This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
External Descriptors
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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
Not applicable. No biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the product data. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.
Biological Roles
This compound is a synthetic small-molecule building block rather than a metabolite or biopolymer constituent. No inherent physiological role is established for 4-(4-bromophenyl)piperidine.
General context (non-clinical, literature-based):
Piperidine motifs are common in bioactive molecules and can modulate basicity, solubility, and receptor binding in medicinal chemistry campaigns. The presence of an aryl bromide enables rapid diversification for structure–activity relationship (SAR) studies without implying any specific bioactivity for this substance itself.
In biochemical assay development, such scaffolds may be used as reference chemotypes or as precursors to tagged derivatives (e.g., biotin/fluorophore conjugates) through amide/carbamate formation and subsequent cross-coupling on the aryl bromide.
Note: Any biological testing or use should be conducted strictly within research settings. This product is supplied for research use only (Product Data) and is not intended for diagnostic, therapeutic, or clinical applications.
Buffer Applications
4-(4-Bromophenyl)piperidine is not used as a buffering agent. Although it is a basic secondary amine, it is not part of standard biological/analytical buffer systems. For aqueous work, converting the free base to a defined salt (e.g., hydrochloride) may improve solubility or crystallinity, but this is a purification/handling tactic rather than a buffering application.
For pH control in experiments involving this compound, select a conventional buffer (e.g., phosphate, HEPES, Tris) appropriate to your system, and treat the compound as a solute added to that buffered medium.
Green Alternatives
Sustainable choices focus on solvent and catalyst systems for transforming the aryl bromide while managing the basic amine.
Greener solvent swaps (literature guidance):
Replace dioxane/THF with 2-MeTHF or CPME in Suzuki/Buchwald couplings; both tolerate water and allow easier recovery.
Use ethanol or water–ethanol mixes for reductive amination or salt formation steps when feasible.
Avoid NMP/DMF where possible; acetonitrile, propylene carbonate, or 2-MeTHF often provide comparable outcomes.
Catalyst/base considerations:
Employ ligand-efficient Pd precatalysts (e.g., PEPPSI, Buchwald precatalysts) at ≤0.5 mol% to reduce metal footprint.
Explore nickel-catalyzed Suzuki or amination protocols as Pd alternatives for activated partners.
Utilize aqueous bases (K2CO3/K3PO4) in biphasic or micellar media to reduce organic solvent use.
Cross-coupling solvent | Dioxane/DMF | 2-MeTHF/CPME or Me-THF–H2O | Sometimes longer reaction times; solubility of inorganic base must be managed.
Base | NaOtBu | K2CO3/K3PO4 (aq) | May require higher temperature.
Catalyst | Pd(PPh3)4 (1–3 mol%) | Pd-precatalyst (0.1–0.5 mol%) or Ni | Sensitivity to air/moisture can increase.
Waste minimization:
Capture Pd/Ni residues via metal scavengers post-reaction.
Prefer salt-switch crystallizations over chromatographic purification to reduce silica/solvent consumption.
Pharmaceutical Uses
No pharmacopeial or excipient role is indicated for this substance. 4-(4-Bromophenyl)piperidine is primarily a synthetic intermediate for research and development.
Formulation/manufacturing context (general R&D use only; not for human/clinical use):
As a free base, it can be converted to well-defined salts (e.g., HCl, sulfate) to modulate solubility and facilitate isolation/crystallization during intermediate handling.
The aryl bromide allows late-stage diversification en route to candidate molecules; the piperidine nitrogen provides a handle for forming amides, carbamates, or quaternary ammonium species for purification tags.
Regulatory note: This product is supplied for research use only and is not manufactured under GMP for drug substance/drug product. Any use in regulated manufacturing would require independent qualification and sourcing to appropriate standards.
Physical state: typically a crystalline solid or low-melting solid/oil for closely related 4-arylpiperidines; exact MP not widely reported (check CoA).
Basicity: secondary amine; pKaH of piperidinium typically ~10.5–11.5 (literature, piperidine family). Expect similar range given the para-aryl substituent.
