This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
207.270 g/mol
XLogP3
0.700
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
207.126 Da
Monoisotopic Mass
207.126 Da
Topological Polar Surface Area
32.700 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
180.000
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
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Application Protocols
Not applicable. No bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic uses, refer to the Reaction Conditions and Synthetic Utility sections.
Biological Roles
This compound is a synthetic small-molecule building block and is not known as a natural metabolite.
General context (literature):
Morpholine is commonly used in medicinal chemistry to increase aqueous solubility and modulate basicity; embedding morpholine into aromatic scaffolds is a standard strategy to balance lipophilicity and clearance. Here, the morpholinomethyl substituent can serve as a solubilizing handle or interaction vector in SAR studies.
The benzylic alcohol provides a handle to access aldehyde/acid derivatives that can engage in covalent or reversible interactions in biochemical probe design.
Enzymatic interactions: No specific biological targets are inherently addressed by this scaffold; any biological activity would derive from further derivatization and context within a larger molecule.
Metabolic considerations (general):
Typical Phase I pathways would include benzylic oxidation to the corresponding aldehyde/acid and N-oxidation or N-dealkylation of the morpholine ring.
Phase II conjugation might include glucuronidation/sulfation of the benzylic alcohol once oxidized to phenolic/acidic handles in derivative structures.
All uses are for laboratory research only. No medical, diagnostic, or therapeutic applications are claimed or supported.
Buffer Applications
This product is not a buffering agent and is not typically used to prepare biological buffers. The tertiary amine can be protonated to form water-soluble salts, but dedicated buffer systems (e.g., phosphate, acetate, Tris, HEPES) are preferred for pH control.
Practical note: If handling in aqueous media is needed, convert to a defined salt (e.g., hydrochloride) and dissolve in the appropriate buffer. Avoid relying on the compound itself for buffering capacity or pH control.
Green Alternatives
Although this compound is a reagent/intermediate (not a solvent), greener choices impact the steps in which it is used.
Greener solvent swaps (general guidance):
Replace chlorinated solvents (DCM, CHCl3) with EtOAc, 2-MeTHF, or CPME when solubility and kinetics permit.
Use MeOH/EtOH or water/EtOH mixtures for salt manipulations rather than DMF/DMSO where feasible.
For oxidations, select catalytic systems (e.g., TEMPO/NaOCl in water/EtOAc biphasic, or O2 with catalytic TEMPO/Cu) instead of stoichiometric chromium reagents.
EtOAc: bio-based availability, readily biodegradable, higher bp; may require mild heating to match rates.
Swern/DMP vs. TEMPO/NaOCl for alcohol oxidation:
Swern/DMP: low-temperature control or hypervalent iodine waste; precise, broadly applicable.
TEMPO/NaOCl: aqueous biphasic, catalytic, minimized hazardous waste; pH control is critical with amines (protonate amine to suppress side reactions).
Process intensification:
Consider crystallization-induced purification as a salt (e.g., HCl) to avoid chromatographic solvent use.
Employ telescoped sequences (e.g., in situ mesylation → displacement) to reduce solvent and intermediate handling.
Note: Always verify that greener alternatives deliver the required selectivity in the presence of a tertiary amine.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item.
General context (for research/manufacturing development only, not clinical use):
The morpholinomethyl substituent is widely used in medicinal chemistry to enhance polarity and adjust basicity; this scaffold can function as an intermediate for generating lead-like compounds.
The primary alcohol can be transformed into aldehydes, acids, esters, or carbamates used in prodrug or linker strategies in conjugates (e.g., polymer–drug conjugates) during research.
For GMP or clinical manufacturing, specification of residual solvents, identity/purity by orthogonal methods, and nitrosamine risk assessments (for tertiary amines under certain conditions) would be required; none of these are specified for this catalog item.
All references here pertain to research and development contexts only. No therapeutic claims are made.
Physical Properties
Item-specific specifications (this catalog item):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (See computed value under Structure & Identity.)
