This compound belongs to the class of organic compounds known as pyrrolidines. These are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
135.630 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Exact Mass
135.081 Da
Monoisotopic Mass
135.081 Da
Topological Polar Surface Area
12.000 Ų
Heavy Atom Count
8
Formal Charge
0
Complexity
52.100
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
2
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Application Protocols
Not applicable.
No immunoassay or bioassay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical laboratory use, see Reaction Conditions and Synthetic Utility for preparative protocols.
Biological Roles
Scope
This product is intended strictly for research use. No clinical or in vivo claims are made.
General biochemical context (literature)
Pyrrolidine rings are common in natural products and bioactive molecules; they modulate basicity, solubility, and conformational preferences.
3-Ethyl substitution alters steric environment at nitrogen and adjacent carbons, impacting pKa and receptor/enzyme binding interactions in medicinal chemistry SAR studies.
As a small aliphatic amine, it can serve as a fragment in fragment-based lead discovery or as a solubilizing/basic handle in probe design.
Notes
No endogenous biological role is attributed to 3-ethylpyrrolidine or its hydrochloride salt.
Any statements about binding targets or pathways would be system- and substituent-dependent; consult primary literature for specific derivatives synthesized from this scaffold.
Buffer Applications
Not typically applicable.
3-Ethylpyrrolidine hydrochloride is not a standard buffering agent and lacks a defined, narrow buffer range compared with dedicated buffers (HEPES, MES, phosphate).
If used to modulate pH, it behaves as a simple Brønsted acid/base pair (amine/ammonium), but dedicated buffers are recommended for precise pH control. Refer instead to Solvent Selection and Reaction & Applications for relevant use cases.
Green Alternatives
Context
As a small organic hydrochloride salt, the main sustainability lever is solvent and process choice rather than the reagent itself.
Greener handling strategies (literature/guidance)
Use water or water-lean solvent systems when feasible. Many reactions involving amine salts can be run in aqueous ethanol, isopropanol, or water with phase-transfer catalysts.
Avoid chlorinated solvents where possible. Liberate the free base and extract into 2-MeTHF, CPME, or EtOAc instead of DCM/CHCl3.
Employ catalytic, high-atom-economy transformations (e.g., catalytic hydrogenation for reductive amination instead of excess hydride reagents) to reduce waste.
Telescoping: Generate amide/carbamate salts directly from the hydrochloride without isolating the free base by using organic bases in situ (e.g., DIPEA, triethylamine) to minimize solvent-intensive workups.
Comparison of solvent options (general)
DCM: Excellent extraction efficiency for free amines but chlorinated and less desirable environmentally.
2-MeTHF/CPME: Bio-based or more benign ethers with good partitioning for free amines; higher boiling points allow convenient temperature control.
EtOAc/iPrOAc: Readily biodegradable esters suitable for extractions and crystallizations; limited for strongly basic reactions.
Waste and safety
Neutralize and properly dispose of acidic aqueous layers containing chloride. Consider salt recovery/minimization strategies in scale-up.
Pharmaceutical Uses
Formulation/context (general; no therapeutic claims)
Aliphatic amine hydrochlorides are sometimes used as intermediates in the synthesis of drug substance candidates or as counterion forms to enhance crystallinity and handling.
3-Ethylpyrrolidine motifs may appear in medicinal chemistry as solubilizing/basic fragments; however, this listing does not specify compliance with pharmacopeial monographs (USP/EP/JP) or GMP status.
Item-specific status
Pharmacopeia status: Not specified for this item; refer to CoA/Spec Sheet.
Residual solvent/elemental impurity controls aligned to ICH Q3C/Q3D: Not specified for this item; refer to CoA/Spec Sheet.
Practical considerations
Salt selection: The HCl salt increases aqueous solubility and reduces volatility/odor, facilitating handling during scale-up.
For preclinical formulation work or as a process intermediate, request detailed impurity profiles, water content, and stability data under ICH conditions before use.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula and molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for 3-ethylpyrrolidine hydrochloride
Physical state: Typically an off-white to white crystalline solid for small aliphatic amine hydrochloride salts (literature trend; specific to this item not confirmed).
Solubility: High in water and polar protic solvents; soluble in alcohols; poor in nonpolar solvents (literature for aliphatic amine hydrochlorides).
Hygroscopicity: Many low-mass amine HCl salts are moderately hygroscopic and deliquescent under high humidity (literature trend).
pKa (conjugate acid of 3-ethylpyrrolidine): Expected pKaH ~10–11 for pyrrolidinium-type amines (literature range; exact value for this specific derivative not verified).
LogP (free base): Small, basic amines of this class generally show low to moderate logP as free bases; the HCl salt is effectively non-lipophilic in water (literature trend).
