5-Fluoroadamantan-2-one - ≥95% , CAS No.41171-83-9

CAS: 41171-83-9 Cat. No.: F952442 Formula: C₁₀H₁₃FO Peso molecolare: 168.210 Numero EC: 995-902-2

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

C1C2CC3CC(C2)(CC1C3=O)F

IUPAC Name

5-fluoroadamantan-2-one

InChIKey

ZBDVRJNXUKDRAZ-UHFFFAOYSA-N

INCHI

1S/C10H13FO/c11-10-3-6-1-7(4-10)9(12)8(2-6)5-10/h6-8H,1-5H2

Peso molecolare

168.210

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Cyclic ketones
            • Level7 Adamantanones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Cyclic ketones
• Direct Parent: Adamantanones
• Alternative Parents: Organofluorides Organic oxides Hydrocarbon derivatives Alkyl fluorides
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Adamantanone - Organic oxide - Hydrocarbon derivative - Organofluoride - Organohalogen compound - Alkyl halide - Alkyl fluoride - Aliphatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as adamantanones. These are organic compounds containing a ketone group is attached to the adamantane (tricyclo[3.3.1.1]decane) ring.
• 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: 168.210 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 168.095 Da
• Monoisotopic Mass: 168.095 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 230.000
• 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

Not applicable. No antibody/assay application protocols are associated with this small-molecule reagent. For synthetic use, see the Reaction Conditions and Synthetic Utility sections for practical guidance.

Biological Roles

Item-specific biological roles: Not specified for this item; refer to primary literature if needed.

General context (no clinical claims):

• Adamantane cores are common in chemical biology due to their rigid, hydrophobic nature, which can increase binding affinity to hydrophobic pockets and influence membrane interactions. Fluorination further tunes lipophilicity, dipole moments, and metabolic stability.
• 5-Fluoroadamantan-2-one itself is best viewed as a synthetic intermediate or fragment: the carbonyl allows elaboration to amines, alcohols, oximes, or lactones, enabling rapid access to libraries of fluorinated adamantyl derivatives for target-agnostic screening.
• Enzyme interactions: carbonyl-containing adamantyl fragments may serve as probes in fragment-based discovery; the C–F bond is typically metabolically stable, aiding in tracing and SAR.

Note: Any biological testing should be conducted under appropriate approvals and is outside the scope of Aladdin’s research-use-only supply. No therapeutic or diagnostic use is implied.

Buffer Applications

This compound is a neutral, water-insoluble organic ketone and is not typically used to prepare aqueous buffer systems. For lab workflows, dissolve in an appropriate organic solvent (e.g., DMSO, MeCN, EtOAc, THF, or CH2Cl2) before introducing to biphasic or assay systems as applicable.

Green Alternatives

Context: 5-Fluoroadamantan-2-one is a substrate/intermediate; its “greenness” is driven largely by solvent and reagent choices.

Greener solvent choices (general guidance):

• Prefer 2-MeTHF or CPME over THF/Et2O for organometallic additions when feasible; they offer higher boiling points, partial bio-origin, and reduced peroxide formation risk vs Et2O.
• Ethyl acetate or Me-THF can replace CH2Cl2 in many workups and some reactions; assess reactivity and selectivity with peracids before wholesale substitution in oxidations.
• IPA/EtOH as protic media for NaBH4 reductions can replace MeOH or mixed aqueous systems, balancing safety and removal.

Illustrative comparison (general):

• THF vs 2-MeTHF: similar polarity; 2-MeTHF often allows room-temperature operations with easier phase separation and improved sustainability metrics.
• DCM vs EtOAc: EtOAc is less toxic, biodegradable, and widely accepted in green solvent guides; volatility is higher than many alternatives but manageable.

Reagent considerations:

• Baeyer–Villiger: consider urea–hydrogen peroxide (UHP) with catalytic acids in greener solvents as an alternative to mCPBA in DCM, where compatible.
• Reductive amination: employ NaBH(OAc)3 in toluene/AcOH or EtOAc/AcOH systems to avoid halogenated solvents.

