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
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
155.240 g/mol
XLogP3
1.100
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
155.131 Da
Monoisotopic Mass
155.131 Da
Topological Polar Surface Area
21.300 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
123.000
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
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Application Protocols
No standardized bioassay or diagnostic application protocols apply to this chemical building block. For synthetic applications, consider the general procedures outlined under Reaction Conditions and Synthetic Utility.
If employing in parallel synthesis or library production
Establish stock solutions (free base in dry DMSO/MeCN) under inert atmosphere.
Validate stoichiometry by titration or qNMR to account for any salt content or adventitious water.
Use acid/base switching and antisolvent addition to streamline isolations (e.g., form HCl salts for crystallization, then liberate free base as needed).
Biological Roles
No intrinsic biological role is assigned to 3-cyclobutoxypiperidine; it is a synthetic small molecule used as a research building block. The following notes provide general context for related motifs (literature/general):
Piperidine motif in biochemistry/medchem
Piperidine rings are common in natural products and pharmaceuticals, functioning as basic, protonatable centers that influence solubility and target engagement via ionic and H-bonding interactions.
Substitution at C3 modulates pKa, lipophilicity, and conformational preferences, which can adjust permeability and metabolic stability.
Ether and cycloalkyl features
Alkyl ethers often improve solubility and attenuate basicity through inductive effects; they are generally metabolically stable but can undergo oxidative O-dealkylation in vivo (general observation for ethers).
Cyclobutyl groups can impart “escape from flatland,” potentially improving 3D shape and reducing aromatic content in lead series (a medicinal chemistry design principle).
Research use restriction
As stated in Product Data: For research use only. Not intended for human or veterinary use, diagnostic procedures, or therapeutic applications.
Practical implication
When incorporated into screening libraries or SAR series, properties such as cation pKa, clogP, and polar surface area should be measured or predicted to ensure the desired ADME profile; however, no biological activity is claimed or implied for this specific compound.
Buffer Applications
3-Cyclobutoxypiperidine is not a standard buffering agent and is not commonly used to formulate biochemical buffers.
Applicability
While secondary amines can accept protons, this compound is typically employed as a synthetic intermediate rather than a buffer component. Dedicated buffer systems (e.g., phosphate, HEPES, Tris, MOPS) are recommended for pH control.
Guidance
If a temporary pH adjustment is required during a reaction or workup, use conventional acid/base additives (e.g., aq. HCl, NaHCO3) rather than relying on this compound’s intrinsic basicity.
For robust buffer recipes and pH ranges, consult standard buffering agents; this section is not typically applicable to this product.
Green Alternatives
While the compound itself is a target building block, greener choices are often possible in the processes where it is used.
Greener solvent selection (general guidance)
Replace DCM with EtOAc or Me-THF when acylations are sufficiently reactive; workups are simplified and EHS footprint is reduced.
Substitute DMF/NMP with acetonitrile, 2-MeTHF, CPME, or propylene carbonate where solubility and coupling kinetics permit.
Favor alcohols (EtOH, i-PrOH) for reductive aminations with NaBH(OAc)3; water-tolerant protocols can reduce solvent load.
Energy and waste reduction
Use catalytic coupling systems (Pd–biaryl phosphines for C–N coupling) at lower loadings and higher turnover numbers to minimize metal waste.
Employ micellar aqueous media (TPGS-750-M or similar) for certain amide formations or alkylations to reduce organic solvent usage.
Comparison snapshot (process choices)
THF vs 2-MeTHF: similar performance; 2-MeTHF offers bio-based sourcing, higher boiling point (fewer losses), and easier separations.
DCM vs EtOAc: DCM excels in rate and substrate scope; EtOAc is biodegradable, lower toxicity, and supports streamlined extractions.
Tradeoffs
Greener solvents can impact solubility or reactivity; small-scale scouting (DoE) is recommended to validate conversion, selectivity, and crystallization behavior for salt forms of 3-cyclobutoxypiperidine derivatives.
Pharmaceutical Uses
This product is supplied for research use only. It is not an excipient and is not intended for clinical or therapeutic use. The following notes refer to typical roles of similar compounds in pharmaceutical R&D (no medical claims):
Role in development pipelines (general)
Commonly used as a building block/intermediate during medicinal chemistry campaigns to access amides, ureas, sulfonamides, and N-alkylated analogs.
Facilitates structure–property tuning by introducing a basic center (piperidine) and a compact lipophilic ether moiety (cyclobutoxy).
