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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
171.280 g/mol
XLogP3
1.700
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Exact Mass
171.162 Da
Monoisotopic Mass
171.162 Da
Topological Polar Surface Area
21.300 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
108.000
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
1
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Recensioni
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Application Protocols
No antibody/biological assay protocols are applicable to this small-molecule building block.
General synthetic handling protocol (for reference; not a product test):
Inspect container; if crystallized or viscous, gently warm to room temperature and vortex/sonicate to homogenize.
For reactions, dry over molecular sieves or distill bases/solvents; the amine itself can be used as received unless water-sensitive chemistry is planned.
For chromatography, pre-treat silica with 1% Et3N in eluent or use basic alumina to minimize tailing.
For bioassay usage or target testing, develop assay-specific protocols independently; none are provided or validated for this item.
Biological Roles
Item-specific biological/biochemical roles are not established; this product is supplied for research use only.
General context (literature) for structural class:
Piperidine is a prevalent motif in natural products and bioactive small molecules. Its secondary amine is typically protonated at physiological pH (pKaH ~11), enhancing aqueous solubility of drug-like molecules.
Installation of an aliphatic ether (isobutoxymethyl) at C4 modulates lipophilicity and can influence membrane permeability and metabolic soft spots (e.g., potential O-dealkylation by oxidative enzymes in biological systems). These are general ADME considerations rather than established properties of this specific compound.
As a stand-alone small molecule, 4-[(2-methylpropoxy)methyl]piperidine has no known endogenous role. It may serve as an intermediate or fragment in the synthesis of ligands for receptors, transporters, or enzymes where piperidine nitrogen participates in ionic or H-bond interactions.
Important: No claims of biological activity, efficacy, or clinical use are made or implied for this item. Any use in assays or target screening should be accompanied by appropriate controls, and the compound should be handled under institutional chemical safety protocols.
Buffer Applications
This compound is not a dedicated buffering agent. While secondary amines are basic and can accept protons, 4-[(2-methylpropoxy)methyl]piperidine is not typically employed to prepare defined buffer systems in biochemical workflows.
If a protonated form (e.g., hydrochloride salt) is generated, it may temporarily contribute to solution pH, but it lacks the conjugate-acid/conjugate-base pair properties and pKa alignment required for robust buffering capacity near physiological pH.
For buffer preparation, select established systems (HEPES, MOPS, phosphate, Tris) with known pKa values and recipes. Use this compound instead as a synthetic building block where its basicity is a reactivity handle, not a buffering feature.
Green Alternatives
Because this product is a building block rather than a solvent, “green alternatives” focus on greener process choices when using it, not on replacing the molecule itself.
Greener solvent choices for common transformations (general guidance):
Replace dichloromethane with 2-MeTHF, CPME, or EtOAc for acylations/couplings when feasible; control temperature to manage exotherms.
Favor ethanol, isopropanol, or MeOH (with caution for transesterification) as media for reductive amination, minimizing chlorinated and dipolar aprotic solvents.
For SN2 alkylations, consider propylene carbonate or Cyrene as safer dipolar aprotics where compatible.
Comparison (typical trade-offs):
2-MeTHF vs THF: 2-MeTHF offers higher hydrophobicity and partial immiscibility with water aiding workup; both support organometallics. THF is more established and broadly miscible.
EtOAc vs DCM: EtOAc is biodegradable and less toxic but has higher boiling point and can participate in transesterification under strong base.
MeOH/EtOH vs MeCN: Alcohols are greener but can reduce rates/selectivity in some condensations and may react with acylating agents.
Process intensification and waste minimization:
Use catalytic rather than stoichiometric coupling activators where possible (e.g., CDI or green peptide-coupling reagents over acid chlorides).
Implement in-line salt formation (e.g., isolating as an HCl salt) to reduce solvent use from chromatography.
Recycle amine-containing mother liquors by back-extraction (acid/base) to recover unreacted starting material.
Note: No item-specific “green grade” or stabilizers are specified for this product.
Pharmaceutical Uses
No pharmacopeial monograph or excipient status is specified for this item; it is offered for research use only.
General formulation/manufacturing context (literature/good practice):
Role as an intermediate: 4-[(2-methylpropoxy)methyl]piperidine can be incorporated into APIs or lead compounds during medicinal chemistry campaigns to modulate physicochemical properties (basicity, solubility, lipophilicity) of target molecules.