Process tips:

• Maximize atom economy by choosing direct carbonyl transformations. Exploit the inherent stability of the C–F bond to minimize protecting group steps.
• Evaluate solvent recycling and crystallization-driven purifications (EtOAc/hexanes) to reduce silica waste.

Pharmaceutical Uses

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

General formulation/manufacturing context (no medical claims):

• Role in discovery: fluorinated adamantyl motifs are frequently incorporated into small-molecule leads to modulate permeability, potency, and metabolic stability. 5-Fluoroadamantan-2-one is a convenient precursor for installing such motifs via carbonyl derivatization.
• Intermediate synthesis: the ketone can be elaborated to amines (via reductive amination) or alcohols/ethers (via reduction), furnishing handle-rich derivatives for salt screening and pre-formulation studies.
• Solid-state benefits: adamantyl-containing compounds often crystallize well, aiding purification and polymorph exploration during early development.

If you require GMP, pharmacopoeial testing, or extended impurity profiling, contact Aladdin to discuss custom manufacturing and quality packages.

Physical Properties

Item-specific physical specifications (this lot):

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

Literature/computed properties for the neat compound (for reference only; not product specifications):

• Physical state: typically a crystalline solid for adamantanone derivatives of this size.
• Molecular weight: ~168.21 g/mol (from formula C10H13FO).
• Expected solubility profile: low solubility in water; good solubility in chlorinated solvents (CH2Cl2, CHCl3), ethyl acetate, ethers (THF, diethyl ether), aromatic hydrocarbons (toluene) due to a compact hydrophobic cage and a single carbonyl (literature trend for adamantanones).
• Volatility: low; high lattice energy of adamantane cage reduces vapor pressure (general diamondoid behavior).
• Partitioning: adamantane frameworks are lipophilic; addition of one carbonyl moderates but maintains overall hydrophobicity; logP expected in the moderate-to-high range (literature trend).
• Melting/boiling points, density, refractive index, pKa: Not widely consolidated in public sources for this exact fluorinated ketone; consult primary literature or measure as needed.

Notes:

• Provide your application and temperature needs when requesting a CoA; item-specific MP, residual solvents, water content, and other QC attributes are batch-dependent and will appear on the Aladdin CoA/Spec Sheet when available.

Quality and Grades

Item-specific quality information:

• 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 on interpreting grades (general):

• Research grade indicates suitability for most synthetic and discovery workflows. If HPLC/LC–MS applications require low UV background or metal trace control, request HPLC grade or LC–MS-tailored material when available.
• For structure–activity studies, typical controls include: identity by 1H/13C NMR and HRMS; purity by HPLC/GC; water content by Karl Fischer; and residual solvents per ICH. These specifics are batch-dependent and will be listed on the CoA.

Ketone stability considerations (general):

• 5-Fluoroadamantan-2-one is not prone to self-condensation or peroxide formation; no stabilizer is typically required. However, trace acids/bases can catalyze side chemistry in aggressive conditions; maintain standard clean, dry storage.

If you require a particular purity threshold (e.g., ≥98% assay by HPLC) or analytical panel, contact Aladdin to source or qualify material to your specification.

Reaction and Applications

Use profile (general for 5-fluoro-2-adamantanone):

• Scaffold: fluorinated adamantane is a valuable, conformationally locked, lipophilic core for materials and medicinal chemistry discovery, enabling SAR exploration where the C–F bond modulates electronics and lipophilicity.
• Carbonyl chemistry: the 2-one enables a wide range of transformations without disturbing the robust C–F bond under standard conditions.

Representative transformations (literature/general guidance):

• Nucleophilic addition to the ketone: Grignard or organolithium reagents to afford tertiary alcohols on the adamantyl core; typical solvents THF/Et2O at −78 to 0 °C.
• Reduction: NaBH4 (MeOH/EtOH) or LiAlH4 (Et2O/THF) to the corresponding secondary alcohol; the C–F bond is retained.
• Oxime/hydrazone formation: reaction with hydroxylamine or hydrazines; precursors for further rearrangements or reductions.
• Reductive amination: carbonyl to tertiary amines using amines + NaBH3CN/NaBH(OAc)3 (DCM/MeOH, pH-controlled).
• Baeyer–Villiger oxidation: peracids (e.g., mCPBA) convert adamantanones to the corresponding lactones; the rigid framework often gives high regioselectivity.
• Carbonyl protection/derivatization: acetals/ketals under acid catalysis in suitable solvents; note that strong superacid conditions can also activate substitutions on adamantane (advanced methods).

