Spiro[3.3]heptan-2-ylmethanol - ≥95% , CAS No.4483-67-4

CAS: 4483-67-4 Cat. No.: S1021663 Fórmula: C₈H₁₄O Peso molecular: 126.200 Número CE: 828-564-0

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

• Sorrisos canónicos: C1CC2(C1)CC(C2)CO
• IUPAC Name: spiro[3.3]heptan-2-ylmethanol
• InChIKey: GYVSAPVZLUZCBL-UHFFFAOYSA-N
• INCHI: 1S/C8H14O/c9-6-7-4-8(5-7)2-1-3-8/h7,9H,1-6H2
• Peso molecular: 126.200

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Alcohols and polyols

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Not available
• Direct Parent: Primary alcohols
• Alternative Parents: Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Hydrocarbon derivative - Primary alcohol - Aliphatic homopolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as primary alcohols. These are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
• 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

Propriedades químicas e físicas

• Peso molecular: 126.200 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 126.104 Da
• Monoisotopic Mass: 126.104 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 9
• 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

Application Protocols

Not applicable. There are no immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) associated with this small-molecule building block. For synthetic use, refer to the Reaction Conditions, Synthetic Utility, and Solvent Selection sections.

Biological Roles

Item-specific biological roles are not provided for this SKU. This compound is a synthetic, saturated spirocyclic primary alcohol and is not known as a natural metabolite.

General context (no clinical claims)

• Spirocyclic motifs: Frequently employed in medicinal chemistry to increase three-dimensionality (high sp3 fraction), modulate lipophilicity, and improve physicochemical properties (e.g., reducing aromaticity while maintaining potency). The spiro[3.3]heptyl group can act as a conformationally constrained hydrophobic substituent.
• Metabolic considerations (literature): Primary alcohols are typically oxidized in biological systems to aldehydes/acids by alcohol/aldehyde dehydrogenases; however, the rigid bicyclic framework may slow oxidation or alter membrane partitioning relative to linear analogs.
• Bioconjugation utility: After suitable activation (e.g., as carbonate or succinate), the alcohol can be linked to probes or polymers to introduce a compact, lipophilic tag.

Note: Any use in biological systems should be limited to research laboratory studies. No pharmacology or therapeutic claims are made or implied for this product.

Buffer Applications

Not typically applicable. Spiro[3.3]heptan-2-ylmethanol is a non-ionic organic building block and does not serve as a buffering agent. For work in aqueous systems, prepare stock solutions in a compatible organic cosolvent (e.g., DMSO, EtOH) and dilute into buffered media if solubility and compatibility permit.

Green Alternatives

Consider greener choices primarily in the context of reactions performed on this alcohol, not as a solvent itself.

Greener solvent substitutions (general guidance)

• Replace DCM/chloroform with:
  • 2‑MeTHF (biorenewable, water‑separable), CPME (low peroxide formation, hydrophobic), or EtOAc (readily biodegradable) when compatible with reagents.
• Replace DMF/DMAc/NMP with:
  • MeCN (if acceptable), propylene carbonate, Cyrene, or dimethyl isosorbide depending on reaction class.
• Replace toluene with:
  • Cyclopentyl methyl ether (CPME) or methyl tert‑butyl ether (MTBE) where volatility and safety are manageable.

Greener oxidation strategies

• TEMPO/NaOCl (aqueous bleach) for alcohol→aldehyde/acid under biphasic conditions; or catalytic TEMPO with O2/air where feasible.
• Electrochemical alcohol oxidation (flow or batch) avoids stoichiometric oxidants; requires apparatus.

Waste and energy considerations

• Use room‑temperature or flow protocols (e.g., flow Swern alternatives, catalytic oxidations) to reduce energy footprint.
• Minimize halogenated solvent use; implement in‑process solvent recovery.

Trade‑offs

• 2‑MeTHF/CPME can alter selectivity/solubility relative to DCM/THF; check reaction rates and workup (salting out often easier).
• Aqueous oxidations may require careful phase transfer control and can increase emulsions; design extraction accordingly.

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient role is not specified for this SKU; refer to CoA/Spec Sheet.

General formulation/manufacturing context (no therapeutic claims)

• Intermediate: The primary alcohol can be elaborated to carbamates, carbonates, esters, or oxidized to carbonyls as an intermediate in API or agrochemical synthesis, leveraging the rigid spiro scaffold to explore SAR.
• Pro-moiety potential: The alcohol may be masked as a carbonate/ester for temporary modification of physicochemical properties during discovery; such use requires full safety and regulatory evaluation.
• Solid form/handling: If the material is a low-melting solid or viscous liquid (appearance not specified), consider formulation aids (pre-dissolve in EtOH/PEG or adsorb onto inert carriers) for dose-form screening in preclinical research.

