2-azaspiro[4.6]undecane - ≥95% , CAS No.184-14-5

CAS: 184-14-5 Cat. No.: A731079 Formula: C₁₀H₁₉N Molecular Weight: 153.27 EC Number: 993-522-1 PubChem CID: 23282818

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1CCCC2(CC1)CCNC2

IUPAC Name

2-azaspiro[4.6]undecane

InChIKey

UYUUEEXDJGLCLY-UHFFFAOYSA-N

INCHI

1S/C10H19N/c1-2-4-6-10(5-3-1)7-8-11-9-10/h11H,1-9H2

Isomeric SMILES

C1CCCC2(CC1)CCNC2

PubChem CID

23282818

Molecular Weight

153.27

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azaspirodecane derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Azaspirodecane derivatives
• Alternative Parents: Pyrrolidines Dialkylamines Azacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Azaspirodecane - Pyrrolidine - Azacycle - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aliphatic heteropolycyclic compound
• Description: 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

Chemical and Physical Properties

• Molecular Weight: 153.260 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 153.152 Da
• Monoisotopic Mass: 153.152 Da
• Topological Polar Surface Area: 12.000 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 123.000
• 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

• Not applicable. There are no assay protocols (e.g., WB, IHC, IF, FC) validated for this small-molecule building block in the Product Data.

• For synthetic use, refer to the Reaction & Applications and Reaction Conditions sections for general preparative guidance, and consult primary literature for exact procedures tailored to your substrates.

Biological Roles

• Item-specific biological/biochemical role: Not specified.

• General considerations (informative only):

  • 2-azaspiro[4.6]undecane is a synthetic, saturated spirocyclic amine without a known natural biological role.
  • As a protonatable amine, its conjugate acid can engage in ionic interactions and hydrogen bonding, which is why such scaffolds are explored in biochemical probe and materials design research; however, no biological function is inherent to the parent scaffold.
  • Spirocyclic amines are valued for introducing 3D shape and conformational restriction, properties that can modulate permeability, basicity, and binding in structure–activity exploration (general medicinal chemistry principles; not a claim of biological activity for this item).

• Use context reminder:

  • This product is supplied strictly for research use only (per Product Data) and is not intended for use in humans or diagnostics.

Buffer Applications

• Not typically used as a defined buffering agent. Secondary aliphatic amines can act as weak bases with pKaH typically around 10–11 (literature, class value), but 2-azaspiro[4.6]undecane is not a standard buffer component.

• Practical note (general):

  • If a basic environment is needed transiently, the amine can be protonated with mineral acids to form a soluble ammonium salt; however, for precise pH control, use established buffer systems (e.g., Tris, phosphate, HEPES) rather than this building block.

Green Alternatives

• Context: The compound itself is a reagent/building block rather than a solvent. Greener choices mainly concern the reaction medium and activation chemistry used alongside this amine.

• Greener solvent options (general guidance):

  • Replace chlorinated solvents (e.g., DCM) with ethyl acetate, 2-MeTHF, CPME, toluene, or MeCN where compatible.
  • Favor alcohols (EtOH, i-PrOH) for reductive aminations and hydrogenations.

• Greener activation and coupling strategies:

  • Prefer enzymatic or catalytic reductive amination (H2 with Pd/C or Raney Ni) over stoichiometric borohydrides when feasible.
  • Use carbonyldiimidazole (CDI) or anhydrides instead of acid chlorides to reduce HCl generation and corrosivity.

• Comparison snapshot (general, not item-specific):

  • DCM vs. 2-MeTHF: 2-MeTHF offers lower toxicity and can be derived from biomass; may provide similar solubility for amide couplings involving amines.
  • DMF/NMP vs. Acetonitrile/CPME: MeCN/CPME have more favorable hazard profiles; assess solubility and catalyst compatibility.

• Waste minimization:

  • Capture and neutralize amine-containing offgases in acidic scrubbers when applicable.
  • Opt for salt formation to crystallize products, reducing reliance on silica chromatography and high volumes of solvent.

• Trade-offs:

  • Greener solvents may alter rates/selectivity; perform small-scale screens to balance EHS benefits with process robustness.

Pharmaceutical Uses

• Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet.

