2-Chloro-4'-morpholinomethyl benzophenone , CAS No.898770-29-1

CAS: 898770-29-1 Cat. No.: C947403 Summenformel: C₁₈H₁₈ClNO₂ Molekulargewicht: 315.8 PubChem CID: 24724245

Storage

Room temperature

Spezifikationen

Storage

Room temperature

Namen und Kennungen

Kanonisches Lächeln

C1COCCN1CC2=CC=C(C=C2)C(=O)C3=CC=CC=C3Cl

IUPAC Name

(2-chlorophenyl)-[4-(morpholin-4-ylmethyl)phenyl]methanone

InChIKey

JKPBLYDSZACPQS-UHFFFAOYSA-N

INCHI

1S/C18H18ClNO2/c19-17-4-2-1-3-16(17)18(21)15-7-5-14(6-8-15)13-20-9-11-22-12-10-20/h1-8H,9-13H2

Isomere SMILES

C1COCCN1CC2=CC=C(C=C2)C(=O)C3=CC=CC=C3Cl

PubChem CID

24724245

Molekulargewicht

315.8

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Aryl-phenylketones Diphenylmethanes Benzoyl derivatives Benzylamines Phenylmethylamines Chlorobenzenes Aralkylamines Morpholines Aryl chlorides Vinylogous halides Trialkylamines Dialkyl ethers Azacyclic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives Organochlorides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzophenone - Diphenylmethane - Aryl-phenylketone - Phenylmethylamine - Aryl ketone - Benzylamine - Benzoyl - Aralkylamine - Chlorobenzene - Halobenzene - Aryl chloride - Morpholine - Oxazinane - Aryl halide - Vinylogous halide - Ketone - Tertiary aliphatic amine - Tertiary amine - Oxacycle - Azacycle - Dialkyl ether - Organoheterocyclic compound - Ether - Organic oxygen compound - Organic nitrogen compound - Amine - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Aromatic heteromonocyclic compound
• Beschreibung: 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 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: 362.000
• 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

Not applicable. No validated bioassay or immunoassay protocols are associated with this small-molecule reagent. For synthetic uses, refer to the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for guidance.

Biological Roles

This product is a synthetic organic intermediate and is not a biological molecule. No endogenous biological role is expected.

General considerations (literature/chemistry-focused)

• Tertiary amines like morpholine can engage in acid–base interactions and may affect membrane partitioning in model systems, but this compound is not intended for biological function studies unless used as a synthetic precursor.
• Benzophenone moieties are frequently used as photoaffinity labels due to their triplet-state reactivity; derivatives can covalently capture nearby C–H sites upon irradiation. If adapted as a photo-crosslinking probe, appropriate linkers/bioconjugation handles are typically required.

Research Use Note

• For research use only. Not for human or veterinary use, diagnostics, or clinical applications.

Buffer Applications

Not typically applicable. This compound is a hydrophobic aryl ketone with a tertiary amine and is not used as a buffering agent. For experiments involving this reagent in aqueous systems, choose an appropriate external buffer (e.g., phosphate, HEPES) and introduce the compound via a cosolvent (DMSO, EtOH) or as a soluble acid salt of the amine when compatible.

Green Alternatives

Greener choices relate primarily to solvent and process selection; the core molecule itself contains chlorine (aryl chloride) and a tertiary amine.

• Solvent substitution (literature guidance)

  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or propylene carbonate when feasible.
  • For Pd-catalyzed couplings, consider aqueous micellar media (e.g., TPGS-750-M) or bio-derived solvents (2-MeTHF) instead of dioxane/toluene.

• Workup and purification

  • Favor crystallization or trituration (e.g., as an amine salt) over silica chromatography to reduce solvent consumption.
  • Use greener eluents (heptane/EtOAc) if chromatography is required.

• Energy and light usage

  • Photochemical steps: employ LED sources at 350–365 nm with narrow bandwidth; minimize UV excess and heat load.

Comparison snapshot (general)

• DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; DCM offers faster kinetics for some steps but carries higher environmental and health concerns.
• THF vs 2-MeTHF: 2-MeTHF (from hemicellulose) is more sustainable and forms fewer peroxides; however, it can contain water and has a higher boiling point, affecting concentration and drying.

