can often replace DCM; for recrystallizations, favor ethanol/isopropanol over toluene/benzene.

Photochemistry process improvements

• Use LED sources (365–405 nm) with narrow bands to reduce energy consumption and off-target photolysis compared to broadband mercury lamps.
• Conduct reactions in flow photoreactors to enhance photon efficiency and minimize solvent volumes (literature best practice).

Trade-offs (balanced view)

• 2-MeTHF is bio-based and has favorable safety vs THF but can contain peroxides; institute peroxide monitoring.
• Cyrene/propylene carbonate have higher viscosity and may slow mass transfer; heating or dilution may be required.

Mini comparison (general)

• DCM vs 2-MeTHF: similar solvating power for many organics; 2-MeTHF is less toxic, higher bp, partially water immiscible—beneficial for extractions but may complicate removal.

Pharmaceutical Uses

This item is supplied for research use only. No therapeutic or clinical use is claimed or implied.

General formulation context (literature/general)

• Benzophenone-containing intermediates are sometimes encountered during discovery-stage synthesis of photoaffinity probes or analytical reagents. The tertiary amine allows formation of salts (e.g., HCl) to enhance crystallinity and handling.
• As an excipient or approved additive: Not applicable for this specific item; no pharmacopoeial status is indicated. Any use in GMP or regulated settings would require full specification, validation, and regulatory review.

Manufacturing note

• When used as a process intermediate, control of residual solvents, related substances, and inorganic residues should be verified by batch CoA and in-house QC. UV-absorbing nature may aid in-process monitoring by HPLC/UV (general practice).

Physical Properties

Item-specific data

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index / density / BP / MP / UV cutoff / water content / residual metals: Not specified for this item; refer to CoA/Spec Sheet.

Literature- and structure-informed expectations (not specifications)

• Phase at ambient conditions: likely a solid or viscous oil for benzophenone derivatives of this size; exact form varies by purity and solvate content (literature/general).
• Solubility (qualitative): expected to be soluble in polar organic solvents (e.g., DCM, THF, acetonitrile, acetone) and in protic solvents like methanol/ethanol due to the tertiary amine; limited solubility in water (literature/general for morpholine-bearing benzophenones).
• Acid–base behavior: contains a tertiary amine (morpholine) that can be protonated under acidic conditions; no phenolic OH (methoxy is not ionizable under neutral conditions) (literature/general).
• UV–vis: benzophenone chromophores typically show strong absorption in the 240–260 nm region and a band around 330–360 nm depending on substitution (literature/general for benzophenones). Exact λmax/ε for this item: Not specified; refer to CoA/Spec Sheet.

Note: The above values are general guidance based on the named structure; consult the product CoA/SDS for item-specific physical data.

Quality and Grades

Item-specific

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and implications (general)

• Research-grade organics are commonly supplied at ≥95% purity unless otherwise specified; exact assay, residual solvents, and related-substance limits are batch-dependent and should be verified on the Certificate of Analysis (CoA).
• If offered in HPLC grade (not specified for this item), that would imply low UV background and minimal nonvolatile residues suitable for analytical work. If labeled AR/ACS grade, this would refer to meeting broadly recognized reagent standards; again, not specified here.
• Stabilizers: None are specified for this item. For benzophenone derivatives, no stabilizer is typically required, but protection from light is prudent to minimize photochemical side reactions (general practice).
• What to check on receipt:
  • Identity confirmation (e.g., NMR, MS) and assay from CoA.
  • Appearance matches CoA description (solid vs oil).
  • Residual solvents, water (Karl Fischer), and related substances if critical to your process.

For regulated applications or critical synthesis steps, request full spec sheet/CoA for the lot to confirm suitability.

Reaction and Applications

Notes below are general/literature guidance for benzophenone-based, morpholine-bearing building blocks; they are not item-specific specifications.

Photochemistry and labeling

• The benzophenone unit is a classic triplet-state photoreactive group used in photo-crosslinking/photoaffinity labeling. Substitution (methoxy, morpholinomethyl) can tune absorption and triplet energies; practitioners often irradiate around 350–365 nm (literature practice for benzophenones).

