2-(Morpholin-4-yl)-2-phenylethan-1-amine - ≥95% , CAS No.31466-44-1

CAS: 31466-44-1 Cat. No.: M1072856 Formula: C₁₂H₁₈N₂O Peso molecolare: 206.29 Numero EC: 894-458-6 PubChem CID: 3158583

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1COCCN1C(CN)C2=CC=CC=C2

IUPAC Name

2-morpholin-4-yl-2-phenylethanamine

InChIKey

WSNSRJWLIVDXDI-UHFFFAOYSA-N

INCHI

1S/C12H18N2O/c13-10-12(11-4-2-1-3-5-11)14-6-8-15-9-7-14/h1-5,12H,6-10,13H2

Isomeri SMILES

C1COCCN1C(CN)C2=CC=CC=C2

PubChem CID

3158583

Peso molecolare

206.29

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Classe Organonitrogen compounds
      • Subclass Amines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Classe: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Not available
• Direct Parent: Aralkylamines
• Alternative Parents: Morpholines Benzene and substituted derivatives Trialkylamines Oxacyclic compounds Dialkyl ethers Azacyclic compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Aralkylamine - Monocyclic benzene moiety - Morpholine - Oxazinane - Benzenoid - Tertiary amine - Tertiary aliphatic amine - Oxacycle - Ether - Dialkyl ether - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Primary amine - Organooxygen compound - Hydrocarbon derivative - Primary aliphatic amine - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 206.280 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 206.142 Da
• Monoisotopic Mass: 206.142 Da
• Topological Polar Surface Area: 38.500 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 174.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 standardized bioassay or immunoassay protocols apply to this small-molecule building block.

• Synthetic use suggestions (general)
  • For library synthesis, prepare 0.1–0.5 M stock solutions in dry DMSO or MeCN, dispense under inert gas, and react with acylating/sulfonylating agents in parallel format.
  • For aqueous screening, convert to a defined acid addition salt (e.g., HCl) to improve solubility; filter-sterilize solutions through 0.22 μm PTFE or PES as needed for biochemical assays.

All application conditions should be optimized experimentally for the intended research use.

Biological Roles

This compound is a synthetic, non-natural small molecule diamine.

• General biochemical relevance (literature-based, not specific to this item)
  • The morpholine motif is widely used in medicinal chemistry to modulate basicity, solubility, and PK properties; it is not a natural metabolite.
  • Primary amines at benzylic positions often serve as anchors for conjugation to biomolecules (e.g., forming amide/urea/sulfonamide linkages) for probe or ligand synthesis.
  • As a dialkylamine-bearing aromatic, it can form protonated species under physiological pH, increasing aqueous solubility—useful for designing cationic ligands.

No endogenous biological function is attributed to 2-(morpholin-4-yl)-2-phenylethan-1-amine itself. Any biological testing should be conducted under appropriate approvals and is strictly for research use only.

Buffer Applications

Not typically used as a defined buffer component.

• Practical notes
  • The molecule contains two basic sites and can accept protons (forming mono- or di-cations), but it lacks the well-characterized pKa separation and low UV background preferred for standard biological buffers.
  • If a protonated salt is required to enhance water solubility for screening or assay preparation, prepare a defined acid addition salt (e.g., HCl) and standardize concentration by titration or weight-by-assay. Buffering capacity and pKa values should be measured experimentally for the salt solution if used in any pH-sensitive context.

Green Alternatives

This product is a solid/liquid organic building block rather than a process solvent; “green alternatives” pertain to the choice of reaction media and workup methods when using it.

• Greener solvent choices for typical transformations (literature-guided)

  • Acylations/couplings: Replace DCM/DMF with EtOAc, 2-MeTHF, Me-THF/EtOAc mixtures, or dimethyl carbonate when feasible. For peptide-type couplings, consider green coupling media like EtOAc/MeCN and newer coupling reagents with improved atom economy.
  • Reductive amination: Perform in EtOH or i-PrOH with solid acid catalysts where possible; use NaBH(OAc)3 in EtOAc/MeOH mixed solvents instead of cyanoborohydride in MeCN.
  • Workups: Favor aqueous EtOAc extractions over chlorinated solvents; use carbonate buffers rather than strong mineral acids when appropriate.

