Piperidine-3,5-diol - ≥95% , CAS No.1792-72-9

CAS: 1792-72-9 Cat. No.: P992497 Formula: C₅H₁₁NO₂ Peso molecolare: 117.150

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1C(CNCC1O)O
• IUPAC Name: piperidine-3,5-diol
• InChIKey: QCQKTGJRAPFKRX-UHFFFAOYSA-N
• INCHI: 1S/C5H11NO2/c7-4-1-5(8)3-6-2-4/h4-8H,1-3H2
• Peso molecolare: 117.150

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Piperidines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Piperidines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Piperidines
• Alternative Parents: Secondary alcohols 1,2-aminoalcohols Dialkylamines Azacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Piperidine - Secondary alcohol - 1,2-aminoalcohol - Azacycle - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Amine - Alcohol - Aliphatic heteromonocyclic compound
• Descrizione: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 117.150 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 117.079 Da
• Monoisotopic Mass: 117.079 Da
• Topological Polar Surface Area: 52.500 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 68.800
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No specific biological assay protocols are provided for this small-molecule building block. It is intended for research and synthetic use. For general handling:

• Prepare stock solutions in DMSO, water (as an acid salt), MeOH, or EtOH as compatible with your assay or reaction (verify solubility empirically).
• Filter solutions (0.22–0.45 µm) for analytical or biological studies.
• For stereochemical studies, consider pre-separation of cis/trans or enantiomers by chromatography or crystallization.

Assay-specific parameters (WB, IHC, IF, FC) and recommended dilutions are not applicable to this chemical.

Biological Roles

No specific biological role is assigned to Piperidine-3,5-diol itself in standard metabolic pathways (not a canonical metabolite; literature note). However, the piperidine scaffold is ubiquitous in natural products and bioactive small molecules, and 3,5-disubstitution patterns are common in alkaloid frameworks.

• The presence of a basic nitrogen (secondary amine) and two hydrogen-bond-donating –OH groups creates a polyfunctional pharmacophore that can engage in ionic and H-bond interactions with biomacromolecules (general medicinal chemistry principle).
• As a synthetic intermediate, it can serve to construct conformationally restricted ligands, where cis/trans relationship of the 3,5-diol stereocenters modulates 3D shape and binding vectors.
• Salt formation (e.g., hydrochloride) can improve aqueous solubility and may be leveraged in biochemical assay preparation (general note; not item-specific).

All statements above are general, literature-based context for the scaffold and not claims of biological activity for this product. For any biological testing, ensure appropriate controls and recognize the product is supplied for research use only.

Buffer Applications

Piperidine-3,5-diol is not a standard biological buffer. While secondary amines can, in principle, provide buffering capacity near the pKa of their conjugate acids, this compound is typically used as a synthetic building block, not as a dedicated buffering agent.

• If used in biochemical contexts, it may be dissolved as an acid salt (e.g., HCl) to improve stability and solubility; pH will then be governed by the counterion and added buffer system.
• For reliable and reproducible pH control, employ established buffers (HEPES, phosphate, Tris) and treat Piperidine-3,5-diol as a solute, not a buffer component.

Buffer recipes, capacity ranges, ionic strengths, and compatibility are therefore not applicable to this item. Refer instead to the Solvent Selection and Storage tabs for practical handling guidance.

Green Alternatives

This product is a multifunctional building block, not a process solvent. Greener practice therefore focuses on synthetic choices surrounding its use (literature-based):

• Solvent selection: Prefer low-toxicity, biobased or recyclable solvents (e.g., 2-MeTHF, CPME, EtOAc, Me-THF/H2O biphasic systems) over chlorinated solvents when compatible with the reaction.
• Protection economy: Minimize protecting group steps; when necessary, choose benign deprotection strategies (e.g., carbonate protections removable under mild conditions). Avoid stoichiometric hazardous reagents.
• Catalysis: Use catalytic acylations (DMAP-catalyzed Steglich with benign solvents) and electrocatalytic/photocatalytic oxidations instead of Cr(VI) oxidants when converting –OH to carbonyls.
• Energy efficiency: Conduct reactions at ambient temperature where possible; exploit microwave or flow to reduce time/energy.

Illustrative comparison (general):

• DCM vs 2-MeTHF for Boc protection
  • DCM: excellent solubility, but chlorinated and less green.
  • 2-MeTHF: biorenewable, water-tolerant; often effective for Boc2O + base with careful control of water content.

