2-Piperidineethanamine - ≥95% , CAS No.15932-66-8

CAS: 15932-66-8 Cat. No.: P1353815 분자식: C₇H₁₆N₂ 분자량: 128.22 PubChem CID: 27568

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

사양 및 순도

≥95%

보관 조건

Room temperature

배송

Normal

순수함

≥95%

이름과 식별자

정식 스마일

C1CCNC(C1)CCN

IUPAC Name

2-piperidin-2-ylethanamine

InChIKey

IEVJVQXLBZUEMH-UHFFFAOYSA-N

INCHI

1S/C7H16N2/c8-5-4-7-3-1-2-6-9-7/h7,9H,1-6,8H2

이성체 SMILES

C1CCNC(C1)CCN

PubChem CID

27568

분자량

128.22

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 분류 Piperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 분류: Piperidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Piperidines
• Alternative Parents: Dialkylamines Azacyclic compounds Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Piperidine - Azacycle - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Primary aliphatic amine - Amine - Aliphatic heteromonocyclic compound
• 설명: This compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

화학 및 물리적 특성

• 분자량: 128.220 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 128.131 Da
• Monoisotopic Mass: 128.131 Da
• Topological Polar Surface Area: 38.100 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 73.300
• 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: 1

Application Protocols

No assay‑type application protocols (e.g., WB, IHC, IF, FC) are applicable to this small‑molecule reagent.

• Tested applications: Not specified for this item; refer to CoA/Spec Sheet.
• General lab protocols where this reagent is commonly used:
  • Reductive amination workflow: carbonyl + 2‑piperidineethanamine (1.2–3.0 equiv), AcOH (0.2–0.5 equiv), MeOH, rt 1–2 h; then NaBH3CN (1.2–1.5 equiv), rt 2–16 h; aqueous workup and purification.
  • Selective acylation: cool 0 °C, add acyl chloride (1.0–1.2 equiv) to amine (1.0 equiv) and base (2.0 equiv) in DCM; warm to rt, monitor by TLC/LC–MS; quench and extract.
  • Salt formation for isolation: bubble HCl(g) or add 4 M HCl/dioxane to an anhydrous ether/alcohol solution at 0–5 °C until pH strongly acidic; filter and dry salt.

For any item‑specific recommended procedures, consult the product’s CoA or technical note.

Biological Roles

This product is sold strictly for research use. The notes below reflect general biochemical properties of piperidine‑containing aliphatic diamines; they are not clinical or therapeutic claims.

• Structural motif: piperidine is a prevalent saturated heterocycle in bioactive small molecules. Adding an ethylamine side chain provides two protonation sites, enabling pH‑dependent charge states that influence membrane interaction and solubility.
• Acid–base behavior (literature): dual pKaH values typically place at least one nitrogen protonated near physiological pH, with both protonated under acidic conditions. This can promote salt formation and aqueous solubility.
• Interactions: primary amines readily form imines with aldehydes (e.g., in biochemical derivatization protocols). Protonated amines can engage in ionic interactions with polyanions (e.g., nucleic acids, acidic polysaccharides) in model systems.
• Metabolic considerations (general): aliphatic amines undergo oxidative dealkylation, N‑oxidation, and conjugation pathways in microsomal systems. Piperidine rings can be oxidized at alpha positions or open under harsh oxidative stress.
• Use in biochemistry labs:
  • As a model polyamine mimic for studying amine–polyanion binding in vitro.
  • As a derivatization reagent or spacer for bioconjugation after appropriate protection strategies.

Caution: actual bioactivity, cytotoxicity, and biocompatibility of this specific item have not been established here. Perform your own assessments and consult the SDS/CoA before any biological handling.

Buffer Applications

2‑Piperidineethanamine is not a standard biological buffer. It lacks a defined buffering range/package typical of Good’s buffers. However, general guidance for amine bases in lab settings includes:

• Potential buffering windows (literature/general): primary/secondary aliphatic amines can provide buffering capacity in the alkaline range (approximately pH 9–11 near their pKaH values), but specificity and stability are inferior to dedicated buffers.
• Practical use cases:
  • Temporary pH adjustment in organic/aqueous synthesis (e.g., during reductive amination or acylation) rather than as a dedicated buffer.
  • Formation of ammonium salts to modulate solubility/extraction but not for maintaining a fixed pH in biological assays.
• Recommendations:
  • For biochemical applications, select validated buffers (e.g., Tris, HEPES, MOPS) with known pKa and low interference profiles.
  • If using this amine to control pH in organic synthesis, monitor with calibrated pH/probe or acid–base titration; avoid in systems sensitive to nucleophilic amines.