Lipophilicity: logP for analogous 4-phenyl/4-bromophenyl piperidines commonly in the ~2–3.5 range (literature trends), increased by the aryl bromide; exact value varies among computational methods.
Solubility: free base is moderately polar and often soluble in organic solvents (EtOAc, DCM, toluene, MeOH, acetonitrile, DMF/DMSO); limited water solubility in free-base form but soluble as salts (e.g., HCl, TsOH) (general behavior of secondary amines).
Refractive index/density/UV cutoff: Not broadly standardized in literature for this specific compound.
Notes for use:
Convert to a crystalline salt (e.g., HCl) when aqueous handling or isolation as a solid is desired.
The aryl bromide absorbs in the UV; for chromatography detection, 254 nm monitoring is typically effective (general aromatic behavior).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet. Aladdin typically supplies research-grade materials suitable for synthetic and analytical laboratory use. Actual assay, impurity profile, and residual solvents are defined on the CoA.
What grade implies (general guidance):
Research grade: intended for R&D; not certified for GMP manufacture or clinical applications. Typical acceptance criteria include identity (NMR/IR/HRMS), assay, and limits on related substances.
If offered as HPLC grade (not indicated here), that designation would refer to low non-volatile residue and low UV background for chromatographic use, not applicable unless stated on the label.
Stabilizers/additives:
None specified for this item; refer to CoA/Spec Sheet. Secondary amines are usually shipped neat; if a salt form (e.g., hydrochloride) is needed for crystallinity/handling, it will be labeled explicitly.
Release documentation and QC (typical):
Identity: 1H/13C NMR, MS; optionally IR.
Purity: qNMR or HPLC/GC area%.
Appearance and water content: Not specified for this item; refer to CoA/Spec Sheet.
Practical note:
For air/moisture-exposed free bases, assay may drift slightly due to adventitious CO2/H2O uptake. If critical, convert a portion to a defined salt and back-extract to the free base immediately prior to use.
Reaction and Applications
4-(4-Bromophenyl)piperidine is a versatile bifunctional scaffold combining a cross-coupling handle (aryl bromide) with a nucleophilic/basic secondary amine.
Aryl–Br functionalization (literature examples):
Suzuki–Miyaura cross-coupling: installation of aryl/heteroaryl groups para to the piperidine substituent. Typical systems: Pd(PPh3)4 or Pd-PEPPSI, base K2CO3/K3PO4, dioxane–H2O or 2-MeTHF–H2O, 60–100 C.
Buchwald–Hartwig amination: formation of para-anilines using Pd2(dba)3 with BrettPhos/XPhos or precatalysts (e.g., Pd-G3), base NaOtBu or Cs2CO3, toluene or dioxane, 80–110 C.
Sonogashira: coupling with terminal alkynes to yield para-alkynyl derivatives; Pd/CuI, Et3N or iPr2NH, 25–80 C.
Carbonylations: Pd-catalyzed carbonylative coupling to give para-amides/esters under CO.
Lithiation–borylation is less favored at aryl bromide in presence of basic amine; protection of N (e.g., Boc) mitigates side reactions.
Nitrogen-directed chemistry:
N-acylation/alkylation to tune basicity and physicochemical properties. Protect the amine (Boc, Cbz) before strong-base metalations or when selectivity is required in cross-coupling.
Salt formation (e.g., HCl, TsOH) for purification, crystallization, or to facilitate aqueous processing.
Applications:
Scaffold elaboration for SAR libraries, particularly CNS/GPCR-focused chemotypes (general medicinal chemistry context; no clinical claims).
Linker into bifunctional molecules where the amine serves as an attachment point and the aryl para position enables modular diversification via Pd catalysis.
Tips:
Use degassed solvents and inert atmosphere in Pd-catalyzed transformations.
If the free base poisons catalysts, pre-form the Boc-carbamate and deprotect after coupling.
Reaction Conditions
General literature conditions for key transformations of 4-(4-bromophenyl)piperidine (for planning; not item specifications):
Suzuki–Miyaura arylation:
Catalyst: 1–3 mol% Pd(PPh3)4 or 0.5–1 mol% Pd-PEPPSI.
