This compound belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
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.
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Application Protocols
No assay or bioanalytical protocols are specified for this item in the Product Data.
General lab use suggestions (non‑validated, literature‑style):
Stock solutions: prepare 10–100 mM in DMSO, DMF, ethanol, or methanol; filter (0.22 µm PTFE) for analytical work.
Salt formation for aqueous tests: dissolve in minimal ethanol, add 1–2 eq HCl in ethanol to form the hydrochloride; concentrate and triturate with MTBE/Et2O; dry thoroughly.
Purity check: 1H NMR (CDCl3), LC–MS; confirm absence of unreacted 2‑naphthol and bis‑alkylated materials.
For application‑specific SOPs (e.g., catalysis screens, materials modification), develop and validate internally.
Biological Roles
This product is supplied for research and laboratory use only. No biological activity or clinical utility is claimed.
General literature context (not item‑specific, no medical claims):
Mannich bases of 2‑naphthol can serve as intermediates to o‑quinone methides, which are reactive electrophiles in bioconjugation studies. Tertiary amines may form salts that increase aqueous compatibility for assay development.
The morpholine motif is common in medicinal chemistry scaffolds due to its balanced basicity and polarity; however, any biological function of this exact compound is not established here.
Practical note: If used in biochemical experiments (e.g., probe synthesis), prepare fresh stock in DMSO or ethanol, filter sterilize if required for in vitro systems, and confirm purity by LC–MS to avoid confounding results.
For any biological testing, consult institutional safety and ethics guidelines; this reagent is not intended for human or animal therapeutic use.
Buffer Applications
Not typically used as a buffer component. This compound lacks the defined conjugate acid/base pairs with narrow pKa spacing required for standard biochemical buffers.
If handling in aqueous systems is needed: prepare as a dilute acid salt (e.g., hydrochloride) to enhance water solubility, and use an established buffer (e.g., phosphate, HEPES, acetate) for pH control.
Recommended approach: dissolve the compound in a compatible co‑solvent (DMSO, ethanol) and dilute into the working buffer below 1–2% v/v organic where the biology tolerates it.
Green Alternatives
Context: This compound is a specialty building block/catalyst, not a bulk solvent or reagent with common green alternatives. Greener choices relate to the reaction medium and transformation rather than replacing the molecule itself.
Greener solvent choices (literature, when applicable):
Replace DCM/CHCl3 with ethyl acetate, 2‑MeTHF, CPME, or toluene where solubility/reactivity allow.
Favor alcohols (EtOH, i‑PrOH) over MeOH/DMF/DMSO when compatible with the chemistry.
Example comparison (general):
DCM vs. 2‑MeTHF: 2‑MeTHF is bio‑based, higher boiling (safer handling), and water‑immiscible; DCM offers faster extractions and lower viscosity but is a chlorinated solvent.
DMF/DMSO vs. CPME/EtOAc: DMF/DMSO provide superior polarity for generating phenoxide in situ; CPME/EtOAc are greener but may require higher temperatures or bases.
Process considerations:
Salt formation for isolation can reduce solvent volumes (crystallization from EtOH/EtOAc/MTBE systems).
Employ catalytic rather than stoichiometric bases when feasible (e.g., tertiary amines or carbonate bases recycled in flow).
Waste minimization:
Segregate amine‑containing organic waste; neutralize acids/bases before disposal per local regulations.
These are general green chemistry practices; specific feasibility should be verified experimentally.
Pharmaceutical Uses
No excipient or pharmacopeial role is specified for this item; it is provided for research use only.
General context (literature): morpholine‑containing aromatics are common in discovery chemistry. Compounds of this class may be used as intermediates during lead optimization or as synthetic handles (e.g., for quaternization to ionic liquids or for probe attachment). These statements do not imply suitability for GMP manufacturing.
Regulatory status: Not specified for this item; refer to CoA/Spec Sheet. There is no claim of USP/Ph. Eur./JP compliance.