Salt formation for handling: If conversion to a crystalline salt (e.g., HCl, fumarate, besylate) is desired for isolation or purification, standard salt-screening can be performed. Selection depends on downstream synthetic steps and target solid-state properties.
Impurity profiling: Secondary amines warrant nitrosamine risk assessment during process development. Control nitrite sources, use low-nitrite acids, and define hold times/temperatures to minimize nitrosation risk.
Residuals and quality: If used as an intermediate in GMP settings, establish specifications for identity (NMR/IR/HRMS), assay, related substances, residual solvents (per ICH Q3C), water content, and, where applicable, chiral purity (not expected here).
Note: No medical or therapeutic claims are made. Any incorporation into clinical supply chains requires appropriate regulatory assessment and GMP controls.
Physical Properties
Item-specific specifications (this lot/product):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
Other analytical limits (water, metals, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed properties for the named structure (reference only; not product specs):
Approximate molecular formula: C9H19NO (see Structure & Identity).
Approximate molecular weight: ~157.26 g/mol.
Basicity: conjugate acid pKaH for piperidine ~11.2; a 4-(alkoxymethyl) substituent is not expected to significantly alter basicity (literature trend for 4-substituted piperidines).
Polarity/partitioning: secondary amine base; neutral form expected to be moderately lipophilic, protonated form water-soluble (qualitative, literature behavior of alicyclic amines).
Physical state: Many low-MW substituted piperidines are liquids near ambient temperature; exact MP/BP for this specific compound were not located in standard references and are not specified for this item.
Solubility (qualitative, literature expectations):
Miscible with many organic solvents (DCM, THF, EtOAc, MeOH, toluene).
Forms water-soluble salts with mineral/organic acids (e.g., HCl, TsOH).
Note: Do not treat literature/computed values as product specifications. Always consult the CoA/Spec Sheet for certified properties of SKU M998534.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvents, and chromatographic purity.
Context for common grades (general guidance):
Research/technical grade: Suitable for synthetic research workflows. Typical QC includes identity confirmation (NMR/GC–MS/LC–MS) and purity by GC/LC.
HPLC grade/UV-cut specifications: Tailored for low background in chromatographic detection; not applicable here unless explicitly stated.
Stabilizers/inhibitors: None indicated for this item. If present in a particular lot, the CoA will describe stabilizer type and implications for downstream reactions.
What to check on receipt (practical tips):
Verify physical appearance against CoA; small color changes are generally acceptable for amines due to air exposure, but significant discoloration may indicate oxidation or contamination.
Confirm purity and identity in-house if your application is sensitive (e.g., medicinal chemistry SAR). Typical tools: 1H/13C NMR, HRMS, GC/LC purity, water by Karl Fischer if moisture-sensitive transformations are planned.
If salt form is desired for handling or crystallinity (e.g., HCl salt), verify whether the supplied material is free base or a salt. This listing appears to refer to the free base based on the name; however, the actual form is not specified for this item.
Reaction and Applications
Practical roles of 4-[(2-methylpropoxy)methyl]piperidine in synthesis (general, literature-based):
As a nucleophilic secondary amine:
Amide formation: Rapid acylation with acid chlorides/anhydrides to give N-acyl piperidines; use non-nucleophilic base (Et3N, DIPEA) in DCM/THF at 0–25 °C.
Urea/thiourea/carbamate formation: Reaction with isocyanates/isothiocyanates or chloroformates to modulate basicity and lipophilicity in medicinal chemistry.
Reductive amination: Condense with aldehydes/ketones (NaBH3CN, NaBH(OAc)3, or hydrogenation) to access tertiary amines with the 4-(isobutoxymethyl) handle retained.
Alkylation/quaternization: SN2 alkylation to tertiary amines in MeCN/DMF with mild base; exhaustive alkylation affords ammonium salts (phase-transfer agents or intermediates).
Leveraging the ether side chain:
The –CH2–O–iPr group is typically inert under many coupling conditions, offering a polarity/lipophilicity handle. Under strong acidic conditions (HI/HBr) or with specialized cleavage methods, aliphatic ethers can be deprotected, but this is not generally a mild handle.
The benzylic-like CH2 next to nitrogen (C4 of piperidine) is not present; substitution is on carbon, not nitrogen. Therefore, use N-protection (Boc, Cbz) as needed for selective C–N vs N–functionalization downstream.
Medicinal chemistry context: Piperidine cores are ubiquitous in screening libraries. The isobutoxymethyl at C4 tunes basicity and cLogP while offering a metabolically addressable ether.
