3-Ethyl-2-pyrrolidinone - Reagent grade

Cat. No.: E481588

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Especificações e pureza

Reagent grade

Condições de armazenamento de armazenamento

Room temperature

Grau

Reagent Grade

Application Protocols

No assay application protocols are specified for this SKU.

Guidance for laboratory use (general):

• Solvent use: If employing as reaction medium, document drying method (e.g., 3 Å sieves, KF endpoint), temperature program, and removal/workup approach for reproducibility.
• Substrate use: When 3‑ethyl‑2‑pyrrolidinone is the reactive substrate, outline base selection, temperature control, and quench procedure to mitigate competitive side reactions (e.g., over‑alkylation or ring opening).
• Materials processing: For polymer dissolution/film casting, report solids content, temperature, stir time, and drying conditions (vacuum/temperature) to allow reproducibility.

For chromatographic or spectroscopic uses:

• UV background and absorbance cutoffs for this item are not specified; if using for HPLC or UV‑sensitive analytics, confirm suitability experimentally or request additional specifications.

Always defer to method‑specific SOPs in your laboratory; the above are general considerations only.

Biological Roles

This product is a synthetic lactam solvent/building block and is not typically used as a biological reagent per se.

General chemistry/biochemistry context (literature):

• Lactams are common motifs in biology (e.g., β‑lactam antibiotics, proline derivatives), but 3‑ethyl‑2‑pyrrolidinone itself is not a known endogenous metabolite.
• As a polar aprotic medium with hydrogen‑bond acceptor capacity, lactams can influence protein and nucleic acid solubility and conformation in vitro; however, such uses require careful toxicity and denaturation assessments.
• The secondary amide N–H can engage in hydrogen bonding; thus, in biochemical extractions, related lactams (e.g., 2‑pyrrolidone, NMP) have been examined as solubilizers for recalcitrant matrices. Whether 3‑ethyl‑2‑pyrrolidinone affords advantages will depend on hydrophobicity and compatibility with the biomolecules of interest.

Important note for users:

• No biological activity or role is specified for this SKU. For any work involving biological systems, thoroughly evaluate cytotoxicity/denaturation and ensure compliance with institutional safety protocols.
• Research use restriction: For research use only (from Product Data). Not for diagnostic or therapeutic use.

Buffer Applications

3‑Ethyl‑2‑pyrrolidinone is not a buffering agent and is not typically used to prepare pH buffers or electrophoresis running buffers.

Practical guidance:

• If used as a co‑solvent in biochemical assays, buffer capacity must be provided by a true buffering system (e.g., phosphate, Tris, HEPES). Assess effects of the lactam on pKa and ionic strength, and validate assay performance across the intended solvent fraction.
• For standard buffer recipes and pH ranges, refer to dedicated buffering agents rather than this solvent.

Green Alternatives

Sustainability considerations (literature/green-chemistry guidance):

• Lactam solvents deliver excellent solvation but may raise concerns around persistence and worker exposure (as with NMP/NEP). While specific regulatory status for 3‑ethyl‑2‑pyrrolidinone varies, consider greener substitutions when performance allows.

Potential alternatives and trade‑offs (general comparison):

• Propylene carbonate (PC):

  • Pros: Biodegradable profile, low vapor pressure, high BP, often REACH‑friendlier.
  • Cons: Less coordinating/basic than lactams; may not dissolve polyamides/salts as effectively.

• Dimethyl isosorbide (DMI):

  • Pros: Bio‑based, low toxicity profile, good solvency for many organics.
  • Cons: Lower polarity than lactams; limited salt solubility.

• Cyrene (dihydrolevoglucosenone):

  • Pros: Bio‑derived, strong dipolarity, good replacement for DMF/NMP in some cases.
  • Cons: Reactive under strong base/nucleophiles; odor and viscosity considerations.

• Sulfolane:

  • Pros: High polarity and thermal stability; good for SNAr and gas treating.
  • Cons: Sulfone handling and potential environmental persistence; needs stringent drying.

