1，5-Dioxa-9-azaspiro[5.5]undecane， tech - ≥95% , CAS No.180-94-9

CAS: 180-94-9 Cat. No.: D700071 Formula: C₈H₁₅NO₂ Peso molecolare: 157.21 Numero EC: 827-488-5 PubChem CID: 2737216

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

C1COC2(CCNCC2)OC1

IUPAC Name

1,5-dioxa-9-azaspiro[5.5]undecane

InChIKey

ZQGLEEFGEZLSAJ-UHFFFAOYSA-N

INCHI

1S/C8H15NO2/c1-6-10-8(11-7-1)2-4-9-5-3-8/h9H,1-7H2

Isomeri SMILES

C1COC2(CCNCC2)OC1

PubChem CID

2737216

Peso molecolare

157.21

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Azaspirodecane derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Azaspirodecane derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Azaspirodecane derivatives
• Alternative Parents: Ketals Piperidines 1,3-dioxanes Oxacyclic compounds Dialkylamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Azaspirodecane - Ketal - Meta-dioxane - Piperidine - Oxacycle - Azacycle - Secondary amine - Acetal - Secondary aliphatic amine - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Amine - Organic oxygen compound - Organopnictogen compound - Aliphatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.
• 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: 157.210 g/mol
• XLogP3: 0.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 157.11 Da
• Monoisotopic Mass: 157.11 Da
• Topological Polar Surface Area: 30.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 124.000
• 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

Application Protocols

No standardized biological assay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent.

General laboratory handling suggestions:

• For moisture-sensitive work, pre-dry the reagent under vacuum or by azeotrope with a dry solvent.
• If forming salts (e.g., HCl), generate in situ in anhydrous ether/EtOAc by passing dry HCl gas or adding ethanolic HCl, then isolate by filtration and dry under vacuum.
• For reaction screening, prepare stock solutions at known concentration in MeCN or DMSO and store aliquots tightly sealed to minimize water uptake.

Biological Roles

This product is intended strictly for research use and is not intended for human or veterinary use.

General note (not specific to this item): 1,5-dioxa-9-azaspiro[5.5]undecane is a synthetic, non-natural spirocyclic heterocycle. It does not have a recognized endogenous biological role. In medicinal chemistry and chemical biology, related spirocyclic amine–acetal motifs are sometimes explored to adjust physicochemical properties (e.g., basicity, polarity, 3D shape) of probe molecules or leads.

Potential biochemical relevance (literature-level, scaffold-based):

• Protonation behavior: tertiary amines can be protonated under physiological pH, influencing membrane permeability and target engagement in designed ligands.
• Hydrogen-bond accepting ability: the ether oxygens can participate in noncovalent interactions when this motif is embedded in larger structures.

No claims are made about biological activity, safety, efficacy, or therapeutic use. Any biological testing should be designed and interpreted under appropriate institutional guidelines and safety oversight.

Buffer Applications

Not typically applicable. Although tertiary amines can exhibit buffer capacity near the pKa of their conjugate acids, this spirocyclic amine–acetal is not a standard laboratory buffer component and lacks established Good’s buffer characteristics (defined pKa, low metal binding, high water solubility, minimal biological interference).

If a pH-modulating role is considered in a specific protocol:

• Verify the compound’s aqueous solubility and exact pKa from literature before use.
• Prefer established buffering agents (e.g., HEPES, MOPS, TRIS, phosphate) for robust, reproducible biological or analytical systems.

Green Alternatives

Greenness considerations for using a spirocyclic tertiary amine–acetal revolve around solvent choice, energy input, and lifecycle of the nitrogenous heterocycle.

• Feedstock and synthesis: If your route uses this scaffold as a base/ligand only, consider catalytic loadings or recyclable, immobilized amine catalysts to reduce mass intensity.
• Solvent optimization: Favor greener media (ethyl acetate, 2-MeTHF, cyclopentyl methyl ether, dimethyl carbonate, propylene carbonate, water/biobased alcohols where compatible) to replace chlorinated or high-toxicity solvents.
• Workup/waste: Tertiary amines can complicate aqueous waste (high COD, amine odor). Salt out and recover/reuse where possible; use CO2-free acid scrubbing to control emissions.