Base: K2CO3 or K3PO4 (2–3 equiv), often with 5–20% H2O as co-solvent.
Solvent: dioxane/H2O, 2-MeTHF/H2O, or toluene/H2O.
Temperature/time: 70–100 C, 2–16 h. Typical isolated yields: 60–90% depending on partner.
Buchwald–Hartwig amination (to para-anilines):
Catalyst/ligand: 1–2 mol% Pd2(dba)3 with 2–4 mol% BrettPhos or XPhos; or precatalyst (0.5–1 mol%).
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: toluene, dioxane, or CPME.
Temperature/time: 80–110 C, 4–18 h. Typical yields: 55–85%.
Sonogashira coupling:
Catalyst: 1–2 mol% Pd(PPh3)2Cl2, 2–5 mol% CuI.
Base/solvent: iPr2NH or Et3N in THF/MeCN/EtOH.
Temperature/time: 25–70 C, 2–12 h. Typical yields: 50–80%.
Solvent/temperature: DCM/THF, 0–25 C, 0.5–3 h. Often >80%.
Practical notes:
Protect the amine (Boc) if it deactivates Pd catalysts or competes in coupling; Boc-piperidines often show cleaner cross-couplings.
Degas solvents and employ inert atmosphere to maintain catalyst activity.
If using aqueous bases, ensure sufficient solubility or use phase-transfer (e.g., TBAB) in biphasic media.
Safety and Handling
Item-specific hazard data (GHS/CLP) are not provided in this listing. Always consult the product SDS for authoritative information.
General safety guidance for 4-(4-bromophenyl)piperidine and related aryl-bromide secondary amines (literature/analog-based):
Likely hazards: may cause skin/eye irritation; harmful if swallowed or inhaled; amines can be corrosive to mucous membranes at higher concentrations. Aryl bromides are not typically highly volatile but can be irritants.
PPE: use lab coat, nitrile gloves, and safety glasses as minimum. Employ chemical splash goggles and face protection for scale-up or operations with splashing potential.
Engineering controls: handle in a fume hood to control vapors/aerosols and to avoid exposure during reagent charging or solvent removal.
Incompatibilities: strong oxidizers; acid chlorides/anhydrides and isocyanates (react vigorously with amines); strong bases may induce side reactions during metal-catalyzed couplings; avoid sodium/peroxide-forming agents during storage.
Handling tips: for moisture- or CO2-sensitive free bases, keep containers tightly closed under dry air or nitrogen. If preparing salts (e.g., HCl), note exotherm on acid addition.
First aid (overview; defer to SDS): eye/skin contact—rinse with water for at least 15 minutes; inhalation—move to fresh air; ingestion—rinse mouth, seek medical attention.
Fire safety: use CO2, dry chemical, or alcohol-resistant foam. Combustion may produce HBr, NOx, and CO/CO2—firefighters should wear SCBA.
Waste: collect amine-containing and halogenated waste streams separately per institutional and regulatory guidance.
Solvent Selection
Solvent choice for 4-(4-bromophenyl)piperidine is governed by two handles: a basic secondary amine (polar, H-bond accepting/donating) and an aryl bromide (nonpolar, coupling handle).
Aqueous media: free base has poor water solubility; salt forms (e.g., HCl) are water-soluble.
For cross-couplings at the aryl–Br:
Common media: dioxane/water, toluene, 2-MeTHF, CPME, or DMF/DMAc depending on catalyst/boron partner.
Aqueous base promotes transmetalation in Suzuki couplings; biphasic systems (toluene–water with phase-transfer) can work well.
For N-functionalization (acylation/alkylation):
Use anhydrous, aprotic solvents (DCM, THF, MeCN) with non-nucleophilic bases (DIPEA, Et3N) to suppress over-alkylation.
Purification considerations:
Free bases can tail on silica; adding a trace of base (0.1–1% Et3N) to eluents or converting to a salt for crystallization often improves handling.
Comparison snapshot (general):
DMF/DMAc: dissolves everything; high-boiling, harder to remove.