Conclusion: Not typically applicable as a buffer. Prefer dedicated buffering agents and refer to Synthesis/Reaction sections for more relevant uses.

Green Alternatives

Consideration of greener choices depends on whether the molecule is used as a reagent, base, or structural building block.

• If used primarily as a base/nucleophile:
  • Greener bases such as carbonate/bicarbonate or biobased tertiary amines (e.g., N‑methylated amino alcohols) may substitute when nucleophilicity is not required.
  • For phase‑transfer or ionic media needs, choline‑derived salts or amino acid‑based ionic liquids can reduce toxicity/odor, albeit with performance tradeoffs.
• If used as a building block (unique nitrogen scaffold):
  • Functional equivalence is often not achievable with greener reagents; instead, adopt greener solvents and workups (2‑MeTHF, CPME, EtOAc; water‑lean crystallizations; minimal chlorinated solvent use).
• Process intensification options:
  • Telescoping reductive amination without isolation of intermediates, aqueous‑organic biphasic extractions with CO2‑generated salts (reversible capture/release), and continuous flow for exotherm control.

Comparison snapshot (general considerations):

• 2‑Piperidineethanamine vs triethylamine as base
  • Performance: higher nucleophilicity and chelation ability (often overkill for acid scavenging).
  • EHS: stronger odor/irritation potential; consider TEA when pure base function suffices.
• 2‑Piperidineethanamine vs piperidine as building block
  • Performance: added handle for diversification (ethylamine) reduces step count in multi‑N targets.
  • EHS: similar amine hazards; choose salt forms to cut vapor/odor and improve handling.

Net guidance: retain the reagent when its bifunctionality is essential; otherwise, evaluate simpler, lower‑impact bases and greener solvent systems.

Pharmaceutical Uses

For research use only. No medical or therapeutic claims.

• Role in development/manufacturing (general):
  • Serves as a versatile intermediate for constructing piperidinyl‑ethyl motifs frequently found in small‑molecule drug candidates (enhancing basicity, solubility, and binding vectors).
  • Useful handle for preparing salts (e.g., dihydrochlorides) that crystallize readily, aiding purification of advanced intermediates.
  • Can act as a transient base or nucleophile in process steps such as acylations, carbamate formation, and reductive aminations.
• Excipient status: Not a common excipient. No compendial monograph is indicated for this specific amine; verify pharmacopeial status if a salt or derivative is intended for GMP contexts.
• Process considerations:
  • Control residual amine via validated purge steps and sensitive analytical methods (GC, derivatization for UV/LC detection).
  • Odor and amine bleed‑through can be mitigated by converting to nonvolatile salts during workup.
  • For late‑stage API work, impurity fate and purge (e.g., nitrosamine risk assessment with secondary amines) should be assessed per current regulatory guidance.

Note: Consult your QA unit and request full CoA/impurity profile if evaluating for regulated development. This catalog item is intended for laboratory research only.

Physical Properties

Only item-specific values appearing on the Product Data may be listed as specifications. Where values are provided below, they are general literature ranges for closely related 2‑piperidine‑ethanamine isomers and are not specifications for this catalog item.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point (literature, aliphatic diamine of this class): typically high, often >200 °C at 1 atm; can be distilled under reduced pressure to limit decomposition/amine loss.
• Melting point (literature): generally liquid at ambient temperature for low‑molecular‑weight piperidinyl ethylamines; salts (e.g., hydrochlorides) are crystalline solids with higher Tm.
• Density (literature): often in the 0.85–0.93 g/mL range at 20–25 °C for related piperidinylalkylamines; verify on CoA for this item.
• Refractive index (literature): typical nD20 ~1.45–1.49 for similar tertiary/secondary aliphatic amines; item-specific value not established here.
• Solubility (general):
  • Water: miscible to highly soluble as a free base; forms water‑soluble salts with mineral acids.
  • Organic: miscible with polar organics (alcohols, acetone) and many ethers; variable in nonpolar hydrocarbons depending on isomer and temperature.
• Basicity (literature): two basic sites. Primary amine pKaH typically ~9.5–10.5; ring nitrogen pKaH typically ~10.5–11.5 (values vary by isomer and ionic strength).
• LogP/logD (literature): cationic forms are hydrophilic; neutral base expected to have moderate logP (~0.5–1.5) depending on isomer and temperature.