• General context (non-clinical, no therapeutic claims):

  • Spirocyclic amines like 2-azaspiro[4.6]undecane are primarily used as intermediates or scaffolds in discovery and process research to explore structure–property relationships.
  • The formation of pharmaceutically acceptable salts (e.g., hydrochloride, sulfate, maleate) is commonly employed to tailor crystallinity, hygroscopicity, and solubility during intermediate handling and purification.
  • Any use in GMP or clinical settings would require dedicated quality systems, impurity profiling, and regulatory documentation that are not implied by this catalog offering.

Physical Properties

• Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature expectations for saturated secondary amines of similar size (informative, not item specifications):

  • Physical state: Often low-melting solids or high-boiling liquids (oily) at ambient temperature for C9–C12 secondary alicyclic amines.
  • Basicity: Secondary alicyclic amines typically have conjugate acid pKaH ~10–11 (literature, class value), indicating ready protonation under mildly acidic conditions.
  • Solubility: The free base is usually miscible with many organic solvents (e.g., alcohols, ethers, chlorinated solvents) and sparingly to moderately soluble in water; the hydrochloride or other mineral acid salts are highly water-soluble.
  • Volatility and odor: Lower volatility than small amines; characteristic amine odor may be present (literature, class behavior).
  • Partitioning: As a protonatable amine, logP is pH-dependent; the free base is more lipophilic than its protonated salts (general principle).

• Practical notes (general):

  • For analytical development, determine exact boiling point, melting point, and refractive index on the specific lot; do not rely on class estimates. These values should be taken from the product’s CoA or experimentally measured under your lab conditions.

Quality & Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret typical grades (general guidance):

  • Research/ACS/AR grade: Indicates suitability for general laboratory synthesis; specific impurity thresholds (e.g., metals, residual solvents) vary by supplier and lot.
  • HPLC or LC/MS grade (if applicable): Focuses on low background and UV absorbance; generally not assigned to neat amines unless provided with UV-cutoff data.
  • Pharmaceutical or GMP-grade: Requires stringent quality systems and documentation; not implied unless explicitly stated.

• Considerations specific to spirocyclic amines:

  • Monitor potential residual starting materials (e.g., lactams, cyclic ketones) and amine-related byproducts via GC/GC–MS or LC–MS.
  • Check water content (KF) and residual solvents for reactions sensitive to moisture; for this item, exact values are not specified.
  • If chiral or diastereomeric variants are possible, confirm stereochemical purity. For 2-azaspiro[4.6]undecane as presented (no stereocenters except the spiro carbon), stereochemical specification may be unnecessary unless substituted derivatives are prepared.

• Documentation:

  • For release criteria (purity assay, identification, residual solvents, water, metals), consult the CoA/Spec Sheet for the specific lot supplied under SKU A731079.

Reaction & Applications

• Role in synthesis (general): 2-azaspiro[4.6]undecane is a compact, conformationally restricted secondary amine frequently employed as a scaffold or nucleophilic partner to introduce spirocyclic topology into targets. Its rigidity can improve physicochemical profiles in materials and discovery chemistry.

• Representative transformations (literature/general; not item-specific performance):

  • N-Acylation/Carbamylation: Formation of amides, carbamates, and ureas using acid chlorides, anhydrides, CDI, or isocyanates. Control stoichiometry and temperature to avoid overacylation.
  • Reductive Amination: Coupling with aldehydes/ketones using NaBH(OAc)3 or catalytic hydrogenation to generate tertiary amines while retaining the spiro core.
  • Alkylation: SN1/SN2 alkylation with suitable electrophiles (alkyl halides, sulfonates); suppress over-alkylation by base choice and slow addition of electrophile.
  • Aryl C–N Cross-Coupling: Buchwald–Hartwig amination with aryl (pseudo)halides under Pd catalysis to install aryl substituents on nitrogen.
  • Sulfonylation: Reaction with sulfonyl chlorides to give sulfonamides for further diversification.
  • Salt/Prodrug-like handles: Formation of ammonium salts (e.g., HCl, fumarate) can modulate crystallinity and handling.

• Application domains (general, non-clinical):

  • Building block for libraries exploring 3D-rich, non-flat chemical space.
  • Polycation templating in materials/supramolecular studies where a rigid cation is beneficial.

