2-piperidinonicotinaldehyde - Reagent grade

Cat. No.: P481962

QUALITÉ & PURETÉ Reagent Grade

Storage

Room temperature

Spécifications

Spécifications et pureté

Reagent grade

Conditions de stockage de stockage

Room temperature

Grade

Reagent Grade

Application Protocols

No vendor-tested biological application protocols are provided for this small-molecule reagent. Typical laboratory protocols relevant to this scaffold include:

• General reductive amination workflow (outline; literature guidance):
  • Dissolve the aldehyde and amine (1.0–1.5 equiv) in MeOH or EtOH; add AcOH (0.2–0.5 equiv) and stir 0.5–2 h to form the imine.
  • Add NaBH(OAc)3 (1.2–2.0 equiv) portionwise at 0–25°C; stir until completion by TLC/LC–MS.
  • Quench with saturated NaHCO3, extract with EtOAc, dry, and purify on base-modified silica.
• Oxime formation (outline): Dissolve aldehyde and hydroxylamine hydrochloride (1.2–1.5 equiv) in EtOH with pyridine or NaOAc as base, stir at rt–50°C until complete; isolate oxime by filtration or extraction.
• Olefination (outline): For HWE, combine phosphonate (1.2–1.5 equiv) with base (NaH/DBU) in MeCN or THF at 0–25°C, then add aldehyde; quench and purify.

These outlines are for experienced chemists to adapt; they are not item-specific validated protocols. Always consult primary literature and perform small-scale optimization.

Research Use Note: For research use only.

Biological Roles

This product is supplied strictly for research use as a synthetic building block. No biological role or function is assigned in the Product Data.

General perspective (not item-specific and not implying therapeutic use):

• Heteroaryl aldehydes such as nicotinaldehyde derivatives are commonly employed in medicinal chemistry programs to construct libraries via reductive amination, imine formation, and olefination. The pyridine motif is prevalent in bioactive scaffolds due to its tunable basicity and ability to engage in hydrogen bonding and metal coordination.
• The presence of a pendant tertiary amine (piperidine) increases basicity and aqueous solubility upon protonation, aiding in lead optimization SAR studies where cationic centers are desirable for target engagement or PK tuning.
• Derivatized imines (Schiff bases) of pyridyl aldehydes can function as ligands in bioinorganic models; however, the parent aldehyde is not itself a biological buffer or metabolite.

Important: No claims are made regarding biological activity, safety, or suitability for clinical/diagnostic use. Any biochemical experiments should include appropriate controls and comply with institutional safety and ethics policies.

Buffer Applications

This compound is not a conventional buffering agent. As a heteroaryl aldehyde with basic nitrogens, it does not provide a defined conjugate acid/base pair with a narrow buffering range suitable for biochemical buffers.

Practical notes:

• If dissolved in aqueous systems, protonation under acidic conditions may increase solubility, but this is not “buffering” in the analytical sense.
• For experimental workflows requiring pH control, employ established buffers (e.g., phosphate, acetate, HEPES, MOPS) and use this compound only as a substrate or reagent within that buffered medium.

Refer to the sections on Reaction & Applications and Synthetic Utility for relevant uses. No buffer recipes are provided for this item.

Green Alternatives

Greener considerations focus on solvent and reagent choices for typical transformations of heteroaryl aldehydes; the product itself is a research building block and not replaced by a single “green” analogue.

Greener solvent substitutions (general guidance):

• Replacement of chlorinated solvents in workup/purification: Use ethyl acetate or 2-MeTHF instead of DCM/CHCl3 when polarity allows. Heptane/EtOAc systems frequently separate well.
• Reaction media alternatives:
  • For reductive amination: EtOH or i-PrOH with catalytic acid and sodium triacetoxyborohydride can reduce DMF usage; aqueous micellar media (e.g., TPGS-750-M) are reported for some imine reductions (literature) but require compatibility checks with basic heteroarenes.
  • For olefination: HWE reactions often proceed in MeCN or EtOH with carbonate bases instead of THF/DMF.
  • For Grignard additions: 2-MeTHF is a preferred alternative to THF due to higher boiling point and partial biorenewability.

