This compound belongs to the class of organic compounds known as piperidinones. These are compounds containing a piperidine ring which bears a ketone.
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
No application protocols are specified for this SKU. As a general solvent/reagent, protocols will be reaction‑ or process‑specific.
General usage guidance (literature/practice)
Solvent conditioning: Dry over 3 Å sieves before moisture‑sensitive work; filter before use if particulate control is required.
Reaction setup: Charge base/salts last to minimize localized precipitation; ensure efficient stirring due to higher viscosity than low‑bp solvents.
Workup: Dilute with water and extract if product partitions into organics; for polymer films, stepwise temperature ramps under vacuum reduce defects.
Analytics: Residual solvent by headspace GC; water content by Karl Fischer.
For standardized, step‑by‑step protocols, adapt published procedures for your specific transformation (e.g., SNAr, Suzuki coupling, polymer casting) and validate at the intended scale.
Biological Roles
This product is supplied for research use as a chemical solvent/reagent. No biological activity or clinical utility is claimed for this SKU.
General/literature context
Structural motif: The piperidone scaffold (piperidin‑2‑one) is a common intermediate in medicinal chemistry campaigns, and the piperidine ring is prevalent in natural products and pharmaceuticals. However, N‑methyl‑2‑piperidone itself is primarily employed as a process/analytical solvent rather than as a bioactive entity.
Biocompatibility: Polar aprotic lactams can interact with biological membranes and proteins through dipolar and hydrogen‑bond accepting interactions; they are widely used as formulation/process solvents in R&D. Specific ADME/tox or biological pathway interactions for N‑methyl‑2‑piperidone should not be inferred from NMP without direct data.
Enzymatic interactions: Cyclic amides may serve as substrates/analogues for amidases or lactamases in biochemical studies, but no specific role is established for this compound.
For any biological experiments, ensure that residual solvent levels are controlled and that appropriate vehicle controls are included. Consult institutional EHS and SDS guidance before in vitro or ex vivo use.
Buffer Applications
N‑Methyl‑2‑piperidone is not a buffering agent and is not typically used to prepare pH buffers. As a polar aprotic solvent, it can be used as a cosolvent to dissolve poorly soluble analytes or reagents in predominantly aqueous buffer systems.
Practical notes (general)
Cosolvent use: Introduce gradually to the aqueous buffer while stirring; verify that the final cosolvent fraction does not disrupt buffer capacity or biological assays.
Compatibility: High cosolvent fractions can alter protein stability and enzymatic rates; run controls if used in biochemical assays.
For buffer preparation recipes and pH ranges, refer instead to dedicated buffering systems (e.g., phosphate, Tris, HEPES).
Green Alternatives
Selecting greener solvents depends on the transformation and performance constraints. N‑methyl‑2‑piperidone shares many considerations with NMP regarding regulatory and EHS scrutiny; alternatives may be viable where extreme solvency/high‑bp are not mandatory.
Potential alternatives (literature/general):
Cyclic carbonates: Propylene carbonate (PC), ethylene carbonate (EC) — high polarity and bp; often lower toxicity profiles; limited water miscibility (PC) can aid workups.
Bio‑derived dipolar aprotics: Cyrene (dihydrolevoglucosenone) — strong polarity, limited base stability window; good for SNAr and some couplings.
Ethers: 2‑MeTHF, CPME — greener profiles and facile removal; lower polarity; may require salt‑solubilizing cosolvents/biphasic conditions.
Sulfoxides/sulfones: DMSO (readily available, biodegradable) and sulfolane (very high bp; check process safety).
Esters: Propylene glycol monomethyl ether acetate (PGMEA) for coatings where solvency and film formation are key.
Comparison snapshot (literature/general)
Polarity/bp trade‑offs: N‑methyl‑2‑piperidone offers very high bp and strong solvency; greener ethers/esters reduce hazard but may underperform for salts/polymers.
Workup/energy: Lower‑bp alternatives reduce drying energy and residual solvent risk; cyclic carbonates balance bp with improved profiles.
Process strategy: Consider cosolvent systems (e.g., PC + alcohol) or solvent‑free/solid‑state methods where feasible; apply solvent selection guides (e.g., CHEM21, PMI reduction) and pilot trials to confirm performance.
Note: Selection must consider EHS, regulatory acceptance, and product quality. Validate extractables/leachables and residual solvent limits for your application.
