This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
248.150 g/mol
XLogP3
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
247.053 Da
Monoisotopic Mass
247.053 Da
Topological Polar Surface Area
21.300 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
163.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
2
Lösungsrechner
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Application Protocols
No manufacturer application protocols are provided for this item.
General laboratory usage examples (illustrative, not product-specific):
Stock solutions: Prepare at 10–100 mM in water, methanol, ethanol, or DMSO depending on downstream application. Filter (0.22 µm) if particulate is present.
Basification/extraction to free base: Dissolve the HCl salt in water, basify to pH ~11 with Na2CO3, extract with EtOAc (3×), dry (Na2SO4), concentrate. Use immediately.
Coupling setup: In anhydrous DCM, add substrate acid (1.0 equiv), HATU (1.1 equiv), DIPEA (3 equiv total, including HCl neutralization), then add a solution of the amine salt at 0–5 °C; warm to RT and stir to completion.
For precise, validated procedures, consult the peer-reviewed literature and optimize for your substrate.
Biological Roles
This material is intended strictly for laboratory research use. No medical or clinical use is implied.
General context (literature):
Structural class: Aryloxy-piperidines are prevalent scaffolds in medicinal chemistry libraries due to their balance of basicity and lipophilicity and their capacity to form salts with favorable solid-state properties.
Biological role: 4-(4-chlorophenoxy)piperidine itself is a synthetic small molecule; it does not have a known endogenous biological role or participation in native metabolic pathways.
Physicochemical attributes relevant to discovery:
Basic center (piperidine) enabling salt formation for formulation and solubility tuning.
Aromatic chlorine can modulate metabolic stability and binding interactions in SAR campaigns (literature trend), but effects are context-dependent.
Use in biology labs (general):
If used as a tool compound precursor or in fragment elaboration, ensure endotoxin/inorganics are not critical; this is not a GMP material.
Handle solutions under aseptic conditions only if required by your protocol; no sterility is claimed.
Buffer Applications
Not typically applicable. 4-(4-Chlorophenoxy)piperidine HCl is an organic building block, not a dedicated buffering agent.
Practical notes (general):
The HCl salt can acidify aqueous solutions slightly due to the conjugate acid; however, it does not provide a defined buffering range.
For biochemical assays, prepare stock solutions (e.g., in water, methanol, or DMSO) and dilute into an appropriate biological buffer (PBS, HEPES, etc.) selected for your assay’s pH, ionic strength, and compatibility.
Green Alternatives
Although this product is a solid reagent, greener choices can be made in solvents, bases, and workups involving 4-(4-chlorophenoxy)piperidine HCl.
Opportunities (general, literature-based):
Solvent substitution:
Replace DMF/DCM where possible with 2-MeTHF, EtOAc, IPA, or ethanol for acylations, alkylations, and reductive aminations.
Conduct reductive aminations in ethanol or water/ethanol mixtures using NaBH3CN alternatives like picoline borane or catalytic hydrogenation.
Base selection:
Use carbonate bases (K2CO3, Cs2CO3) or organic bases with lower environmental impact (e.g., DBU/DIPEA in greener solvents) instead of strong inorganic bases that complicate waste streams.
Workup/waste minimization:
Favor aqueous base liberation of the free base followed by extraction with EtOAc/2-MeTHF, avoiding chlorinated solvents.
Employ salt-switch crystallizations (e.g., HCl ↔ organic acid salts) to purify without chromatography.
Small comparison (illustrative):
DMF vs 2-MeTHF: 2-MeTHF is biorenewable and easier to remove; may require optimizing temperature or base to achieve comparable rates.
DCM vs EtOAc: EtOAc is less toxic and has favorable EHS profile; polarity differences may affect solubility—pre-form the free base to maintain dissolution.
Caveats:
Reaction scope/kinetics may shift in greener solvents; run small-screen DoE to confirm yields and impurity profiles.
Ensure amine salt is sufficiently dissolved; consider in situ neutralization to improve rate while maintaining greener solvent.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is supplied for research use only.