Illustrative comparison (general; not item-specific):

• Conventional: DCM/DMF for N-alkylation — effective but with environmental/health concerns.
• Greener alternative: MeCN or 2-MeTHF for alkylation; ethyl acetate or CPME for extractions and crystallizations; MeOH/EtOH for hydrogenations.

Trade-offs:

• Water and biobased solvents may promote acetal hydrolysis under acid; maintain neutral/basic pH.
• Ethers like 2-MeTHF/CPME offer greener profiles but still require peroxide management and proper ventilation.

Recommendation: Map the most material-intensive steps (solvent, workup, purification) and prioritize substitution with higher GHS/hazard scores first, maintaining conditions that preserve the acetal integrity.

Pharmaceutical Uses

Formulation/excipient context: This material is not a recognized pharmacopeial excipient and is not typically used directly in pharmaceutical formulations.

R&D context (general, non-clinical):

• As a medicinal chemistry building block, spirocyclic amine–acetal motifs can be introduced to modulate lipophilicity, basicity, and 3D shape of discovery compounds. Any such use remains at the research stage.
• Potential roles in process development include serving as a ligand or transient protecting element in synthetic sequences that generate API intermediates.

Compliance note:

• No therapeutic, diagnostic, or clinical claims are made. For GMP or clinical manufacturing, use only after full qualification, impurity profiling, and supplier quality assessments. Consult internal QA and regulatory groups before any regulated use.

Physical Properties

Item-specific specifications (this lot):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for this scaffold (not lot-specific):

• Physical state: typically a colorless liquid or low-melting solid for small spirocyclic aminal/acetals; exact form depends on purity and temperature.
• Boiling/melting points: Spirocyclic tertiary amine acetals of comparable size often show moderate boiling points and may distill under reduced pressure to limit decomposition; exact values for this CAS should be confirmed from primary literature or the CoA.
• Solubility: expected miscibility with many polar organic solvents (e.g., acetonitrile, alcohols, chlorinated solvents, ethers). Limited solubility in nonpolar hydrocarbons; generally low solubility in water but sufficient basicity may afford some water solubility upon protonation.
• Basicity: tertiary amines commonly show pKb in the 3–5 range (pKa of the conjugate acid typically 7–11, literature), but exact pKa for this compound should be verified in the literature.

Notes:

• All numerical values not explicitly listed in Product Data are not specified for this item and should be taken from the CoA/Spec Sheet or primary references for CAS 180-94-9 before use in regulated work.

Quality and Grades

• Listed grade/purity for this SKU: Not specified for this item; refer to CoA/Spec Sheet. The designation “tech” indicates technical grade material suitable for general synthetic and process development work, where ultra-trace impurity control (e.g., LCMS/HPLC, metal speciation, UV cutoffs) is not required.

What “tech” typically implies (general guidance):

• Purity: often adequate for routine organic synthesis; minor residual solvents or related spirocyclic byproducts may be present.
• Analytical expectations: lot-specific GC/HPLC area% and water content may be provided on the CoA, but ultra-low UV background or chromatographic purity standards of HPLC/UV grade materials are not implied.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If any stabilizer is used, it will be disclosed on the CoA.

When to choose a higher grade:

• Catalysis sensitive to amine/basic impurities, kinetic studies, or analytical reference use may require upgraded grades (e.g., ≥98% assay, low water) or additional in-house purification (distillation over base/drying agents, recrystallization).

Quality notes specific to this scaffold:

• Tertiary amine acetals may pick up CO2/H2O on standing (forming ammonium carbamate-like films or increasing water content). For most precise work, pre-dry and, if applicable, distill under reduced pressure immediately before use.

Reaction and Applications

This spirocyclic tertiary amine–acetal is primarily used as a conformationally restricted, polar building block and basic ligand. The following applications are based on general literature for related spirocyclic aminal/acetal systems and should be adapted to your specific protocol.