General/literature expectations for the neat compound (for reference only; not product specifications):
Physical state: typically a colorless to pale liquid or low-melting solid for comparable ortho-morpholinomethyl benzyl alcohols (literature/general expectation).
Approximate molecular weight: ~208.28 g/mol (computed from C12H18NO2).
Acid-base: tertiary amine pKaH of morpholine ~8.3–8.5 (literature, for morpholine; the N within a benzylated morpholine is similar). Free-base is neutral; forms water-soluble salts with mineral acids.
Solubility: free base expected to be soluble in polar organics (MeOH, EtOH, MeCN, DCM, THF) and sparingly soluble in water; salt forms (e.g., HCl) are water soluble (general guidance; verify experimentally).
LogP/logD: benzylic alcohol + tertiary amine suggests moderate lipophilicity as free base; substantially reduced logD at acidic pH due to protonation (literature trend for morpholine-containing benzyl alcohols).
Density, refractive index, melting/boiling points, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. If required for process design, determine experimentally or consult primary literature for this exact CAS.
Note: Do not treat these general values as specifications; confirm with the lot-specific CoA when planning analytical or process work.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Context and implications (general guidance for this class of reagent):
Analytical vs. synthetic grade: For quantitative synthesis or analytical use, specifications often include assays by GC/HPLC/NMR, residual solvents, and trace metals. In the absence of a declared grade, verify suitability by reviewing the lot CoA and performing incoming QC (1H NMR for identity/purity; GC/HPLC for assay; water by KF if moisture-sensitive transformations are planned).
UV profile: If intended for use in photochemical steps or as an HPLC mobile phase additive, ensure low UV absorbance specifications; otherwise, typical synthetic-grade materials may contain UV-active impurities (aromatics, amines). Not specified for this item.
Stabilizers: No stabilizer is indicated in Product Data. If long-term storage is planned, a small headspace of inert gas and amber glass are good practices for benzylic alcohols to minimize slow oxidation.
Salt form vs. free base: This listing appears to be the free base (no salt stated). For work in aqueous media, consider preparing or procuring the hydrochloride salt to enhance water solubility and to simplify handling; confirm with supplier if a salt option exists.
Reaction and Applications
As a bifunctional aryl–CH2OH/tertiary amine, (2-(Morpholinomethyl)phenyl)methanol is a versatile intermediate.
Alcohol derivatization: conversion to halides (SOCl2, PBr3), sulfonates (MsCl/TsCl), or carbonates; facilitates subsequent SN2 reactions for side-chain elaboration.
Oxidation: benzylic alcohol to aldehyde (Dess–Martin periodinane, Swern, TEMPO/bleach) or to acid (Jones, Pinnick) while monitoring the basic N; acid salts can moderate amine basicity during oxidation.
Reductive amination/alkylation on the amine: quaternization or N-alkylation of the morpholine nitrogen to tune solubility or create phase-transfer intermediates.
Carbamate/urethane formation: reaction with chloroformates to protect or tag the alcohol.
Mitsunobu (alcohol substitution): with DEAD/DIAD and PPh3 to install O-, N-, or S- nucleophiles at the benzylic position (note: tertiary amine may require protonation to minimize side reactions).
Orthogonal reactivity and site selectivity:
The benzylic position is activated toward oxidation and substitution; neighboring tertiary amine can assist as an internal base but may also require protection (as HCl salt or Boc) to avoid competing reactions.
The aryl ring is ortho-disubstituted; electrophilic aromatic substitution is deactivated relative to anilines but still feasible under strong conditions (e.g., nitration is discouraged due to overreaction/oxidation).
Use cases:
Linker/tether in medicinal chemistry to append a morpholine solubilizing group to aromatic scaffolds.
Precursor to ortho-aminomethyl benzaldehydes/benzoic acids for ligand design, polymer modifiers, or surfactant-like amphiphiles.