Do not treat literature values as product specifications. For authoritative, lot-specific data (e.g., melting point, water content, residual solvents, metal traces, UV cutoff), consult the product CoA/Spec Sheet.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grades (general)
Research grade: Suitable for exploratory synthesis, method development, and routine laboratory work. Impurity profiles and trace metals may not be tightly controlled unless specified.
High-purity/assay grades (e.g., ≥98–99%): Offer reduced byproducts and residual solvents, aiding reproducibility in asymmetric catalysis or analytical method development.
HPLC/UV grades (solvents): Emphasize low UV absorbance and particulate count; not directly applicable to solid reagents like this salt unless stated.
What to check on the CoA for amine hydrochlorides
Assay method (e.g., potentiometric titration vs. qNMR), residual solvent levels, water content (Karl Fischer), halide content confirmation (chloride assay), and optical rotation if a defined stereochemistry is claimed.
Inorganic impurities (Na+, K+, heavy metals) and halide identity where relevant.
Recommendation
For sensitive applications (e.g., chiral synthesis, pharmaceutical intermediate work), request a current CoA/Spec Sheet for lot-specific assay, water content, and impurity profile before use.
Reaction and Applications
General roles (literature)
Building block: 3-Ethylpyrrolidine is a saturated, secondary cyclic amine motif found in agrochemical and medicinal chemistry libraries. The hydrochloride form is a convenient, bench-stable source of the amine.
Salt metathesis/neutralization: Conversion to the free base enables direct use in nucleophilic substitution (SN2 on alkyl halides), acylation (to amides/carbamates), and reductive amination workflows.
Typical transformations (literature examples)
Amide formation: Reaction with acid chlorides/anhydrides (or via coupling agents such as EDCI/HATU) after liberating the free base; tertiary amide formation is straightforward.
Carbamate/urethane synthesis: With chloroformates or carbonates to access protected derivatives for downstream transformations.
Reductive amination: As the amine component with aldehydes/ketones in the presence of NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
Alkylation: N-alkylation to tertiary amines under basic conditions; phase-transfer or solvent selection governs selectivity and suppresses over-alkylation.
Quaternization: Formation of quaternary ammonium salts using alkyl halides or MeOTf, enabling ionic liquid or phase-transfer catalyst precursors.
Practical considerations
Pre-generate the free base with Na2CO3/K2CO3 in biphasic media (water/organic) to limit emulsions; verify pH >11 to ensure full deprotonation.
Dry the liberated free base (e.g., over KOH pellets or molecular sieves) before moisture-sensitive couplings.
For stereochemical studies, note that C-3 is a stereocenter; racemization at carbon is not expected under mild conditions, but enantiospecific syntheses may require chiral resolution or asymmetric routes.
Reaction Conditions
General guidance (literature; not product specifications)
Free-base generation: Dissolve the hydrochloride in water or MeOH/H2O, basify to pH ≥11 with Na2CO3 or NaOH, extract the free base into MTBE/Et2O/EtOAc, dry, and use promptly.
Acylation to amides: DIPEA or triethylamine (2–3 equiv) in DCM, DMF, or THF; 0–25 C; 1–4 h with acid chlorides or 6–16 h with coupling reagents (HATU/EDCI) and carboxylic acids. Typical isolated yields for analogous pyrrolidines: 70–95% (literature).
Reductive amination: Aldehyde/ketone (1.0 equiv), amine (1.2–2.0 equiv), AcOH (0.2–0.5 equiv) in MeOH, DCM, or iPrOH; NaBH(OAc)3 or NaBH3CN added portionwise at 0–25 C; 2–18 h. Typical yields: 60–90% (literature, substrate-dependent).
N-Alkylation: K2CO3 or Cs2CO3 in acetonitrile/DMF, 20–80 C; or phase-transfer (toluene/50% NaOH, TBAB). Monitor to avoid over-alkylation.
Quaternization: Alkyl halide (1.1–2.0 equiv) in MeCN or acetone, reflux; 2–24 h; isolate quaternary ammonium halide by precipitation.
Tips
For stereochemical integrity at C-3, avoid strong base at elevated temperatures that might promote ring-opening or elimination in substituted systems.
If conducting metal-catalyzed couplings on N-acyl derivatives, ensure rigorous base control; residual HCl from the salt can impact catalyst performance.
Safety and Handling
Item-specific GHS details
Signal word, H-statements, pictograms, and classification: Not specified for this item; refer to SDS.
General safety information for aliphatic amine hydrochloride salts (literature/generic)
Hazards: May cause irritation to skin, eyes, and respiratory tract. Dust may be irritating. Avoid inhalation of particulates and contact with eyes/skin.
PPE: Use lab coat, safety glasses or chemical goggles, and suitable gloves (e.g., nitrile). Employ local exhaust ventilation or work in a fume hood when handling powders or preparing solutions.
Incompatibilities: Strong bases (which can liberate the free base), strong oxidizers. Contact with strong alkali may release free amine vapors with a strong odor.