• Practical notes:

  • Ensure adequate base scavenging of HX byproducts; DIPEA or Na2CO3 are common choices.
  • For volatile derivatization reagents, maintain low temperatures to control exotherm and avoid amine evaporation losses.

Reaction Conditions

• Item-specific conditions: Not specified for this item; refer to CoA/Spec Sheet and your internal methods.

• General condition ranges from literature (informative, adjust to your system):

  • Reductive amination: Aldehyde/ketone (1.0 eq), 2-azaspiro[4.6]undecane (1.2–2.0 eq), AcOH (0.2–1.0 eq), NaBH(OAc)3 (1.5–3.0 eq); solvent MeOH/EtOH/MeCN; temperature rt–40°C; time 2–16 h.
  • Amide formation (acid chloride): Base (DIPEA, Et3N, 2–3 eq); solvent DCM/THF; temperature 0°C to rt; add acyl chloride slowly to control exotherm.
  • Urea formation (isocyanate): Solvent DCM/THF/MeCN; catalytic DMAP may accelerate; 0°C–rt, 1–4 h.
  • Buchwald–Hartwig amination: Aryl bromide/chloride (1.0 eq), amine (1.2–1.5 eq), Pd2(dba)3 or Pd(OAc)2 (1–3 mol%), ligand (XPhos, RuPhos, BrettPhos, 2–6 mol%), base (NaOtBu, Cs2CO3), solvent toluene/dioxane/CPME, 80–110°C, 4–24 h under inert atmosphere.
  • Sulfonylation: R–SO2Cl (1.0–1.2 eq), base (NaHCO3, Et3N), solvent DCM/MeCN; 0°C–rt, 1–3 h.

• Workup/purification (general):

  • Quench carefully; partition between water and organic solvent; for amine-containing mixtures, acid/base extraction is efficient. Consider isolation as HCl salt for crystallization.

• Analytics:

  • Track by TLC with base additive, LC–MS, or GC–MS. For free bases, suppress streaking by adding 0.5–1% NEt3 in eluent.

Safety & Handling

• Item-specific GHS data: Not specified for this item; refer to SDS for definitive hazard and precautionary statements.

• General hazards for aliphatic secondary amines (informative):

  • May cause skin and eye irritation; vapors/aerosols can irritate respiratory tract.
  • Can be harmful if swallowed; may be corrosive to some materials when concentrated and basic.
  • Amines can form amine salts with acids and may react with acylating agents, isocyanates, acid anhydrides, and strong oxidizers; avoid such incompatibilities unless intended.

• Recommended PPE and controls (good practice):

  • Lab coat, safety glasses, and nitrile gloves. Work in a chemical fume hood to control vapors/odors and minimize exposure.
  • Use inert atmosphere if conducting moisture- or CO2-sensitive reactions; dry glassware for moisture-intolerant transformations.

• First-aid overview (general guidance; consult SDS):

  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; seek medical attention.
  • Inhalation: Move to fresh air; monitor breathing; seek medical advice if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; get medical attention.

• Storage incompatibilities and stability (general):

  • Keep away from strong oxidizers and strong acids (unless preparing salts under controlled conditions). Amines may absorb CO2 and moisture from air; keep container closed.

Solvent Selection

• Applicability: As a neutral-to-basic, saturated secondary amine, solvent choice is driven by reaction type and whether the free base or a salt form is used.

• General polarity/miscibility (general knowledge):

  • The free base is typically miscible with polar organic solvents (alcohols, acetone, acetonitrile), good solubility in ethers and chlorinated solvents, and limited water solubility. Its mineral acid salts are highly water-soluble and less soluble in nonpolar media.

• Selection guidance by use case:

  • N-acylation/carbamylation/urea formation: Use anhydrous DCM, THF, MeCN, or DMF; include base (e.g., Et3N, DIPEA) if acyl chloride/anhydride is used.
  • Reductive amination (as amine nucleophile): MeOH, EtOH, i-PrOH, or MeCN with NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
  • Aryl amination (Buchwald–Hartwig): High-boiling polar aprotics (toluene, dioxane, t-BuOH, CPME) with Pd catalysts and strong bases.
  • Salt formation/purification: Dissolve free base in ether or EtOAc; gas with HCl(g) or add alcoholic HCl to precipitate the hydrochloride salt.