Pharmaceutical Uses
No pharmacopeial grade or excipient classification is specified for this item; consult the CoA/Spec Sheet for quality attributes.
General/formulation context (literature)
Role: High‑boiling polar aprotic solvent for process development — extraction, reaction medium, polymer/drug coating applications, and cleaning validation studies. It can dissolve a broad range of polymers (e.g., polyimides, polyurethanes) used in device and coating R&D.
Residual solvents: As a high‑bp solvent, removal may require elevated temperature/vacuum and extended drying; establish validated residual‑solvent limits and analytical methods (e.g., headspace GC) appropriate to your dosage form or device.
Materials compatibility: Generally compatible with stainless steel and glass; may swell certain elastomers and plastics (e.g., some fluoropolymers show resistance, while others may swell). Conduct extractables/leachables assessments when contacting polymers or seals.
Alternative solvent strategies: Where regulatory or toxicological drivers exist, evaluate cyclic carbonates (propylene carbonate) or bio‑derived dipolar aprotics (e.g., Cyrene) as potential substitutes in early development.
This product is provided for research use only and is not intended for human or veterinary use or for use in diagnostic procedures.
Physical Properties
Item-specific specifications are not provided in the Product Data. Values below are typical literature figures for N-methyl-2-piperidone and should be used as guidance only (not as specifications).
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~113.16 g/mol (literature)
Boiling point: typically reported ~265–275 °C at 1 atm (literature)
Melting point: typically reported below room temperature; liquid at ambient conditions (literature)
Density (20/25 °C): ~1.02–1.04 g/mL (literature)
Refractive index (nD20): ~1.485–1.495 (literature)
Vapor pressure: low at 25 °C (literature; consistent with high bp lactams)
Solubility: completely miscible with water and many polar organics (alcohols, ketones, esters, chlorinated and aromatic solvents) (literature)
LogP (octanol/water): around −0.4 to −0.2 (literature, indicative of high polarity)
Dielectric constant: estimated high, on the order of ~30 (literature, analogous to NMP)
Viscosity: moderately viscous relative to low‑bp solvents; increases at lower temperature (literature)
Notes
These values can vary with impurity level and water content. For exact property and analytical acceptance ranges of this specific lot/SKU, consult the CoA/Spec Sheet.
As a polar aprotic lactam, the solvent exhibits strong dipolar interactions and good salt/polymer solvency compared with ethers or esters of similar volatility.
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
UV/LC suitability: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general)
Analytical vs. synthetic grades: For chromatography or spectroscopic applications, low UV‑absorbing, low‑particulate material is preferred. For general synthesis, water and metal content often dominate performance; dry, low‑base/acid background is typically desirable for moisture‑sensitive reactions.
Water content: Polar lactams are hygroscopic to varying degrees. If Karl Fischer water limits are critical (e.g., for organometallic chemistry or high‑performance polymerizations), verify the actual lot value on the CoA. If lower water is needed, dry over 3 Å molecular sieves or by azeotropic removal (literature best practices).
Residual amines/basicity: Tertiary amide background is generally low‑basicity but can affect acid‑sensitive substrates. If acid number or amine content is relevant, consult the Spec Sheet.
Metals/peroxides/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
What the storage and shipping imply
The specified 2–8 °C storage and wet‑ice shipping suggest quality stewardship for materials where hydrolysis/volatility are minimal but oxidative/thermal history is controlled to preserve low impurity background and consistent viscosity/water content.
Reaction and Applications
This solvent’s high polarity, thermal window, and amide functionality underpin broad synthetic and processing uses.
Nucleophilic aromatic substitution (SNAr) on activated aryl halides/nitroarenes; polar aprotic medium accelerates rates and solubilizes inorganic bases.
Transition‑metal catalysis (Heck, Suzuki–Miyaura, Sonogashira): Good solubility for catalysts, bases, and aryl partners; supports elevated temperatures.
Condensations and cyclizations: Amidations, urea/urethane formation, lactamizations where solvation of reagents/additives is critical.
Heterocycle functionalizations: As medium for strong bases (e.g., K2CO3, Cs2CO3) with minimized proton donation.
Polymer chemistry: Casting and imidization of polyamic acids to polyimides; dissolution of engineering polymers; polyurethane prepolymer processing.
Practical tips (general):
Drying/degassing: Sparge with inert gas or vacuum‑argon cycles; 3 Å sieves for water control. Avoid strong reducing agents that may attack the amide.