Applications:

• Discovery chemistry: installation of adamantyl groups is known to tune membrane affinity and metabolic stability; this fluorinated variant further modulates properties for tool compounds and materials building blocks.
• Materials: rigid, bulky substituent for tuning Tg/plasticization in polymers and for constructing dense molecular architectures.

Tip: The adamantyl framework lacks facile beta-elimination pathways, improving chemoselectivity during strong nucleophile additions.

Reaction Conditions

General literature conditions for representative transformations on adamantan-2-one derivatives (adapt to the fluorinated analog; verify on small scale):

• Reduction to alcohol: NaBH4 (0.5–2.0 eq) in MeOH or EtOH, 0–25 °C, 0.5–4 h; or LiAlH4 (1–2 eq) in Et2O/THF, 0–25 °C, 1–3 h. Quench carefully.
• Grignard addition: RMgX (1.2–2.0 eq) in anhydrous THF/Et2O, −78 to 0 °C, 1–6 h; yields of tertiary alcohols typically good to excellent with adamantanones (literature precedent).
• Reductive amination: ketone + amine (1.2–2.0 eq) with NaBH3CN (1.5–2.0 eq) in MeOH/DCM (pH ~5–6 with AcOH), 0–25 °C, 2–16 h; or NaBH(OAc)3 in DCE/MeCN/EtOAc.
• Oxime formation: hydroxylamine·HCl (1.2–2.0 eq), pyridine or NaOAc as base, EtOH/MeOH, reflux 1–4 h.
• Baeyer–Villiger oxidation: mCPBA (1.2–2.0 eq) in CH2Cl2, 0–25 °C, 2–24 h; or peracetic acid in MeCN. Monitor for regioselective lactone formation common to adamantanones.

Notes specific to the fluorinated scaffold (general):

• The C–F bond is robust and typically survives the above conditions. Avoid strong nucleophiles at elevated temperatures in polar aprotic media if undesired SN1/SN2-like substitutions on the cage are a concern (rare but possible under forcing/superacidic conditions).
• Rigorously dry conditions are recommended for organometallic additions; the cage tolerates low temperatures well.

All parameters are general literature guidance and should be optimized per substrate and scale.

Safety and Handling

Item-specific hazard information (from Product Data):

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

General safety guidance for adamantane ketones (literature/industry practice; defer to this product’s SDS):

• Likely hazards: irritant potential to skin/eyes; avoid inhalation of dust/particulates; carbonyl-containing organics may cause reversible CNS effects at high solvent exposures when handled in volatile solvents.
• PPE: lab coat, safety glasses, and appropriate chemically resistant gloves (nitrile). Use in a fume hood to avoid inhalation of dust or solvent vapors during processing.
• Handling: avoid generating dust; minimize static. For synthetic use, ensure dry glassware and anhydrous solvents when moisture-sensitive reagents are present.
• Incompatibilities: strong oxidizers (risk of exotherm), strong bases in the presence of halides that could induce undesired side reactions; avoid strong Lewis acids with the fluorinated cage unless intended, as superacids can activate adamantyl substitution.
• First aid (overview): on skin/eye contact, rinse with water for ≥15 min; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention in all cases of exposure.
• Fire: treat as an organic combustible; suitable extinguishing media include CO2, dry chemical, or foam. Combustion may produce toxic fumes (HF, CO/CO2).
• Spill response: collect solids with minimal dust; avoid discharge to drains. Dispose of in accordance with local regulations.

Always consult the Aladdin SDS for authoritative, product-specific safety information.

Solvent Selection

Compound type and polarity (general):

• Rigid, compact polycyclic ketone with a single polar carbonyl and a C–F bond; overall moderately lipophilic and non-ionizable under neutral conditions. Not water-miscible.

Solubility/miscibility tendencies (literature trends for adamantanones):

• Good: CH2Cl2, CHCl3, THF, diethyl ether, MTBE, EtOAc, acetone, acetonitrile (moderate), toluene, hexanes (moderate to low, may require warming).
• Poor: water and aqueous buffers.