Synthetic applications as a building block

• Nucleophilicity/basicity: The morpholine nitrogen acts as a tertiary amine base/nucleophile; it can be quaternized (e.g., with MeI) to generate ammonium salts useful for phase-transfer.
• Redox chemistry: The diaryl ketone can undergo chemoselective reductions to benzhydrols (NaBH4, hydrosilanes, catalytic hydrogenation) or Wolff–Kishner/Clemmensen conditions to the diarylmethane (literature/general).
• Derivatization: Formation of oximes/hydrazones with hydroxylamine/hydrazines; Baeyer–Villiger oxidation to aryl benzoates may be feasible depending on substituent orientation.
• Demethylation: The 2-methoxy group can be transformed to phenol via BBr3 or AlCl3/thiols (literature), opening routes to ether formation or further coupling.
• C–C coupling on aryl rings: If halogen handles are introduced, standard Suzuki/Heck/Buchwald–Hartwig chemistry can elaborate the scaffold.

Practical tips

• Protect from intense light during manipulations not intended to be photochemical to avoid side reactions.
• When protonated (acidic media), the amine may enhance aqueous workup and facilitate salt-based crystallization for purification.
• For photochemical work, degassing (N2/Ar sparge) improves reproducibility by minimizing oxygen quenching (general photochemistry practice).

Reaction Conditions

General, literature-based conditions for transformations of benzophenone derivatives with tertiary amines (guidance only; optimize per application)

• Photocrosslinking/photoactivation:

  • Solvents: acetonitrile, ethanol, or aqueous buffer with ≤5% DMSO/MeOH cosolvent.
  • Atmosphere: degassed (N2/Ar) to reduce oxygen quenching.
  • Light: 350–365 nm LEDs; intensity 10–50 mW/cm².
  • Temperature: 0–25°C to limit side reactions.
  • Time: minutes to hours depending on geometry and concentration (literature general for benzophenones).

• Carbonyl reduction to benzhydrol:

  • Reagents: NaBH4 in MeOH/EtOH; or catalytic hydrogenation (Pd/C, H2 1–3 bar) in EtOH/EtOAc.
  • Temperature: 0–25°C (NaBH4) or rt–50°C (H2).
  • Typical outcome: high conversion within 0.5–4 h (literature/general).

• Demethylation of aryl methoxy to phenol:

  • Reagent: BBr3 (1–3 equiv) in DCM at −78 to 0°C, then warm to rt.
  • Workup: quench with MeOH/H2O; isolate phenol (literature).

• Quaternization of morpholine N:

  • Alkyl halides (e.g., MeI, benzyl bromide) in acetonitrile or acetone; rt–50°C, 2–24 h; precipitated ammonium salts often isolate readily (literature/general).

These conditions are representative of the scaffold class; verify compatibility with all substituents and scale. Item-specific parameters are not provided—consult primary literature and perform trials.

Safety and Handling

Item-specific hazard data

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification/Pictograms: Not specified for this item; refer to SDS.
• Research use: For research use only.

General safety guidance (literature/practice; defer to SDS for authoritative instructions)

• Likely hazards: Aromatic ketones and tertiary amines are commonly classified as irritants; avoid inhalation, ingestion, and skin/eye contact.
• PPE: Use lab coat, safety glasses, and nitrile gloves. Handle in a fume hood to minimize vapor/aerosol exposure.
• Light sensitivity: Benzophenone chromophores can undergo photochemical reactions; handle/store away from strong UV sources. Use amber glassware when practical (general guidance for benzophenones).
• Incompatibilities: Separate from strong oxidizers, strong acids (which can form ammonium salts), and acid chlorides/anhydrides (which may react with the tertiary amine). Avoid bases/alkoxides when undesired N-alkyl cleavage is possible (general guidance).
• First aid (overview): In case of contact, rinse affected area with water for 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. Seek medical attention as needed. Always consult the SDS.
• Spills/waste: Absorb small spills with inert material; dispose of in accordance with local regulations. Prevent release to drains.

Always consult the current SDS for definitive hazard and response information.

Solvent Selection

Compound type and polarity (general expectation)

• Mixed polarity: an aryl ketone with a tertiary amine (morpholine) and methoxy group; overall moderately polar, favoring dissolution in polar aprotic and many alcohols.

Miscibility/solubility tendencies (literature/general for similar structures)

• Good: dichloromethane, chloroform, THF, acetonitrile, acetone, ethyl acetate, DMF/DMAc/DMSO, methanol/ethanol/isopropanol.
• Limited: nonpolar hydrocarbons (hexanes, heptane) unless co-solvent used.
• Aqueous: typically low water solubility at neutral pH; solubility increases under acidic conditions via protonation of the morpholine nitrogen.