Important: For exact physical properties and release criteria of SKU P1353815, consult the Aladdin CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• What grade means in practice (general guidance):
  • For building‑block amines, “AR/Analytical” or “Reagent” grade typically addresses assay (GC, titration), color, and limits on volatile/basic impurities. “High‑purity” or “HP” material may also have tighter limits on water, residual solvents, and amine titer. “LC/MS or HPLC” grade, when provided, emphasizes low UV background and low nonvolatile residue for analytical workflows.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Many aliphatic amines are shipped neat without stabilizers; salts (e.g., hydrochloride) can enhance stability and handling.
• QC considerations for diamines (general):
  • Identity by NMR (distinct signals for ring CH2 and ethyl chain), IR (N–H stretches), MS (M+H+ of the free base), and GC purity. Water by Karl Fischer may be relevant due to hygroscopicity.
  • Residual mineral acid/base content matters if supplied as a salt or partially neutralized form; verify assay method on the CoA.
• Suitability notes:
  • For moisture/CO2‑sensitive applications (e.g., precise stoichiometry in coupling reactions), freshly distill under reduced pressure from base (KOH) to remove water and CO2 adducts.
  • For bioconjugation or pharmaceutical intermediate work, request full impurity profiling and elemental analysis if required by your QA system.

Reaction and Applications

2‑Piperidineethanamine (a piperidine‑based diamine) is a versatile, bifunctional nucleophile/base. Common research applications include:

• Nucleophilic substitutions and alkylations:
  • Formation of tertiary amines via alkyl halide displacement; control over mono‑ vs di‑alkylation by stoichiometry and protecting groups.
  • Quaternization to ammonium salts for phase‑transfer or ionic‑liquid precursors.
• Carbonyl derivatizations:
  • Reductive amination with aldehydes/ketones to form secondary/tertiary amines (NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation). The second amine site allows either intramolecular cyclization (with dialdehydes) or orthogonal protection.
  • Amide/carbamate/urea synthesis with acyl chlorides, chloroformates, or isocyanates; tosylation for protecting‑group strategies.
• Heterocycle construction:
  • Acts as a tethered nucleophile to build bicyclic or spiro frameworks via intramolecular SN2 or Michael additions.
  • Mannich and aza‑Michael chemistry on activated alkenes/acrylates, leveraging the ring amine as a base and the side‑chain amine as the nucleophile (or vice versa).
• Catalyst/ligand roles (literature):
  • Serves as an organobase for transesterifications or Knoevenagel reactions in polar solvents.
  • Coordinates to transition metals; can function as a simple bidentate nitrogen ligand in exploratory catalysis.
• Materials/intermediate use:
  • Precursor to ion‑exchange resins, crosslinkers, and polyurethane/epoxy curing components after appropriate functionalization.

Practical notes:

• Dry the amine over KOH or CaH2 and distill under reduced pressure for water‑sensitive applications.
• Protect one amine (e.g., Boc on the ring nitrogen) to enable site‑selective transformations.
• For reductive amination, buffer near pH 5–6 to favor imine formation while minimizing over‑protonation, then reduce at 0–25 °C.

Reaction Conditions

Generalized conditions drawn from literature for piperidinyl‑ethylamines; adjust to the specific isomer and substrate set. These are not item specifications.

• Reductive amination:
  • Solvent: MeOH, EtOH, or MeCN; sometimes DCE if water‑sensitive.
  • Conditions: Condense carbonyl + amine at pH 5–6 (AcOH), then reduce with NaBH3CN (rt, 2–16 h) or NaBH(OAc)3 (rt, 2–24 h). Catalytic hydrogenation (H2, 1–5 bar, Pd/C, rt–40 °C) is an alternative.
  • Tip: Use 2–3 equiv of the diamine to suppress iminium polymerization; remove excess by acid extraction.
• Acylation/sulfonylation:
  • Solvent: DCM, THF, or DMF; base: DIPEA, NaHCO3, or pyridine.
  • Temperature: 0 °C to rt; time: 0.5–4 h. For selective mono‑acylation, protect the other amine or run at low temperature with slow addition.
• Urea/carbamate formation:
  • Reagents: CDI or triphosgene; solvent: DCM/THF.
  • Conditions: 0–25 °C, 1–6 h; quench with water/alcohol to avoid over‑carbonylation.
• Alkylation (SN2):
  • Solvent: MeCN, DMF, or acetone; base: K2CO3/Na2CO3.
  • Temperature: rt–60 °C; time: 2–24 h. Employ protecting groups to prevent over‑alkylation.
• Salt formation/crystallization:
  • Add dry HCl in IPA/Et2O to a cooled (0–5 °C) solution of the amine in IPA/EtOH; isolate the hydrochloride salt by filtration; dry under vacuum.