General context (non-clinical, literature-based):
Aryloxy-piperidines serve as intermediates and scaffolds in medicinal chemistry synthesis. The hydrochloride salt form is often chosen for improved crystallinity, handling, and measured assay accuracy.
Process considerations:
Salt selection (HCl vs. organic acid salts) influences hygroscopicity, solubility, and crystallization behavior during API intermediate handling.
Lot-to-lot control of salt stoichiometry and residual solvents is essential in scale-up; for this research-grade item, consult CoA/Spec Sheet for available controls (not specified here).
No therapeutic claims are made or implied. For GMP/process development, source appropriate grade and specifications.
Physical Properties
Item-specific (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Physical state: typically a crystalline solid as the hydrochloride salt.
Solubility: HCl salts of piperidines are usually freely soluble in water and polar protic solvents (e.g., methanol, ethanol) and in DMSO; the corresponding free base is more soluble in organic solvents (EtOAc, MTBE, toluene) and less in water.
pKa: secondary piperidine conjugate acid pKa typically ~10.5–11.5 (for free base; literature range for piperidines). As an HCl salt, the amine exists predominantly as ammonium.
LogP (free base, literature): aryl-oxy piperidines often exhibit moderate lipophilicity (estimated clogP ~2–3), while the HCl salt is more hydrophilic (reported as logD-dependent on pH).
Melting point: Many amine HCl salts melt/decompose >180 °C; specific MP for this item is Not specified; consult CoA.
Density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Notes for practitioners:
If precise solubility, MP, or spectral data are critical, request the lot-specific CoA/Spec Sheet. Salt form, hydration, and polymorph can shift MP and handling profile.
Quality and Grades
Item-specific (from Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
Without a declared grade, assume research-use quality suitable for synthetic and analytical laboratory applications. For trace analyses (e.g., pharmacology SAR, GLP), request a detailed specification including assay basis (anhydrous vs. as-is), residual solvents, and counter-ion content.
HCl salt considerations:
Assay reporting: Salt forms may be reported as free-base or salt-basis; verify when calculating equivalents.
Counter-ion content: Chloride and residual water (hydrate level) affect molecular weight and stoichiometry; Karl Fischer and chloride titration can be informative. Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: None indicated for this product. If present in other lots, stabilizers can influence reactivity (e.g., amines with antioxidant traces). Not specified for this item; refer to CoA/Spec Sheet.
UV profile/LC use: If planning HPLC/UV analysis, confirm low-UV impurity profile for your method. Not specified for this item; refer to CoA/Spec Sheet.
Recommendations:
Request CoA/Spec Sheet for current lot to confirm identity (1H/13C NMR, IR), purity (HPLC/GC), and water content. Verify salt stoichiometry before scale-up or analytical quantitation.
Reaction and Applications
Scope: 4-(4-Chlorophenoxy)piperidine HCl is a versatile nitrogenous building block. Aryloxy-piperidines are common motifs in discovery chemistry. The HCl salt is convenient for handling and weighing but is less nucleophilic until neutralized.
Typical applications (literature/general):
N-Acylation and carbamate/urea formation: Convert to free base with DIPEA/TEA in situ; acylate with acyl chlorides/anhydrides or react with chloroformates/CO2-derived reagents to form carbamates/ureas.
N-Alkylation: SN2 with primary alkyl halides or sulfonates under basic conditions (K2CO3 in DMF/MeCN; or DIPEA in DCM for more reactive electrophiles). Monitor for over-alkylation to tertiary amines.
Amide coupling: As a nucleophile with activated carboxylic acids (HATU/EDC/DIC with HOAt/DMAP). Salt form requires base to liberate free amine.
Reductive amination: With aldehydes/ketones using NaBH(OAc)3, picoline borane, or H2/Pd. Often conducted in DCE/MeOH with AcOH or in EtOH; adjust pH to balance imine formation vs. salt formation.
Ether stability/transformations: The aryl–O–alkyl ether is typically stable to base and mild acid; harsh Lewis acids or strong nucleophiles (e.g., BBr3, HBr/heat) can cleave aryl ethers (literature), enabling deprotection to 4-chlorophenol derivatives.
