This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
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
Not applicable. No assay-specific protocols (e.g., WB, IHC, IF, FC) are relevant to this small-molecule reagent. For synthetic and preparative uses, refer to the Reaction & Applications and Reaction Conditions tabs for general guidance, and consult primary literature for substrate-specific procedures.
Biological Roles
Item-specific biological data are not provided. The compound is intended for research use only and is not an endogenous metabolite.
General context (literature)
Structural motif: the morpholine ring is a common polarity-enhancing, solubility-improving heterocycle in chemical biology probes and small-molecule libraries. The pendant primary amine enables conjugation to carboxylates (amide formation), activated esters, and electrophilic linkers.
Protonation and cell compatibility: dual basic centers typically confer high aqueous solubility and can influence membrane permeability and lysosomal accumulation (cationic amphiphiles). Such properties are often tuned rather than relied upon as intrinsic biological functions.
Metal binding: weaker bidentate binding than diamines like ethylenediamine; can still coordinate metals under certain conditions, which may be exploited in probe design.
Biodegradation: aliphatic amines are generally biodegradable, but specific rates and pathways for this compound are context-dependent and not provided.
No claims are made regarding pharmacology, toxicity thresholds, or clinical relevance. For any biological experiments, determine biocompatibility and cytotoxicity empirically under your specific conditions.
Buffer Applications
This compound is not a standard biological buffer. While the presence of two basic nitrogen centers provides buffering capacity in alkaline-to-near-neutral ranges, it lacks the well-characterized pKa separation, ionic strength behavior, and spectral transparency data typical of dedicated Good’s buffers.
Item-specific buffer parameters: Not specified for this item; refer to CoA/Spec Sheet.
If a custom buffer is desired (general guidance)
Prepare as the conjugate acid/salt (e.g., hydrochloride) to achieve defined ionic strength and pH control.
Empirically determine the titration curve in your matrix, as apparent pKa values and buffering range will differ from canonical buffers (HEPES, MOPS, Tris).
Consider using established buffers for reproducibility unless a reactive primary amine is specifically needed for conjugation chemistry.
Green Alternatives
Although 2-(aminomethyl)morpholine (AMM) is itself a reagent rather than a solvent, greener choices can be made in how it is used and what alternatives are selected for functionally similar roles.
Greener media when employing AMM (general guidance)
Prefer water, ethanol, or isopropanol for reductive aminations and salt formations when compatible, instead of chlorinated solvents or high-boiling dipolar aprotics.
Consider 2-MeTHF or ethyl acetate as greener alternatives to DCM/THF for acylations and extractions where feasible.
Functional alternatives (role-based)
As a polar, solubilizing amine fragment in medicinal chemistry: morpholine alternatives include piperazine or N-methylpiperazine, but note their different basicities/chelation and potential persistence. Greener selection often weighs synthetic step count, avoidance of hazardous reagents, and biodegradability rather than simple substitution.
As an organic base: if only base is required (no incorporation), inorganic bases (K2CO3, NaHCO3) in aqueous or alcoholic media may reduce solvent and amine emissions.
Incorporation into product: yes (building block) | typically no | no
Trade-offs: AMM adds structural polarity and H-bonding capacity but requires amination steps. Greener process design emphasizes solvent choice, telescoped sequences (avoiding isolations), and salt-switch crystallizations to minimize energy-intensive distillations.
Pharmaceutical Uses
No pharmacopeial grade or excipient status is provided for this item. The material is for research use only.
General process-chemistry context (literature)
Synthetic intermediate: 2-(Aminomethyl)morpholine is commonly employed to introduce the morpholine motif into discovery and process intermediates via amide formation, reductive amination, or SNAr. The morpholine ring improves aqueous solubility and ADME-related physicochemical properties in screening compounds.
Salt formation and isolation: the amine readily forms crystalline salts (e.g., hydrochloride, p-toluenesulfonate), which can aid in purification, solid handling, and polymorph screening during route scouting (no specific salt form is indicated for this item).
Process considerations: compared with more volatile amines, it generally presents reduced fugitive emissions and odor; however, residual amine can persist in mother liquors due to high water miscibility. Robust washing and pH-switch protocols are recommended.
No claims are made regarding therapeutic application, safety in humans, or clinical utility. For any cGMP use, source an appropriate grade and confirm compliance with relevant pharmacopeial monographs if available.