• 2‑MeTHF/CPME (for less polar needs):

  • Pros: Greener ether solvents, easy workup.
  • Cons: Much lower polarity; not suitable when salt/polymer solvation is critical.

Implementation strategy:

• Map the solubility/function requirement (salt/polymer vs. neutral organics), then run small solvent screens against greener candidates. Combine co‑solvents (e.g., PC with an alcohol or ether) to tune viscosity and evaporation rate while maintaining performance.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is specified for this SKU; consult the CoA/Spec Sheet if required.

General formulation context (literature/industry):

• Related lactams such as 2‑pyrrolidone and N‑methyl‑2‑pyrrolidone (NMP) have been used as solvents/penetration enhancers in certain topical or transdermal research formulations. Regulatory scrutiny of NMP/NEP has increased in some jurisdictions due to worker‑exposure concerns.
• 3‑Ethyl‑2‑pyrrolidinone is less commonly cited in pharmaceutics; any use would be as a high‑boiling polar solvent or processing aid in research settings only, subject to toxicological qualification.

Important restrictions:

• From Product Data: For research use only. Not for human or veterinary use, not for diagnostic or therapeutic applications.
• If evaluating as a processing solvent, ensure residual-solvent controls, extractables/leachables studies, and toxicology clearance per ICH guidelines. Absent such validation, select established pharmacopeial excipients instead.

Physical Properties

Item-specific specifications (this SKU):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, water/peroxide/metal content, UV cutoff, and similar specs: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general reference values for 3‑ethyl‑2‑pyrrolidinone (for context; not product specs):

• Physical state: typically a colorless to pale liquid at ambient temperature (literature/general observation for C‑substituted pyrrolidinones).
• Boiling point: often reported in the high‑boiling range for lactam solvents; qualitative expectation: >200 °C (literature). Exact value varies by source and should be verified on CoA.
• Melting point: usually well below room temperature for ethyl‑substituted lactams (literature trend).
• Polarity: polar aprotic amide; strong hydrogen‑bond acceptor, weak donor via N–H (lactam) (literature characterization).
• Solubility: lactams are generally miscible with many polar organics (alcohols, ketones, esters, chlorinated solvents) and show high affinity for water; 3‑ethyl substitution may reduce water miscibility relative to 2‑pyrrolidone but still affords substantial aqueous solubility (literature trend).
• LogP/logD: expected higher than 2‑pyrrolidone due to the ethyl substituent; specific values vary by source (literature; check CoA).
• pKa (lactam N–H): typically ~15–17 in DMSO; conjugate acid pKa ~−0.5 to 0 in water for related lactams (literature ranges; solvent dependent).

Practical notes:

• Drying: like N‑alkyl/alkyl‑substituted pyrrolidones, it is hygroscopic to a degree; drying over activated 3 Å molecular sieves or by azeotropic removal can lower water content (general practice).
• Viscosity increases at lower temperatures; warm gently for accurate volumetric handling.

Quality and Grades

• Grade for this SKU: Reagent Grade (from Product Data).

What “Reagent Grade” generally signifies:

• Intended for laboratory use in general synthesis and analytical procedures.
• Typical impurity control suitable for most synthetic and preparative applications; may not meet the stricter UV absorbance or trace‑metal specifications required for chromatographic or semiconductor uses.
• UV cutoff, water content, residual solvents, and trace metals are not specified here. If these parameters are critical to your work (e.g., photochemistry, battery materials, catalysis), request the current CoA/Spec Sheet.

Stabilizers and additives:

• None stated for this item. If stabilizers or inhibitors are present, they would be listed on the CoA. For moisture‑sensitive uses, consider in‑house drying (e.g., activated 3 Å sieves) and document Karl Fischer values as needed.

Batch-to-batch considerations:

• Lactam solvents can absorb moisture; measured water content may vary after container opening. For reproducibility, record water content at use and standardize pre‑treatment.

