2-methyl-2-morpholinopropanal - Reagent grade

Cat. No.: M481977

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Specifications & Purity

Reagent grade

Storage

Room temperature

Grade

Reagent Grade

Application Protocols

No antibody/assay application protocols apply to this small-molecule reagent. For practical use, see synthetic protocols in Reaction Conditions and Reaction & Applications.

• Tested applications (WB, IHC, IF, FC): Not applicable.
• Recommended dilutions: Not applicable.
• Positive controls: Not applicable.

General handling protocol (synthetic use):

• Bring to room temperature (if stored cold), open under inert gas if possible. For moisture-sensitive transformations, transfer via syringe or cannula. Use dry, amine-compatible solvents and monitor reactions by TLC/LC–MS.

Biological Roles

• This compound is a synthetic organic reagent/building block combining a morpholine tertiary amine and an aldehyde. It is not a known natural metabolite or cofactor.
• Morpholine-containing motifs appear in many synthetic auxiliaries and materials; however, 2-methyl-2-morpholinopropanal itself has no established endogenous biological role.
• The tertiary amine could form salts with physiological acids, increasing water compatibility, but any biochemistry would be dominated by nonspecific interactions (electrostatic/hydrogen bonding) rather than receptor-selective binding.
• Due to the reactive aldehyde functionality, the compound can form Schiff bases with primary amines (e.g., lysine side chains) in proteins under suitable conditions; in biological matrices this is typically reversible and non-selective. Such reactivity is a general property of aldehydes and should not be interpreted as a targeted biological function.
• Research use only (from Product Data). Any exploration of biochemical reactivity should be performed in controlled in vitro settings with appropriate quenching/derivatization to manage aldehyde–amine equilibria.

Item-specific biological data (targets, pathways, EC numbers, etc.): Not specified for this item; refer to CoA/Spec Sheet if available.

Buffer Applications

This product is not a buffering agent. As a reactive aldehyde/amine-containing building block, it is generally unsuitable for preparing pH buffers or for routine buffer components in biochemical assays.

• If used in biochemical experiments, avoid standard buffer systems that may react with aldehydes (e.g., Tris contains a primary amine and can form imines/hemiaminals). Phosphate or acetate buffers without primary amines are less reactive but may protonate the tertiary amine, altering solubility.
• For carbonyl derivatization studies, employ amine-free buffers and control pH to moderate imine formation (typically mildly acidic to neutral).

No validated buffer formulations are provided for this item. For operational use, see sections Reaction & Applications and Reaction Conditions.

Green Alternatives

This product is a specialty building block, not a process solvent. Green chemistry considerations focus on solvent/reagent choices and waste minimization when employing it.

• Greener solvent choices (general guidance):

  • Replace chlorinated solvents with ethyl acetate, 2‑MeTHF, CPME, or propylene carbonate where compatible.
  • For reductive amination, ethanol or isopropanol can be effective, reducing toxicity compared with MeCN or DMF in some cases.

• Oxidation/reduction choices:

  • Use TEMPO/bleach (aqueous NaOCl) or oxygen with catalytic TEMPO for oxidation to acids/aldehyde derivatives instead of chromium(VI) reagents.
  • Prefer NaBH(OAc)3 or catalytic hydrogenation over pyrophoric hydrides when feasible; consider transfer hydrogenation (HCO2NH4, HCO2Na) with supported catalysts.

• Energy and safety:

  • Conduct reactions at ambient temperature/pressure when possible; the built-in tertiary amine can sometimes obviate external bases.
  • Employ continuous-flow or microreactor setups for hazardous steps (e.g., handling of cyanoborohydride or hydrogenation), improving safety and scalability.

• Comparison snapshot (general, application-focused)

  • THF vs 2‑MeTHF/CPME: greener ethers offer higher boiling points and lower peroxide tendencies; check solubility and rate effects.
  • MeCN vs EtOH: EtOH is renewable and less toxic; however, iminium formation may be slower and equilibria differ—optimize acid loading.

Note: No alternative exists for the molecular function of this specific aldehyde; greening focuses on the surrounding process.

Pharmaceutical Uses

• Role: Potential intermediate/building block in medicinal chemistry and process development owing to the morpholine motif and aldehyde handle. It can be used to assemble morpholine-bearing scaffolds, β‑amino alcohols, and quaternary‑center frameworks.
• Regulatory/compendial status: Not specified for this item; refer to CoA/Spec Sheet. No pharmacopeial monograph is indicated in the provided data.
• Formulation/excipient use: Not typical. Reactive aldehydes are generally not excipients due to reactivity toward amines and proteins.
• Process considerations:
  • Salt formation with mineral or organic acids can modulate handling (reduced vapor, increased crystallinity), but will also deactivate the amine’s basicity until neutralized.
  • For GMP contexts, control residual aldehyde content in downstream intermediates and ensure purge of potential nitrosamine precursors; tertiary amines are generally less prone than secondary amines, but risk assessments are recommended.
• Analytics (general suggestions):
  • Assay by GC or HPLC with derivatization (e.g., DNPH or oxime formation) to stabilize the aldehyde for quantitation.
  • Impurities: over-oxidation to the acid, hydration/acetalization by solvents, and N‑oxide formation of the tertiary amine under strong oxidants.