When to choose which solvent:

• Reaction medium for nucleophilic additions/reductions: THF/Et2O (for organometallics), or MeOH/EtOH/IPA (for NaBH4 reductions) as compatible.
• Oxidations (e.g., Baeyer–Villiger): CH2Cl2, CHCl3, or MeCN with peracids (mCPBA) or peroxyacids.
• Workup/Crystallization: Ethyl acetate/hexanes or toluene/hexanes pairs often enable efficient trituration or crystallization of adamantane derivatives.

Comparison notes:

• Versus highly polar aprotic solvents (DMSO/DMF): those enhance solubility for polar reagents but may be unnecessary and harder to remove. Prefer mid-polarity ethers/esters for ease of isolation when compatible.

Always verify actual solubility with a small-scale test, as substituent patterns can shift behavior.

Storage and Reconstitution

Item-specific storage conditions (from Product Data):

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

General guidance:

• Keep container tightly closed in a dry, well-ventilated place. Protect from strong acids/bases and oxidizers. Avoid prolonged exposure to light and heat.
• If weighing frequently, consider splitting into aliquots to minimize ambient exposure; the solid is expected to be stable under dry, ambient conditions.
• Solution stability: in anhydrous, oxygen-free organic solvents (e.g., CH2Cl2, THF, EtOAc), solutions are typically stable for days at 2–8 °C; prepare fresh solutions for moisture/oxygen-sensitive reactions.
• Reconstitution: not applicable (supplied as a neat solid). Dissolve directly in a compatible organic solvent appropriate to the intended reaction or assay.

Research use only: not for human or animal use.

Structure and Identity

Brief overview: 5-Fluoroadamantan-2-one is a rigid, polycyclic ketone of the adamantane family bearing a fluorine substituent. The framework is a diamondoid cage; the carbonyl resides at the 2-position, with F at the 5-position.

• Item-specific identifiers (from Product Data):

  • SKU: F952442
  • Product Name: 5-Fluoroadamantan-2-one
  • CAS: 41171-83-9
  • PubChem CID: 12653455
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity data (for reference; not item-specific specs):

  • Molecular formula (literature): C10H13FO
  • Molecular weight (literature): ~168.21 g/mol
  • Core structural features: adamantane cage (tricyclo[3.3.1.13,7]decane) with a ketone at C2 and a fluorine at C5; no stereogenic centers in the parent framework; highly symmetrical, conformationally locked scaffold.
  • 2D description: a fused tricyclic hydrocarbon (adamantane) where one bridgehead-adjacent carbon bears a carbonyl (C=O), and a non-adjacent tertiary carbon on the opposite face bears F.

Synthetic Utility

Functional groups and reactivity (general):

• Ketone at C2: engages in nucleophilic additions (RMgX, RLi), reductions (NaBH4, LiAlH4), imine/oxime/hydrazone formation, and Baeyer–Villiger oxidation to lactones. The rigid cage often affords high stereocontrol in additions to the carbonyl carbon.
• C–F at C5: typically inert under standard nucleophilic/electrophilic conditions, serving as an electronic modifier and lipophilicity dial; under superacidic conditions, adamantyl C–X bonds can be replaced, but such methods are specialized.

Strategic roles:

• Late-stage introduction of the adamantyl group: use the ketone to append diverse sidechains that project from a sterically demanding core.
• Protecting-group-lite synthesis: the stability of C–F and the cage minimizes side reactions, enabling concise routes.
• Scaffold diversification: oxime → Beckmann rearrangement; Baeyer–Villiger → lactone → further ring-openings to access functionalized fluorinated adamantane derivatives.

Retrosynthetic value:

• Target tertiary alcohols or amines bearing 5-fluoroadamantyl as a bulky, metabolically robust substituent. Trace back through carbonyl chemistry to 5-fluoroadamantan-2-one as a convergent hub.

Target Specificity

Not applicable. This product is a small-molecule chemical, not a biological targeting reagent (e.g., antibody, enzyme, nucleic acid). No antigen/epitope or species reactivity applies.