If considering use in preformulation research: evaluate salt forms (hydrochloride, mesylate) to improve solubility, and characterize hygroscopicity, polymorphism, and stability under ICH conditions as part of internal R&D only.
Physical Properties
Item-specific (Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations (do not treat as item specs):
Physical state: typically a solid or viscous oil for related Mannich bases of 2‑naphthol; exact form depends on purity and solvate content. Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: commonly cited ~244 g/mol for C15H18NO2; verify on CoA.
Melting point / boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable unless liquid; not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative, literature):
Organic: good solubility in polar aprotic and protic solvents (e.g., DMSO, DMF, dichloromethane, ethyl acetate, methanol, ethanol); moderate in acetonitrile; limited in aliphatic hydrocarbons.
Aqueous: limited at neutral pH; solubility increases in acidic media (tertiary amine protonation) and decreases in strong base (phenoxide formation may increase water miscibility but depends on counter‑ion).
pKa (phenol): typically ~9–10 for 2‑naphthol derivatives (literature, substituent dependent). Tertiary ammonium pKaH of morpholine derivatives often ~6–7 (literature). Exact values for this specific compound: Not specified for this item; refer to CoA/Spec Sheet.
LogP: aromatic Mannich bases of 2‑naphthol are moderately lipophilic; exact value Not specified for this item; refer to CoA/Spec Sheet.
Always consult the item’s CoA/SDS for definitive specifications.
Quality and Grades
Item-specific (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research/technical grade Mannich bases are typically provided with NMR/LC or HPLC purity; low‑level residual solvents or inorganic salts may be present depending on workup.
Where “analytical” or “HPLC” grade is indicated, expectations include high assay and low UV background/fluorescence. In the absence of a stated grade, verify suitability for sensitive applications (e.g., photophysics, trace catalysis) by consulting the CoA/SDS.
Stabilizers/inhibitors: None are indicated in the Product Data. If stabilizers were used (e.g., antioxidant for phenolics), they would be listed on the CoA. Not specified for this item; refer to CoA/Spec Sheet.
What to check on receipt:
Identity: 1H/13C NMR consistent with benzylic CH2 (~3.5–4.5 ppm), phenolic OH (variable), and morpholine ring signals; HRMS for [M+H]+ around m/z ~244–245 (literature guidance only).
Purity: chromatography or qNMR; look for unreacted 2‑naphthol or morpholine adducts.
Residual solvents/water: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
Functional profile: a benzylic tertiary amine adjacent to a phenolic ring (Mannich base). The phenol can be deprotonated to a nucleophilic phenoxide; the tertiary amine can be protonated, quaternized, or serve as a non‑nucleophilic base/ligand.
Representative applications (literature/general; expand per project needs):
Building block for quaternary ammonium salts by alkylation at nitrogen (e.g., MeI, benzyl halides), yielding phase‑transfer catalysts or ionic materials.
Precursor to o‑quinone methide chemistry: under acidic/thermal conditions, Mannich bases of 2‑naphthol can undergo C–N bond cleavage to generate electrophilic o‑quinone methide intermediates, enabling Friedel–Crafts‑type additions or cycloadditions.
Ligand/base in organocatalysis: tertiary amine can catalyze acylations, transesterifications, or Morita–Baylis–Hillman‑type activations; phenolic OH may participate in H‑bonding activation.
Protecting/activating handle: benzylic –CH2–N(morpholine) can be transformed (e.g., oxidation to aldehyde/acid after demannich), or displaced in electrophilic substitution sequences.
Polymer/additive chemistry: tertiary amine phenols are used as stabilizers and curing accelerators; this scaffold can be tailored by further functionalization (quaternization, acylation) for materials applications.
Practical tips:
For clean Mannich chemistry downstream, control acidity to avoid premature demannich (formation of colored quinone methides).
Phenoxide generation (K2CO3, Cs2CO3) enhances O‑alkylation/arylation; nitrogen is less nucleophilic (tertiary) but can be quaternized by strong electrophiles.
Oxidants (e.g., DDQ) may selectively target the benzylic position; monitor by TLC/UPLC (aromatic UV 254 nm).