Selection tips by use case

• Reaction medium: choose DCM or THF for photochemical or electrophilic steps where the amine remains unprotonated; MeOH/EtOH if protonation is acceptable or desired.
• Purification: reverse-phase LC (MeCN/H2O + 0.1% formic acid) can help if silica shows strong retention due to H-bonding; otherwise normal-phase silica with DCM/MeOH mixtures is typical.
• Spectroscopy: for UV–vis studies, choose acetonitrile or ethanol with known low background; avoid strongly absorbing/aromatic solvents if measuring in the 240–360 nm range.

Comparison (general)

• Versus unsubstituted benzophenone: the morpholine substituent increases polarity and basicity, improving solubility in polar media and enabling salt formation for handling.

Storage and Reconstitution

Item-specific

• Storage Conditions: Room temperature (as provided).
• Shipped In: Normal (ambient) conditions.

General best practices (literature/practice; not specifications)

• Protect from light to minimize unintended photochemical reactions of the benzophenone chromophore (store in amber container or cabinet).
• Store in a tightly closed vial under dry conditions; if long-term storage is planned, consider under inert gas to limit oxidative degradation.
• Avoid prolonged exposure to strong acids/bases in storage which can lead to salt formation or degradation.
• If solidifies or is highly viscous, gently warm (30–40°C) to aid dissolution; do not overheat or expose to strong UV.

Reconstitution/solution handling (general)

• Solvents: DMSO, acetonitrile, ethanol, methanol, or dichloromethane typically dissolve benzophenone derivatives well.
• Prepare fresh solutions when possible for photochemical work; if storing solutions, keep in amber vials at 2–8°C and use within a few days.

Always refer to the product’s CoA and SDS for lot-specific stability, appearance, and handling guidance.

Structure and Identity

Brief overview: 2-Methoxy-3'-morpholinomethyl benzophenone is a benzophenone (diaryl ketone) bearing a methoxy group on one ring and a morpholinomethyl substituent on the other. The scaffold is useful where a benzophenone chromophore and a tertiary amine handle are desired.

Item-specific (from Product Data)

• SKU: M1253277
• Product Name: 2-Methoxy-3'-morpholinomethyl benzophenone
• CAS: 898765-05-4
• InChIKey: 68145 (as provided)
• 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/literature-based description of the named structure)

• Core: benzophenone (diphenyl ketone) with a central carbonyl bridging two phenyl rings.
• Substitution pattern: one ring 2-methoxy-substituted; the other ring bears a benzylic –CH2–morpholine at the 3′-position (meta to the carbonyl).
• Functional groups: aryl ketone (photoreactive chromophore), aryl ether (methoxy), tertiary amine (morpholine).
• Heteroatoms: O (carbonyl and methoxy) and O/N within the morpholine ring.
• Stereochemistry: none (achiral as named; no stereocenters expected).

2D verbal depiction (general)

• Two phenyl rings linked by a carbonyl (Ph–C(=O)–Ph). One ring carries an ortho-methoxy. The opposite ring carries a benzylic –CH2– tether to a 1,4-oxazacyclohexane (morpholine).

Synthetic Utility

Functional elements and reactivity (general)

• Diaryl ketone (benzophenone): platform for reduction (to benzhydrol), imine/oxime formation, Baeyer–Villiger oxidation, and photochemical transformations.
• Methoxy (Ar–OMe): can be a directing group in electrophilic aromatic substitution; removable via BBr3 demethylation to phenol, enabling further derivatization (ether/ester formation).
• Morpholinomethyl: tertiary amine can be protonated, quaternized, or engaged in Mannich-type elaborations; the benzylic methylene may undergo selective oxidation to the corresponding benzyl alcohol/aldehyde under mild conditions (literature/general).

Retrosynthetic value

• Serves as a convergent node combining a photoactive aryl ketone and a solubilizing/basic handle. Useful in constructing photoaffinity probes, polymer modifiers, or surface-anchoring ligands where post-functionalization through the amine is desired.

Named reactions/platforms (examples)

• Reductive amination (installing or modifying the –CH2–N functionality on the aryl ring).
• Formation of oxime/semicarbazone derivatives for characterization or further transformations.
• Photoinitiated radical coupling or crosslinking leveraging the benzophenone triplet (general benzophenone chemistry).

Separation/handling

• Formation of amine salts (e.g., HCl) can aid crystallization/purification; free-basing regenerates the neutral amine for further reactions.

Target Specificity

Not applicable. This product is a small-molecule organic reagent, not an antibody, enzyme, or biorecognition reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.