Physical Properties
Item-specific specifications were not provided for this catalog entry. Do not treat the following as product specifications; verify with the CoA/SDS for your lot.
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Physical state: typically a colorless to pale yellow, hygroscopic liquid with amine odor (literature for low-MW alkanolamine/morpholine derivatives).
Acid–base: bifunctional base (one primary, one secondary amine); commonly forms stable monoprotonated or diprotonated salts with mineral acids (e.g., HCl, H2SO4).
Solubility: expected to be freely miscible with water and polar organic solvents (MeOH, EtOH, acetone); high solubility in DMSO/DMF (literature, qualitative).
Partitioning: strongly hydrophilic; logP expected to be negative to near-zero for the free base; becomes even more water-soluble upon protonation (literature, qualitative).
Volatility: low to moderate; substantially less volatile than simple alkylamines of comparable mass (literature, qualitative).
Boiling point, melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes (general)
Hygroscopic/basic liquids can absorb CO2 and moisture from air; keep containers tightly closed to limit carbonate/salt formation.
Protonation state will strongly affect apparent pKa and solubility; adjust pH accordingly in aqueous systems.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grade meaning (general, for reference)
Research grade: suitable for most synthetic and preparative work, where ultra-trace impurities are not critical. Verify residual water, metals, or UV-absorbing impurities via CoA if your application is sensitive (e.g., catalysis, photophysics).
High-purity/low-water grades (when offered): beneficial for air/water-sensitive transformations (e.g., strong base-mediated alkylations, moisture-sensitive coupling reagents). For amines, trace water and peroxides are less common concerns than for ethers; however, residual metals and carbonyls can affect catalytic reactions and reductive aminations.
Titration/assay: For amines, acidimetric assay or NMR qNMR is often used to determine active base content. If exact base equivalents are critical, standardize with HClO4 in acetic acid or use qNMR with an internal standard.
Practical QA recommendations
If employing as a nucleophile/base in quantitative synthesis, determine amine content and residual water (Karl Fischer) for stoichiometric accuracy.
For salt-sensitive processes, confirm whether the supplied material is free base or a salt form; adjust stoichiometry accordingly.
For low-UV applications (e.g., HPLC mobile-phase modifiers), verify UV cutoff and amine-related baseline noise; item-specific values are required from the CoA.
Reaction and Applications
As a bifunctional nucleophile (primary amine side chain) with an embedded secondary amine in a morpholine ring, 2-(aminomethyl)morpholine is an exceptionally versatile building block.
Reductive amination: couples with aldehydes/ketones to form secondary amines; NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation are common. The ring N can remain unmodified, or both nitrogens can participate with appropriate protection.
Amide/urea/thiourea formation: acylation or carbamoylation of the primary amine using acid chlorides/anhydrides/coupling reagents (EDC/HOBt, HATU). Useful for preparing morpholine-containing amide fragments for medicinal chemistry campaigns.
Nucleophilic aromatic substitution (SNAr): displacement of activated aryl fluorides/chlorides (e.g., on nitro- or CN-activated aryls) to introduce the morpholinylmethylamino motif.
Alkylation: formation of N-alkylated derivatives (e.g., quaternization or tertiary amines) using alkyl halides or sulfonates; chemoselectivity can be tuned via protection of one nitrogen (Boc, Cbz) or transient protonation.
Sulfonylation/carbamate formation: installation of sulfonamides or carbamates for further diversification; useful handles for SAR exploration.
Metal-catalyzed cross-couplings: the amine can be converted to amides/ureas that participate in C–N couplings (Buchwald–Hartwig) after appropriate functionalization.
Roles in synthesis
Fragment in linker chemistry: the morpholine ring imparts polarity and aqueous solubility to linker scaffolds.
Auxiliary/base: can serve as a mild organic base or nucleophilic catalyst in some transformations, though sterically and electronically distinct from tertiary amines like DIPEA.
Practical tips
Control protonation: free base is required for nucleophilic substitutions; slight excess base (e.g., K2CO3) helps in SNAr.
Protecting-group strategy: Boc-protect either the primary or ring amine to direct chemoselectivity.
Workup: convert to HCl salt for crystallization/purification; reverse to free base with NaHCO3/NaOH as needed.
Reaction Conditions
General, literature-based guidance for common transformations employing 2-(aminomethyl)morpholine (AMM). These are NOT item-specific specifications.