Salt exchange and crystallization: Formation of alternate acid salts (e.g., tosylate, mesylate) can tune solubility and crystallinity for purification.
Practical tips:
Drying: Prepare the free base immediately before moisture-sensitive reactions; azeotrope with toluene or use solid-phase base (K2CO3) to minimize water.
Equivalents: When using the HCl salt, include one equivalent of base to neutralize HCl, plus the stoichiometric base needed for reaction.
Reaction Conditions
General literature guidance (not item-specific; optimize per substrate):
Liberation of free base:
Aqueous workup: Dissolve HCl salt in water, basify to pH ~11 (Na2CO3/NaOH), extract with EtOAc/MTBE. Dry and use immediately.
In situ: Add 1.1–2.0 equiv organic base (DIPEA/TEA) in anhydrous solvent.
N-Acylation:
Solvent: DCM, THF, 2-MeTHF, or EtOAc.
Base: DIPEA (2–3 equiv total, accounting for HCl neutralization).
Temperature: 0–25 °C; time: 0.5–4 h. Monitor by TLC/LCMS.
Reductive amination:
Solvent: MeOH/EtOH or DCE/MeOH mixtures; AcOH (0.5–1.0 equiv) to drive imine formation.
Reductant: NaBH(OAc)3 (2–3 equiv) at 0–25 °C; 2–16 h. Alternative: H2 (1–3 bar), Pd/C (5–10 wt%) in EtOH, 25–50 °C.
N-Alkylation (SN2):
Solvent: MeCN or DMF (or greener: acetone/2-MeTHF with phase-transfer).
Temperature: 25–80 °C; 2–18 h. Beware dialkylation.
Carbamate formation:
With chloroformates in DCM/Et3N at 0–25 °C; 1–3 h. For CDI coupling to alcohols/CO2-derived methods, use DMF/MeCN.
Ether stability:
Stable to base; avoid strong Lewis acids (BBr3/AlCl3) if ether integrity must be retained.
Expected yields: Highly substrate-dependent; many N-acylation/alkylation examples report 60–90% under optimized conditions (literature). Always confirm by small-scale trials.
Safety and Handling
Authoritative safety information must be taken from the SDS for this product/lot.
Item-specific (from Product Data):
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
Storage: Room temperature.
General laboratory guidance (literature/good practice; not product-specific):
Likely hazards: Amines and their hydrochloride salts may cause skin/eye irritation; dust may be irritating if inhaled. Avoid generating dust/aerosols.
PPE: Use lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Handle in a fume hood when weighing large quantities or when basifying to the free base (amine vapors/odors possible).
Incompatibilities: Strong oxidizers; strong bases liberate the free base and HCl (acidic fumes possible). Avoid contact with acyl/alkylating agents unless controlled for synthesis.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill response: Avoid dust; collect mechanically; wash area with mild detergent. For solutions, absorb with inert material.
Waste: Dispose according to local regulations; salts containing amines are typically collected as organic/amine-containing waste.
Always consult the SDS for definitive hazard classification and response.
Solvent Selection
Relevance: This compound is a solid building block (amine HCl salt), not a solvent. Solvent choice impacts isolation, coupling efficiency, and basification.
General solvent behavior (literature):
Polarity class: As an HCl salt, behaves as a polar, ionic species; excellent solubility in water, methanol, ethanol; good in DMSO; variable in acetonitrile; limited in nonpolars.
Free-base form: After basification, solubility increases in moderately polar organics (DCM, EtOAc, THF, toluene) and decreases in water.
Typical use scenarios:
N-acylation/alkylation: Convert to free base in situ with an organic base (DIPEA, TEA) in DMF, DCM, THF, or MeCN, or pre-generate the free base and use anhydrous solvents.
Nucleophilic substitutions and carbamate formation: DMF or MeCN often provide good solubility with base; for greener options, 2-MeTHF or ethanol may be suitable when compatible with reagents.
Salt exchange/extraction: Dissolve in water, basify (Na2CO3/NaOH), extract free base into EtOAc/MTBE. Back-salt with HCl in ether/IPA if required.
DMF/DMSO: Pros—high solubility; Cons—difficult workup; not green.
