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
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.
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Application Protocols
Not applicable. No bioassay or immunoassay application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For chemical usage, see the Reaction & Applications and Reaction Conditions tabs for general synthetic guidance.
Biological Roles
No specific biological role is assigned to 1-(2-bromophenyl)piperidine in this product listing. It is supplied strictly for research use as a synthetic intermediate.
General context (literature; not product-specific and not implying biological activity):
The piperidine ring is a ubiquitous motif in natural products and bioactive small molecules, often modulating basicity and solubility.
N-Aryl piperidines can serve as scaffolds for SAR exploration in medicinal chemistry; the tertiary amine may engage in salt-bridge interactions in protein binding sites, while ortho substituents modulate conformational preferences and electronics of the aniline moiety.
The aryl bromide is a synthetic handle rather than a biological determinant; it allows rapid diversification (e.g., replacing Br through cross-coupling) to probe structure–activity relationships.
Important: This product is provided for laboratory research use only. It is not intended for use in humans or animals, diagnostics, or therapeutic applications.
Buffer Applications
This compound is a hydrophobic tertiary amine building block, not a buffering agent. It does not form a defined conjugate acid/base pair suitable for precise pH buffering in aqueous systems.
Not typically used to prepare laboratory buffers or electrophoresis media.
If aqueous handling is required, converting to a water-soluble salt (e.g., hydrochloride) can aid dissolution, but this is for solubility, not buffering.
For pH control and buffering, select established buffer systems (e.g., phosphate, HEPES, Tris) appropriate to your pH and compatibility needs.
Green Alternatives
This item is a halogenated building block, not a solvent or auxiliary. A direct “green substitute” for the molecule itself typically does not exist when the ortho-bromo handle is required for synthesis. Nevertheless, greener choices can be made in how it is used (literature guidance):
Greener process choices for transformations of aryl bromides like 1-(2-bromophenyl)piperidine:
Solvent selection: Prefer 2-MeTHF, CPME, propylene carbonate, or water/ethanol mixtures for cross-coupling when compatible, in place of DMF, NMP, or dioxane.
Catalysis: Employ highly active Pd catalysts at ppm levels or Ni catalysis to reduce precious metal loading; consider ligand systems enabling room-temperature couplings.
Base and additives: Use milder inorganic bases (K3PO4, K2CO3) or aqueous carbonate to reduce hazards relative to alkoxides.
Energy efficiency: Microwave or flow chemistry can cut reaction times and energy input; flow also enhances heat/mass transfer for o-substituted substrates.
Waste minimization: Select boron partners that generate benign byproducts (e.g., boronic acids/esters over stannanes). Recover and recycle Pd where feasible.
Greener-leaning: 2-MeTHF or aqueous ethanol, 100–1000 ppm Pd or Ni, 40–80°C, K3PO4, with solvent recycling.
Note: If a non-halogenated precursor could be functionalized via C–H activation, that may avoid halogenated intermediates; applicability is case-dependent.
Pharmaceutical Uses
No pharmacopeial or excipient role is specified for this item. It is offered as a research chemical/intermediate only.
Process chemistry context (general, non-clinical):
1-(2-Bromophenyl)piperidine can serve as a key intermediate en route to drug-like molecules containing the N-aryl piperidine motif. The ortho-bromo substituent enables late-stage diversification via cross-coupling to introduce aryl, heteroaryl, alkynyl, or other groups.
Salt formation (e.g., HCl, fumarate) is commonly leveraged during process development to enhance crystallinity, enable purification, and modulate handling properties of piperidine-containing intermediates.
Typical quality considerations prior to scale-up include assay by qNMR/GC, control of residual solvents, identification of halogen-containing impurities, and light/air stability assessment.
Compliance notes:
No compendial monograph or pharmaceutical-grade designation is provided for this listing. Any use in GMP settings would require independent qualification, vendor assessment, and specification setting based on your internal quality system.
Research use only; not for human or veterinary use.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values and expectations (for guidance only; not product specifications):
Phase/appearance: N-aryl piperidines of comparable structure are typically colorless to pale yellow oils at ambient temperature.