2-MeTHF/CPME: greener alternatives; good for Pd couplings; easier workup.
Toluene: low polarity; ideal for ligand/catalyst stability in some couplings.
MeOH/EtOH: useful for salt formation and reductive amination steps.
Storage and Reconstitution
Storage (as supplied): Room temperature (Product Data). Store tightly closed in a dry place. For best long-term integrity of a free-base amine, minimize exposure to moisture and CO2 by purging headspace with dry air or nitrogen after use.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution: Not applicable; supplied neat unless otherwise specified. If a solution is required for your workflow, prepare fresh in a suitable dry solvent (e.g., DCM, THF, MeCN, EtOH, DMF) immediately before use.
Salt handling: If converting to a salt (e.g., HCl) for crystallinity or aqueous work, prepare under controlled conditions (dry solvent, slow addition of acid) and document stoichiometry. Free-base the salt with aqueous base and extract into an organic solvent when the free base is needed.
Freeze–thaw: Not applicable. If storing prepared solutions, keep in sealed, inerted vials at 2–8 C and use within days to minimize degradation or solvent loss.
Stability notes (general): Secondary amines are generally stable at ambient conditions; avoid strong oxidizers. The aryl bromide is stable under neutral conditions but participates in metal-catalyzed reactions—store away from metal catalysts/finely divided metals to prevent unintended reactions.
Research use only: This product is intended for laboratory research use and is not for human or veterinary use.
Structure and Identity
4-(4-Bromophenyl)piperidine is a para-brominated anilide-like scaffold in which a 4-bromophenyl group is bonded directly to the 4-position of a saturated piperidine ring.
Molecular Formula: C11H14BrN (literature; typical for this structure)
Molecular Weight: ~240.14 g/mol (literature, calculated from C11H14BrN)
Structural features (descriptive):
Aromatic ring: para-bromobenzene (the bromine is para to the piperidine substituent).
Saturated heterocycle: piperidine (six-membered, secondary amine), substituted at C4 by the aryl ring.
Functional groups: aryl bromide (C–Br on sp2 carbon), secondary amine (basic nitrogen, can be protonated to a piperidinium salt).
Stereochemistry: achiral as drawn; the 4-substituted piperidine can adopt chair conformations without creating stereocenters.
2D verbal depiction: a benzene ring bearing bromine at the para position relative to the bond that links the ring to the axial/equatorial C4 of a piperidine chair. The piperidine nitrogen is secondary (one hydrogen) and positioned three carbons away from the aryl junction (–Ar–CH–CH2–CH2–N–).
Synthetic Utility
Functional group handles and reactivity profile:
Aryl bromide (para to the piperidine substituent):
Amenable to Pd/Ni-catalyzed cross-couplings (Suzuki, Sonogashira, Heck, Buchwald–Hartwig) to introduce aryl, alkynyl, vinyl, or amino groups.
Carbonylative variants give amides/esters under CO.
Secondary amine (piperidine nitrogen):
Rapidly derivatized via acylation (acid chlorides, anhydrides), sulfonylation, or reductive alkylation.
Protectable (Boc, Cbz, Fmoc) to control chemoselectivity during cross-couplings or strong-base chemistry.
Retrosynthetic value:
Serves as a convergent node: diversify the aryl bromide first to a library of para-substituted phenyl derivatives, then orthogonally elaborate the piperidine nitrogen (or vice versa), enabling matrix libraries.
The 4-linkage on piperidine spaces the amine three atoms from the aryl ring, often beneficial for tuning basicity and sterics in lead optimization.
Sonogashira: Ar–Br + HC≡CR → Ar–C≡CR; Pd/CuI, iPr2NH, 25–60 C.
N-Acylation: R–COCl, base (Et3N/DIPEA), DCM, 0–25 C.
Workup/purification tips:
Convert to salt (e.g., HCl in Et2O) for crystallization, then free-base as needed.
During silica chromatography, add 0.1–1% Et3N to prevent streaking/tailing of the free base.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, enzyme inhibitor with defined biological target in this listing). No antigen/epitope or species reactivity information is relevant.
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