Selection guidance:

• For demanding applications (e.g., low‑ppm water or low UV background), evaluate fit-for-purpose by small‑scale trials or consider higher‑spec solvent grades (HPLC/Anhydrous/Spectro) if available for closely related solvents (e.g., NMP/NEP) and your chemistry tolerates the substitution.

Reaction and Applications

General reaction/application domains for 3‑ethyl‑2‑pyrrolidinone (literature-based; expand/adjust per project needs):

• Solvent for high‑temperature transformations requiring polar aprotic media, including SNAr, Ullmann‑type couplings, and heteroaromatic functionalizations where substrate/catalyst solubility is limiting.
• Polymeric materials work: dissolution of polar polymers or precursors (e.g., imide formers), resin processing, and film casting where slow evaporation and strong solvation are beneficial.
• Electrochemistry/materials: lactams often show wide electrochemical stability windows and high salt solvation; can be explored as co‑solvents or processing solvents (verify compatibility with your electrolyte and electrodes).
• Organometallic/cross‑coupling: coordinates to metal centers; can act as a benign cosolvent to increase polarity and maintain catalyst activity. Evaluate against catalyst sensitivity to amide donors.
• H‑bonded catalysis and selectivity: the N–H of the secondary lactam can engage in H‑bond networks, sometimes altering selectivity relative to N‑alkyl analogs (NMP/NEP).

Practical tips:

• Dry thoroughly for moisture‑sensitive steps; water suppresses strong nucleophile reactivity and many organometallics.
• For base‑promoted α‑functionalization, the C‑3/C‑5 positions are enolizable; ensure that amide anion formation or ring functionalization is not competing with your intended transformation.
• Removal: due to high BP and hydrogen‑bonding, solvent stripping may require high vacuum, co‑evaporation with a lower‑boiling solvent (e.g., toluene/ethyl acetate), or aqueous workup followed by extraction.
• Compatibility: avoid strong dehydrating reagents (e.g., SOCl2, POCl3) or aggressive acylation conditions that can open or functionalize the lactam ring unless desired.

Reaction Conditions

General conditions and ranges (literature guidance; adjust to your system):

• As solvent: 0.1–1.0 M substrate concentration is typical; temperatures from ambient to 150–200 °C are accessible due to high BP. Use oil bath or sealed tube/pressure vessel as needed. Employ inert atmosphere for air‑/moisture‑sensitive transformations.
• Drying/degassing: Dry over activated 3 Å sieves (≥24 h) or distill under reduced pressure if appropriate. Degas by N2 sparging or three freeze‑pump‑thaw cycles when required.

Use in base‑promoted α‑functionalization of the lactam:

• Base: LDA, LiHMDS, or NaHMDS (0.9–1.5 equiv) at −78 to 0 °C to form the enolate, then electrophile addition at low temperature to room temperature. Quench with buffered aqueous workup.
• Solvent system: Often THF/toluene are used; however, the compound can serve as substrate rather than solvent in these steps. If used as solvent, consider competitive deprotonation.

Metal‑catalyzed couplings (when used as cosolvent):

• Pd or Cu catalysts for C–N/C–O coupling: 60–140 °C; base (K2CO3, Cs2CO3, or organic bases). Evaluate catalyst tolerance to amide donors.

Workup and isolation:

• High BP and strong hydrogen bonding make removal challenging. Strategies: co‑evaporate with toluene/EtOAc under high vacuum; salt out with brine followed by extraction into less polar solvents; employ solid‑phase workup when applicable.

Expected outcomes:

• Yields and rates are system‑dependent; literature reports for analogous lactam media often show improved conversions where solubility limits are the bottleneck. Validate on small scale before scale‑up.

Safety and Handling

Authoritative safety classification for this SKU:

• Signal word, GHS classification, hazard (H) statements, and pictograms: Not specified for this item; refer to the SDS for authoritative information.