Small comparison (literature/tradeoffs):

• DCM vs EtOAc: EtOAc is less toxic and bio-derived; DCM offers superior solvency and low boiling point for delicate separations.
• DMF/DMSO vs MeCN/EtOH: MeCN and ethanol are generally easier to remove and have more favorable environmental scores, but DMF/DMSO dissolve salts and polar substrates more effectively.

Process hygiene:

• Minimize excess reagents in imine formations; use solid-supported scavengers for amines/aldehydes to reduce solvent volumes.
• Recycle chromatography solvents where permitted; adopt reverse-phase purification for scale to reduce halogenated waste.

Always validate green substitutions on small scale to confirm selectivity and impurity profiles.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this item. This product is for research use only and is not intended for human or veterinary applications.

Research and development context (general):

• Heteroaryl aldehydes are widely used as intermediates in discovery chemistry to prepare amine-bearing analogues through reductive amination or as precursors to heteroaryl olefins via Wittig/HWE methodologies.
• The 2-piperidino substituent can be leveraged to modulate basicity and solubility of downstream analogues, which is often explored in lead optimization campaigns.
• Process considerations: When translating to scale, attention to residual aldehyde content, imine formation during storage, and control of amine salts is important for impurity profiles.

Compliance note:

• This SKU is not accompanied by GMP documentation or pharmacopeial monographs. It is not suitable as an API, excipient, or in clinical manufacturing without additional qualification and regulatory clearance.

For formulation or process development efforts in a regulated context, obtain appropriate quality documentation and perform full internal qualification prior to any non-research use.

Physical Properties

Item-specific physical constants are not supplied in the Product Data. For specifications used for lot release, consult the CoA/Spec Sheet.

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

General/literature expectations for a 2-(piperidin-1-yl)-substituted nicotinaldehyde (for planning only):

• Polarity: Moderately polar aromatic aldehyde containing two basic nitrogens (pyridine and tertiary amine). The free base is often soluble in polar organics (MeOH, EtOH, MeCN, acetone, DCM, DMF, DMSO). The conjugate acid is typically water-soluble under acidic conditions.
• Acid–base behavior: The aldehyde is non-ionizable; the pyridine N and the piperidine N are basic (tertiary). Protonation state will strongly affect solubility and chromatographic behavior.
• Stability: Aldehydes can undergo air oxidation, aldol/imine formation, and polymerization under strongly basic or nucleophilic conditions. The tertiary amine may absorb CO2/H2O forming ammonium salts on standing.

Important: Do not treat the above as specifications; verify with analytical data for your lot if exact constants (bp/mp, assay, water, residual solvents) are critical.

Quality and Grades

• Grade/Purity: Reagent Grade (per Product Data). Reagent Grade generally denotes material suitable for standard laboratory synthesis and analytical work, meeting common impurity thresholds for routine research tasks. It is not necessarily low-UV HPLC grade or trace-metal certified unless explicitly stated.

What Reagent Grade means in practice:

• Typical intent: Organic synthesis, method development, and general lab use where ultra-trace impurities and ultra-low UV background are not critical.
• Impurities: Specific limits (e.g., water content, residual solvents, metals, UV cutoffs) are NOT specified for this item; refer to CoA/Spec Sheet for lot-specific data if required by your application.
• Stabilizers: None are listed in the Product Data; if stabilization is present (e.g., acidification or antioxidant), it will be indicated on the label/CoA.
• Documentation: For GMP or regulated environments, this product is intended for research use only; it is not accompanied by pharmacopeial monographs or GMP documentation.