Representative uses:

• N-Functionalization: the tertiary amine can undergo quaternization (alkyl halides) to give ammonium salts, or N-oxide formation (mCPBA) to tune polarity and reactivity.
• Acylation/Carbamoylation: introduction of amide/carbamate handles at nitrogen (via quaternization–dequaternization strategies or by using activated chloroformates under carefully controlled conditions when a secondary amine is present in derivatives).
• Ligand/organocatalyst scaffold: the basic, sterically defined spiro center can act as an ancillary ligand in coordination chemistry or as an organocatalyst platform after suitable derivatization.
• Protective chemistry: the acetal-like portion is generally stable to base and nucleophiles but can be cleaved under strong aqueous acid, enabling temporary masking strategies in multistep synthesis.
• Building block incorporation: the rigid spirocyclic core is valued in medicinal chemistry to modulate 3D shape, reduce lipophilicity, and affect solubility; coupling typically proceeds via N-derivatization or through appended side chains installed onto the core.

Practical tips:

• Maintain neutral to basic conditions to preserve the acetal; avoid strong mineral acids unless cleavage is desired.
• For clean N-alkylations, employ polar aprotic solvents and slow addition of alkyl halide; consider phase-transfer conditions for less reactive substrates.
• Prior to sensitive steps, dry the material (e.g., azeotrope or vacuum) to minimize variability.

Reaction Conditions

General conditions for common transformations of spirocyclic tertiary amine–acetals (literature guidance; not item-specific):

• N-alkylation (quaternization):

  • Solvent: MeCN, acetone, or DCM.
  • Base: none required for tertiary amine; use mild base (e.g., K2CO3) if needed to scavenge HX in situ.
  • Temperature: 20–60°C; monitor to avoid over-alkylation byproducts.
  • Workup: precipitate quaternary ammonium salt or concentrate and triturate with ether.

• N-oxidation (amine N-oxide):

  • Reagent: mCPBA (1.1–1.5 equiv).
  • Solvent: DCM or MeCN; 0–25°C to control exotherm.
  • Quench: aqueous Na2SO3/NaHCO3; standard extractive workup.

• Acidic deprotection/cleavage of acetal (if desired):

  • Reagent: HCl(aq) or p-TsOH in aqueous alcohol.
  • Conditions: typically 0.5–2 M acid, 25–60°C; monitor by TLC/LC for ring opening.
  • Caution: extended exposure may lead to complex mixtures; optimize stoichiometry and time.

• Metal coordination/ligand applications:

  • Combine with metal salts (e.g., Cu, Pd) in alcohols or MeCN under inert atmosphere as needed; screen stoichiometry 1:1 to 2:1 (ligand:metal).

Yields/timeframes are substrate- and setup-dependent; consult primary literature for CAS 180-94-9 for quantitative benchmarking before scale-up.

Safety and Handling

Authoritative safety data must be taken from the product SDS. The following is general guidance for tertiary amines and cyclic acetal/ether derivatives.

Item-specific safety fields:

• Signal word: Not specified for this item; refer to SDS.
• H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.

General precautions (literature/experience-based):

• Likely hazards: organic tertiary amines may cause skin/eye irritation and respiratory irritation; strong odors are possible. Cyclic acetals are usually combustible liquids/solids.
• PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and avoid inhalation.
• Incompatibilities: strong oxidizers; strong mineral acids (which can protonate the amine and potentially hydrolyze the acetal under acidic, aqueous conditions). Avoid nitrosating agents.
• Peroxide formation: not typically a concern for this structural class (non-allylic, non-benzylic ethers in a cyclic acetal), but standard periodic testing is prudent for long-stored ethers; follow SDS guidance.
• First aid (overview; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; get medical attention.
• Fire safety: treat as combustible; use CO2, dry chemical, or foam. Thermal decomposition may release irritating vapors (e.g., amine-containing fumes).

Solvent Selection

This product is a heterocyclic reagent/building block rather than a general-purpose solvent. That said, selecting an appropriate solvent for reactions involving 1,5-dioxa-9-azaspiro[5.5]undecane is important.

General polarity/miscibility profile (literature-based expectations):

• Polarity: polar, basic, hydrogen-bond acceptor; expected to dissolve well in polar aprotic media (MeCN, DMF, DMSO) and moderately in ethers and alcohols.
• Water: limited solubility as the free base; good solubility upon protonation (e.g., as the HCl salt), depending on ionic strength.

