2-Phenyladamantane - ≥95% , CAS No.19066-24-1

CAS: 19066-24-1 Cat. No.: P1361819 Formula: C₁₆H₂₀ Molecular Weight: 212.34 PubChem CID: 527341

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Shipped In

Normal

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1C2CC3CC1CC(C2)C3C4=CC=CC=C4

IUPAC Name

2-phenyladamantane

InChIKey

MWQZYLIXDPNHFG-UHFFFAOYSA-N

INCHI

1S/C16H20/c1-2-4-13(5-3-1)16-14-7-11-6-12(9-14)10-15(16)8-11/h1-5,11-12,14-16H,6-10H2

Isomeric SMILES

C1C2CC3CC1CC(C2)C3C4=CC=CC=C4

PubChem CID

527341

Molecular Weight

212.34

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Monocyclic benzene moiety - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• 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: 212.330 g/mol
• XLogP3: 5.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 212.157 Da
• Monoisotopic Mass: 212.157 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 233.000
• 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.

• No validated immunoassay or diagnostic application protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic and materials applications, refer to Reaction Conditions and Synthetic Utility for guidance.

Biological Roles

Applicability note

• 2-Phenyladamantane is a synthetic hydrocarbon research chemical with no inherent biological function. The following points address general biochemical context without implying clinical use.

General context (literature/general)

• Adamantane motif: The rigid, hydrophobic cage is used in chemical biology as a probe or lipophilic tag to modulate membrane interactions or to engage host–guest systems (e.g., adamantane–cucurbituril complexes) for sensing and assembly.
• Structure–property effects: Incorporation into small molecules can increase hydrophobic surface area and steric bulk, which may affect binding in hydrophobic pockets or alter permeability in model membranes; such effects are system-dependent and must be empirically validated.
• Metabolic stability: The saturated adamantyl cage is known for metabolic robustness in vitro; attaching a phenyl group often further increases resistance to oxidative degradation on the cage, shifting any biotransformations toward the aromatic ring (general trend; actual outcomes are context-specific).

Research use only

• Any evaluation of biochemical interactions, labeling, or host–guest studies should be conducted under laboratory research protocols. No medical or therapeutic claims are made for this product.

Buffer Applications

Not typically applicable.

• 2-Phenyladamantane is a hydrophobic, non-ionic solid and does not function as a buffering agent. It is essentially insoluble in aqueous buffers and is not used to control pH.
• For work involving this compound, focus on organic solvent handling and derivatization strategies (see Solvent Selection, Reaction & Applications).

Green Alternatives

Context

• 2-Phenyladamantane is itself a hydrocarbon building block; “greenness” considerations pertain primarily to its synthesis, solvents, and workup rather than to substituting the molecule.

Greener processing choices (general guidance)

• Solvent selection: Prefer methyl tert-butyl ether (MTBE), 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), or ethyl acetate over chlorinated solvents when feasible for dissolution, reactions on the aryl ring, and extractions.
• Catalysis: Use catalytic halogenation (e.g., NBS with photoredox) or electrochemical methods in place of stoichiometric halogens when appropriate; adopt Pd-catalyzed couplings in green solvents (e.g., aqueous micelles, 2-MeTHF).
• Energy: Conduct reactions at ambient temperature and employ flow chemistry to improve heat/mass transfer for exothermic electrophilic substitutions.
• Workup/waste: Aim for solvent recycling, minimize silica usage via crystallization-driven purifications, and apply greener recrystallization pairs (EtOAc/hexane or MeOH/water for derivatives bearing polar groups).

Illustrative comparison (general)

• Chlorinated solvents (DCM/CHCl3): Strong dissolving power; higher toxicity/volatility; difficult waste stream.
• Aromatic hydrocarbons (toluene): Effective solvency; flammable VOC; widely recoverable by distillation.
• Ethers (2-MeTHF/CPME): Good balance of solvency and sustainability; peroxide formation risk over time—manage via testing/scavenging.

Note

• Select greening strategies consistent with your route; maintain product quality and safety while reducing environmental footprint.

Pharmaceutical Uses

Applicability note

• This product is offered for research use only. No medical or clinical uses are claimed or supported.