Reductive amination
Solvents: MeOH, EtOH, i-PrOH, MeCN.
Conditions: mix carbonyl (1.0 eq) + AMM (1.2–2.0 eq) + AcOH (0.5–1.0 eq) to form imine/iminium; reduce with NaBH3CN (pH 5–6) or NaBH(OAc)3 (rt to 40°C), 2–16 h.
Notes: control water content; monitor by LC–MS; neutralize and extract or crystallize as an acid salt.
Amide formation (EDC/HOBt or HATU)
Solvents: DMF, DCM, MeCN, or greener EtOAc/2-MeTHF when compatible.
Base: DIPEA or i-Pr2NEt alternative; or use inorganic base (NaHCO3) in biphasic systems.
Conditions: 0–25°C, 1–12 h; quench with dilute base and extract.
SNAr on activated aryl fluorides
Solvents: DMSO, DMF, NMP, MeCN.
Base: K2CO3, Cs2CO3 (1–2 eq).
Temperature: 60–120°C (depending on activation), 2–24 h; monitor by HPLC.
Alkylation (to tertiary amines)
Electrophiles: alkyl halides/sulfonates.
Solvents: MeCN, acetone, DMF.
Base: K2CO3 or Na2CO3; 25–60°C, 2–16 h.
Protection strategies
Boc protection (primary amine): Boc2O, base (NaHCO3 or DIPEA), DCM/MeCN, 0–25°C.
Selective protection of ring N may require stronger bases or distinct protecting groups (e.g., Cbz, nosyl) with orthogonal deprotection.
Yields vary with substrate/electrophile; consult primary literature for substrate-specific optimization. Ensure amine is in the free-base form for nucleophilic steps; salts can be neutralized in situ with base.
Safety and Handling
Item-specific hazard classifications were not provided. Always consult the SDS for authoritative guidance.
GHS classification (item-specific): 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 low-molecular-weight polyamines/morpholine derivatives (literature/good practice)
Hazards: may be corrosive/irritating to skin, eyes, and respiratory tract; strong, persistent amine odor is possible. Amines can form nitrosamines with nitrosating agents—avoid nitrite-acid mixtures.
PPE: laboratory coat, chemical-resistant gloves (e.g., nitrile), splash goggles; use in a fume hood to control vapors/odors.
Incompatibilities: strong oxidizers; acyl halides and anhydrides (exothermic acylation); isocyanates, epoxides, and CO2 (salt/carbamate formation); avoid contact with nitrites under acidic conditions.
Handling: keep tightly closed; purge headspace with inert gas when feasible; dispense under anhydrous conditions when water-sensitive reactions are planned.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye: immediate decontamination with copious water for ≥15 min; remove contaminated clothing; obtain medical evaluation.
Ingestion: rinse mouth; do not induce vomiting; seek medical assistance.
Spill response: absorb with inert material; avoid neutralization with strong acids in-situ due to heat and fumes; collect for disposal according to institutional procedures.
Fire: amines are combustible; use CO2, dry chemical, or alcohol-resistant foam; firefighters should wear SCBA.
Storage (see also Storage & Reconstitution tab): store at 2–8°C, tightly sealed. Protect from air and moisture to minimize CO2 uptake and degradation.
Solvent Selection
This product is a reactive amine reagent, not a general-purpose solvent. However, solvent choice strongly affects its reactivity and handling.
Polarity/miscibility (general)
Highly polar and strongly hydrogen-bonding; freely miscible with water and polar organics (MeOH, EtOH, acetone, acetonitrile, DMSO, DMF). Limited solubility expected in nonpolar hydrocarbons.
In aqueous media, protonation enhances solubility further; buffering near its basic pKa(s) tunes nucleophilicity versus solubility.
Choosing media for typical uses
Nucleophilic substitution (e.g., SNAr on activated aryl halides): use polar aprotic solvents (DMF, DMSO, NMP, MeCN) or alcoholic media; ensure base capture of HX if using an aryl halide.
Reductive amination: alcoholic solvents (MeOH, EtOH, i-PrOH) or MeCN are common; control water content to favor imine formation.
Amide/urethane formation (acylation/carbamoylation): use dichloromethane, THF, or MeCN with base; for greener options, EtOAc or 2-MeTHF may be suitable.
Salt formation/purification: use anhydrous Et2O/MTBE/EtOAc for precipitating amine salts from alcoholic or acetonitrile solutions.