Acid–base: tertiary amine; expected to form salts with strong acids (e.g., HCl), increasing aqueous solubility (literature).
Solubility: expected to be miscible with common organic solvents (DCM, EtOAc, THF, MeOH, toluene) and sparingly soluble in water as the free base; protonated salts are water-soluble (literature).
LogP: N-aryl tertiary amines with a single halogen substituent typically exhibit moderate lipophilicity (estimated cLogP ~2–3; literature/computational estimates for analogs).
Boiling/melting points and density: Not specified for this item; values vary with purity and are not provided here. Consult CoA/Spec Sheet or primary literature for exact measurements.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes (general):
As a tertiary amine, it may absorb CO2/H2O from air; handling under dry conditions helps maintain material quality.
Formation of crystalline salts (e.g., HCl, p-TsOH) can facilitate handling, purification, or analytical characterization when needed.
Quality & Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
When provided, organic intermediate grades (e.g., 95%, 97%, 98%) indicate assay by qNMR, GC, or HPLC. For cross-coupling chemistry, higher assay and low halide impurities can improve reproducibility and yields.
Stabilizers: None specified for this item. Tertiary aryl amines generally do not require inhibitors; however, storage under inert atmosphere and dry conditions can help preserve purity by limiting moisture/CO2 uptake and oxidative discoloration.
Trace analysis: If your application is catalyst-sensitive (e.g., ppm-level Pd in subsequent steps), request ICP-MS data for residual metals or halides. Not specified for this item; refer to CoA/Spec Sheet.
Documentation: Aladdin provides a Certificate of Analysis (CoA) batch-by-batch. Use the CoA to confirm assay, identification (NMR/GC/MS), residual solvents, and water (if reported) for your received lot.
Suitability notes:
For medicinal chemistry: verify assay, identity (1H/13C NMR), and ensure minimal aromatic impurities prior to SAR studies.
For scale-up: request stability profile, mass balance closure, and impurity characterization; ensure the chosen grade meets your process specifications.
Reaction & Applications
As an ortho-brominated N-aryl piperidine, 1-(2-bromophenyl)piperidine functions as a versatile aryl bromide electrophile and tertiary amine scaffold. Typical research and process applications (literature):
Cross-coupling at the aryl bromide:
Suzuki–Miyaura: installation of diverse (hetero)aryl fragments via Pd catalysis with boronic acids/esters; ortho substitution can sometimes require elevated temperature or bulky ligands (e.g., SPhos, XPhos).
Buchwald–Hartwig C–N coupling: introduction of anilide/diarylamine motifs; the pre-existing tertiary amine is not usually the coupling partner but can be tolerated under optimized conditions.
Sonogashira: coupling with terminal alkynes to introduce ethynyl substituents, enabling further transformations (hydrogenation, cycloadditions).
Negishi/Kumada/Stille: where compatible organozinc, Grignard, or stannane partners are available.
Directed ortho chemistry and metalation:
Lithium–halogen exchange (n-BuLi, t-BuLi) at low temperature can generate the corresponding aryllithium for trapping with electrophiles (formylation, carboxylation, intramolecular cyclization). Use strictly anhydrous conditions and cryogenic control.
Electrophilic aromatic substitution on the ring is deactivated by bromine but activated by the anilino substituent; regiocontrol is influenced by the ortho bromo.
N-Functionalization of the piperidine:
Quaternization (e.g., MeI, MeOTf) to form quaternary ammonium salts.
Acylation to form amide salts, useful for purification or property tuning.
Medicinal chemistry scaffold: The piperidine–aniline motif is prevalent; the ortho-bromo handle accelerates library diversification via rapid couplings.
Practical tips:
Drying: If needed, dry over K2CO3 or molecular sieves; minimize air/moisture exposure.
Base sensitivity: Strong bases used in coupling (e.g., NaOtBu) are generally tolerated but can lead to minor N-dealkylation in harsh conditions—monitor by LC/MS.
Reaction Conditions
General literature guidance for typical transformations of aryl bromides like 1-(2-bromophenyl)piperidine (not product specifications):
Suzuki–Miyaura coupling:
Catalyst/ligand: Pd2(dba)3 (0.5–1 mol%) with SPhos/XPhos or Pd(PPh3)4 (1–3 mol%).