Bases: Carbonates, tertiary amines, or alkoxides are commonly compatible; monitor for potential ring opening only under forcing basic/nucleophilic conditions at high T.
Workup: Due to high bp and water miscibility, aqueous extractions are effective; salting‑out can improve phase separation. Co‑evaporation with toluene/EtOAc assists removal.
Analysis: Residual solvent in polymers/actives can be quantified by GC with headspace; validate method due to high bp/low vapor pressure.
Manufacturer Applications: Not specified in Product Data. Typical uses (literature) include high‑temperature polar solvent media for synthesis, coatings, and polymer processing. Always validate suitability for your specific process.
Reaction Conditions
Typical literature guidance for using N‑methyl‑2‑piperidone as solvent (not specifications for this item):
General ranges
Temperature: Ambient to 160 °C (oil bath), limited by apparatus/seal compatibility; autogenous pressure may develop in closed vessels at high T.
Concentration: 0.1–1.0 M for small‑molecule couplings/condensations; higher for polymer processing/casting.
Atmosphere: Inert (N2/Ar) recommended for air/moisture‑sensitive reagents.
Named transformations (examples)
SNAr of activated aryl fluorides/chlorides: K2CO3 or Cs2CO3, 60–120 °C, 2–16 h; high conversions reported when nucleophile is solubilized.
Pd‑catalyzed Suzuki–Miyaura: Pd(PPh3)4 or Pd(dppf), base (K3PO4, K2CO3), 80–120 °C, 2–12 h; good solubility of aryl partners.
Heck coupling: Pd(OAc)2/PPh3 or Pd2(dba)3/ligand, Et3N or carbonate base, 100–140 °C.
Polyimide formation: Chemical imidization (acetic anhydride/triethylamine) at 20–80 °C or thermal imidization 150–250 °C post‑casting (solvent removal prior to high‑T step).
Drying/conditioning
Dry over 3 Å molecular sieves (activated at 250–300 °C) for 12–24 h; or strip under vacuum (≤10 mbar) at 60–80 °C with inert sparge.
Removal
Rotary evaporation may be inefficient due to high bp; prefer high‑vacuum (≤1–5 mbar) at 60–90 °C, co‑evaporating with toluene/IPA/EtOAc. Aqueous workup often expedites removal due to full water miscibility.
Note: Optimize conditions to the specific substrate/catalyst system; verify compatibility with bases, electrophiles, and seals/gaskets at target temperature.
Safety and Handling
Safety information specific to this item is not provided in the Product Data; consult the product SDS for authoritative guidance.
GHS/CLP classification, signal word, H‑statements, pictograms: Not specified for this item; refer to SDS.
General hazards (literature/general): Polar aprotic lactams can cause skin and eye irritation and may be harmful if inhaled or ingested. Prolonged or repeated contact may defat skin. Avoid aerosol formation and unnecessary exposure.
Storage conditions (from Product Data): Store at 2–8 °C.
Shipping (from Product Data): Shipped on wet ice.
Incompatibilities (general): Strong oxidizers; strong reducing agents; reactive acid chlorides/anhydrides; powerful dehydrating agents. Avoid bases or reagents that can induce ring‑opening under forcing conditions.
Handling practices (general):
Use in a chemical fume hood to minimize inhalation exposure, especially during heating.
Wear appropriate PPE: lab coat, safety glasses or goggles, and chemical‑resistant gloves (e.g., nitrile). Change gloves regularly due to potential permeation by polar solvents.
Prevent moisture uptake to maintain consistent solvent performance; tightly recap immediately after use.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with plenty of water for ≥15 minutes; 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 advice.
Fire safety (general): Combustible liquid with high flash point relative to common solvents; use CO2, dry chemical, or alcohol‑resistant foam. Cool containers with water spray in fire conditions.
Solvent Selection
N‑Methyl‑2‑piperidone is a high‑boiling, polar aprotic solvent in the lactam family, offering solvency similar to N‑methyl‑2‑pyrrolidone (NMP) but with a larger ring and higher thermal window.
Polarity/miscibility (literature/general):
High dipole moment; strong hydrogen‑bond acceptor; no donor capacity (tertiary amide).
Miscible with water and most organic solvents (alcohols, ketones, esters, aromatics, chlorinated solvents).
When to choose it
When higher boiling range and thermal stability than NMP/DMF are advantageous (e.g., elevated‑temperature polymer processing, high‑solids coatings, difficult dissolutions).