No therapeutic claims are made. For research and development use only (per Product Data).

Physical Properties

Item-specific specifications have not been provided. Do not construe the following as product specifications; consult the CoA/Spec Sheet for release values.

• Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point, melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general expectations, literature-based reasoning)
  • Likely high solubility in polar aprotic organic solvents (e.g., acetonitrile, DMF, DMSO, EtOAc) due to the polar tertiary amine and aldehyde.
  • Partial to good miscibility with alcohols (MeOH, EtOH); water solubility may be moderate because the morpholine increases polarity, but aldehydes can hydrate—handle under controlled pH to avoid side reactions.
• Acid/base behavior (general)
  • Contains a tertiary amine (morpholine; conjugate acid pKa typically ~8.3–8.6 for morpholine, literature), suggesting basicity and salt formation in acidic media.
  • Aldehyde is not appreciably deprotonated under neutral conditions; the α‑carbon here is quaternary (no α‑H), so no enolization.
• Partitioning (general)
  • Expect intermediate polarity; the morpholine ring reduces lipophilicity relative to simple aliphatic aldehydes, aiding handling in polar media.

For any numeric property (BP, MP, density, nD, water content, peroxide content, metal content, UV cutoffs): Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade/Purity (from Product Data): Reagent Grade.

• What Reagent Grade typically indicates (general explanation):

  • Suitable for routine laboratory synthesis and preparative work where trace-absorptivity, metal content, or ultra-low impurity levels are not critical, in contrast to HPLC/LC–MS grades.
  • Reasonable control of common impurities, but not necessarily specified for parameters such as UV cutoff, water (Karl Fischer), peroxides, or trace metals unless stated on the CoA.

• Implications for this item:

  • As a bifunctional aldehyde/tertiary amine, impurity profile can influence reactivity (e.g., presence of acids can protonate the amine; peroxides are less relevant than for ethers, but oxidation to the corresponding carboxylic acid is a common degradant for aldehydes). Check the CoA for aldehyde assay and related-substances profile.
  • If your application is moisture- or acid-sensitive (e.g., reductive amination with cyanoborohydride, organometallic additions), consider additional in-lab purification (e.g., vacuum distillation under inert gas) if permissible.

• Stabilizers:

  • Stabilizer presence is Not specified for this item; refer to CoA/Spec Sheet. If none is present, handle under inert atmosphere and keep dry to limit oxidation/hydration.

• Release specifications:

  • Any item-specific numeric specifications (assay %, UV, water, metals): Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As a non-enolizable, sterically congested aldehyde bearing a tertiary amine, 2-methyl-2-morpholinopropanal is a versatile building block in amine and carbonyl chemistry.

• Key reaction manifolds (general, literature-based):

  • Reductive amination: Formation of iminium ions with primary/secondary amines followed by reduction (e.g., NaBH3CN, NaBH(OAc)3, catalytic hydrogenation) to furnish β-tertiary-amine alcohols or diamines depending on partner; the internal tertiary amine remains as a pendant base.
  • Nucleophilic additions to the aldehyde: Organometallic reagents (RMgX, RLi, R2CuLi) provide tertiary carbinols adjacent to a morpholine substituent; strong base and rigorously anhydrous conditions recommended.
  • Oxime/hydrazone/semicarbazone formation: For temporary protection or analytical derivatization of the aldehyde.
  • Acetal/ketal formation: Acid-catalyzed acetalization with diols or alcohols; tertiary amine protonation must be controlled to avoid over-acidification.
  • Oxidation: To the corresponding carboxylic acid or amide derivatives (e.g., Pinnick oxidation for mild conversion to acid; TEMPO/bleach systems also feasible).

• Strategic features:

  • α-Quaternary center (no α‑H): No enolization or self-aldol—useful when an electrophilic aldehyde is desired without aldol side reactions under base.
  • Built-in tertiary amine: Can enhance solubility in polar media and enable phase-transfer-like behavior; also offers a handle for quaternization or salt formation.

• Applications (examples):

  • Synthesis of β-amino alcohols, tertiary carbinols, and morpholine-containing scaffolds for catalysis ligands, materials, or discovery chemistry.
  • Use as a Mannich electrophile equivalent in multicomponent condensations (e.g., iminium-mediated couplings).