Practical tip: Dry the material (vacuum over P2O5 or molecular sieves-compatible approach) if using in moisture-sensitive couplings; tertiary amines can absorb CO2 forming carbamates on prolonged air exposure.
Reaction Conditions
General literature-guided conditions for common transformations of benzylic alcohols bearing tertiary amines (for planning; verify experimentally):
Oxidation to aldehyde:
Dess–Martin periodinane (1.3–1.5 equiv), DCM, 0–25 °C, 1–3 h; typical isolated yields 70–90% for benzylic alcohols.
TEMPO (2–5 mol%), NaBr (10 mol%), NaOCl (bleach), pH 8.6 buffer, EtOAc/H2O biphasic, 0–5 °C then rt; 70–90% typical. Keep amine protonated to suppress side reactions.
Conversion to benzylic chloride/mesylate:
SOCl2 (1.2–2.0 equiv), DCM, 0–25 °C, 1–2 h; add base (pyridine) cautiously given tertiary amine presence; 60–85% typical for substrates of this class.
MsCl (1.2–1.5 equiv), Et3N (2.0 equiv), DCM, 0 °C→rt, 1–2 h; follow with SN2 nucleophile in polar aprotic solvent (DMF, MeCN) at 25–60 °C.
Carbamate formation (alcohol):
p-Nitrophenyl chloroformate (1.1 equiv), Et3N (2 equiv), DCM, 0–25 °C; then amine coupling step in DMF/Et3N at rt–40 °C.
N-alkylation (morpholine N):
Alkyl halide (1.2–2.0 equiv), MeCN or acetone, K2CO3 (2–3 equiv), rt–50 °C, 2–16 h; monitor for over-alkylation to quaternary salt if desired.
N-oxide formation:
mCPBA (1.1 equiv), DCM, 0–25 °C, 1–3 h; quench with Na2SO3; useful for further functionalization.
Notes:
Control acid/base carefully; protonating the tertiary amine can enhance chemoselectivity for alcohol-centered reactions.
Dry, oxygen-free conditions may be required for air-sensitive reagents; otherwise, the substrate itself is not highly air-sensitive.
The values above are general for benzylic alcohols/morpholine derivatives and should be optimized for this exact structure.
Safety and Handling
Item-specific hazard data:
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General safety considerations for benzyl alcohols bearing tertiary amines (literature/analog-based guidance; not a substitute for SDS):
Likely hazards: may cause skin/eye irritation; amine odor possible; harmful if swallowed; avoid aerosol generation. Tertiary amines can be irritating and may be corrosive to some plastics.
Peroxide formation: Not expected (no ether solvent functionality prone to peroxidation outside the morpholine ring). Nonetheless, follow standard solvent/additive compatibility practices.
Incompatibilities: strong oxidizers (risk of exotherm/oxidation); acylating/alkylating agents (react with the amine or alcohol); strong acids/bases (can protonate/deprotonate and lead to salt formation or elimination under forcing conditions).
PPE: lab coat, nitrile gloves, safety glasses or face shield when splashing is possible. Handle in a fume hood to control vapors/aerosols.
First aid (overview):
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; monitor for respiratory irritation; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill/cleanup: Absorb with inert material, collect in compatible container. Neutralize residues appropriately; avoid release to drains.
Fire: Use CO2, dry chemical, or foam. Combustion may produce NOx/CO/CO2. Ensure grounding/bonding if handling flammable co-solvents.
Always consult the product-specific SDS for authoritative guidance.
Solvent Selection
This product is an organic building block (not used as a bulk solvent). The following guidance concerns selecting solvents to dissolve or process it:
Polarity/ionization:
Free base is moderately polar with a tertiary amine and a benzylic alcohol; dissolves well in polar aprotic and many protic solvents (MeOH, EtOH).
Protonated (salt) forms are highly polar and water soluble; choose aqueous buffers or alcohol/water mixtures for salt forms.
Variable: EtOAc, toluene (often improved with a small amount of polar co-solvent).
Poor: Alkanes (hexanes/heptane) for the free base; salts effectively insoluble.