• Comparison snapshot (general)

  • DCM vs 2-MeTHF: 2-MeTHF is renewable and has lower environmental impact; DCM offers superior solubilization for some acyl chlorides—test small-scale first.
  • DMF/DMSO vs Cyrene/PC/propylene carbonate: Emerging dipolar aprotics can replace DMF/DMSO in some couplings; verify compatibility with amine bases and reagents.

• Waste minimization

  • Use in-situ protection strategies to reduce steps, adopt telescoped imine–reduction sequences in alcohols, and leverage crystallization of acid salts to avoid chromatography.

Pharmaceutical Uses

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

• General roles (non-clinical; research/manufacturing context only)

  • Intermediate/building block: The morpholine/benzylic primary amine motif is prevalent in discovery chemistry; this scaffold can be diversified by acylation, sulfonylation, reductive amination, and urea/carbamate formation.
  • Salt formation: Formation of hydrochloride, mesylate, or tosylate salts can improve crystallinity, hygroscopicity control, and handling during process development.
  • Enabling functionality: The tertiary morpholine often enhances aqueous solubility and reduces lipophilicity of candidate molecules, aiding formulation screening.

No therapeutic claims are made. Any use is restricted to research and laboratory development.

Physical Properties

• Item-specific values (specs): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/General expectations for the neutral free base (for reference only)

  • Aggregation state: Typically a colorless to pale yellow liquid or low-melting solid for analogous benzylic morpholine diamines; salts tend to be crystalline.
  • Solubility profile: Free base expected to be soluble in polar organic solvents (MeOH, EtOH, MeCN, DMF, DMSO) and partially in less polar solvents due to the phenyl ring; protonated salts (e.g., HCl, TsOH) are highly water-soluble.
  • Basicity: Two basic sites. Tertiary morpholine nitrogen pKaH typically ~8.2–8.6 (literature, morpholine); primary benzylic amine pKaH typically ~9–10 (literature, aliphatic primary amines). Overall, readily forms mono- and di-protonated salts under acidic conditions.
  • Volatility: As a multifunctional diamine with an aryl ring, volatility is low to moderate; vacuum can aid solvent removal after workups.
  • Partitioning: Presence of both aryl and polar centers suggests moderate polarity; cationic salts are hydrophilic.
  • UV: Aromatic ring provides UV absorbance in the 200–280 nm region (literature, aryl amines). Exact UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.

Note: Numerical values for bp, mp, density, refractive index, water content, and metal/peroxide levels are not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting common grades for this molecule type (general guidance)
  • Research-grade/≥95–98%: Suitable for synthetic chemistry, SAR, and method development. May contain trace residual solvents or regioisomeric/enantio impurities.
  • HPLC grade (when applicable to solvents) is not relevant here; however, “HPLC assay ≥99%” on a solid/liquid amine would indicate low UV-absorbing impurities—useful for bioactive library synthesis.
  • Enantiomeric specification: The benzylic center can be chiral. Unless an ee/er is specified, material should be assumed racemic. Verify if a single enantiomer is required for asymmetric studies.
• Stabilizers/inhibitors: None are typically added to amine building blocks. If an acid salt is supplied (e.g., HCl salt), this improves stability and handling; confirm on the CoA.
• What to check on receipt
  • Identity (1H/13C NMR, HRMS), assay/purity (HPLC/GC), water content (KF) for moisture sensitivity in downstream steps, and residual solvents. For chiral work, check ee/er. All item-specific values: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• Role in synthesis
  • Bifunctional diamine and heteroaryl-alkyl linker used as a building block in medicinal and materials chemistry. The primary benzylic amine is highly nucleophilic and readily derivatized; the morpholine nitrogen provides tertiary amine character and tunable basicity/solubility.
• Representative transformations (literature/general)
  • Amide/carbamate formation: Acylation with acid chlorides/anhydrides or coupling (EDC/HATU/DIC) to give amides and ureas; Boc/CBZ protection can be applied selectively to the primary amine.
  • Reductive amination: The primary amine condenses with aldehydes/ketones; reduction (NaBH3CN, NaBH(OAc)3, catalytic H2) affords secondary amines while retaining the morpholine.
  • Sulfonylation: Reaction with sulfonyl chlorides yields sulfonamides (excellent handles for SAR and as leaving groups).
  • Quaternization/functionalization of morpholine N: Alkyl halides or methyl triflate generate quaternary ammonium salts; N-oxide formation with m-CPBA provides distinct polarity for separation.
  • Cross-coupling adjunct: The benzylic center adjacent to the aryl ring is compatible with downstream aryl functionalization when the phenyl bears halogen substituents (in analogs).
• Practical tips
  • Chemoselectivity: The primary amine is generally more reactive than the tertiary morpholine N toward acylation/sulfonylation; use stoichiometry and base choice to maintain selectivity.
  • Silica tailing: Add 0.1–1% Et3N to eluents. Alternatively, isolate as an acid salt, then basify at the end.
  • Salt strategies: Forming crystalline HCl or p-TsOH salts can aid purification, stability, and handling of oils.
• Application domains
  • Common in fragment-based libraries, solubilizing linkers, and as a polar headgroup for amphiphilic constructs in probe development.