Comparison notes (general)
Versus simple alkylamines: higher water miscibility and lower volatility/odor; often easier to handle.
Versus diamines (e.g., ethylenediamine): lower basicity per nitrogen and reduced metal chelation strength; may be advantageous in metal-catalyzed reactions where strong chelation is undesirable.
Storage and Reconstitution
Item-specific storage (from Product Data)
Storage Conditions: Store at 2–8°C.
Shipped In: Wet ice.
Container/handling guidance (general best practice)
Keep tightly closed under air-free or low-CO2 headspace to minimize absorption of moisture and carbon dioxide (which forms amine salts/carbamates).
Use amber or opaque containers if prolonged light exposure is anticipated, although significant photolability is not typical for this class.
If received as a viscous liquid, warm gently to ambient temperature to ensure homogeneity; mix thoroughly before aliquoting.
Reconstitution
Not applicable; the product is typically supplied neat (free base) unless otherwise specified. If a solid salt form is supplied in a specific lot, dissolve in water, alcohols, or polar aprotic solvents as needed.
Freeze–thaw and stability
Avoid repeated freeze–thaw cycling; instead, prepare small aliquots for long-term use.
For long-term storage beyond routine timelines, consider inert-gas blanket and desiccant. Monitor by 1H NMR or LC–MS for signs of degradation or adventitious salt formation.
Always defer to the lot-specific CoA and SDS for definitive storage, stability, and handling instructions.
Structure and Identity
2-(Aminomethyl)morpholine is a small, bifunctional, aliphatic heterocycle featuring a morpholine ring bearing a pendant aminomethyl group at the 2-position.
Item-specific identifiers (from Product Data)
SKU: A481712
Product Name: 2-(Aminomethyl)morpholine
CAS: 116143-27-2
PubChem CID: 4542027
InChIKey: 270445 (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.
Literature/general identity (non-item-specific; for reference only)
Common structural description: a six-membered morpholine ring (tetrahydro-1,4-oxazin-4-ium framework in conjugate-acid form) comprising one ring oxygen and one ring nitrogen, substituted at the carbon alpha to oxygen with a –CH2–NH2 group.
Ring system: saturated morpholine (–O–CH2–CH2–NH–CH2–CH2–) with two heteroatoms separated by two carbons.
Functional groups: one secondary amine (ring nitrogen), one primary amine (pendant –CH2NH2), and an ether oxygen within the ring (cyclic ether).
Stereochemistry: none (achiral in the free base; no stereocenters).
Note: Literature identifiers are provided for context only and are not item-specific specifications. Always verify with the CoA/SDS for this catalog lot.
Synthetic Utility
Key reactive elements
Primary amine (pendant): highly nucleophilic; forms amides, sulfonamides, ureas, carbamates; participates in reductive aminations and imine/enamine chemistry.
Secondary amine (ring nitrogen): less nucleophilic due to adjacent oxygen (morpholine attenuates basicity); can be selectively protected, alkylated, or acylated to control chemoselectivity.
Ether oxygen (ring): generally inert; enhances polarity/solubility; can engage in H-bonding and weak coordination.
Strategic uses (literature)
Bifunctional linker: provides a handle for conjugation (primary amine) while retaining the morpholine ring that modulates solubility and basicity in the final construct.
Divergent synthesis: orthogonal protection (e.g., Boc on primary amine, nosyl/alloc on ring N) enables stepwise derivatization, giving access to libraries of analogs.
Quaternization: formation of ammonium salts can yield ionic liquids or phase-transfer catalysts for specialized applications.
Named/typical reactions (general)
Reductive amination (NaBH3CN, NaBH(OAc)3), Eschweiler–Clarke (for tertiary amines from primary/secondary N centers), Buchwald–Hartwig after prior functionalization, and sulfonamide formation (e.g., with TsCl, MsCl).
Practical notes
Selectivity control: transient protonation or protection of one nitrogen guides N-alkylation/acylation to the desired site.
Purification: form crystalline salts for trituration; regenerate free base at basic pH during workup.
Analytics: 1H/13C NMR in D2O or CDCl3 (with acid additive) provides clear diagnostics for both amines; potentiometric titration quantifies base content.
Target Specificity
Not applicable. This product is a small-molecule amine reagent and is not an antibody, enzyme, or affinity reagent. No antigen, epitope, clone, isotype, or species reactivity information applies.
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