To solvate polar polymers (polyimides, polyurethanes, some acrylates) and inorganic salts more effectively than esters/ethers.
For challenging SNAr and cross‑couplings where a strongly polar medium enhances rates/solubility.
Comparison (literature/general):
Versus NMP (bp ~202 °C): N‑methyl‑2‑piperidone offers higher bp and sometimes higher viscosity; similar polarity; potentially slower drying.
Versus DMF/DMAc: Higher boiling and often lower volatility/odor; comparable polarity; lower basicity than DMAc.
Versus DMSO: Comparable polarity; less protophilic basicity; different odor and drying behavior; higher lipophilicity than DMSO.
Practical notes
Drying: 3 Å molecular sieves or vacuum stripping at mild heat; avoid strong dehydrating agents that may induce ring reactions.
Removal: Vacuum at elevated bath temperature; residual films may require co‑evaporation with lower‑bp solvent (e.g., toluene, IPA) or aqueous workup.
Storage and Reconstitution
Storage conditions (from Product Data): Store at 2–8 °C in a tightly closed container.
Shipping (from Product Data): Shipped on wet ice.
Container recommendations (general): Use amber glass or compatible metal containers with PTFE‑lined caps to minimize permeation and extractables. Avoid containers/seals that may swell in strong polar aprotic solvents.
Handling to maintain quality (general):
Minimize headspace and reseal promptly to limit moisture uptake; consider inert gas backfill for long‑term storage.
For high‑purity needs, store over activated 3 Å molecular sieves in a sealed bottle (do not leave sieves in shipping container).
Reconditioning before use (general):
If water content is critical, dry by stirring over 3 Å sieves 12–24 h, or vacuum‑strip at 60–80 °C with inert sparge, then cool under inert atmosphere.
Filter to remove drying agents or particulates before use (0.2–0.45 µm as needed).
Stability (general): Chemically stable under recommended storage. Avoid strong oxidizers and reactive acid chlorides/anhydrides. Protect from prolonged heating in the presence of strong bases.
Note: For lot‑specific acceptance criteria (water, acidity/alkalinity, UV, metals), consult the CoA/Spec Sheet. This product is for research use only.
Structure and Identity
N-Methyl-2-piperidone is a six‑membered cyclic amide (lactam), structurally analogous to N‑methyl‑2‑pyrrolidone (NMP) but with an expanded ring (piperidin-2-one core).
Item identifiers (from Product Data):
SKU: N335945
CAS: 931-20-4
CID: 13603
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature structural data (for the named compound; informational):
Structural description (2D, literature): A six‑membered ring with one nitrogen (position 1) and a carbonyl at C2 (lactam). The nitrogen bears a methyl substituent; the remaining ring positions are methylene groups, giving a conformationally flexible, polar aprotic scaffold. No stereocenters present; achiral.
Notable structural features (general):
Polar, hydrogen‑bond acceptor (amide carbonyl); very weak H‑bond donor character absent due to N‑methylation (tertiary amide).
High dipole due to amide bond; good solvating power for salts and polar organics compared with many common ethers/esters.
Medium for polar/ionic chemistry: Enhances solubility of inorganic bases/nucleophiles for SNAr, alkylations of acidic methylenes, and heteroarene functionalizations.
Transition‑metal catalysis: Supports Pd‑, Ni‑, and Cu‑catalyzed couplings by dissolving aryl halides, boronates, and bases simultaneously; useful at 100–160 °C when higher bp is advantageous.
Polymer enabling: Dissolves polyamic acids and facilitates thermal imidization to polyimides; solubilizes diisocyanates and polyols for urethane chemistry.
Lactam chemistry: Although generally inert as solvent, under forcing conditions the lactam ring can participate in ring‑opening or N‑acylation; this reactivity is typically avoided in solvent roles but can be leveraged synthetically when used as a reagent.
Retrosynthetic perspective
Choice of solvent can shift reaction manifold from diffusion‑ to solvation‑limited; N‑methyl‑2‑piperidone often enables single‑phase operation where DMF/DMAc would require elevated pressure or suffer from volatility.
Workup and purification
High bp/water miscibility favors aqueous extractions; salting‑out may assist phase split. Co‑evaporation with toluene/EtOAc and high‑vacuum finishing minimize residues.
Target Specificity
Not applicable. This product is a small‑molecule solvent/reagent and is not an antibody, enzyme, oligo, or affinity reagent. No antigen/epitope or species reactivity applies.
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