General safety guidance for lactam solvents (literature/industry practice):

• Likely hazards: May cause skin and eye irritation; prolonged or repeated exposure can lead to defatting and dermatitis. High‑boiling polar aprotic solvents can facilitate dermal uptake of dissolved solutes—avoid skin contact.
• Inhalation: Vapors are typically low at room temperature due to high BP but can increase on heating; use local exhaust when warming or in large‑scale operations.
• Combustibility: Organic liquid; keep away from ignition sources. Check flash point on SDS; high‑boiling lactams often have elevated flash points but are still combustible.
• Peroxide formation: Not typically prone (amide), unlike ethers; routine peroxide testing is generally unnecessary.

PPE and handling:

• Wear safety glasses or goggles, lab coat, and appropriate chemical‑resistant gloves (e.g., nitrile). For heated operations or splash risk, use face shield and apron.
• Work in a fume hood. Avoid breathing vapor/mist and avoid skin contact.
• Storage incompatibilities: Strong oxidizers, strong acids/bases (can catalyze ring‑opening or aminolysis under forcing conditions), acylating agents.

First aid (summary—defer to SDS):

• Skin: Wash with soap/water; remove contaminated clothing.
• Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
• Inhalation: Move to fresh air; seek medical attention if symptoms occur.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Waste disposal: Collect as halogen‑free organic waste unless contaminated; follow institutional and local regulations.

Solvent Selection

Solvent class and polarity (literature/general):

• Class: Polar aprotic cyclic amide (γ‑lactam).
• Hydrogen‑bonding: Strong acceptor (carbonyl oxygen), weak donor via N–H; overall behaves as polar aprotic in most reactions.
• Dielectric behavior: High relative permittivity typical of lactams; promotes dissolution of salts and polar reagents.

Miscibility profile (general trends):

• Broad miscibility with polar organics (alcohols, ketones, esters, chlorinated solvents) and strong solvating power for polymers and inorganic salts. Substantial solubility in water; 3‑ethyl substitution increases hydrophobicity relative to 2‑pyrrolidone/NMP.

When to choose 3‑ethyl‑2‑pyrrolidinone:

• Need for a high‑boiling, polar aprotic medium that can improve solubility of polar substrates, polymers (e.g., polyamides, polyimides precursors), or salts.
• Desire to avoid N‑alkyl lactams (e.g., NMP/NEP) due to regulatory or reaction‑compatibility considerations; the secondary amide N–H can be advantageous in certain hydrogen‑bonding solvation scenarios.

Comparison (literature, qualitative):

• NMP: Lower viscosity and very well‑characterized; 3‑ethyl‑2‑pyrrolidinone is more hydrophobic and may offer different selectivity/solubility profiles.
• DMF/DMSO: Lower boiling (DMF) or similar solvency (DMSO) but with different coordinating properties and odor profiles; lactams often dissolve polymers and salts better.
• Propylene carbonate: Green, high‑BP alternative; less basic/less coordinating than lactams; poorer amide/heteroaromatic solvation in many cases.

Practical tips:

• Dry before moisture‑sensitive chemistry (3 Å sieves). Degas by sparging or freeze‑pump‑thaw if needed for air‑sensitive catalysis.
• Elevated temperatures can be used due to high BP; monitor for amide participation under strongly basic or strongly acidic conditions.

Storage and Reconstitution

Storage conditions (from Product Data):

• Store at room temperature.

Additional practical guidance:

• Keep container tightly closed to minimize moisture uptake and contamination. Store in a cool, well‑ventilated place away from strong oxidizers and strong acids/bases. Amber or opaque containers can reduce light exposure, though lactams are generally light‑stable.
• After opening, consider blanketing headspace with dry nitrogen to slow moisture ingress, especially if performing moisture‑sensitive chemistry.

Stability:

• Lactam solvents are typically stable under ambient conditions. Avoid prolonged exposure to high heat in the presence of strong acids/bases that can catalyze ring opening or degradation.