General formulation/manufacturing context (literature/general)

• Role in discovery chemistry: The adamantyl–phenyl motif is used as a hydrophobic pharmacophore fragment during hit-to-lead optimization to modulate physicochemical properties (lipophilicity, steric profile). Any such use remains within nonclinical research.
• Excipient status: 2-Phenyladamantane is not a common pharmaceutical excipient, and there is no established pharmacopeial monograph known for this specific compound. Regulatory specifications for use in drug products are therefore not established.
• Processing: If formulated into research materials, dissolve in appropriate organic media or embed in polymer matrices; avoid aqueous vehicles unless a solubilization strategy (e.g., cyclodextrin inclusion complexes with adamantane-binding hosts) is intentionally developed for research purposes.

Note

• For any application intersecting GMP or preclinical development, define material controls (identity, purity, residual solvents, and potential catalysts) and obtain a detailed CoA.

Physical Properties

Item-specific (Product Data)

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

Literature/General (for reference only; not item specifications)

• Physical state: Typically a crystalline, nonpolar hydrocarbon solid (literature).
• Molecular weight: 212.33 g/mol (C16H20) (literature).
• Solubility: Expected to be insoluble in water; soluble in nonpolar/low-polarity organic solvents (e.g., hexanes, toluene, DCM) (general chemical knowledge).
• Density, melting point, boiling point, refractive index, logP, pKa/Brønsted basicity: Not specified here; consult primary literature or measure experimentally for your application.

Practical notes (general)

• The adamantane cage confers high thermal stability and low volatility relative to simple alkylbenzenes. The phenyl ring allows standard aromatic functionalization (e.g., halogenation, nitration under controlled conditions). For chromatographic handling, normal-phase systems with nonpolar eluents are typically effective. For precise specifications needed for process design (e.g., melting point, DSC onset, Hansen parameters), refer to peer-reviewed sources or determine experimentally.

Quality & Grades

Item-specific (Product Data)

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

Guidance for this compound class (general)

• Hydrocarbon building blocks like 2-phenyladamantane are commonly offered as research-grade organics. When grade is unspecified, assume general laboratory/research use; verify suitability for analytical or synthetic needs by reviewing the CoA (e.g., NMR purity, GC assay, residual solvents, and identity confirmation by MS/IR).
• UV background: As an aromatic hydrocarbon, it absorbs in the UV; if using in photophysical studies or as a chromatography standard, evaluate UV cutoffs empirically.
• Impurities of concern: Unreacted adamantane or polyalkylated benzenes, trace halogenated byproducts if halogen-mediated synthesis was used, and residual catalysts/acid residues from Friedel–Crafts routes. Request metals/halide content if your process is catalyst-sensitive.
• Stabilizers: None are typically required for saturated hydrocarbons of this type; product is generally shipped neat without additives unless otherwise stated in the CoA.

Recommendation

• For critical applications (e.g., materials research, mechanistic studies), specify analytical criteria (GC/NMR purity thresholds) in your purchase order or request a detailed CoA.

Reaction & Applications

General research applications (literature/general)

• Hydrophobic scaffold: Widely used as a rigid, bulky hydrocarbon appendage to modulate lipophilicity, steric profile, and conformational restriction in organic molecules and materials.
• Precursor to substituted derivatives: The phenyl ring enables downstream transformations (e.g., halogenation, nitration, sulfonation) to create handles for cross-coupling or further functionalization while retaining the adamantyl core.
• Cation chemistry: Under superacidic conditions, adamantyl centers can generate stabilized tertiary carbocations; 2-phenyl substitution influences cation rearrangements and has been studied mechanistically.
• Materials/host–guest: Adamantane motifs are used in supramolecular chemistry (e.g., binding with cucurbiturils or β-cyclodextrin derivatives) and as bulky spacers in polymers; the phenyl group can improve compatibility with aromatic matrices.

Synthesis/derivatization notes

• Electrophilic aromatic substitution on the phenyl ring (e.g., Br2/Fe, NBS/benzoyl peroxide, nitration under controlled conditions) installs leaving groups or nitro groups for subsequent cross-couplings or reductions.
• Metal-catalyzed cross-couplings: After aryl halogenation, apply Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira protocols to elaborate the aromatic periphery.
• Benzylic oxidation on suitably substituted derivatives and C–H functionalization strategies may be explored, but the adamantane cage is resistant toward many radical/oxidative conditions, aiding chemoselectivity.