Salt formation and handling (general)
Drug-like candidates derived from this scaffold may be isolated as salts (e.g., HCl, mesylate, fumarate) to improve crystallinity, hygroscopicity, and dissolution rate.
Regulatory notes
No pharmacopeial monograph is associated with 3-cyclobutoxypiperidine. Any GMP or regulatory use would require bespoke specification setting, impurity profiling (including nitrosamines risk assessment), and validated analytical methods.
Manufacturing considerations
For scale-up, attention to residual solvents, metals (from Pd-catalyzed couplings), and salt stoichiometry is recommended; however, such specifications are process- and program-specific and are not provided for this catalog item.
Physical Properties
Item-specific numeric specifications (bp, mp, density, refractive index, UV cutoff, assay) are not provided in the Product Data for SKU C1283024.
Item-specific values
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
State: Typically a low-melting solid or colorless to pale liquid for small N-alkyl/alkoxy piperidines of this size.
Basicity: Secondary piperidines exhibit conjugate-acid pKaH around ~10.5–11.5 (literature, piperidine analogs). Substitution at C3 with an ether is not expected to abolish basicity.
Solubility profile: Expected to be miscible with many organic solvents (EtOAc, DCM, MeCN, alcohols, THF). Water solubility is moderate as the free base; high as protonated salts (e.g., HCl salt).
Volatility: Lower than piperidine; still amenable to removal by high-vacuum or short-path distillation if liquid.
Partitioning: Ether substitution increases lipophilicity vs parent piperidine (qualitative).
Practical notes (general)
Free bases of amines can absorb CO2/H2O from air; measured mass and concentration may drift upon prolonged exposure to humid air. For analytical work, prepare a defined salt or standardize by acidimetric titration.
Quality and Grades
The Product Data for SKU C1283024 does not specify an assay value, grade designation, stabilizers, or impurity limits.
Item-specific 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.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance)
Research/technical grade: Suitable for most synthetic applications; typical GC/NMR purity ≥95%.
High-purity or screening grade: Tighter controls on residual solvents, water, and common inorganic/organic impurities; preferable for medicinal chemistry SAR and sensitive transformations.
HPLC grade (for solvents) or LC/MS grade (for analytes): Controlled UV background and low metal content—relevant when compound doubles as mobile phase modifier or analytical standard (usually not the case here).
What to check on the CoA for this item
Identity: 1H/13C NMR consistency with 3-substitution; HRMS within tolerance; optional IR (amine/ether bands).
Purity: GC or HPLC area %; residual solvents; Karl Fischer water (if applicable).
Form: Free base vs defined salt (e.g., HCl)—impacts solubility, assay by weight, and handling.
Batch-to-batch considerations (general)
Secondary amines can form trace nitrosamines if exposed to nitrosating agents; ensure manufacturing and storage minimize nitrite contamination. Verify nitrosamine testing if application context requires it.
Reaction and Applications
3-Cyclobutoxypiperidine is a versatile, saturated nitrogen heterocycle frequently used as a building block in discovery chemistry and fragment-to-lead campaigns.
Amide formation: Rapid acylation with acid chlorides/anhydrides; peptide-like couplings via HATU/HBTU/EDC in DMF/MeCN.
Carbamates/ureas: CDI, triphosgene, or chloroformates (Boc, Cbz) on the secondary amine; subsequent deprotection routes enable diversification.
Sulfonamides: Reaction with sulfonyl chlorides (e.g., TsCl, MsCl) in DCM or MeCN with base (Et3N, pyridine).
N-alkylation: Reductive amination with aldehydes/ketones (NaBH3CN/NaBH(OAc)3) or SN2 with primary halides (requires careful base selection to limit over-alkylation).
Cross-coupling as amine partner: Buchwald–Hartwig C–N coupling to aryl/vinyl halides/triflates using Pd/XPhos/BippyPhos/AdBrettPhos systems.
Oxidation/state edits: N-oxidation (mCPBA) to the amine N-oxide (useful in late-stage diversification); quaternization to ammonium salts.
Reactivity notes
Secondary amine remains nucleophilic/basic; proximal ether is typically inert under mild conditions but can be cleaved by strong Lewis acids (e.g., BBr3/AlCl3) or under harsh protic acid at elevated temperatures.
The cyclobutane ring introduces subtle conformational and lipophilicity effects valued in medicinal chemistry for tuning pKa, solubility, and metabolic stability.