Regulatory note

• No USP/Ph.Eur. monograph is known for this specific structure (literature context). For GMP applications, define in-house specs and validated analytical methods. This catalog item is sold for research use only.

Physical Properties

Item-specific specs

• Boiling point, melting point, density, refractive index, water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for this scaffold (for planning only; verify experimentally)

• State/appearance: Small, saturated aliphatic primary alcohols of this size are commonly colorless liquids or low-melting solids; exact appearance is not specified for this item.
• Solubility: Expected to be miscible with many organic solvents (e.g., ethers, chlorinated solvents, alcohols) and poorly soluble in water due to the compact hydrophobic spiro core (literature trend for C8 primary alcohols). Quantitative solubilities are not specified for this item.
• Volatility: Moderate, with vapor pressure lower than corresponding C6–C7 alcohols but higher than long-chain alcohols; handle in a fume hood.
• Partitioning: Likely positive logP given hydrophobic skeleton; exact logP not specified.

Practical notes

• Drying: Primary alcohols can retain moisture; if anhydrous conditions are critical, dry over molecular sieves (3Å/4Å) and verify KF.
• Spectra: Alcohol O–H stretch (broad) typically 3200–3600 cm−1 (IR); 1H NMR shows –CH2OH (≈3.3–3.7 ppm) and exchangeable OH; 13C NMR: spiro quaternary carbon downfield vs methylenes. Exact values depend on solvent and temperature.

Quality and Grades

Item-specific details

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

Guidance for interpreting grades (general)

• Research/technical grade: Suitable for most synthetic and exploratory work; impurity profiles may vary. Verify by NMR/GC/LC as needed.
• High-purity/assay-specified grade: Tighter assay (e.g., ≥98–99%) and lower residual solvents/water; beneficial for kinetic studies or sensitive catalysis.
• Chromatography/HPLC grade (when applicable to solvents): Low UV background and particulates; not typically relevant to a solid/liquid building block like this.

Practical quality control suggestions

• Identity confirmation: 1H/13C NMR, HRMS/GC‑MS, and IR. For spiro frameworks, pay attention to the characteristic spiro quaternary carbon in 13C NMR and diagnostic –CH2OH signals.
• Purity assessment: GC or LC (evaporable under GC if sufficiently volatile; otherwise LC). Titrate water by Karl Fischer if moisture-sensitive transformations are planned.
• Residuals: If used in cross-coupling or sensitive organometallic steps, screen for peroxide (unlikely for alcohols vs ethers), residual acids/bases, and metals as needed for your process.

Documentation

• For exact specifications, acceptance criteria, and analytical methods for this SKU, consult the product CoA/Spec Sheet.

Reaction and Applications

As a sterically encumbered primary alcohol on a rigid spiro[3.3]heptane scaffold, this compound serves as a conformationally constrained, lipophilic handle for synthesis.

Representative transformations (general literature practices)

• Oxidations:
  • To aldehyde: Dess–Martin periodinane (DCM, 0–25 °C), Swern (DMSO/oxalyl chloride, −78→0 °C), or TEMPO/bleach (biphasic, RT). The spiro core minimizes β‑fragmentation pathways typical of more flexible systems.
  • To acid: Pinnick oxidation from the aldehyde (NaClO2/NaH2PO4, 2‑methyl‑2‑butene), or direct TEMPO/NaOCl/NaClO2.
• Activation/substitution:
  • Halides: Appel (PPh3/CX4), SOCl2 or PBr3 (control for rearrangement/elimination; mild conditions recommended due to ring strain).
  • Sulfonates: MsCl/TsCl in DCM or MeCN with Et3N or pyridine; subsequent SN2 to introduce N, O, S, or C nucleophiles.
• Protection/deprotection:
  • Silyl ethers (TBS, TBDPS) in dry DMF/DCM with imidazole; benzyl ethers via NaH/benzyl bromide or Mitsunobu with PhCH2OH.
• C–C bond formation via alcohol derivatives:
  • Oxidation to aldehyde followed by Wittig/HWE/organometallic additions to elaborate side chains while retaining the spiro core.
• Mitsunobu reactions:
  • Inversion-enabled ether or ester formation using DIAD/DEAD and PPh3; consider sterics around the primary center which is slightly hindered by the bicyclic framework.