Reaction Conditions

General, literature-based guidance for this scaffold (optimize per substrate and scale):

• Amide/carbamate formation
  • Solvent: DCM, THF, or EtOAc (greener) under anhydrous conditions.
  • Base: DIPEA or Et3N (2–3 equiv).
  • Reagents: Acid chlorides/anhydrides, or EDC/HATU with HOAt/HOBt alternatives.
  • Temperature/time: 0–25°C, 1–16 h. Typical isolated yields: 70–95% for clean systems.
• Reductive amination on the primary amine
  • Solvent: MeOH, EtOH, or MeCN.
  • Conditions: Aldehyde/ketone (1.0–1.5 equiv), AcOH (0.5–1.0 equiv) to form imine, then NaBH(OAc)3 (1.5–2.5 equiv). 0–25°C, 2–18 h. Yields: 60–90% depending on sterics/electronics.
  • Alternative: Catalytic hydrogenation (H2, 1–3 bar) over Pd/C in EtOH for imine/hydrogenation telescopes.
• Sulfonamide formation
  • Solvent: DCM or MeCN; base: NaHCO3/Et3N; sulfonyl chloride (1.05–1.2 equiv); 0–25°C. Yields: 70–95%.
• Quaternization of morpholine nitrogen
  • Solvent: MeCN/acetone; alkyl halide (e.g., MeI, 1.2–2.0 equiv); reflux 4–24 h. Isolation as iodide/bromide salt by precipitation.
• Purification
  • Add 0.1–1% Et3N to silica eluents to prevent tailing, or isolate as crystalline acid salts (HCl, TsOH), then free-base as needed.

All values above are literature-type ranges for analogous amines and are provided as general guidance only.

Safety and Handling

• Item-specific GHS information: Not specified for this item; refer to SDS.
• General hazards for aliphatic/aromatic diamines (literature-based guidance)
  • May cause skin and eye irritation; vapors/aerosols can irritate respiratory tract.
  • Amines are basic and can be corrosive to some materials in concentrated form; may be harmful if swallowed.
  • Not a strong peroxide former; however, general good practice is to store away from oxidizers.
• PPE and engineering controls
  • Wear suitable gloves (e.g., nitrile), lab coat, and splash goggles. Handle in a fume hood to avoid inhalation of vapors/aerosols.
  • Avoid contact with acids unless forming a deliberate salt; neutralization can be exothermic.
• Incompatibilities
  • Strong oxidizers, acid chlorides/anhydrides (violent acylation possible), isocyanates (rapid urea formation), and carbonyl-activating agents that can react exothermically with amines.
• First-aid overview (defer to SDS for authoritative steps)
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor for respiratory distress.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Storage and handling tips
  • Store tightly closed at room temperature (per Product Data). Protect from moisture and CO2 to minimize adventitious salt formation; for long-term storage, consider inert atmosphere and amber container if extended light exposure is expected.