Base: K3PO4, K2CO3, or Cs2CO3 (2–3 equiv).
Solvent: dioxane/H2O, toluene/H2O, or 2-MeTHF/H2O.
Temperature/time: 60–100°C, 2–16 h. Ortho-bromo substrates may require the higher end of temperature or catalyst loading.
Buchwald–Hartwig amination (C–N coupling at the aryl bromide):
Catalyst/ligand: Pd2(dba)3/BrettPhos or Pd-PEPPSI precatalysts (0.5–2 mol%).
Base: NaOtBu, KOtBu, or K3PO4.
Solvent: toluene, dioxane, or t-AmOH.
Temperature: 80–110°C; monitor for possible competitive N-dearylation under harsh conditions.
Sonogashira coupling:
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) with CuI (2–5 mol%).
Solvent: MeCN or DCM; 0–25°C; monitor by LC/MS for clean conversion.
Yields are substrate- and condition-dependent; consult primary literature for optimization with ortho-brominated anilines.
Safety & Handling
Authoritative safety data: Not specified for this item in the product data. Always consult the product-specific SDS for GHS classification, hazard statements, and response measures.
General safety considerations for tertiary aryl amines and aryl bromides (informational, not a substitute for the SDS):
Likely hazards: may cause skin/eye irritation and respiratory tract irritation; harmful if swallowed; combustible liquid risk depending on flash point (literature for similar compounds). No GHS classification provided here—defer to SDS.
Personal protective equipment (PPE): lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a functioning chemical fume hood.
Handling practices:
Avoid inhalation of vapors/aerosols; minimize skin contact.
Keep containers tightly closed; minimize exposure to air/moisture to prevent amine carbonation.
Ground/bond containers if transferring flammable liquids; eliminate ignition sources if solvent is present.
Incompatibilities: strong oxidizers; strong acids/bases (will form salts with acids); reactive halide chemistry may occur under metalation/coupling conditions—store away from reactive metals/reducing agents.
First aid (overview):
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention as needed.
Inhalation: move to fresh air; monitor breathing; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire response: use CO2, dry chemical, or foam; cool containers with water spray. Consult SDS for flash point and specific firefighting advice.
Regulatory/labeling in this listing:
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
Solvent Selection
This product is a nitrogen-containing aryl bromide/tertiary amine building block rather than a process solvent. Solvent choice pertains to its use in synthesis, purification, and analysis.
General solvent compatibility (literature):
Miscibility: expected to dissolve well in polar aprotic solvents (DMF, DMAc, DMSO, NMP), moderately polar ethers (THF, 2-MeTHF), halogenated solvents (DCM, chloroform), esters (EtOAc), and aromatics (toluene). Limited solubility in water as the free base; water solubility increases upon protonation (e.g., as HCl salt).
Dielectric/polarity considerations:
Cross-coupling (Suzuki, Buchwald–Hartwig, Sonogashira): DMF, dioxane, toluene, or mixed aqueous-organic systems (e.g., dioxane/H2O) are commonly used to solubilize aryl bromides and bases.
Metal–halogen exchange/lithiation: anhydrous ethers (THF, MTBE) or hydrocarbons (hexanes/toluene) at low temperature are typical.
Alkylation/acylation at nitrogen (to form quaternary or amide derivatives): acetonitrile, DCM, or THF with non-nucleophilic bases (e.g., DIPEA) are often suitable.
Purification and workup tips:
The tertiary amine can tail on silica; pre-treat silica with 1–2% triethylamine or use basic alumina. Alternatively, convert to its salt for crystallization, then basify to recover the free base.
For LC analysis, mobile phases with 0.1% amine modifiers (e.g., Et3N) can improve peak shape on silica-based columns.
Selection guidance:
Choose higher boiling polar aprotics (DMF/DMSO) for challenging couplings; choose ethers/aromatics for low-temperature organometallic steps. Consider greener alternatives (e.g., 2-MeTHF, CPME) where feasible; see Green Alternatives tab.
Storage & Reconstitution
Storage conditions (item-specific): Store at 2–8°C (as provided in product data). Protect from light and moisture. Keep container tightly closed.