Use considerations

• The bulky, lipophilic nature can dramatically affect solubility and phase behavior of target molecules; small structural changes may yield large ADMES-like property shifts in discovery settings (research use only).

Reaction Conditions

General literature guidance (not item specifications)

• Electrophilic aromatic bromination (to enable cross-coupling):
  • Solvent: CHCl3, DCM, or acetic acid; greener options include EtOAc or toluene.
  • Reagents: Br2/FeBr3 or NBS with radical initiator or photochemical activation.
  • Temperature: 0–25 °C (monitor to avoid polybromination). Typical times: 0.5–4 h.
• Suzuki–Miyaura coupling (using a pre-brominated derivative):
  • Catalyst/base: Pd(dppf)Cl2·DCM or Pd(PPh3)4; K2CO3 or K3PO4.
  • Solvent: Dioxane/water, 2-MeTHF, or toluene/EtOH/H2O mixtures.
  • Temperature: 60–100 °C; time: 2–12 h.
• Buchwald–Hartwig amination (from aryl bromide):
  • Catalyst/ligand: Pd2(dba)3 with BINAP/XPhos; base: NaOtBu or Cs2CO3.
  • Solvent: Toluene, dioxane, or 2-MeTHF.
  • Temperature: 80–110 °C; time: 6–18 h.
• Nitration (controlled):
  • Reagents: HNO3/H2SO4 at low temperature (−10 to 0 °C) to limit overreaction.
  • Workup: Quench into ice/water, extract with toluene or DCM; neutralize carefully.

Operational tips

• Ensure complete dissolution in a suitable organic solvent before adding reagents; the bulky hydrophobe benefits from good mass transfer.
• Because the adamantyl cage is robust, chemoselectivity usually favors the aromatic ring; nonetheless, avoid excessively harsh conditions that could crack the cage (strong oxidants at high temperature).
• For scale-up, monitor exotherms during electrophilic substitutions and provide efficient stirring due to low polarity and high viscosity of some media.

Safety & Handling

Item-specific (Product Data)

• GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature (store tightly closed, per good lab practice). Shipped at ambient temperature.

General safety guidance (not a substitute for SDS)

• Likely hazards: Hydrocarbon solids of this class are generally combustible; dust generation should be minimized. Not expected to be corrosive or strongly irritating, but avoid inhalation of dust and contact with skin/eyes.
• PPE: Wear lab coat, safety glasses, and appropriate gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or solvent vapors from solutions.
• Incompatibilities: Strong oxidizers (risk of exothermic oxidation); chlorinating/nitrating agents may cause vigorous electrophilic substitution on the aromatic ring. Avoid strong acids in the presence of oxidants.
• First aid (overview): If inhaled, move to fresh air; for skin/eye contact, rinse with water for at least 15 minutes; if ingested, rinse mouth and seek medical attention. Always follow institutional protocols.
• Fire-fighting: Use CO2, dry chemical, or foam. Cool containers with water spray. Combustion may produce soot and CO/CO2.

Always consult the product-specific SDS for authoritative hazard classification and response measures.

Solvent Selection

Applicability note

• 2-Phenyladamantane is a solid building block, not a solvent. This section focuses on solvents suitable for dissolving/processing this compound.

General solvent guidance (literature/general)

• Polarity class: Nonpolar, hydrophobic aromatic–alicyclic hydrocarbon.
• Expected solubility profile: Good in nonpolar to moderately polar organic solvents; poor in protic and strongly polar media.
• Typical choices:
  • Excellent: Hexanes, heptane, cyclohexane, toluene, xylene, chlorobenzene.
  • Good: Dichloromethane, chloroform, ethyl acetate.
  • Limited: Alcohols (MeOH/EtOH/i-PrOH) and acetonitrile; heating may be required.
  • Poor: Water and aqueous buffers.
• Dielectric/interaction rationale: The rigid adamantyl core plus phenyl ring favors dispersion-dominated solvation; aromatic solvents can provide favorable π–π/dispersion interactions.