Solvent Selection

• Polarity and solubility considerations (general)
  • The free base is polar, hydrogen-bond basic, and typically miscible/soluble in polar protic (MeOH, EtOH, i-PrOH) and polar aprotic solvents (MeCN, acetone, DCM/CHCl3 to a degree, THF, DMF, DMSO). Water solubility is enhanced upon protonation (e.g., as HCl salt).
• Choosing solvents by operation
  • Reaction media: For acylations/carbamate formations, use anhydrous DCM, THF, EtOAc, or DMF with base (DIPEA/Et3N). For reductive amination: MeOH, EtOH, or MeCN with NaBH3CN/NaBH(OAc)3.
  • Workup: Extract free base into organic (EtOAc/MTBE) from basic aqueous; switch to aqueous phase by acid extraction (e.g., 1–2 M HCl) to isolate salts.
  • Purification: Amines can tail on silica. Add 0.1–1% Et3N to mobile phase or use neutral alumina/reverse-phase chromatography.
• Comparison notes
  • DCM vs. EtOAc: DCM offers faster kinetics and better solubilization of both amine and acylating agents; EtOAc is greener but may require longer times.
  • MeOH/EtOH vs. MeCN: Alcohols facilitate imine formation/reduction; MeCN provides cleaner baselines for HPLC monitoring.
• Salt handling
  • If supplied/converted to an acid salt, aqueous processing and crystallization from alcohol/ether mixtures often give improved handling and stability.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Keep container tightly closed. Store in a dry place away from strong oxidizers and acids.
• General handling
  • Protect from atmospheric CO2 and moisture to avoid adventitious salt formation and viscosity changes. For long-term storage, consider inert atmosphere and an amber vial if light-sensitive partners are present.
• Reconstitution/preparation of solutions
  • Solubility: Readily soluble in polar organic solvents such as MeOH, EtOH, MeCN, DMF, and DMSO (literature, diamines). Water solubility is greatly increased as an acid addition salt.
  • Stock solutions: Prepare at 10–500 mM in dry solvent depending on application. For biological assays, filter-sterilize and store aliquots at 2–8°C to minimize microbial growth; avoid repeated freeze–thaw of aqueous stocks.
• Stability notes
  • Free base amines can absorb CO2 and form carbamates on prolonged air exposure; cap promptly after use. Avoid strong oxidants.
• Any item-specific stability/shelf-life parameters: Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

Brief description: 2-(Morpholin-4-yl)-2-phenylethan-1-amine is an aromatic, bifunctional diamine featuring a primary benzylic amine and a tertiary morpholine nitrogen within a six-membered N,O-heterocycle.

• Item-specific (from Product Data)
  • CAS: 31466-44-1
  • InChIKey: 406993 (as provided)
  • Storage conditions: Room temperature
  • Research Use: For research use only
• Literature/Computed identifiers and features (for reference; not item-specific specs)
  • Synonyms: 2-Phenyl-2-(morpholin-4-yl)ethan-1-amine; β-amino tertiary morpholine derivative
  • Molecular formula (neutral free base, literature): C12H18N2O
  • Molecular weight (literature, free base): ~206.29 g/mol
  • SMILES (literature, non-stereo): NCC(c1ccccc1)N2CCOCC2
  • Functional groups: primary aliphatic amine (benzylic), tertiary morpholine nitrogen, aryl ring, ether (in morpholine)
  • Structural description (2D): a chiral benzylic carbon (C2) bearing three substituents—phenyl, morpholin-4-yl (N-attached), and a methylene terminating in a primary amine (–CH2–NH2). The morpholine is a six-membered ring containing one nitrogen and one oxygen atom in a 1,4-relationship.
  • Stereochemistry: The benzylic center is prochiral/chiral when resolved; commercial material is typically racemic unless specified (not specified for this item; refer to CoA/Spec Sheet).

Synthetic Utility

• Functional group handles and selectivity
  • Primary amine (benzylic): Highly nucleophilic; undergoes acylation, sulfonylation, urea/carbamate formation, and reductive amination. Typically reacts faster than the tertiary morpholine nitrogen, enabling chemoselective derivatization.
  • Tertiary morpholine nitrogen: Amenable to quaternization (alkyl halides), N-oxidation (m-CPBA), and occasionally Mannich-type reactions when activated. Provides a built-in solubilizing group.
  • Aromatic ring: Platform for π–π interactions in ligands; can be further functionalized in appropriately substituted analogs.
• Protection strategies
  • Protect the primary amine (e.g., Boc, CBZ, Fmoc) to manipulate the morpholine nitrogen selectively. Boc protection is robust to many conditions and removable under mild acid.
• Linker chemistry
  • Serves as a spacer connecting an aryl pharmacophore to a solubilizing tertiary amine; useful in conjugate and probe synthesis.
• Retrosynthetic value
  • Accessible via reductive amination of benzaldehyde derivatives with 2-(morpholin-4-yl)ethylamine, or via addition of morpholine to styrene oxide followed by amination—routes allow late-stage diversification on the aryl component.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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

The CAS Number is 31466-44-1, the molecular formula is C12H18N2O, and the molecular weight is 206.29 g/mol. InChIKey WSNSRJWLIVDXDI-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.