Note: These are general green chemistry practices; optimize case-by-case for your specific transformation with Piperidine-3,5-diol.

Pharmaceutical Uses

There are no item-specific pharmacopeial listings or excipient roles provided. This material is supplied for research use only.

General formulation/manufacturing context (literature-based):

• Piperidine-3,5-diol is most relevant as a synthetic intermediate for the preparation of drug-like piperidine derivatives rather than as a formulated excipient.
• The amine can form salts (e.g., hydrochloride, mesylate) that may influence solubility/crystallinity during API intermediate processing and crystallization studies.
• The diol functionality enables prodrug-like derivatization (e.g., carbonate or ester masks) during medicinal chemistry campaigns (research stage).

No therapeutic or clinical claims are made. For GMP considerations, consult your quality system; any regulatory specifications, residual solvent limits, or elemental impurity controls are: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature rationale suggests a small-molecule mass consistent with a dihydroxy piperidine scaffold.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point / Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: Hydroxylated piperidines are often solids with moderately high melting points (literature generalization, not item-specific).
• Density / Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature expectation: good solubility in polar protic solvents (water, methanol, ethanol) and DMSO due to one secondary amine and two alcohol groups; reduced solubility in nonpolar hydrocarbons.
• pKa (conjugate acid of the amine): Not specified for this item; refer to CoA/Spec Sheet.
  • Literature note: hydroxyl substitution on a piperidine ring typically lowers basicity vs piperidine (pKaH ~11.2) by inductive effects.
• LogP / partitioning: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature expectation: low logP (increased polarity and H-bonding).

All numeric values not explicitly provided above should be verified against the item’s CoA/Spec Sheet. Do not use literature trends as specifications.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance for interpreting grades (general information for researchers):

• If supplied as research grade, expect suitability for synthetic and analytical R&D. Trace metal/UV specifications are typically not controlled unless stated.
• If provided as >95–98% purity (example ranges used in the field), this commonly refers to HPLC or GC area normalization; verify actual method on the CoA.
• For stereochemically complex materials (cis/trans, racemate/enantiomer): • Confirm whether the material is a mixture or an isomerically defined compound.
  • If chiral purity matters, request enantiomeric/diastereomeric ratio data.
• Stabilizers/inhibitors: None are listed for this item. If stability is a concern in your workflow, perform a small-scale pretest and consult our technical team for current stability/impurity profiles.

Item-specific specifications such as water content (KF), residual solvents, metals, and UV cutoffs are: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Piperidine-3,5-diol is a versatile bifunctional nucleophile (secondary amine + two alcohols) offering rich derivatization for medicinal and complex-molecule synthesis (literature/general chemistry):

• N-functionalization: • Acylation/carbamylation to amides/ureas/carbamates (e.g., Boc, Cbz, Fmoc protections).
  • Alkylation via reductive amination or SN2 on activated electrophiles.
  • N-oxide formation enabling Polonovski-type rearrangements or selective oxidations.
• O-functionalization: • Esterification (acid chlorides, anhydrides, Steglich conditions) and carbonate formation.
  • Silylation (TBDMS/TBS/TBDPS) to protect alcohols selectively; potential to exploit differential reactivity at C3 vs C5 (diastereotopic environment).
• Selective protection strategies: Orthogonal protection of N and one/both OH groups allows divergent synthesis of 3- or 5-monosubstituted derivatives; Mitsunobu can effect stereochemical inversion at a chosen center when applicable.
• Ring transformations: Oxidation of secondary alcohols to ketones (Dess–Martin, PCC) affords 3- or 5-keto piperidinones enabling enolate chemistry and further C–C bond formation.
• Cross-coupling handles: Conversion of –OH to triflates/mesylates permits subsequent SN2 substitutions or Pd-catalyzed couplings via amination/alkylation after displacement.
• Scaffold role: 3,5-disubstituted piperidines are prevalent motifs in alkaloids and drug leads; the diol provides a convergent entry to libraries via parallel N/O derivatizations.

Applications span medicinal chemistry hit elaboration, chiral ligand development (after resolution), and materials monomer design where H-bonding capacity is desired. For stereochemically defined outcomes, consider starting from or resolving cis/trans and enantiomeric forms.