Selecting the appropriate grade:

• Use this Reagent Grade material for discovery chemistry, route scouting, and non-quantitative workflows.
• For applications demanding tight spectroscopic backgrounds (e.g., LC-UV method development) or very low metal content (e.g., sensitive catalysis screening), request the CoA for your lot or contact us to discuss alternate grades.

Bottom line: This SKU supplies reliable research-grade material. Confirm lot-specific attributes via CoA/SDS if your process is sensitive to moisture, UV baseline, or trace ions.

Reaction and Applications

As a 2-(piperidin-1-yl)-substituted nicotinaldehyde (inferred from the name), this molecule is a versatile heteroaryl aldehyde building block combining a conjugated carbonyl with two basic nitrogens. Typical research applications include:

• Carbonyl transformations:
  • Imine/enamine formation with primary/secondary amines; downstream reductive amination to generate benzylic/pyridylalkyl amines. Catalysts: NaBH3CN, NaBH(OAc)3, or hydrogenation (Pd/C) after imine formation.
  • Wittig/HWE/Julia–Kocienski olefinations to install (hetero)aryl vinyl units with control over E/Z via reagent choice.
  • Cyanohydrin, bisulfite, hydrazone, oxime formation for derivatization or protection.
  • Nucleophilic additions (Grignard/organolithium) to access secondary/tertiary alcohols; protect or protonate basic nitrogens to avoid competitive deprotonation/coordination.
• Electrophilic aromatic chemistry: The 2-piperidino substituent is a strong electron donor, modulating the pyridine ring electronics and potentially directing metalation or cross-coupling on appropriately functionalized congeners.
• Condensation chemistry: Knoevenagel condensations with active methylenes (e.g., malononitrile, cyanoacetates) under mild base to install push–pull chromophores or conjugated acceptors.
• Coordination and materials: The pyridyl nitrogen can act as a ligand site; imine derivatives can serve as Schiff-base ligands in coordination chemistry studies.

Practical tips:

• Aldehyde compatibility: Exclude strong bases or free primary amines until intentional condensation; store and handle under neutral conditions to minimize background imine formation.
• Workup: Exploit acid/base toggling for phase separations (protonate to move into water; basify to recover the free base). Use base-modified silica for chromatographic purification to minimize tailing and decomposition.

Reaction Conditions

No item-specific recommended conditions are provided. The following are general literature-style conditions for common transformations of heteroaryl aldehydes containing basic nitrogens; verify and optimize for your substrate.

• Reductive amination: Form imine/enamine in MeOH, EtOH, or MeCN with a catalytic acid (e.g., AcOH) followed by NaBH3CN or NaBH(OAc)3 at 0–25°C. For secondary amines, NaBH(OAc)3 in DCE or MeOH often affords clean conversions. Maintain pH ~5–6 to balance imine formation and suppress amine over-protonation.
• Wittig/HWE olefination: Use stabilized ylides or phosphonates in THF, toluene, or MeCN with bases such as NaH, KOtBu, or DBU at 0–25°C (Wittig) or 0–40°C (HWE). Coordinate-basic nitrogens may slow reactions; temporary protonation or Lewis acid additives can modulate rates/selectivity.
• Nucleophilic additions: Grignard reagents in 2-MeTHF/THF at −78 to 0°C; pre-form amine salts with HBF4·Et2O or HCl in ether when necessary to reduce substrate basicity and prevent catalyst/metal scavenging.
• Knoevenagel condensations: Piperidine or ammonium acetate catalysis in EtOH, toluene, or acetonitrile at rt–80°C with active methylene partners (malononitrile, cyanoacetates). Water removal (azeotrope or molecular sieves) improves E/Z control and conversion.
• Oxime/hydrazone formation: Hydroxylamine hydrochloride or hydrazine derivatives in EtOH/AcOH or MeOH at rt–50°C.

Analytics:

• Monitor by LC–MS with acidic or basic modifiers to manage peak shape. 1H NMR typically shows an aldehyde singlet around 9–10 ppm (literature, solvent-dependent) unless derivatized.