First aid (overview; defer to SDS): If inhaled, move to fresh air. In case of skin contact, wash with soap and water. For eye exposure, rinse cautiously with water for several minutes; remove contact lenses if present and easy to do. If ingested, rinse mouth; seek medical advice.
Fire safety: Combustible organic salt; use water fog, CO2, dry chemical, or foam. Thermal decomposition may produce HCl and nitrogen oxides.
Always consult the official SDS for this product for definitive hazard classification and emergency measures.
Solvent Selection
Applicability to this compound type
3-Ethylpyrrolidine hydrochloride is an ionic, water-soluble organic salt. Solvent choice determines whether it remains as the protonated salt or is converted to the free base.
General guidance (literature/generic)
To use as the salt (protonated): Choose polar protic solvents (water, methanol, ethanol) or polar aprotic solvents containing a small amount of acid to maintain protonation.
To access the free base in situ: Treat with a stoichiometric base (e.g., Na2CO3, K2CO3, NaOH) and extract into a nonpolar or moderately polar organic solvent (e.g., MTBE, Et2O, DCM) where the free base is more soluble.
Dielectric/miscibility: As a hydrochloride, highly miscible in water; solubility in acetonitrile/DMF/DMSO is often good, especially with some water. In nonpolar solvents, the salt is typically insoluble.
Comparison (literature)
Hydrochloride salt vs. free base:
Salt: Easier handling, reduced volatility/odor, better stability; ideal for aqueous phase chemistry and salt-coupling operations.
Free base: Required for nucleophilic substitutions, metal-catalyzed couplings, and base-promoted reactions in organic media.
Practical tip
If measuring stoichiometry in organic reactions, either pre-neutralize to the free base and assay by qNMR, or account for the HCl equivalent when charging bases.
Storage and Reconstitution
Item-specific instructions (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for amine hydrochloride salts (literature/generic)
Keep tightly closed in a dry, well-ventilated place. Protect from excessive humidity to prevent caking/deliquescence.
If long-term storage is required in humid environments, consider desiccation (e.g., over silica gel or P2O5) and reseal promptly after use.
Reconstitution: Readily dissolves in water and alcohols. For use as the free base, dissolve the salt in minimal water/alcohol, basify with Na2CO3/NaOH, and extract into a suitable organic solvent; dry and use immediately.
Freeze–thaw: Not relevant for a solid; for prepared solutions, store at 2–8 C and use within a few days, or validate stability by analytical testing.
Always consult the product CoA/Spec Sheet and SDS for lot-specific stability, compatibility, and handling information.
Core scaffold: Saturated five-membered azacycle (pyrrolidinium) bearing an ethyl substituent at the 3-position; present as the protonated ammonium chloride salt.
Stereochemistry: Substitution at C-3 creates a stereogenic center; unless stated otherwise, commercial material is often racemic. This item’s enantiomeric state is not specified.
2D structural description
A five-membered ring containing one nitrogen (pyrrolidine). The ring nitrogen is protonated in the hydrochloride, forming an ammonium center. An ethyl group is attached to the ring carbon adjacent to the nitrogen (3-position in the conventional numbering), and chloride is the counterion.
Synthetic Utility
Functional group features
Secondary cyclic amine (pyrrolidine) presented as the ammonium chloride salt. The nitrogen is nucleophilic upon neutralization; the ring imparts conformational constraint and basicity typical of saturated azacycles.
Key transformations (literature)
N-Acylation and sulfonylation to access amides and sulfonamides (HATU/EDCI or acid chloride/sulfonyl chloride routes).
Reductive amination to elaborate side chains at nitrogen, forming tertiary amines with controlled steric bias from the 3-ethyl substituent.
Alkylation/quaternization to generate tertiary amines and ammonium salts—useful for phase-transfer catalyst prototypes.
Carbamate formation for protecting-group strategies and as handles for further diversification (e.g., Mitsunobu on carbamates).
Retrosynthetic value
The 3-ethylpyrrolidine motif can be viewed as a cyclized 1,4-diamine equivalent; it provides a compact, lipophilicity-tuning element when introduced into scaffolds.
The C-3 stereocenter allows for chiral pool/exploration if enantioenriched material is obtained; this product does not specify enantiomeric form.
Handling for synthesis
Convert the HCl salt to the free base immediately prior to use to maximize reactivity. Remove adventitious water (e.g., drying over K2CO3 or molecular sieves) for moisture-sensitive couplings.
Account for the HCl equivalent in stoichiometry to avoid overconsumption of base or catalyst poisoning in metal-catalyzed reactions.
Target Specificity
Not applicable.
This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies to this item.
Foire aux questions
What is the purity of this product?
This product is supplied at ≥98% 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 1384431-43-9, the molecular formula is C6H14ClN, and the molecular weight is 135.630 g/mol. InChIKey YGRGUQNCCWBFNJ-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.
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