Workup considerations:

• Partition between organic and 1–2 M HCl to remove excess amine, then basify to recover product if needed.
• Dry organic layers over K2CO3 to neutralize trace acid and remove water.

Note: Strongly basic amines may poison certain metal catalysts; pre‑complexation or temporary protection can improve outcomes.

Safety and Handling

• GHS information (item-specific):
  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H‑codes): Not specified for this item; refer to SDS.
  • Pictograms/classification: Not specified for this item; refer to SDS.
• General hazards for aliphatic diamines (literature/typical):
  • Corrosive/irritant to skin, eyes, and respiratory tract; can cause burns on contact with concentrated free base.
  • Harmful if swallowed or inhaled; vapors may be irritating, especially when warmed.
  • Strong base; reacts exothermically with acids and may absorb CO2 from air forming carbamates/salts.
• Incompatibilities (general): strong oxidizers, acid chlorides/anhydrides, isocyanates, epoxides (vigorous addition), aldehydes/ketones (Schiff base formation), and carbon dioxide/moisture for long-term storage of the free base.
• Recommended PPE/controls: chemical‑resistant gloves (e.g., nitrile), lab coat, eye/face protection; handle in a fume hood to control vapors/odors. Use secondary containment for bulk transfers.
• First aid (overview; defer to SDS):
  • Skin/eye: immediate decontamination with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention.
  • Inhalation: move to fresh air; support breathing; medical evaluation recommended.
  • Ingestion: rinse mouth; do not induce vomiting; get medical attention.
• Fire safety: amines are combustible; use alcohol‑resistant foam, CO2, dry chemical. Heating can increase vapor and irritation risk.
• Waste: collect as organic amine waste; neutralize carefully if required by local procedures; follow institutional and regulatory disposal rules.

Always consult the product’s SDS for authoritative, item‑specific safety information.

Solvent Selection

As a strongly basic, polar organic base, 2‑piperidineethanamine is both a reagent and a solute. Solvent choice depends on reaction class and desired protonation state.

• Polarity/miscibility (general):
  • Free base is miscible with water and polar organics (alcohols, acetone, acetonitrile) and dissolves well in ethers (THF, MTBE) and chlorinated solvents (DCM) to varying degrees.
  • As an ammonium salt (e.g., HCl), it is water‑soluble but poorly soluble in many nonpolar organics; DMF/DMSO and aqueous media are suitable.
• Typical solvent choices by application:
  • N‑acylation, carbamate/urea formation: DCM, THF, or toluene with a base (e.g., DIPEA, Na2CO3) and controlled temperature.
  • Reductive amination/alkylation: MeOH, EtOH, or MeCN; consider buffered conditions to balance imine formation and reduction.
  • Metal‑catalyzed couplings as a ligand/base: alcoholic or glycol ethers and polar aprotic media (DMF, DMAc) as required by catalyst solubility.
  • Salt formation/purification: IPA/Et2O antisolvent systems for crystallizing acid salts (HCl, TsOH) of the amine.
• Practical tips:
  • Avoid strong protic acids in the presence of acid‑labile partners; generate salts intentionally at the end for isolation.
  • For anhydrous transformations, dry solvents rigorously; amines readily pick up moisture and CO2.
• Comparison (general):
  • Versus triethylamine: stronger nucleophile and bidentate; higher coordination tendency to metals and carbonyls.
  • Versus piperidine: enhanced basicity/equivalents available and tunable bifunctionality for step‑economical synthesis.