These are starting points; run small-scale screens to tailor to this substrate’s electronics and basicity.

Safety and Handling

Hazard classification details (GHS, H/P statements, pictograms) are not provided in the Product Data for this SKU. Always consult the product SDS for authoritative safety information.

General safety guidance for heteroaromatic aldehydes bearing tertiary amines (good laboratory practice):

• Anticipated hazards: Irritation to skin/eyes/respiratory tract is common with aldehydes and amines; sensitization is possible with some aldehydes. Handle in a fume hood to avoid inhalation of vapors or aerosols.
• PPE: Safety glasses or splash goggles, lab coat, and suitable chemically resistant gloves (e.g., nitrile). Use a fume hood or local exhaust ventilation. Avoid contact with acids/bases that can lead to exothermic neutralization or side reactions.
• Incompatibilities: Strong oxidizers (risk of over-oxidation), strong acids (may form ammonium salts; possible exotherm), strong bases and nucleophiles (can promote aldol/imine formation or Cannizzaro-like side processes in non-enolizable contexts), acid chlorides/anhydrides (acylation of amine). Aldehydes may react with primary amines, hydrazines, and hydroxylamines to form imines/hydrazones/oximes.
• First aid (overview; follow SDS): If on skin or in eyes, rinse cautiously with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical advice.
• Fire safety: Treat as a combustible organic. Use CO2, dry chemical, or foam. Combustion may produce NOx and CO/CO2.
• Spill response: Absorb with inert material, avoid dust/vapor; collect for disposal per institutional and local regulations.

Note: SDS supersedes all general guidance. No medical or clinical use; for research use only.

Solvent Selection

This compound is a heteroaromatic aldehyde bearing a tertiary amine (piperidine) and a pyridine nitrogen. While item-specific solubility data are not provided, the following general guidance applies to similar structures:

• Polarity class: Moderately polar, basic aromatic aldehyde. Typically dissolves in polar aprotic solvents (MeCN, DMF, DMSO, acetone) and chlorinated solvents (DCM, CHCl3). Often soluble in short-chain alcohols (MeOH, EtOH). Protonation under mildly acidic conditions enhances water miscibility.
• Acid–base tuning: In basic media, the free base is lipophilic and extracts into organic layers. In acidic media (e.g., 0.1–1 M HCl), the ammonium salt shifts to aqueous phase—useful for workups and purifications.
• Chromatography: On silica, basic sites cause tailing. Add a volatile base (e.g., 0.1–1% Et3N) to the eluent or use base-deactivated silica/alumina. Reverse-phase methods benefit from pH control (e.g., 0.1% formic acid or ammonium formate) to modulate retention.
• Moisture sensitivity: Aldehyde functionality is moisture-tolerant but can form hydrates and imines with amines; dry solvents help minimize side reactions in base- or nucleophile-rich conditions.

When to choose alternatives:

• If UV transparency is critical (e.g., analytical LC), prefer MeCN or MeOH mobile phases and verify UV background from your lot’s CoA.
• If greener processing is desired, consider 2-MeTHF, CPME, or EtOAc for extractions and carbonyl reactions; replace DMF/DMSO where feasible with MeCN/EtOAc or alcohols.

Storage and Reconstitution

• Storage conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to air and moisture to mitigate aldehyde hydration/imine formation with adventitious amines.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/solubility: Not specified for this item; refer to CoA/Spec Sheet. General guidance: dissolve in common polar organic solvents (e.g., DCM, MeCN, MeOH, EtOH, acetone, DMF, DMSO) as compatible with your application. For aqueous handling, prepare acidic solutions to protonate the amine(s) and enhance solubility, then neutralize as needed during workup.
• Stability after opening: Aldehydes can slowly oxidize or form imines; minimize headspace oxygen and store in amber containers if light-sensitive impurities are a concern. If long-term storage is needed, consider inert atmosphere and desiccation.
• Freeze–thaw: Not typically required for small-molecule solids/liquids; if preparing stock solutions, aliquot and store under inert gas at appropriate temperatures to avoid repeated freeze–thaw cycles.