Note: No greener structural analogue of this exact reagent is proposed here; optimization focuses on solvent/base/catalyst choices, waste minimization, and energy-efficient irradiation.

Pharmaceutical Uses

No pharmacopeial grade or excipient role is specified for this item; refer to CoA/Spec Sheet.

General context (non-clinical, discovery-focused)

• Morpholine-bearing benzophenones serve as versatile intermediates in medicinal chemistry campaigns to explore SAR around aryl ketone pharmacophores.
• The tertiary amine allows salt formation (e.g., HCl, maleate) to modulate solubility during intermediate handling and purification.
• The aryl chloride enables late-stage diversification via cross-coupling to access analog libraries.

Compliance reminder

• For research use only. Not for use in humans, veterinary applications, or clinical diagnostics.

Physical Properties

Item-specific specifications (this catalog entry)

• 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.

Literature/computed general properties for this structural class (non-item-specific)

• Expected physical state: aromatic benzophenone derivatives with morpholine substituents are typically crystalline solids or viscous oils depending on substitution pattern.
• Solubility (qualitative):
  • Organic solvents: good solubility in dichloromethane, chloroform, THF, ethyl acetate, acetone; high solubility in polar aprotics (DMF, DMSO).
  • Water: very low (hydrophobic aryl core; tertiary amine may increase only slightly in acidic water due to protonation).
• Lipophilicity: benzophenone core generally confers moderate to high logP; tertiary amines can reduce effective logD under acidic conditions (literature trend).
• UV/Vis: benzophenone chromophore typically shows strong absorption around 240–260 nm and 325–345 nm bands (literature for aryl ketones); substituents may shift maxima.
• Acid–base: tertiary morpholine nitrogen pKaH typically ~8.4–8.6 (literature for morpholine), enabling protonation in mildly acidic media.

Notes

• Do not treat the above as specifications. For exact numerical values (mp, bp, density, refractive index, UV cutoffs, residuals), consult the item’s CoA/SDS.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades (general)

• Research grade: suitable for synthetic and discovery applications; typical impurity controls include identity (NMR/LC–MS), assay, and residual solvents. UV–Vis background may be relevant if used in photochemistry.
• HPLC grade solvents/reagents (if applicable): low UV background and strict particulate/metal control—useful if compound will be analyzed by trace UV or LC–MS.
• Stabilizers: Not specified for this item; if present, stabilizers (e.g., trace acid scavengers) would be listed on the CoA.

What to check on receipt (practical advice)

• Verify identity by LC–MS or 1H NMR; benzophenone signals (singlet near ~7.6–7.9 ppm pattern) and benzylic CH2 adjacent to tertiary amine are diagnostic (literature practice).
• Inspect for discoloration; tertiary amines can darken upon oxidation. If necessary, purify by column chromatography under subdued light to protect the benzophenone chromophore.

Reaction and Applications

Use this benzophenone derivative as a dual-function building block: a photoactive aryl ketone and a tertiary amine handle, plus an aryl chloride suitable for cross-coupling.

• Cross-coupling at the aryl chloride (literature)

  • Suzuki–Miyaura, Buchwald–Hartwig, or Negishi couplings can be performed on aryl chlorides with modern Pd catalysts/ligands (e.g., XPhos, SPhos, BrettPhos). Enables late-stage diversification of the chlorinated ring.
  • Tips: ensure rigorous degassing, employ bases such as K3PO4, Cs2CO3, or NaOtBu; use toluene/dioxane/DMAc at 80–110 °C.

• Mannich/benzyl chemistry at the morpholinomethyl unit (literature)

  • Quaternization: N-alkylation of morpholine nitrogen affords ammonium salts (useful for phase transfer or ionic handles).
  • Dealkylation/derivatization: benzylic CH2 adjacent to tertiary amine can participate in oxidative or reductive manipulations; salts can improve crystallinity for purification.

• Photochemistry of the benzophenone core (literature)

  • Triplet-excited benzophenone abstracts hydrogen from donors; can initiate radical processes or serve as a sensitizer.
  • Paternò–Büchi cycloadditions with alkenes under 320–365 nm light yield oxetanes; substituents modulate regioselectivity.

• Carbonyl transformations (literature)

  • Reductions (NaBH4, catalytic hydrogenation) to benzhydrols; subsequent functionalization possible.
  • Electrophilic activation (e.g., formation of imines/Schiff bases with amines after derivatization) less typical without prior modification.