Shipping: Shipped on wet ice (as provided in product data).
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution: Not applicable for neat liquids/solids. If supplied as a solid or viscous oil, dissolve the required amount in a suitable anhydrous solvent (e.g., DCM, THF, MeCN, DMF) immediately before use.
Inert atmosphere: For long-term storage or if repeated openings are expected, consider storing under nitrogen/argon to minimize oxidative discoloration and uptake of CO2/H2O by the amine.
Freeze–thaw: Avoid repetitive freeze–thaw of solutions; prepare single-use aliquots in dry solvent if solution storage is necessary. Store solutions at low temperature (e.g., −20°C) and use within a short timeframe based on stability studies.
Stability: Item-specific stability data are not provided; refer to CoA/Spec Sheet. As a general rule for tertiary aryl amines, avoid strong light, oxidants, and prolonged exposure to air/humidity.
Research use note: For research use only.
Structure & Identity
Brief description: 1-(2-Bromophenyl)piperidine is an N-aryl piperidine bearing an ortho-bromine on the phenyl ring; it is a tertiary amine and an aryl bromide handle for cross-coupling.
SKU: B167586
Product name: 1-(2-Bromophenyl)piperidine
CAS: 156808-79-6
PubChem CID: 13231828 (literature)
InChIKey: 362710 (as provided in product data); full InChIKey not specified for this item; refer to CoA/Spec Sheet.
SMILES: Brc1ccccc1N2CCCCC2 (literature)
Molecular formula: C11H14BrN (literature)
Molecular weight: ~240.15 g/mol (literature, calculated from formula)
Structural features (general description):
Core ring systems: a six-membered aromatic phenyl ring and a six-membered saturated piperidine ring.
Functional groups: tertiary amine (piperidine nitrogen) directly bonded to an aryl ring (anilino motif); aryl bromide at the ortho position relative to the N–aryl bond.
Regiochemistry: bromine at 2-position of the phenyl ring (o-bromo) with the piperidinyl substituent at position 1.
Stereochemistry: achiral as drawn; no stereocenters.
2D description: a brominated benzene ring (bromine ortho to the anilino linkage) connected through the ring carbon to the nitrogen of a chair-like piperidine (–N–(CH2)5–) tertiary amine.
Synthetic Utility
Key reactivity features enabling synthesis (literature):
Aryl bromide electrophile: The ortho-bromine enables Pd- or Ni-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira) to install diverse functionalities. Ortho substitution may benefit from bulky/electron-rich ligands (SPhos, XPhos, BrettPhos) to overcome steric hindrance.
Tertiary amine: The piperidine nitrogen offers orthogonal chemistry—quaternization, N-oxide formation (with m-CPBA), or acylation—to tune electronics/sterics during multistep sequences. Temporary conversion to the ammonium salt can assist phase behavior and purification.
Directed metalation via halogen–lithium exchange: o-Bromo anilines can be converted to aryllithiums at −78 to −40°C in THF/Et2O, enabling addition to electrophiles (CO2, DMF, aldehydes) or intramolecular cyclizations if tethers are present.
Retrosynthetic value: The molecule can arise from N-arylation of piperidine with 2-bromofluorobenzene (SNAr) or via Buchwald–Hartwig coupling of piperidine with 2-bromoiodobenzene derivatives, followed by halogen editing. Alternatively, N-arylation of piperidine with 2-bromobromobenzene analogs under Ullmann-type conditions (Cu catalysts) is feasible.
Practical considerations:
Protecting-group strategy: Although tertiary, the amine can be transiently protonated or oxidized (N-oxide) to alter directing effects or solubility.
Catalyst poisons: Free amines may coordinate to Pd/Ni; additive bases or catalyst/ligand choices mitigate inhibition.
Analytics: 1H NMR typically shows aromatic multiplets (o-bromo shifts downfield) and characteristic piperidine methylene patterns; HRMS confirms [M+H]+ around m/z 241/243 with the bromine isotopic pair (literature).
Target Specificity
Not applicable. This product is a small-molecule chemical intermediate, not a biological affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
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