Reconstitution/pretreatment:

• If solidification or phase separation is observed at low temperature, warm gently to re‑liquefy and homogenize.
• For anhydrous use, dry over activated 3 Å molecular sieves (freshly regenerated) for 12–48 h with periodic Karl Fischer checks until the desired water content is achieved. Alternatively, perform azeotropic drying with an appropriate co‑solvent, then remove under reduced pressure.

Shipping:

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

Other specifications (water content, metal content, UV cutoff, etc.):

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

Research Use Note:

• For research use only (from Product Data).

Structure and Identity

Brief description: 3‑Ethyl‑2‑pyrrolidinone is a five‑membered γ‑lactam (pyrrolidinone) bearing an ethyl substituent at the 3‑position. It is a polar, aprotic amide solvent/building block.

• Item-specific identifiers (from Product Data):

  • 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.

• Literature identity information (for general reference only; verify against the CoA for this SKU):

  • Core scaffold: 2‑pyrrolidinone (a cyclic secondary amide).
  • Substitution pattern: Ethyl group at C‑3 (α to the carbonyl), ring nitrogen unsubstituted (secondary lactam).
  • Typical empirical formula (literature): C6H11NO.
  • Typical molecular weight (literature): ~113.16 g/mol.

• Structural features and 2D description (general):

  • Five‑membered ring containing one carbonyl carbon (lactam C=O) and one ring nitrogen (secondary amide N–H).
  • The ethyl substituent resides on the carbon adjacent to the carbonyl (C‑3), increasing hydrophobicity versus unsubstituted 2‑pyrrolidinone.
  • Functional groups: cyclic secondary amide (lactam), one acidic N–H (weakly acidic), enolizable α‑positions (C‑3/C‑5) adjacent to the carbonyl.
  • Stereochemistry: None specified; 3‑ethyl substitution introduces a stereogenic center if the ring carbons are nonequivalent; commercial material is typically racemic unless stated otherwise (not specified for this item).

Synthetic Utility

Functional group leverage (literature/general):

• Cyclic secondary amide (lactam) with enolizable α‑positions (C‑3/C‑5) adjacent to the carbonyl enables directed functionalization under strong base (e.g., LDA, NaHMDS). The 3‑ethyl substituent biases further α‑chemistry regioselectivity.
• The lactam carbonyl can undergo reduction (e.g., LAH) to furnish the corresponding 3‑ethylpyrrolidine; partial reductions or activation (e.g., via imidoyl chlorides) open routes to diverse pyrrolidine derivatives.
• N‑functionalization via deprotonation/alkylation or acylation affords access to N‑substituted 3‑ethylpyrrolidinones as building blocks for heterocycle libraries.

As solvent/cosolvent:

• Promotes polar transformations requiring high temperature: SNAr on electron‑deficient aromatics, cyclizations, condensations, and certain metal‑catalyzed couplings where substrate/catalyst solubility is a challenge.

Retrosynthetic value:

• Serves as a masked 1,3‑amino‑alcohol or diamine synthon after appropriate ring opening or reduction.
• The C‑3 stereocenter (introduced by the ethyl) provides a handle for chiral resolution or enantioselective elaboration if stereocontrol is targeted downstream (commercial material is typically racemic unless specified).

Select transformations (examples, literature-level guidance):

• α‑Alkylation/acylation of the lactam under strong base with electrophiles (alkyl halides, Michael acceptors).
• Ring opening under strongly nucleophilic or acidic conditions to ω‑amino acid derivatives.
• Conversion to imidates or Weinreb-like amides for subsequent chemoselective manipulations.

Target Specificity

Not applicable to this product type.

• This SKU is a small‑molecule solvent/building block, not a biological affinity reagent. No antigen/epitope, clone, isotype, or species reactivity is relevant.
• Item-specific target information: Not specified for this item; refer to CoA/Spec Sheet (not expected for this product class).