Workup tips: Quench acylations with saturated bicarbonate; extract amine products into dilute HCl, wash organics, then basify to recover. For chromatography, add 0.5–1% Et3N to eluents to suppress tailing.
Reaction Conditions
General literature guidance for secondary amine transformations (illustrative; not product specifications):
N-Acylation (to amides):
Solvent: DCM or THF (anhydrous).
Reagents: Acid chloride (1.0–1.1 eq), DIPEA or Et3N (2.0–3.0 eq).
Temperature/time: 0 °C to rt, 0.5–4 h, monitor by TLC/LC-MS.
Workup: Quench with sat. NaHCO3; extract; wash with brine; dry; purify on basicized silica.
Reductive amination (to tertiary amines):
Solvent: MeOH, EtOH, or DCM/MeOH mixtures; alternatively, AcOH/MeCN for NaBH(OAc)3.
Conditions: Carbonyl (1.0 eq), amine (1.2–2.0 eq), NaBH3CN (1.2–1.5 eq) or NaBH(OAc)3 (1.5–2.0 eq); pH ~5–6 (AcOH) for NaBH3CN.
Temperature/time: 0–25 °C, 2–16 h.
N-Alkylation (SN2):
Solvent: MeCN or DMF.
Base: K2CO3 or Cs2CO3 (2–3 eq), or use alkyl halide in excess.
Temperature/time: 25–80 °C, 4–24 h; minimize over-alkylation if tertiary amine is the target; otherwise continue to quaternization intentionally.
Carbamate/urea formation:
With chloroformates or isocyanates in DCM/THF, 0–25 °C, base present (Et3N/DIPEA).
Salt formation (for isolation/handling):
Dissolve amine in EtOAc/IPA and gas with HCl or add HCl in dioxane to precipitation; filter and dry. Select acid to tune crystallinity (e.g., fumaric, maleic, p-TsOH).
Notes:
Maintain anhydrous conditions for moisture-sensitive couplings.
Additives: Catalytic DMAP can accelerate acylations (mind competing acylation of DMAP).
Yields and exact conditions depend on partners; optimize based on LC–MS/TLC feedback.
Safety and Handling
Item-specific hazard classification:
Signal word, H-statements, GHS class, pictograms: Not specified for this item; consult the product SDS for authoritative classification.
General safety considerations for secondary alicyclic amines and aliphatic ethers (literature/best practice):
Hazards: Basic, irritant to skin, eyes, and respiratory tract; strong odors possible. Secondary amines may form N-nitrosamines upon contact with nitrosating agents—avoid nitrite contamination in acidic media.
PPE: Use lab coat, nitrile gloves, splash goggles. Handle in a fume hood to avoid inhalation of vapors and to control odor.
Incompatibilities: Strong oxidizers, strong acids (may form salts; vigorous heat upon neutralization), acyl halides/anhydrides (reactive), and nitrosating agents. Avoid prolonged contact with air/CO2 if handling the free base; keep containers tightly closed to limit amine odor and carbonation.
Peroxide formation: Aliphatic ethers can form peroxides upon prolonged air/oxygen exposure; although the ether moiety is internal, good practice is to limit exposure to strong oxidants and UV. Do not distill to dryness.
First aid (overview; defer to SDS): Eye/skin contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Provide SDS to responders.
Spill response: Absorb with inert material (vermiculite), collect in suitable waste container. Neutralize residues with dilute acid if appropriate, then rinse.
Always defer to the official SDS for SKU M998534 for complete and current safety guidance.
Solvent Selection
This product is a basic, moderately polar organic base (secondary piperidine) with an aliphatic ether side chain. Solvent selection depends on the intended transformation and whether you use it as a nucleophile/base or as a substrate.
Polarity/miscibility (general behavior):
Neutral free base is soluble in most organic solvents: DCM, chloroform, THF, MeCN, DMF/DMAc, MeOH/EtOH, toluene/EtOAc.
Protonated form (e.g., HCl salt) is water-soluble; the free base has limited water solubility but can be extracted into aqueous mineral acid.
Acid–base handling: For reactions requiring an anhydrous nucleophile, work in aprotic solvents (THF, toluene, DCM, MeCN) under dry conditions; for salt formation or quenching, use alcohols or water with controlled acid addition.
Chromatography: Amines tail on silica; consider adding 0.1–1% Et3N or NH4OH to eluents (hexanes/EtOAc or DCM/MeOH) to sharpen bands. Alternatively, use basic alumina or pre-neutralized silica.