Applications

• Medicinal chemistry intermediate for morpholine-containing scaffolds.
• Photoinitiator/sensitizer studies where a tertiary amine acts as donor in intramolecular PET.

Note: No manufacturer-specific application text was provided; guidance above is literature-based.

Reaction Conditions

Representative literature conditions (general guidance; not item-specific specifications)

• Suzuki–Miyaura coupling at aryl chloride

  • Catalyst: Pd2(dba)3 (1–2 mol%) with XPhos or SPhos (2–4 mol%), or Pd-PEPPSI (NHC) variants.
  • Base: K3PO4 (2–3 equiv) or Cs2CO3.
  • Solvent: toluene or 1,4-dioxane; alternatives include DMAc or 2-MeTHF.
  • Temperature/time: 90–110 °C, 4–16 h under N2/Ar.
  • Notes: water (5–10%) can accelerate some Suzuki couplings; ensure amine does not coordinate deleteriously—ligand excess helps.

• Buchwald–Hartwig amination (if replacing Cl by amine)

  • Catalyst/ligand: Pd(OAc)2 with BrettPhos/XPhos; NaOtBu or K3PO4 as base.
  • Solvent: toluene, dioxane, or tBuOH.
  • 80–110 °C; 6–18 h.

• Quaternization of morpholine nitrogen

  • Electrophile: alkyl halide (e.g., MeI, benzyl bromide).
  • Solvent: acetonitrile, acetone, or neat; rt to 60 °C; 1–24 h.
  • Workup: triturate with ether to isolate ammonium salt.

• Photochemical transformations of benzophenone core

  • Light source: 320–365 nm LEDs; oxygen-free atmosphere for hydrogen abstraction pathways.
  • Solvent: acetonitrile, isopropanol (as H-donor), or nonpolar hydrocarbons depending on mechanism.
  • Temperature: 0–25 °C; monitor by TLC/LC–MS.

Expected outcomes

• Modern catalyst systems routinely furnish 60–90% isolated yields in couplings of aryl chlorides (literature range). Optimize ligand/base to account for tertiary amine presence.

Safety and Handling

Item-specific hazard information

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• Hazard (H-) Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety guidance for benzophenone-based, tertiary-amine-containing organics (literature/standard practice)

• Likely hazards: eye/skin irritation; harmful if swallowed; combustible solid or liquid depending on form. Avoid inhalation of dust or aerosols.
• Personal protective equipment (PPE): lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood.
• Handling: avoid light exposure during photochemical experiments (benzophenone chromophore is photoactive); minimize contact with oxidizers. Tertiary amines may form salts with strong acids—handle accordingly.
• Incompatibilities: strong oxidizing agents; strong acids (may form ammonium salts); strong bases in presence of alkyl halides can quaternize the amine.
• First aid (overview, defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contact lenses if easy.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: use CO2, dry chemical, or foam. Combustion can produce CO/CO2, HCl, and nitrogen oxides.

Always consult the product-specific SDS for authoritative, up-to-date safety and regulatory information.

Solvent Selection

Polarity and miscibility (general guidance)

• Polarity class: moderately lipophilic aryl ketone with a tertiary amine; exhibits good solubility in mid-polar aprotic media.
• Recommended solvents for dissolution and processing:
  • High solubility: DMSO, DMF, NMP.
  • Good solubility: dichloromethane (DCM), chloroform, THF, ethyl acetate, acetone, toluene (warm).
  • Poor solubility: water at neutral pH; solubility improves in dilute aqueous acid via amine protonation.

Selection scenarios

• For analytical stock solutions: DMSO (for bioassays) or acetonitrile (for LC), possibly with 0.1% acid if a protonated form is desired.
• For cross-coupling at the aryl chloride: toluene, dioxane, or DMAc are common (literature for Pd-catalyzed couplings of aryl chlorides); ensure base compatibility.
• For photochemical transformations (e.g., Paternò–Büchi, H-abstraction): solvents of low UV cut-off (e.g., acetonitrile, cyclohexane, ethyl acetate); avoid strong H-donors unless intentionally used as quenchers.

Quick comparison (literature/typical)

• DCM vs EtOAc: DCM gives faster dissolution and better handling for chromatography; EtOAc is greener and safer.
• THF vs 2-MeTHF: similar solvation; 2-MeTHF offers greener profile and higher hydrophobic partitioning; watch water content.