Selection tips:
For nucleophilic substitutions or acylations at the alcohol: use anhydrous DCM, THF, or DMF; add base (e.g., DIPEA) cautiously since tertiary amines may compete for acylation if over-activated.
For oxidations of the benzylic alcohol: MeCN, DCM, or greener EtOAc; avoid strongly basic media that could lead to benzylic elimination.
For salt workup: dissolve in minimal DCM/EtOAc and extract with dilute HCl to partition the amine into the aqueous phase; basify and re-extract to recover the free base.
Small comparison (general):
DCM vs. EtOAc: DCM offers broader solubility and faster kinetics for many transformations; EtOAc is greener and often suitable with slightly elevated temperature.
Keep container tightly closed in a dry, well-ventilated place. If prolonged storage is expected, consider inert gas headspace and amber glass to minimize slow benzylic oxidation.
For aqueous operations, prepare solutions freshly. If converting to a salt (e.g., hydrochloride) for handling, dry the salt under vacuum after crystallization and store at ambient temperature, desiccated.
Avoid exposure to strong oxidants and acids/bases unless intentionally forming the salt.
If solidification occurs (some benzylic alcohols can supercool), gently warm to room temperature and mix before use.
Shelf-life and retest date: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Structure and Identity
Intro: (2-(Morpholinomethyl)phenyl)methanol is an ortho-disubstituted benzyl alcohol bearing a pendant morpholinomethyl group, useful as a bifunctional building block (alcohol + tertiary amine).
Item-specific (from Product Data):
SKU: M195787
CAS: 91271-63-5
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "165587", which is not a standard InChIKey format.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity (from chemical name; for general reference only):
Molecular formula (computed from name): C12H18NO2
Molecular weight (computed): ~208.28 g/mol
Core structural features: benzene ring bearing (i) a benzylic alcohol group (–CH2OH) and (ii) an ortho –CH2–N(morpholine) substituent. The morpholine is a saturated six-membered heterocycle containing one oxygen and one tertiary nitrogen.
2D description in words: A benzene ring with two adjacent substituents; one is –CH2OH, the other is –CH2–N(R) where N is incorporated in a morpholine ring (–N–CH2–CH2–O–CH2–CH2–).
Stereochemistry: None (achiral, no stereocenters in the named parent).
Synthetic Utility
Key functional elements and reactivity:
Benzylic primary alcohol:
Easily oxidized (Swern, Dess–Martin, TEMPO systems) to aldehyde/acid; benzylic position is activation site for further C–C bond formations (e.g., via Wittig/Horner from aldehyde).
Activation to leaving groups (Ms/Ts/halides) enables SN2 with N-, O-, S-nucleophiles to elaborate the side chain.
Tertiary amine within morpholine:
Can be protonated to form crystalline salts for purification/handling.
Alkylation to quaternary ammonium salt provides phase-transfer capability; N-oxide formation (mCPBA) offers selective oxidative handles and can direct subsequent rearrangements.
Ortho relationship between substituents:
Facilitates intramolecular interactions (hydrogen bonding when protonated) and can influence reactivity/selectivity (anchimeric assistance in some derivatizations). Potential for ortho-directing effects in metalation if strongly activated.
Strategic uses:
Build solubilized benzyl aldehydes/acids for coupling into amide/urea/ether libraries.
Introduce morpholine as a polarity handle onto aromatic frameworks via this prebuilt unit, avoiding late-stage Mannich conditions on sensitive substrates.
Generate cationic materials (quaternization) for ion-pair catalysis or material science (antistatic coatings, compatibilizers) in research settings.
Practical notes:
Protect the amine (as HCl salt or Boc on other amines in the system) when selective acylation/activation of the alcohol is required.
Thoroughly dry before moisture-sensitive steps; tertiary amines can absorb CO2 and moisture.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent/intermediate and is not an antibody, enzyme, or biologic. No antigen/epitope or species reactivity applies.
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