Storage and Reconstitution

• Storage (item-specific from Product Data): Store at room temperature.
• Shipping (item-specific): Shipped under normal conditions.
• Container/atmosphere (general best practice for amines):
  • Keep tightly closed in an air/moisture‑resistant container to minimize CO2 uptake and water absorption.
  • For long‑term storage, consider an inert headspace (nitrogen/argon). Avoid acidic vapors and strong oxidizers nearby.
• Stability: Free bases can slowly discolor from air exposure; salts (e.g., hydrochloride) generally offer improved shelf stability and reduced odor/volatility.
• Reconstitution/handling:
  • If supplied as a solid salt: dissolve in water, alcohols, or polar aprotic solvents to the desired concentration; adjust pH as needed.
  • If supplied as a neat liquid: use directly or prepare stock solutions in dry solvents (e.g., MeOH, EtOH, THF, DCM, DMF) under anhydrous conditions where required.
  • For water‑sensitive operations, dry over KOH pellets or CaH2 and distill under reduced pressure immediately before use.
• Freeze–thaw: Not typically necessary; avoid unnecessary freezing of neat amines due to viscosity and seal stress. For stock solutions, store at 2–8 °C if compatible with solvent and application.

Always refer to the CoA/SDS for item‑specific stability, packaging materials, and any additional storage precautions.

Structure and Identity

Brief overview: 2‑Piperidineethanamine is an aliphatic diamine that combines a saturated six‑membered piperidine ring with an ethylamine functionality. It is commonly encountered as a basic, highly nucleophilic building block for nitrogenous scaffolds.

• Item-specific identifiers from Product Data:
  • CAS: 15932-66-8
  • 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):
  • Contains a saturated piperidine ring (secondary amine within a six‑membered heterocycle).
  • Bears an ethanamine side chain (primary amine), making the molecule a diamino species (one secondary ring nitrogen, one primary exocyclic amine).
  • Typical 2D depiction: a chair‑like piperidine ring with nitrogen in the ring; an ethyl chain terminating in –NH2 is attached to the piperidine framework (isomeric attachment can vary by naming conventions; consult CoA for exact connectivity).
  • Functional groups: primary aliphatic amine (–CH2–CH2–NH2), secondary cyclic amine (piperidine N). Both sites are basic and nucleophilic.
• Stereochemistry: No inherent stereocenters for the N‑substituted ethyl linkage; if the ethylamine is attached at a ring carbon (2‑substituted), a stereocenter may exist. Verify isomer and stereochemistry on the item’s CoA.
• Synonym notes (literature, for context): Compounds described as “piperidine‑ethanamine” may refer to N‑(2‑aminoethyl)piperidine (2‑(piperidin‑1‑yl)ethanamine) or to 2‑(piperidin‑2‑yl)ethanamine. Always match to the CAS/CoA for definitive identity.

Synthetic Utility

Key functional elements and how they can be exploited:

• Dual amine reactivity:
  • Primary exocyclic amine: higher nucleophilicity; ideal for selective acylation, sulfonylation, and reductive amination. Protect with Boc/CBz/Fmoc for orthogonal sequences.
  • Secondary ring nitrogen: more hindered but basic; quaternization or selective alkylation possible under controlled conditions.
• Building‑block value:
  • Introduces a piperidinyl–ethyl vector in one step, avoiding multi‑step homologations of piperidine.
  • Facilitates macrocyclizations or tethered cyclizations (e.g., with diesters/dialdehydes) to generate polycyclic aminated scaffolds.
• Named/typical transformations (literature):
  • Reductive amination (NaBH3CN/NaBH(OAc)3, or H2/Pd) with aldehydes to furnish tertiary amines bearing piperidine and alkyl/aryl substituents.
  • Urea/carbamate formation with CDI, phosgene equivalents, or chloroformates to access linkers and protecting groups.
  • Michael additions to acrylates/acrylamides; subsequent intramolecular cyclizations yield diverse aza‑frameworks.
  • SNAr on activated aryl fluorides/nitroarenes to install the diamine as an anilide or diarylamine after acylation.
• Orthogonality strategies:
  • Protonate one nitrogen (salt) to modulate nucleophilicity and achieve site selectivity.
  • Temporary blocking as amide/carbamate on the more reactive site to direct subsequent transformations.

Overall, 2‑piperidineethanamine is a step‑economical, bifunctional handle for rapidly accessing N‑rich chemotypes and tuning basicity/solubility in medicinal chemistry campaigns.

Target Specificity

This product is a small‑molecule reagent, not a biological targeting reagent or antibody.

• Antigen/epitope: Not applicable.
• Species reactivity/clone/isotype: Not applicable.

Conclusion: Target specificity does not apply. See Synthetic Utility and Reaction & Applications for relevant use cases.