Typical solvent choices by context:

• N-alkylation/acylation: polar aprotic solvents (MeCN, DMF, DCM) to favor SN2 or acyl chloride/anhydride reactions; include a non-nucleophilic base if needed.
• Complexation/ligand uses: alcohols, MeCN, or THF depending on metal salt solubility; control water content to avoid acetal hydrolysis under acid.
• Reductive transformations or hydrogenation of appended substituents: ethanol, MeOH, or EtOAc/MeOH mixtures are common, but avoid acidic conditions that can cleave the acetal.

Comparison notes (when choosing the medium):

• Versus protic alcohols: faster proton transfers possible but increased risk of acetal transacetalization under acid.
• Versus chlorinated solvents: high solubility and easy workup, but monitor for HCl formation in reactions that could risk acetal cleavage.

Storage and Reconstitution

• Storage conditions (as supplied): Room temperature (per Product Data). Protect from strong acids and oxidizers. Keep container tightly closed to minimize uptake of CO2/H2O.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not typically applicable; supplied neat unless otherwise stated. If a solid at ambient conditions, dissolve in a dry, compatible solvent (e.g., MeCN, DCM, EtOAc) to prepare stock solutions.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. As with many tertiary amines, long-term storage in amber, airtight containers is recommended.
• Freeze–thaw: Not applicable for neat liquids/solids. If stored as a solution, avoid repeated freeze–thaw cycles; prepare single-use aliquots.
• Disposal: Treat as an organic amine/ether-containing waste; dispose according to institutional and local regulations.

Research use note: For research use only (per Product Data). Always consult the SDS for authoritative safety, storage, and handling information before use.

Structure and Identity

Brief overview: 1,5-Dioxa-9-azaspiro[5.5]undecane is a saturated spirocyclic heterocycle featuring one nitrogen and two oxygen atoms embedded in a bicyclic, 6/6-membered spiro framework. It is a neutral, tertiary aminal/acetal-type scaffold often used as a polar, conformationally restricted building block.

• SKU: D700071
• Product name: 1,5-Dioxa-9-azaspiro[5.5]undecane, tech
• CAS: 180-94-9 (provided)
• PubChem CID: 2737216 (provided)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Note: a complete InChIKey is not provided in Product Data.)
• SMILES: 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.

Structural features (general description):

• Spiro junction linking two six-membered heterocycles (spiro[5.5]).
• Two ring oxygen atoms (dioxa) consistent with an acetal/ether motif; one ring nitrogen (aza) indicating a tertiary amine embedded in a morpholine-/dioxane-like environment.
• Fully saturated (no formal unsaturation), with a compact 3D shape and limited conformational freedom due to the spiro center.
• Functional groups: tertiary amine (basic Lewis base site), cyclic acetal/ether (generally base-stable, acid-labile under strong Brønsted acid).

2D structure in words (literature-style description): a six-membered morpholine-like ring (containing one O and one N) is fused at a single quaternary carbon (the spiro center) to a second six-membered dioxane-like ring (containing two O atoms).

Synthetic Utility

Key functional elements and reactivity (scaffold-based, literature):

• Tertiary amine center: undergoes quaternization (alkyl halides, dialkyl sulfates), N-oxidation (peracids), and coordination to metals (ancillary ligand). Protonation modulates solubility and reactivity.
• Cyclic acetal/ether ring: generally inert to nucleophiles and bases; cleavable under strong Brønsted or Lewis acidic, aqueous conditions to simpler carbonyl/diol fragments depending on substitution.
• Spiro junction: imparts rigidity and defined 3D geometry, valuable for conformational control in fragment-to-lead evolution.

Typical transformations leveraging this core:

• N-alkylation to access quaternary ammonium salts usable as phase-transfer catalysts or ionic-liquid-like auxiliaries.
• Installation of handles on adjacent carbons (via lithiation or halogenation of appropriately substituted derivatives) followed by cross-coupling.
• Salt formation (e.g., HCl, TsOH) for isolation, purification, or to tune crystallinity.

Retrosynthetic value:

• The spiro center can arise from condensation of amino alcohols with carbonyl equivalents, or via intramolecular acetalization on morpholine/dioxane frameworks—useful when planning scalable routes to related analogs.

Target Specificity

Not applicable to this product. Target specificity parameters (e.g., antigen/epitope, clone, isotype, species reactivity) are relevant to biological affinity reagents such as antibodies or proteins. This item is a small-molecule heterocycle supplied for chemical synthesis and general laboratory research.