Reaction Conditions

Typical conditions reported for transformations of amino-diols and hydroxylated piperidines (literature guidance; adjust to your substrate and verify experimentally):

• N-Boc protection: Boc2O (1.1–1.5 eq), base (Et3N or NaHCO3), solvent DCM, 2-MeTHF, or THF, 0–25 °C, 1–6 h. Monitor by TLC/LC-MS. Workup with aqueous wash; avoid overacylation of –OH by controlling base and temperature.
• O-silylation (TBS/TBDMS): TBSCl (1.1–2.2 eq per –OH), imidazole (2–4 eq), DMF or DCM, 0–25 °C, 2–16 h. For selective mono-protection, use sub-stoichiometric silyl chloride and temperature control.
• Esterification (Steglich): Carboxylic acid (1.2 eq), DCC/EDC (1.2–1.5 eq), catalytic DMAP (0.05–0.15 eq), DCM/EtOAc, 0–25 °C, 2–18 h. Filter urea byproducts; consider EDC·HCl in presence of water-tolerant solvents.
• Oxidation to ketone: Dess–Martin (1.3–2.0 eq) in DCM at 0–25 °C, 0.5–3 h; or PCC on silica in DCM. Quench and reduce residual oxidant; avoid overoxidation at nitrogen (protect N as Boc if necessary).
• Alcohol activation: MsCl or Tf2O (1.1–1.5 eq) with base (Et3N, 2,6-lutidine) in DCM at −20 to 0 °C for triflation; immediate use recommended to minimize elimination.
• Reductive amination (N-alkylation): Aldehyde/ketone (1.2 eq), NaBH(OAc)3 in DCE/MeCN or NaBH3CN in MeOH, 0–25 °C, 2–16 h. Control pH (~5–6 with AcOH) to balance imine formation and reduction rate.
• Mitsunobu inversion: DEAD/DIAD (1.2–1.5 eq), PPh3 (1.5–2.0 eq), nucleophile (e.g., benzoate) in THF/PhMe, 0–25 °C; protect N to avoid side reactions.

Expected yields for well-optimized steps are typically 60–90% depending on selectivity and isomer ratio (literature ranges). Always confirm with small-scale trials.

Safety and Handling

• GHS classification / Signal word / Hazard statements / Pictograms: Not specified for this item; refer to SDS for authoritative safety information.

General safety considerations for amino-diols (literature-based, non-item-specific):

• Irritation/sensitization: Amines and low-MW alcohols may cause skin/eye irritation. Avoid inhalation of dusts or aerosols.
• PPE: Use lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Employ local exhaust ventilation or fume hood when handling powders or during reactions that generate vapors/mists.
• First aid (overview): • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Handling: Hygroscopic tendency is possible for polyfunctional amines/alcohols. Keep containers tightly closed. Avoid contact with strong oxidizers and acylating agents unless intended for reaction.
• Incompatibilities (general): Strong oxidizers, acid chlorides/anhydrides (vigorous acylation), isocyanates (carbamate formation). Bases/acids may affect stability via salt formation or dehydration under forcing conditions.
• Spill/cleanup: Collect solids by sweeping with minimal dust generation; for solutions, absorb with inert material. Dispose according to institutional and local regulations.
• Fire safety: Although not highly volatile, organic solids are combustible. Use CO2, dry chemical, or foam. Thermal decomposition may release nitrogen oxides.

Always consult the product-specific SDS before use.

Solvent Selection

As a polar, hydrogen-bonding amino-diol building block rather than a solvent, Piperidine-3,5-diol is typically dissolved rather than used as the medium. Selection considerations for preparing stock solutions or reaction media (literature-based):

• Polarity/miscibility: Expected to be highly soluble in polar protic solvents (water, MeOH, EtOH) and in DMSO/DMF; limited solubility in nonpolar hydrocarbons (hexanes, toluene).
• Acid/base effects: In acidic media it forms ammonium salts (enhanced aqueous solubility); in basic media it remains as the free base (better solubility in organic polar solvents).
• Compatibility: • For acylation/carbamate formation: use dry DCM/THF/MeCN/DMF depending on reagent (Boc2O, acid chlorides, CDI).
  • For silyl protections of –OH: DCM/DMF with imidazole/amine base.
  • For Mitsunobu inversions: THF/THF–PhMe blends are common (ensure water exclusion).