Reaction Conditions

The following guidance reflects general literature practice for aldehydes bearing tertiary amines; adapt to your system. These are not product specifications.

• Reductive amination (general):

  • Typical solvents: MeOH, EtOH, iPrOH, or MeCN. Buffer to pH ~5.5–6.5 with AcOH to promote iminium formation while preserving NaBH3CN stability.
  • Reagents: NaBH3CN (0.5–1.5 eq) or NaBH(OAc)3 (1.5–2.5 eq); 20–25 °C to start, 2–16 h. Monitor by LC. Workup with aqueous bicarbonate, extract into EtOAc.

• Organometallic additions to the aldehyde:

  • Solvent: anhydrous THF, 2‑MeTHF, CPME, or toluene; −78 to 0 °C initially, then warm to RT. Use 1.1–2.0 eq nucleophile. The tertiary amine may coordinate metals—precomplexation or protonation (as ammonium salt) can be used to tune reactivity.

• Oxime/hydrazone formation:

  • Solvent: EtOH or MeCN; catalyst: a few mol% AcOH. Room temperature to 50 °C, 1–6 h. Remove water (molecular sieves) to drive conversion.

• Acetalization:

  • Solvent: ROH (e.g., MeOH, EtOH) or toluene with Dean–Stark; acid catalyst (TsOH, CSA). Control acid strength to minimize amine salt precipitation; 0–60 °C, 2–12 h.

• Oxidation to acid:

  • Pinnick oxidation (NaClO2, NaH2PO4, 2‑methyl‑2‑butene) in t‑BuOH/H2O; 0–25 °C. Alternatively, TEMPO/NaOCl in biphasic systems.

• Purification notes:

  • Aldehydes may streak on silica; pre-treat silica with base (1–2% Et3N) or use rapid flash. Avoid prolonged exposure to acidic media that can protonate morpholine and alter elution.

• Expected yields: Highly substrate- and partner-dependent; consult the primary literature for analogous morpholine-bearing aldehydes.

Safety and Handling

Authoritative safety information must be taken from the product SDS. The following are general considerations for aldehyde- and tertiary-amine–containing organics.

• GHS/CLP (Product Data):

  • Signal word: Not specified for this item; refer to CoA/Spec Sheet and SDS.
  • H‑statements: Not specified for this item; refer to CoA/Spec Sheet and SDS.
  • GHS classification/pictograms: Not specified for this item; refer to CoA/Spec Sheet and SDS.

• Anticipated hazards (general):

  • Aldehydes can be irritants and sensitizers; may cause eye/skin/respiratory irritation. Tertiary amines can be corrosive/irritant and are often harmful if swallowed or inhaled.
  • May form imines/hemiaminals with amines; avoid unintended reactions with amine-containing PPE and materials.

• PPE and engineering controls:

  • Use chemical-resistant gloves (e.g., nitrile), lab coat, splash goggles.
  • Handle in a chemical fume hood; avoid inhalation of vapors.

• Incompatibilities and reactivity:

  • Avoid strong oxidizers (risk of exothermic oxidation of aldehydes and amines).
  • Avoid strong acids/bases that may induce decomposition, iminium formation, or acetalization; tertiary amines will form salts in acids.
  • Reactive toward nucleophiles (bisulfite, amines, hydrazines) at the aldehyde.

• First aid (overview; follow SDS):

  • Inhalation: move to fresh air, seek medical advice if symptoms persist.
  • Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Fire safety: Treat as a combustible organic liquid/solid; use CO2, dry chemical, or foam. Vapors may be irritating; use SCBA for large fires.

Solvent Selection

This product is a reactive building block rather than a solvent. The following guidance addresses solvent choice when using 2-methyl-2-morpholinopropanal in synthesis.

• Polarity/miscibility (general expectations):

  • The morpholine ring imparts polarity and hydrogen-bond basicity; good solubility is expected in polar aprotic solvents (MeCN, DMF, DMSO) and in alcohols. Solubility in nonpolar hydrocarbons may be limited; use co-solvents if needed.

• Choosing solvents by transformation:

  • Reductive amination: MeOH, EtOH, or MeCN are commonly used; control pH (5.5–6.5) to balance iminium formation with reductant stability (general literature guidance).
  • Nucleophilic additions (e.g., organometallics): Anhydrous ethers (THF, MTBE, CPME) or toluene; strictly anhydrous/inert conditions.
  • Carbonyl protections (acetalization/oxime/hydrazone): Alcoholic solvents with acid catalysts (acetal); EtOH/MeOH or MeCN for oximes/hydrazones.
  • Oxidation to acid: Aqueous-organic biphasic systems (AcOH/H2O, MeCN/H2O) or polar organics depending on oxidant.