Comparison (general):
THF vs DCM: THF better for metalations and reductive aminations; DCM preferred for acylations with acid chlorides at low temperature.
MeCN: good for SN2 alkylations and quaternization reactions; higher dielectric constant aids in dissolving salts.
Alcohols: useful for salt metathesis or as protic media in reductive amination (NaBH3CN/AcOH/MeOH systems), but may compete in acylations.
Choose solvent to balance nucleophilicity of the amine, solubility of partners, and downstream workup/greenness.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Best practices for amine ethers (general guidance):
Atmosphere: Keep container tightly sealed to minimize amine odor and absorption of CO2 or moisture. Inert gas blanket (N2/Ar) is optional for long-term storage.
Light/oxidation: Store away from strong oxidizers and direct light. While aliphatic ethers are relatively stable, prolonged exposure to air/UV can lead to slow degradation.
Compatibility: Avoid contact with acids (may form salts) and acylating agents during storage.
Reconstitution/handling:
Physical form is not specified. If supplied as a neat liquid or viscous oil, use directly. If a solid or salt is provided, dissolve in an appropriate solvent (e.g., DCM, THF, MeOH) or water for salt forms. Warm gently (≤40 °C) and sonicate if needed to aid dissolution.
Avoid repeated freeze–thaw cycling; not required for room-temperature storage materials. For long-term archiving, aliquot to minimize headspace and opening frequency.
Always consult the lot-specific CoA/SDS for definitive storage and handling instructions. Research use only.
Structure and Identity
Brief overview: 4-[(2-Methylpropoxy)methyl]piperidine is a secondary alicyclic amine bearing a pendant alkoxymethyl substituent at the 4-position of piperidine. The ether is the 2-methylpropoxy (isobutoxy) group attached via a methylene linker.
Item-specific identifiers (from Product Data):
CAS: 883530-03-8
SKU: M998534
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 (general, for orientation):
Core ring system: saturated six-membered piperidine (C5–N ring), secondary amine at ring nitrogen (no N-alkyl substituent reported in name).
Substituent: at C4, a –CH2–O–CH(CH3)2 group (isobutoxy methyl). Functional groups present: secondary amine (basic), aliphatic ether (non-activated), aliphatic methylene spacer.
Stereochemistry: none specified; the described structure is achiral overall.
Typical molecular formula for the named structure: C9H19NO (literature/computed, for reference only).
Typical molecular weight for the named structure: ~157.26 g/mol (literature/computed, for reference only).
2D description in words: a chair-like piperidine ring with the nitrogen as a secondary amine; at the para (4-) carbon relative to nitrogen, a methylene connects to an ether oxygen, which in turn bears an isopropyl-like 2-methylpropyl fragment (–O–CH(CH3)2).
Synthetic Utility
Functional group synopsis:
Secondary amine (piperidine): nucleophilic, basic; readily acylated, sulfonylated, alkylated, or engaged in reductive amination. Can be protected (Boc/Cbz/Fmoc) to control chemoselectivity.
Aliphatic ether (–CH2–O–iPr): generally inert under many conditions, serving as a lipophilic handle. Under forcing conditions (e.g., hydriodic/hydrobromic acid, elevated temperature), cleavage to alcohol/alkyl halide is possible but not typically synthetically leveraged.
Strategic uses:
Diversification node at nitrogen: Rapid generation of analog series by N-acyl, N-sulfonyl, and N-alkyl libraries for SAR. The C4 substituent remains intact, providing a constant lipophilicity modifier.
Quaternary ammonium formation: Alkylation to ammonium salts enables phase-transfer catalysis or further Hofmann elimination chemistry from quaternary precursors (substrate-dependent).
Coupling partner: As a nucleophile in amide couplings (via acid chlorides, activated esters, CDI-mediated), or in carbamate/urea formation with chloroformates/isocyanates.
Late-stage functionalization: Reductive amination onto complex carbonyl scaffolds to introduce the piperidine moiety while retaining the isobutoxy side chain.
Practical notes:
Use base additives (Et3N/DIPEA) judiciously; the substrate is itself basic. For acylations, 1.0–1.2 equiv amine with 1.0–1.1 equiv acylating agent often suffices.
For chromatography, add 0.1–1% Et3N or NH4OH to suppress tailing. Alternatively isolate as an acid salt and basify post-purification.
If selectivity issues arise, protect nitrogen (Boc) then functionalize elsewhere; deprotect under mild acid (TFA/DCM).
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.
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