2-MeTHF/EtOAc: Pros—greener, easy workup; Cons—may require pre-basification to free base for solubility.
Storage and Reconstitution
Item-specific (from Product Data):
Storage conditions: Room temperature.
Additional guidance (general; not product-specific):
Container: Store tightly capped in a dry, well-ventilated place. Protect from moisture to avoid caking/hygroscopic uptake typical of amine salts.
Stability: Amine hydrochloride salts are generally stable at ambient temperature for extended periods when kept dry and protected from light. Avoid prolonged exposure to high humidity.
Reconstitution/solubility (general):
Water: Typically freely soluble for HCl salts; prepare aqueous stocks fresh or store refrigerated if required by your protocol.
Organic solvents: Soluble in methanol, ethanol, and DMSO; for less polar solvents, first convert to the free base.
Freeze–thaw: Not routinely applicable to solids. For solutions, minimize freeze–thaw cycles; aliquot if long-term storage is needed.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Note: Exact solubility, water content, and salt stoichiometry are Not specified for this item; refer to CoA/Spec Sheet for lot-specific details. Always allow the closed container to equilibrate to room temperature before opening to reduce moisture condensation.
Structure and Identity
Brief: 4-(4-Chlorophenoxy)piperidine hydrochloride is a protonated piperidine salt bearing a para-chlorophenoxy ether substituent at the 4-position of the piperidine ring.
Item-specific (from Product Data):
SKU: P728964
Product name: 4-(4-CHLOROPHENOXY)PIPERIDINE HCL
CAS: 63843-53-8
InChIKey: 197470 (as provided)
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/computed identity (for reference only; not product specification):
Common name: 4-(4-Chlorophenoxy)piperidine hydrochloride (1:1 salt)
Free-base formula: C11H14ClNO; HCl salt formula: C11H15Cl2NO (literature/computed)
Approx. formula weight (HCl salt): ~248.15 g/mol (computed)
Structural features: one saturated six-membered piperidine ring (secondary amine, protonated in HCl salt), an ether linkage (O–), and a para-chloro-substituted phenyl ring.
2D structure description (general):
A piperidine chair ring with the nitrogen protonated as ammonium (·HCl). At the 4-position of the ring, a methine carbon is bonded via an ether oxygen to a para-chloro phenyl ring (–O–C6H4–Cl at para). No stereogenic centers are specified; the material is typically racemic at C4 if configurationally stable (but in practice interconverts).
Synthetic Utility
Functional group synopsis:
Secondary amine (as HCl salt): Nucleophilic after basification; amenable to acylation, alkylation, sulfonylation, carbamate/urea formation, and coupling to carboxylic acids.
Aryl–O–alkyl ether: Generally robust under basic nucleophilic conditions; can be cleaved under strong Lewis/Brønsted acidic conditions (e.g., BBr3, HBr/heat; literature) if deprotection to p-chlorophenol is desired.
Para-chloro substituent: Modulates electronics of the aryl ring; participates in halogen bonding and can influence lipophilicity; not a reactive handle under mild conditions.
Retrosynthetic value:
Serves as a piperidine nucleophile in convergent assembly of amide-linked libraries, carbamates, and ureas.
The ether linkage offers conformational bias and H-bond acceptor capability often sought in medicinal chemistry.
Representative transformations (literature):
Formation of amides with activated acids (HATU, T3P, EDCI) in DMF/MeCN or greener EtOAc/2-MeTHF with DIPEA.
Reductive amination with aldehydes/ketones using NaBH(OAc)3 in DCE/MeOH or ethanol; for greener practice, use catalytic hydrogenation (Pd/C) in ethanol.
N-Sulfonylation with sulfonyl chlorides in DCM/Et3N to afford sulfonamides (robust handles for further diversification).
Notes:
One equivalent of base is required to neutralize the HCl prior to reaction; adjust stoichiometry accordingly.
If needed, isolate the free base by basification and extraction, then re-salt post-synthesis for purification/crystallinity.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological probe with defined target specificity.
Item-specific data such as antigen/epitope, clone, isotype, or species reactivity: Not applicable/not provided for this item.
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