Applications

• Scaffold incorporation in medicinal chemistry: The spiro[3.3]heptyl motif offers 3D shape, high sp3 content, and metabolic robustness—useful as a lipophilic, non-aromatic vector in SAR exploration.
• Materials/ligand design: Rigid spacer or hydrophobic anchor in polymers and supramolecular hosts.

Note: No manufacturer-specific application text was provided for this SKU; above reflects general synthetic utility.

Reaction Conditions

General literature conditions (illustrative; optimize for your substrate and scale)

• Oxidation to aldehyde:
  • Dess–Martin periodinane (1.3–1.6 equiv) in dry DCM, 0–25 °C, 1–3 h; quench with aqueous NaHCO3/Na2S2O3. Typical isolated yields for unactivated primary alcohols: 80–95% (literature range).
  • Swern (oxalyl chloride, DMSO, −78 °C; then Et3N), 70–90% typical.
• Oxidation to acid:
  • TEMPO (2–5 mol%), NaOCl/NaClO2, buffer pH ~6.8–7.4, biphasic (EtOAc/MTBE–buffer), 0–25 °C; 70–90% typical for primary alcohols.
• Tosylation/mesylation:
  • MsCl or TsCl (1.1–1.5 equiv) in DCM or MeCN with Et3N (2–3 equiv) or pyridine, 0–25 °C, 1–4 h; 80–95% typical.
• Halogenation:
  • Appel (PPh3/CBr4 or CCl4) in DCM, 0–25 °C; 70–90% typical. Alternatively PBr3 (1.1 equiv) in etheral solvent at 0 °C→RT.
• Silyl protection:
  • TBSCl (1.2–1.5 equiv), imidazole (2 equiv) in DMF or DCM, RT, 2–6 h; 85–95% typical.
• Mitsunobu ether/ester formation:
  • DEAD/DIAD (1.1–1.5 equiv) and PPh3 (1.1–1.5 equiv) in THF or toluene, 0–25 °C; yields vary (50–85%) depending on nucleophile and sterics.

Notes specific to spiro systems

• Slightly increased steric hindrance around the primary center may slow SN2; employ more nucleophilic reagents, phase-transfer catalysis, or elevated temperature as needed.
• Avoid prolonged strong acid exposure that could induce ring opening or rearrangements in strained bicyclic frameworks.

All values above are literature/general guidance and not item-specific specifications.

Safety and Handling

Item-specific hazard data

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

General safety guidance for small aliphatic primary alcohols (use as context only; defer to SDS)

• Likely hazards: May cause skin/eye irritation; harmful if swallowed/inhaled; combustible liquid/vapor. Avoid ignition sources.
• PPE: Lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a properly functioning fume hood.
• Handling: Avoid breathing vapors/mist. Prevent contact with strong oxidizers (e.g., chromyl chloride, nitric acid), strong reducing agents/alkali metals (risk of hydrogen evolution), and acid chlorides/anhydrides unless intended.
• Storage: Room temperature as per Product Data, in tightly closed container. Segregate from oxidizers. Use inert gas blanket for long-term storage if moisture/oxidation sensitivity of downstream use is a concern.
• First aid (overview; follow SDS/site protocol):
  • 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; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Fire-fighting: Alcohol-resistant foam, dry chemical, or CO2; water spray to cool containers. Combustion may produce CO/CO2.

Always consult the product-specific SDS for authoritative information.

Solvent Selection

This product is a small aliphatic alcohol building block rather than a solvent. Solvent selection therefore relates to dissolving it for reaction or analysis.

General solubility/miscibility guidance (literature trends for C8 primary alcohols)

• Likely good solubility: Etheral solvents (THF, 2‑MeTHF, MTBE), chlorinated solvents (DCM, chloroform), esters (EtOAc), and alcohols (MeOH, EtOH, i‑PrOH).
• Variable solubility: Acetonitrile and aromatics (toluene) depending on temperature; heating or small alcohol/ether cosolvent can help.
• Poor solubility: Water, especially at ambient temperature, due to hydrophobic spiro core.

Selection tips

• Nucleophilic substitutions/activation (tosylation/mesylation): Use anhydrous DCM, DCE, or MeCN with base (e.g., pyridine, Et3N). Alcoholic co-solvent may lead to transesterification—avoid unless desired.
• Oxidations to aldehyde/acid: Dichloromethane or EtOAc for Dess–Martin/IBX; DMSO/CH2Cl2 for Swern; acetone or MeCN for TEMPO/bleach.
• Protecting group chemistry (silylation/benzylation): Dry THF, DMF, or DCM with appropriate base.
• Purification: Normal-phase silica gel typically effective; add small % Et3N if acid-sensitive.