Reaction Conditions
General literature guidance for this scaffold (verify experimentally for your system):
O‑Alkylation (Williamson ether synthesis):
Typical: substrate (1.0 eq), alkyl halide (1.2–1.5 eq), K2CO3 or Cs2CO3 (2–3 eq) in DMF or acetone, 25–60 °C, 2–16 h. Yields commonly 60–90% depending on electrophile.
Notes: exclude water; tertiary amine can capture HX; monitor for competing N‑quaternization with strong benzylic/allylic halides.
Demannich/quinone methide generation:
Conditions: TFA or p‑TsOH (0.1–1.0 eq) in toluene/CH2Cl2, 0–25 °C; or thermal in non‑nucleophilic solvent. Trap with nucleophiles (arenes, thiols, enamines). Work under inert atmosphere if prone to oxidation (colored byproducts).
Quaternization at nitrogen:
Conditions: alkyl halide (e.g., MeI, BnBr, 1.2–2.0 eq) in MeCN/acetone/EtOAc, 20–50 °C, 1–24 h. Isolate ammonium salt by precipitation with MTBE/Et2O.
Oxidation of benzylic position:
Reagents: DDQ or MnO2 in toluene/CH2Cl2, 0–25 °C. May afford benzyl‑oxidized products; control equivalents to avoid over‑oxidation.
Analytical monitoring:
TLC: strong UV at 254 nm; stains with ninhydrin typically negative (tertiary amine) but positive with universal stains (KMnO4, phosphomolybdic acid).
LC–MS: ESI+ detects [M+H]+ around m/z ~244–245 (literature estimate; confirm for your exact composition).
These are representative conditions from literature precedent for closely related Mannich bases; optimize for scale and substrate.
Safety and Handling
Item-specific (Product Data):
GHS signal word: Not specified for this item; refer to SDS.
H‑statements / classification / pictograms: Not specified for this item; refer to SDS.
General handling guidance (literature/good practice; not item‑specific):
Hazards: Aromatic phenols and tertiary amines can be irritating to skin, eyes, and respiratory tract. Avoid inhalation of dust/aerosols and contact with skin/eyes.
PPE: lab coat, nitrile gloves, safety glasses; handle powders in a fume hood.
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical advice.
Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
Storage: Store tightly closed at room temperature away from light and incompatible reagents. Keep dry to avoid hydrolysis or CO2 uptake upon phenoxide formation.
Spill response: collect solids by damp wiping or HEPA vacuum; for solutions, absorb with inert material; dispose per local regulations.
Always consult the product SDS for authoritative hazard classification and response.
Solvent Selection
This molecule is amphiphilic: aromatic phenol (hydrogen bonding donor/acceptor when deprotonated) and a tertiary amine embedded in morpholine (H‑bond acceptor; protonatable). Solvent choice depends on task (synthesis vs. formulation vs. analysis).
Polarity/miscibility (general):
Good solubility in DMSO, DMF, NMP, dichloromethane, chloroform, methanol, ethanol, acetone, ethyl acetate.
Limited solubility in water at neutral pH; forms water‑soluble salts in dilute mineral acid (e.g., HCl, H2SO4). Phenoxide salts are soluble in polar solvents; aqueous solubility may improve with appropriate counter‑ions.
Selection tips:
For NMR: CDCl3 typically resolves benzylic CH2 and morpholine signals; DMSO‑d6 may broaden phenolic OH via H‑bonding.
For reactions using the phenoxide: use polar aprotics (DMF, DMSO) or alcoholic solvents; add base (e.g., K2CO3) to generate phenoxide in situ.
For quaternization/acylation at nitrogen: polar aprotics (MeCN, DMF) support SN2/acylation; control moisture.
For salt formation (analytical or isolation): dissolve in minimal ethanol/acetone and add ether to precipitate amine salts.
Brief comparison (literature guidance):
DCM vs. EtOAc: DCM offers higher solubility and faster extractions; EtOAc is greener but may give partial crystallization.