• Practical tips:

  • Avoid strongly acidic media that fully protonate the tertiary amine unless amine salification is desired; protonation can change solubility and reactivity.
  • Water promotes aldehyde hydration and Schiff-base equilibria; use dry solvents for nucleophilic additions and protections.

• Quick comparison (general)

  • MeCN: low proticity, good for iminium formation and many oxidations.
  • Alcohols (MeOH/EtOH): enable reductive amination with NaBH3CN/NaBH(OAc)3; watch for acetal formation.
  • Ethers (THF/CPME): preferred for strong nucleophiles; minimize side reactions at the aldehyde.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.

• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Practical storage guidance (general for aldehydes/tertiary amines):

  • Keep tightly closed in an inert atmosphere (nitrogen/argon) to limit oxidation of the aldehyde to the corresponding acid and to avoid moisture-induced hydration or acetalization.
  • Store away from acids, bases, and oxidizers. Use amber glass if the compound is light-sensitive (check CoA/SDS); minimize headspace and consider storing over activated 3 Å molecular sieves in a sealed vial.
  • If extended storage is required, aliquot to minimize repeated air/moisture exposure. Monitor by NMR/GC before critical use.

• Reconstitution/handling:

  • If supplied as a solid or viscous oil, warm gently to room temperature to ensure homogeneity before sampling. If crystallized as a salt (not specified for this item), free-basing may be required prior to use.
  • For moisture-sensitive reactions, pre-dry solvents and glassware; consider brief vacuum/nitrogen cycles after opening.

• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

• Research Use Note (from Product Data): For research use only.

Structure and Identity

Short description: 2-methyl-2-morpholinopropanal is a bifunctional organic building block combining a tertiary amine (morpholine) with an aldehyde on a quaternary α-carbon center.

• Item identifiers (from Product Data)

  • SKU: M481977
  • Product name: 2-methyl-2-morpholinopropanal
  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • 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.

• Structural features (general chemistry description)

  • Core scaffold: a propanal (–CHO) where C2 is tetrasubstituted, bearing a methyl (–CH3) and a morpholin-4-yl group (a six‑membered O,N-heterocycle with one oxygen and one tertiary nitrogen).
  • Functional groups: aldehyde (electrophilic carbonyl) and tertiary amine (basic, Lewis basic site); ring system: morpholine (saturated, heteroatom-rich ring).
  • Stereochemistry: none expected (quaternary α-carbon; no stereocenters indicated by the name).
  • 2D description in words: an aldehyde carbonyl at one end of a three‑carbon chain; the adjacent carbon (C2) carries both a methyl and an N‑linked morpholine substituent, creating a non‑enolizable, congested aldehyde center.

• Notes

  • This identity summary reflects the IUPAC-style name. Exact registry identifiers should be confirmed on the product’s CoA/Spec Sheet.

Synthetic Utility

• Functional group constellation:

  • Aldehyde (electrophile) at a carbonyl carbon adjacent to a quaternary center—resistant to enolization; good acceptor for nucleophilic additions and condensations without self-aldol.
  • Tertiary amine (morpholine) providing basicity, solubilizing character, and a handle for quaternization or N‑oxidation if desired.

• Strategic uses in synthesis (general, literature-based):

  • Construction of tertiary carbinols via addition of organometallic nucleophiles (RMgX, RLi, stabilized carbanions), then downstream elaboration (e.g., activation → substitution, or oxidation → rearrangements).
  • Reductive amination with external amines to furnish β‑substituted tertiary amines; stereochemical control can be introduced via chiral amines or catalysts at the iminium-reduction step.
  • Oxidation to acids, then amide coupling to embed the morpholine-bearing quaternary center in peptide-like or heteroatom-rich frameworks.
  • Derivatization of the morpholine nitrogen (alkylation, acylation, sulfonylation) orthogonally to reactions at the aldehyde.

• Protecting-group and orthogonality considerations:

  • Protonation of the tertiary amine can modulate reactivity during acid-catalyzed steps (e.g., acetalization) but may complicate isolation; choose counterions (e.g., tosylate, HCl) judiciously.
  • Aldehyde protection (acetal/oxime) enables selective N‑chemistry on morpholine without competing carbonyl reactions.

• Advantages:

  • Lack of α‑H eliminates base-promoted side reactions and racemization concerns.
  • Intrinsic polarity aids in chromatographic separation and liquid-phase synthesis workflows.

Target Specificity

Not applicable. This product is a small-molecule building block and not a biological targeting reagent (no antigen/epitope/clone/isotype information).

• Target/epitope: Not specified for this item; refer to CoA/Spec Sheet.
• Species reactivity: Not applicable.
• Assay validations: Not applicable.