• Practical tips:

  • Minimize protic solvent content for moisture-sensitive couplings.
  • For chromatography, amines often tail; add 0.1–1% NEt3 or use amine-modified silica. Alternatively, isolate as a crystalline salt and reconvert to free base.
  • For greener choices, see the Green Alternatives section.

Storage & Reconstitution

• Item-specific storage (from Product Data):

  • Storage Conditions: Room temperature.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for aliphatic amines (informative):

  • Store in a tightly closed container to limit uptake of CO2 and moisture from air.
  • If odor is a concern, keep within a secondary sealed container in a well-ventilated storage cabinet.
  • Protect from strong oxidizers and segregate from acids unless intentionally forming a salt.
  • For long-term storage or for hygroscopic lots, consider converting to a stable mineral acid salt (e.g., HCl salt) for improved shelf life; regenerate the free base before use.

• Reconstitution:

  • Supplied neat; no reconstitution required. If solidification occurs (some amines supercool or crystallize), warm gently to ambient or slightly above and swirl until homogeneous.

• Stability notes:

  • Verify integrity periodically by NMR or LC–MS if stored for extended periods. Follow the lot-specific CoA/Spec Sheet for any additional handling instructions.

• Research Use Note: For research use only (per Product Data).

Structure & Identity

A saturated spirocyclic secondary amine useful as a compact, conformationally restricted building block.

• Item-specific (from Product Data):

  • Product Name: 2-azaspiro[4.6]undecane
  • CAS: 184-14-5
  • CID: 23282818
  • InChIKey: 372718
  • 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 chemistry description):

  • Spirocyclic framework consisting of two fused saturated rings sharing a single quaternary spiro center.
  • Contains one tertiary spiro carbon and one secondary amine nitrogen (–NH–) embedded in one ring.
  • No aromaticity; aliphatic, conformationally constrained scaffold.
  • Expected to present a basic amine center capable of protonation and salt formation.

• 2D description in words (general):

  • Visualize a cycloalkyl ring and a nitrogen-containing cycloalkyl ring meeting at one shared carbon (the spiro junction). The nitrogen is secondary (one hydrogen and two carbon substituents) and lies within the ring system; there are no additional heteroatoms or double bonds in the backbone.

Synthetic Utility

• Functional group reactivity (general):

  • Secondary amine (–NH–): Nucleophilic at nitrogen; undergoes acylation, alkylation, sulfonylation, and condensation reactions.
  • Spirocyclic constraint: Provides a rigid, lipophilicity-modulating scaffold; alters basicity and sterics compared with acyclic analogs.

• Retrosynthetic value:

  • Can serve as a modular amine coupling partner to append the spirocyclic motif late-stage onto electrophilic fragments (acid chlorides, activated esters, aryl halides for Buchwald–Hartwig, aldehydes/ketones for reductive amination).
  • Facilitates SAR exploration by enabling quick generation of tertiary amines, amides, ureas, or sulfonamides while holding the carbon framework constant.

• Named/representative reactions (general literature):

  • Buchwald–Hartwig amination (Pd-catalyzed C–N coupling).
  • Reductive amination (NaBH(OAc)3 or H2/Pd).
  • Urea/carbamate formation (isocyanates, CDI).
  • Amide coupling (EDC/HOBt, HATU, acid chlorides).

• Practical synthesis notes:

  • Employ base selection (e.g., DIPEA vs. inorganic carbonate) to control over-alkylation and minimize side reactions.
  • For purification, convert to a crystalline salt, filter, wash, then basify to regenerate the free base, reducing column chromatography.
  • Verify identity by 1H/13C NMR (amine N–H often broad and exchangeable), IR (N–H stretch), and MS (M+H+ corresponding to exact MW from CoA).

Target Specificity

• Not applicable. This product is a small-molecule chemical (spirocyclic amine), not an antibody, enzyme, nucleic acid, or targeted biological reagent. It does not possess target-binding specificity information in this catalog entry.

Frequently Asked 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.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 184-14-5, the molecular formula is C10H19N, and the molecular weight is 153.27 g/mol. InChIKey UYUUEEXDJGLCLY-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.