MeOH/EtOH vs. i‑PrOH: MeOH dissolves more readily; i‑PrOH can induce crystallization on cooling.
Storage and Reconstitution
Item-specific (Product Data):
Storage conditions: Room temperature
Shipped in: Normal
General guidance:
Container: store in an amber, tightly sealed bottle to limit light and air exposure; include desiccant if long‑term storage is anticipated.
Stability: phenolic Mannich bases are generally stable at ambient conditions when dry; avoid prolonged exposure to acids (risk of demannich/quinone methide formation) and strong oxidants.
Reconstitution/stock preparation:
Organic stocks: dissolve to 10–100 mM in DMSO, DMF, MeOH, or EtOH. For moisture‑sensitive workflows, use anhydrous solvents.
Aqueous use: prepare a soluble salt (e.g., hydrochloride) or dissolve in minimal co‑solvent before dilution; maintain final organic content as low as compatible with your system.
Freeze–thaw: not typically required; if preparing aqueous salts, aliquot and freeze at −20 °C to avoid repeated freeze–thaw cycles.
Always refer to the product’s CoA and SDS for definitive handling and stability information.
Structure and Identity
A Mannich base derived from 2‑naphthol and morpholine; the naphthalene ring bears a phenolic OH at C‑2 and a benzylic morpholinomethyl substituent at C‑1 (–CH2–N(morpholine)). The tertiary amine is embedded in the morpholine ring; the phenol remains free.
Item-specific (Product Data):
CAS: 27438-39-7
CID: 33839
InChIKey: 383500 (as provided; see literature note below)
Storage: Room temperature; shipped under normal conditions
Research use: For research use only
Computed/literature identity (for reference; not item specifications):
Common name: 1‑Morpholinomethyl‑2‑naphthol
Synonyms (literature): 2‑Naphthol, 1‑(morpholinomethyl)‑; Mannich base of 2‑naphthol with morpholine
Molecular formula (literature): C15H17NO2 or C15H18NO2 is reported in the literature depending on tautomeric/analytical conventions; typical assignment: C15H17NO2–C15H18NO2 range. Verify on the CoA.
Approximate formula most commonly cited (literature): C15H17NO2–C15H18NO2; MW ~243–244 g/mol. Not specified for this item; refer to CoA/Spec Sheet.
2D description: a naphthalene bearing OH at C‑2 (ortho to the benzylic substituent); at C‑1, a –CH2–N(R) linkage connects to a six‑membered morpholine ring (–N–CH2–CH2–O–CH2–CH2–). No stereocenters.
SMILES (literature): Oc2ccc1ccccc1c2CN3CCOCC3
InChIKey (literature): Not specified here; refer to authoritative databases; confirm against CoA.
Synthetic Utility
Transformable handles:
Phenol: O‑alkylation/arylation (Williamson ether synthesis, Chan–Lam under Cu), esterification (Steglich), sulfonylation (Ar–O–SO2R), and directed metalation after phenoxide formation.
Tertiary amine: quaternization (R–X), acylation to amide salts under forcing conditions, or conversion to amine oxides (mCPBA) for further rearrangements.
Named/representative reactions (literature):
Demannich/retro‑Mannich to access o‑quinone methides from 2‑naphthol frameworks.
Etherifications via phenoxide in polar aprotics (DMF, DMSO) using alkyl halides/tosylates.
Copper‑mediated O‑arylation (Chan–Lam) from phenol to aryl boronates in the presence of amine ligands.
Retrosynthetic value:
Serves as a masked o‑quinone methide synthon; the morpholinomethyl group can be introduced/removable under mild conditions, providing a traceless activation handle at C‑1 of 2‑naphthol.
The tertiary amine can act as an internal base or ligand in tandem reactions involving the adjacent phenol, enabling intramolecular activation strategies.
Target Specificity
Not applicable. This product is a small organic building block and is not an antibody, enzyme, or targeted biologic. No target, epitope, clone, isotype, or species reactivity is defined in the Product Data.
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