Note

• Item-specific solubility data are not specified for this SKU; verify experimentally on your scale.

Storage and Reconstitution

Item-specific storage

• Storage conditions: Room temperature (from Product Data). Keep container tightly closed in a dry, well-ventilated place. Protect from strong oxidizers.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance

• Inert atmosphere storage (optional): For long-term storage, consider nitrogen/argon headspace to minimize oxidative changes to the alcohol (typically low risk but good practice for sensitive workflows).
• Moisture: While primary alcohols are not highly hygroscopic, cap tightly to prevent water uptake that can affect downstream reactions. Dry over 3Å/4Å sieves if anhydrous use is critical.
• Reconstitution/solutions: Not applicable for solids per se. To prepare stock solutions, dissolve in a compatible dry organic solvent (e.g., DCM, THF, 2‑MeTHF, EtOAc, MeCN, MeOH/EtOH) at a convenient concentration (0.1–1.0 M typical for bench use). Filter if particulates are present.
• Freeze–thaw: Generally not required. If storing solutions, keep in sealed amber vials at 2–8 °C or −20 °C depending on solvent volatility; allow to equilibrate to room temperature before opening to avoid condensation.

Always consult the item’s CoA and SDS for definitive storage and handling instructions.

Structure and Identity

Item-specific (from Product Data)

• Product name: Spiro[3.3]heptan-2-ylmethanol (SKU: S1021663)
• CAS: 4483-67-4
• InChIKey: 115144 (as provided)
• Storage conditions: Room temperature
• Research use: For research use only

Computed/literature structural information (general; not item-specific specs)

• Suggested molecular formula (based on name): C8H14O
• Approximate molecular weight (calculated): ~126.20 g/mol
• Core scaffold: A spiro-bicyclic, saturated hydrocarbon consisting of two cyclobutane rings sharing a single spiro quaternary carbon (spiro[3.3]heptane framework).
• Functional group: Primary alcohol (–CH2OH) at the 2-position of the spiro system; this is a sterically encumbered yet still primary benzylic-analogous position (aliphatic, not benzylic).
• 2D structural description in words: A central spiro carbon connects two four‑membered rings; on the adjacent (2‑) carbon of one ring, a –CH2–OH side chain projects exocyclicly. The molecule is fully saturated (no π-bonds), contains one oxygen as an alcohol, and no heteroaromatic or carbonyl functionalities.

Notes

• SMILES and definitive InChI/InChIKey were not specified for this item; refer to CoA/Spec Sheet for authoritative identifiers.

Synthetic Utility

Functional group and scaffold features

• Primary alcohol at a bridge-adjacent position enables diverse two-electron (oxidation, acylation) and substitution chemistry.
• Rigid spiro[3.3]heptane core provides a compact, lipophilic, conformationally constrained vector to replace aromatic rings or tert‑butyl groups in lead optimization.

Key transformations (general literature)

• Alcohol→Electrophile: Tosylate/mesylate formation (DCM/MeCN, base), followed by SN2 with N/O/S/C nucleophiles; Appel or PBr3/SOCl2 to halides with care to suppress elimination.
• Alcohol→Carbonyl: Swern or Dess–Martin to aldehyde; Pinnick/HNO2-based sequences to carboxylic acid; access to amide/urea libraries via subsequent coupling.
• Protection strategies: TBS/TBDPS ethers for orthogonal protection; carbonate/carbamate installation (e.g., CDI, p‑nitrophenyl chloroformate) for pro-moieties or linkers.
• C–C bond construction: Aldehyde intermediate enables Wittig/Horner–Wadsworth–Emmons, organometallic additions (RMgX/RLi, organozincs), or reductive amination after oxidation to the aldehyde.

Retrosynthetic value

• Serves as a versatile entry to the spiro[3.3]heptyl motif. Divergent synthesis from this handle can rapidly generate ethers, amines (via azide displacement/reduction), and other derivatives.

Analytical/scale-up notes

• Monitor for ring strain-related side reactions under strongly acidic/basic, high-temperature conditions. Use mild conditions and short residence times. Verify integrity of the spiro quaternary center by 13C NMR and HRMS in downstream products.

Target Specificity

Not applicable. This product is a small organic building block, not a biological macromolecule or antibody. No target, epitope, or isotype information applies.