Comparison (literature guidance):

• Water vs DMSO for stock solutions:
  • Water (salt form) – best for bioconjugation screens; may require pH control.
  • DMSO (free base) – best for high-concentration stocks; dilute into buffered aqueous systems.

Always verify solubility empirically with your lot; exact solubility values are not specified for this item.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (as provided in Product Data). Store in a tightly closed container, in a dry place, away from strong oxidizers and reactive acylating agents. Avoid prolonged exposure to moisture and air to minimize potential hygroscopic uptake or surface oxidation.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and solution handling (general guidance):

• Solvents: Water (preferably as an acid salt), DMSO, MeOH, or EtOH are common. Start with small test aliquots to determine maximum solubility for your lot. Exact solubility is not specified for this item.
• Stock solutions: Prepare concentrated stocks (e.g., 10–100 mM in DMSO) as needed; store aliquots to avoid repeated freeze–thaw. For aqueous stocks, adjust pH to enhance solubility if necessary (form the hydrochloride salt in situ).
• Stability: Amino-diols are generally stable at ambient conditions when dry. For long-term storage of solutions, keep at 2–8 °C (aqueous) or ≤−20 °C (DMSO) and protect from light if other chromophores are present. Validate stability by LC/HPLC prior to extended use.

Always refer to the product’s CoA/Spec Sheet and SDS for item-specific details, and follow your institution’s storage and labeling practices. Research use only.

Structure and Identity

Brief description: Piperidine-3,5-diol is a saturated six-membered piperidine ring bearing two alcohol functions at the 3- and 5-positions and a secondary amine at N1. It can exist as cis/trans diastereomers and, in the absence of stereochemical specification, typically as a racemic mixture.

• Product name (SKU): Piperidine-3,5-diol (P992497)
• CAS: 1792-72-9
• PubChem CID (literature): 19781347
• InChIKey (as provided): 293434
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: The unsubstituted piperidine ring is C5H11N; dihydroxy substitution adds two oxygens (literature/computed rationale).
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general chemistry description):

• Ring system: Six-membered saturated heterocycle with one nitrogen (piperidine).
• Functional groups: One secondary amine (–NH–); two aliphatic alcohols (–OH) at C3 and C5.
• Stereochemistry: The 3,5-diol may be present as cis or trans isomers; unless otherwise stated, commercial material may be a mixture (literature note).
• 2D description: Starting from N1, the ring bears –OH substituents at the 3- and 5-carbons relative to nitrogen. Each –OH is bound to an sp3 carbon; the nitrogen is secondary and nucleophilic.

Identity confirmation (general guidance):

• Common analytical handles include 1H/13C NMR (diagnostic –OH and –CH–OH signals), IR (broad O–H and N–H stretches), HRMS, and chiral HPLC if stereochemical resolution is required.

Synthetic Utility

Piperidine-3,5-diol combines a nucleophilic secondary amine with two alcohols, enabling orthogonal and sequential derivatizations central to heterocycle elaboration (literature/general chemistry):

• Protect–functionalize–deprotect strategies: • Install Boc/CBz/Fmoc on N to mask basicity, enabling selective O-chemistry (esterification, carbonate/sulfamate formation).
  • Alternatively, protect one –OH (e.g., TBS) to differentiate C3 vs C5 and direct site-selective transformations.
• Activation of alcohols: Convert –OH to mesylates/tosylates/triflates for downstream SN2 substitutions (azides, halides), ring substitution, or cross-coupling after displacement to suitable handles.
• Oxidation/reduction: • Dess–Martin/PCC oxidation of secondary alcohol(s) to give 3- or 5-keto piperidinones; enables enolate alkylations, Mannich, and reductive stereocontrol on rehydroxylation.
  • Hydrogenation or transfer hydrogenation can adjust protecting groups or reduce intermediates derived from the diol.
• C–N bond formation: Reductive amination on the ring nitrogen (after deprotection) or Buchwald–Hartwig amination on activated side chains introduced via –OH activation.
• Stereocontrol: Mitsunobu inversion at a single center and chelation-controlled acylations can access alternate stereochemical arrays from a single diol precursor (cis/trans interconversion strategies).
• Macrocyclization/oligomerization: The tri-functional nature supports linear or cyclic oligomers via selective amide/ester linkages for materials and probe design.

This scaffold is particularly valuable as a diversity point generator in lead optimization, facilitating rapid generation of 3,5-disubstituted piperidine libraries with controlled polarity and 3D topology.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies to this item.