Note: Exact solubility values and UV cutoffs are not specified for this item; refer to CoA/Spec Sheet as needed.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Store in a tightly closed container, protected from light to preserve the benzophenone chromophore. Keep dry and under inert atmosphere if long-term storage is intended to minimize oxidative discoloration of the tertiary amine.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/stock solutions: Dissolve in anhydrous DMSO, DMF, or dichloromethane to prepare concentrated stocks. For aqueous work, prepare an acidified aqueous solution of its ammonium salt or use a cosolvent system.
• Stability notes (general): Tertiary amines can slowly oxidize on air/light; minimize exposure to strong light and oxidants. Benzophenone moiety is photoactive—store in amber glass if possible.
• Freeze–thaw guidance: Not typically necessary; if storing stock solutions, aliquot and freeze at ≤−20 °C for DMSO solutions to avoid repeated freeze–thaw cycles.

Always consult the CoA/SDS for definitive storage and handling instructions.

Structure and Identity

A benzophenone derivative bearing an ortho-chloro substituent on one ring and a para-morpholinomethyl substituent on the other, providing a photoreactive aryl ketone core with a tertiary amine.

• Item-specific identifiers (from Product Data)

  • SKU: C947403
  • Product Name: 2-Chloro-4'-morpholinomethyl benzophenone
  • CAS: 898770-29-1
  • PubChem CID: 24724245
  • InChIKey: 162870 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (chemistry description)

  • Core: benzophenone (diphenyl ketone) scaffold.
  • Substituents: chlorine at the 2-position of one phenyl ring; morpholinomethyl [–CH2–N(morpholinyl)–] at the 4′-position of the other phenyl ring.
  • Functional groups: aryl ketone (photochemically active), tertiary amine (in morpholine), ether (ring oxygen in morpholine), aryl chloride (cross-coupling handle).
  • Ring systems: two benzene rings plus one morpholine heterocycle (six-membered O,N-heterocycle).
  • Stereochemistry: none (achiral as named).

• Computed/literature identity (non-item-specific)

  • Approximate molecular formula (computed from name): C18H18ClNO2 (literature/computed)
  • Approximate molecular weight: ~315.8 g/mol (literature/computed)

• 2D description in words

  • The carbonyl carbon joins two phenyl rings. On one ring, the ortho carbon (relative to the carbonyl) bears Cl. On the other ring, the para carbon (relative to the carbonyl) is bonded to a –CH2– that connects to the morpholine nitrogen, yielding an N-(benzyl) morpholine.

Synthetic Utility

Key handles and reactivity (literature)

• Aryl chloride: entry point for Pd-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Stille, Negishi) to install (hetero)aryl, vinyl, or amine substituents on the chlorinated ring.
• Benzophenone carbonyl: reducible to benzhydrols; photochemically reactive for radical initiation or Paternò–Büchi cycloadditions; enolate chemistry is limited but possible under strong basic conditions at the benzylic position of substituted analogs.
• Morpholinomethyl tertiary amine: quaternization to generate onium salts; site for further N-functionalization (acylation is not typical on tertiary amines, but N-oxidation to amine N-oxide is possible with mCPBA).

Retrosynthetic value

• Disconnection suggests a Mannich-type introduction of the morpholinomethyl group onto a 4-substituted benzophenone, or N-alkylation of morpholine with a 4-(chloromethyl)benzophenone derivative, followed by selective aryl functionalization.

Practical notes

• Protect from strong acids during reactions intended to keep the amine free base; form salts deliberately for purification/crystallization.
• For cross-coupling, ligand choice is critical to activate aryl chlorides; bulky biaryl phosphines or Pd–NHC systems are effective.
• The benzophenone chromophore can complicate UV-based analytics due to strong absorbance—adjust detector wavelengths accordingly.

Target Specificity

Not applicable. This product is a small-molecule reagent/building block and is not an antibody, enzyme, or affinity reagent. No antigen/epitope or biological target specificity is defined for this catalog item.

Häufig gestellte Fragen

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 898770-29-1, the molecular formula is C18H18ClNO2, and the molecular weight is 315.8 g/mol. InChIKey JKPBLYDSZACPQS-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.