Practical tips

• For recrystallization: Toluene/hexane or ethyl acetate/hexane mixtures often provide good control of crystallinity for aromatic hydrocarbons (optimize empirically).
• For chromatography: Start with hexane-rich eluents; add small percentages of DCM or EtOAc as needed to achieve movement without tailing.
• For kinetics/photophysics: Use high-purity, low-fluorescence aromatic solvents if optical measurements are envisioned.

Storage & Reconstitution

Item-specific (Product Data)

• Storage conditions: Room temperature. Keep container tightly closed in a dry, well-ventilated place. Protect from strong oxidizers.
• Shipped in: Normal (ambient) conditions.

General handling

• Physical form: Neat solid; no reconstitution is typically required. If preparing stock solutions, use dry organic solvents (e.g., toluene, DCM, hexanes) and store in sealed glass vials.
• Solution stability: In anhydrous, oxygen-free conditions, solutions are generally stable for days to weeks depending on solvent. For long-term storage, prefer the neat solid.
• Freeze–thaw: Not applicable to the neat solid. If storing solutions at low temperature, allow to equilibrate to room temperature before opening to avoid moisture ingress/condensation.

Label-specific parameters

• Any item-specific limits (residual solvents, metals, water content, UV cutoff) are Not specified for this item; refer to CoA/Spec Sheet.

Disposal

• Dispose of contents/container in accordance with local/regional regulations for hydrocarbon organic chemicals.

Structure & Identity

Item-specific (Product Data)

• Product name: 2-Phenyladamantane (SKU: P1361819)
• CAS: 19066-24-1; PubChem CID: 527341
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/Computed (general reference only)

• Molecular formula: C16H20 (literature)
• Molecular weight: 212.33 g/mol (literature)
• Structural features: An adamantane cage (triaxial, highly symmetrical polycyclic C10 framework) substituted at the 2-position by a phenyl ring. The adamantane portion contains three fused cyclohexane chairs; the phenyl substituent is attached at a bridgehead carbon, imparting a rigid, bulky, hydrophobic scaffold. No heteroatoms, no formal charges, no stereocenters.
• 2D description: A benzene ring directly bonded to a single carbon of the adamantane cage; remaining adamantane positions are saturated carbons (sp3). The phenyl is sp2; the cage is entirely sp3.

Notes

• Identity confirmation is typically performed by 1H/13C NMR (characteristic adamantyl multiplets and aromatic signals), HRMS (M+ = 212.16 Da), and melting behavior; consult the item’s CoA for actual characterization results.

Synthetic Utility

Functional group and reactivity profile (general)

• Core features: A phenyl ring (amenable to electrophilic aromatic substitution and cross-coupling after halogenation) and an adamantyl cage (sterically bulky, saturated, oxidation-resistant under many conditions).
• Strategic value: Serves as a rigid, lipophilic appendage to modulate conformation, packing, and solubility of target molecules; useful in ligands, monomers, and probes.

Representative transformations (literature/general)

• Aryl halogenation: Electrophilic bromination/chlorination on the phenyl ring to produce 2-(halo)phenyladamantanes as versatile cross-coupling substrates.
• Cross-coupling: Suzuki–Miyaura (with boronates), Buchwald–Hartwig (amines), Sonogashira (alkynes) on the pre-halogenated aryl to append functionality while retaining the adamantyl moiety.
• Nitration/reduction: Controlled nitration of the phenyl followed by reduction affords anilines; subsequent acylation/alkylation provides diverse derivatives.
• Directed metallation: Strong-base-mediated ortho-metalation may be feasible with appropriate directing groups introduced on the phenyl ring.
• Oxidation resistance: The adamantane cage is typically inert towards mild oxidants/ radicals, enabling selective reactions on the aryl substituent.

Practical tips

• Purification: Nonpolar; normal-phase silica with hexane-rich eluents works well. Crystallization from aromatic solvent/alkane pairs can give high purity.
• Analysis: 1H NMR shows characteristic adamantyl multiplets (~1.5–2.1 ppm) and aromatic signals (~7.0–7.5 ppm); GC/MS shows M+ at m/z 212.
• Protecting-group-like behavior: The adamantyl unit can act as a steric shield, sometimes suppressing undesired reactions proximal to the aryl–cage junction.

Target Specificity

Not applicable.

• This product is a small-molecule hydrocarbon building block. There are no biological targets, epitopes, clones, isotypes, or species reactivities associated with this item.