Always verify lot-specific recommendations on the product label and SDS. If critical to your process (e.g., for quantitative assays), confirm concentration and purity of stock solutions by analytical methods (NMR, HPLC, Karl Fischer as applicable).

Structure and Identity

Item-specific identifiers are not provided in the Product Data. Where values are missing below, consult the 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.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• CAS: Not specified for this item; refer to CoA/Spec Sheet.

Structural description (inferred from name; general/literature):

• 2-Piperidinonicotinaldehyde is best interpreted as a nicotinaldehyde (a 3-formylpyridine framework) bearing a piperidino substituent at the 2-position of the pyridine ring, i.e., 2-(piperidin-1-yl)nicotinaldehyde.
• Key functional groups: an aromatic pyridine ring (heteroaromatic nitrogen), an aldehyde (–CHO) directly conjugated to the ring, and a tertiary amine embedded in the piperidine ring attached through the ring nitrogen to C2 of the pyridine (anilide-type C–N bond).
• 2D description: a six-membered pyridine ring with the ring nitrogen at position 1; the aldehyde substituent typically at the 3-position (nicotinaldehyde core), and a –N(piperidinyl) substituent at the adjacent 2-position. The piperidine is a saturated six-membered tertiary amine ring.
• Stereochemistry: none (achiral), assuming no additional stereogenic centers.

Note: Exact regiochemistry and identifiers should be confirmed against the item’s CoA/SDS if needed for regulated workflows or analytical reference.

Synthetic Utility

Functional group set and reactivity (inferred from name; general guidance):

• Aldehyde: Highly versatile handle for C–C and C–N bond constructions. Engages in imine formation, reductive amination, nucleophilic additions, and olefinations (Wittig, HWE, Julia–Kocienski). Oxidation to the acid (or reduction to the alcohol) allows access to divergent oxidation states.
• Basic nitrogens: The pyridine N and tertiary piperidine N modulate electronics and coordination. Protonation state can be exploited for chemoselectivity (e.g., suppressing overaddition of organometallics by temporary salt formation) and purification.
• Heteroaromatic core: The nicotinyl framework provides a directional, coordinating motif, valuable in ligand design and in assembling metal-binding pharmacophores.

Strategic applications:

• Reductive amination with diversified amines to generate focused libraries of benzylic-like amines positioned on a pyridyl ring.
• Construction of push–pull chromophores via Knoevenagel condensation with activated methylenes, leveraging the aldehyde as an acceptor.
• Late-stage diversification: Oxime/hydrazone formation for conjugation or as masked aldehydes; subsequent transformations (e.g., Beckmann-type rearrangements for oximes) can open new vectors.
• Orthogonal manipulation: Temporary protection of the tertiary amine as a salt while performing carbonyl chemistry; conversely, protect the aldehyde (as acetal/oxime) while engaging in N-alkylations elsewhere.

Purification/handling:

• Use base-modified silica or add 0.1–1% Et3N in eluent to minimize tailing. Adjust pH during workups to partition between phases efficiently. Avoid prolonged exposure to strong nucleophiles to limit side reactions.

Target Specificity

Not applicable. This product is a small-molecule research reagent/building block and is not an antibody, enzyme preparation, or biological targeting agent. No antigen, epitope, clone, isotype, or species reactivity information applies.

For intended uses, refer to Reaction & Applications and Synthetic Utility sections.

Foire aux questions

What does Reagent Grade mean?

Reagent Grade is a defined analytical purity tier suitable for general analytical and reagent applications. It specifies a minimum assay percentage, controlled limits on common impurities (water, heavy metals, residue on ignition), and lot-to-lot consistency. Reagent Grade is one of several purity tiers — choose based on the sensitivity and regulatory requirements of your method.

How should this product be stored?

Store at room temperature.

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.