Application domains (general)
Lead optimization: incorporation into scaffolds to modulate basicity and 3D shape.
Linker chemistry: amide, urea, and sulfonamide linkages to heteroaryl warheads.
Salt screening: formation of pharmaceutically acceptable salts (e.g., HCl, fumarate) to improve handling and crystallinity.
Reaction Conditions
The following conditions are general, literature-style guidance for typical transformations of secondary piperidines; they are not specifications for this item.
Amide bond formation
Solvent: DMF, MeCN, or DCM; Base: i-Pr2NEt or NMM; Couplers: HATU/HBTU/EDC–HOAt; Temp: 0–25 °C; Time: 0.5–4 h. Expect rapid conversion with activated acids.
Sulfonamide formation
Solvent: DCM/MeCN; Base: Et3N or pyridine; Temp: 0–25 °C; Time: 1–3 h. Monitor for over-sulfonylation under excess reagent.
Reductive amination
Solvent: MeOH/EtOH/MeCN; Additives: AcOH (cat.) with NaBH3CN or NaBH(OAc)3; Temp: 0–25 °C; Time: 2–16 h. Control pH ~5–6 for selectivity.
N-alkylation (SN2)
Solvent: DMF/MeCN; Base: K2CO3/Cs2CO3; Alkyl halide: 1.1–1.5 eq; Temp: 25–60 °C; Time: 4–18 h. Beware dialkylation; use excess amine or phase-transfer conditions to moderate.
Buchwald–Hartwig amination (as amine partner)
Catalyst: Pd2(dba)3 (1–2 mol%) with XPhos/BrettPhos (2–4 mol%); Base: NaOtBu or Cs2CO3; Solvent: toluene/dioxane/2-MeTHF; Temp: 80–110 °C; Time: 6–18 h.
Protection/deprotection
Boc protection: (Boc)2O, base (NaHCO3/Et3N) in DCM/THF at 0–25 °C.
Boc removal: TFA/DCM (1:1 to 1:4), 0–25 °C, 0.5–2 h; isolate as TFA salt or basify and re-extract.
Notes on the ether moiety
The cyclobutoxy group is robust to bases and typical coupling reagents but can be cleaved by BBr3 or strong protic acids at elevated temperature; avoid such conditions if retention is required.
Safety and Handling
Always consult the product’s SDS for authoritative hazard information. The Product Data for SKU C1283024 does not list specific GHS classifications for this item.
Item-specific hazard fields
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.
General hazards typical for aliphatic amines (literature/analog-based)
May be harmful if swallowed, inhaled, or in contact with skin; causes irritation to skin, eyes, and respiratory tract. Amines can display strong odors and may be sensitizers in some individuals.
Free-base amines are often corrosive to certain plastics and paints; they can attack copper alloys. Avoid contact with acid chlorides/anhydrides (vigorous reactions) unless intentionally used in synthesis.
Handling recommendations (general best practice)
Use in a fume hood. Wear appropriate PPE: lab coat, safety glasses, and nitrile gloves; consider splash protection when charging bulk quantities.
Avoid breathing vapors/mists; keep containers tightly closed to minimize uptake of CO2 and moisture.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye: Rinse with water for several minutes; remove contaminated clothing; seek medical advice for persistent irritation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Solvent Selection
As a secondary amine with an ether substituent, 3-cyclobutoxypiperidine dissolves readily in many organic media. Solvent choice should balance nucleophilicity/basicity control, coupling efficiency, and ease of workup.
Polarity and miscibility (general expectations)
Polar aprotic solvents (DMF, DMAc, NMP, MeCN, DMSO) effectively solvate the amine and are preferred for amide couplings and SNAr.
Ethers (THF, 2-MeTHF, MTBE) offer good solubility and facilitate low-temperature operations, bases, and organometallic steps.
Chlorinated solvents (DCM, DCE) support rapid acylations and carbamoylations with convenient extractions.
Alcohols (MeOH, EtOH, i-PrOH) are useful for salt handling and reductive aminations with NaBH3CN/NaBH(OAc)3.
Water: limited solubility as free base; excellent as protonated salts.
When to choose vs alternatives
Choose MeCN or DCM for fast acylations with acid chlorides/anhydrides; THF or DMF for carbodiimide/HATU couplings.
For Buchwald–Hartwig couplings (aryl halides to amine), toluene, dioxane, or CPME/2-MeTHF often provide robust performance with strong bases at 60–110 °C.
Small comparison (general)
THF vs 2-MeTHF: similar solubility; 2-MeTHF is more hydrophobic and greener, aiding phase splits.
DCM vs EtOAc: DCM speeds acylation; EtOAc is greener and often sufficient for less reactive partners.
Practical tips
Dry aprotic solvents minimize salt formation and maximize nucleophilicity.
If working up as a salt, include an antisolvent step (MTBE/Et2O) to crystallize the amine hydrochloride or tosylate.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Storage conditions: Room temperature.
Shipped in: Normal.
General storage guidance for secondary amines (best practice)
Keep tightly closed in a dry, inert atmosphere if possible to limit CO2/H2O uptake and amine carbonation. Use PTFE-lined caps.
Store away from strong oxidizers, acids, and acylating/alkylating agents. Segregate from food and incompatible chemicals.
For long-term storage, consider converting to a crystalline salt (e.g., HCl) to enhance stability and ease of handling; regenerate the free base prior to use.
Reconstitution and preparation
If provided as a solid or viscous oil, warm gently to ambient and sonicate as needed. Prepare stock solutions in dry solvents (DCM, THF, MeCN, DMF) under nitrogen/argon.
For aqueous work, dissolve as the protonated salt by adding a stoichiometric acid (e.g., HCl in Et2O/IPA), or pre-form the salt and then dissolve in water/alcohol mixtures.
Avoid repeated freeze–thaw cycles of stock solutions; aliquot and store at 2–8 °C (solvent-dependent) if extended use is anticipated.
Appearance and purity checks
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Verify identity/purity by NMR/LC–MS before critical experiments, especially after extended storage.
Structure and Identity
A conformationally flexible, saturated heterocycle bearing a small-ring ether: 3-cyclobutoxypiperidine features a secondary piperidine nitrogen and an O-linked cyclobutyl substituent at the 3-position.
Item identifiers (from Product Data)
SKU: C1283024
Product name: 3-Cyclobutoxypiperidine
CAS: 1250347-74-0
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (not item-specific)
A six-membered piperidine ring with the ring nitrogen at position 1; at carbon-3, an ether oxygen projects to an attached cyclobutyl ring. No stereochemistry is implied by the name; materials may be racemic at C3 if formed via non-stereospecific routes.
Notes on identity and isomerism (general)
Positional isomers (e.g., 2- or 4-cyclobutoxypiperidine) exist but are distinct compounds.
Salts (e.g., HCl, TsOH) may be prepared for handling; this listing refers to the free base unless otherwise indicated.
Synthetic Utility
3-Cyclobutoxypiperidine offers a basic nitrogen center and an adjacent ether substituent, enabling diverse derivatizations while providing favorable 3D topology.
Functional group handles
Secondary amine: readily converted to amides, carbamates, ureas, sulfonamides; amenable to reductive amination and N-alkylation/quaternization.
Ether-linked cyclobutyl: typically inert under standard coupling conditions, serving as a lipophilic, compact substituent that can modulate sterics without aromaticity.
Strategic value in retrosynthesis (general)
Late-stage amine installation: Coupling the free base with aryl/vinyl electrophiles (Buchwald–Hartwig) or via amide bond formation to introduce the piperidine motif proximal to the target pharmacophore.
Protection/deprotection flexibility: Transient protection as Boc, Cbz, or Fmoc allows orthogonal manipulations; C3 substitution remains stable through many protection cycles.
Scaffold diversification
N-alkyl series: libraries accessible by aldehyde/ketone reductive amination.
Acyl/sulfonyl series: rapid parallel synthesis via HATU/EDC (amides) or TsCl/MsCl (sulfonamides).
N-oxide series: oxidative tuning of polarity and H-bonding using mCPBA, with potential for downstream rearrangements.
Compatibility
Generally tolerant of bases (i-Pr2NEt, Cs2CO3), nucleophiles, and many transition-metal catalysts. Avoid strong Lewis acid conditions if the ether must be preserved.
Purification/workup tips
Switch between free base and salt forms to control extraction and crystallization. Silica chromatography often benefits from addition of 1–2% Et3N to prevent tailing of basic compounds.
Target Specificity
Not applicable. 3-Cyclobutoxypiperidine is a small-molecule chemical building block, not a biological reagent with defined target specificity (e.g., antibody/ligand). No antigen, epitope, or species reactivity information applies.
Foire aux questions
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 1250347-74-0, the molecular formula is C9H17NO, and the molecular weight is 155.24 g/mol. InChIKey RRFVKQKMIXFRNL-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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