Cyclohexanone, 2-(phenylmethoxy)- , CAS No.36713-55-0

CAS: 36713-55-0 Cat. No.: C978370 Summenformel: C₁₃H₁₆O₂ Molekulargewicht: 204.260

Storage

Room temperature

Specifications

Storage

Room temperature

Namen und Kennungen

• Kanonisches Lächeln: C1CCC(=O)C(C1)OCC2=CC=CC=C2
• IUPAC Name: 2-phenylmethoxycyclohexan-1-one
• InChIKey: DAAFSJHSNQOYMU-UHFFFAOYSA-N
• INCHI: 1S/C13H16O2/c14-12-8-4-5-9-13(12)15-10-11-6-2-1-3-7-11/h1-3,6-7,13H,4-5,8-10H2
• Molekulargewicht: 204.260

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzylethers
• Alternative Parents: Cyclic ketones Dialkyl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzylether - Cyclic ketone - Ketone - Ether - Dialkyl ether - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 204.260 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 204.115 Da
• Monoisotopic Mass: 204.115 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 207.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 standardized bioassay, immunoassay, or imaging protocols are associated with this small-molecule building block. For synthetic use, see Reaction Conditions for non-binding, literature-style procedures (e.g., hydrogenolysis, enolate alkylation, Baeyer–Villiger oxidation).

Biological Roles

This compound is a synthetic organic intermediate without inherent biological function in standard pathways.

• General context (literature)

  • Benzylic ethers and cyclic ketones of this type are not naturally occurring metabolites and have no established roles in biochemistry. They may be used as precursors to probe molecules or ligands after further functionalization but have no direct signaling or enzymatic relevance.
  • Upon transformation (e.g., debenzylation), the derived 2-hydroxycyclohexanone can participate in enzymatic-like reactions in biomimetic studies (e.g., enolization, hemiacetal formation), yet these are model systems rather than physiological processes.

• Safety note

  • Any mention of biological interaction should be interpreted strictly in a research chemistry context. This product is for research use only and not intended for food, drug, cosmetic, or household use.

Buffer Applications

Not typically applicable. Cyclohexanone, 2-(phenylmethoxy)- is a hydrophobic organic building block, not a buffering agent. It does not participate in conventional aqueous buffer systems. For laboratory use involving this compound, select an appropriate organic solvent system as discussed under Solvent Selection and Reaction & Applications.

Green Alternatives

While this product is a substrate rather than a solvent, greener choices can be made for the media and reagents used with it.

• Greener solvent swaps (literature guidance)

  • Replace DCM/chloroform with EtOAc, 2-MeTHF, or CPME when feasible; these provide adequate solubility and improved environmental profiles.
  • For enolate chemistry, 2-MeTHF often substitutes for THF with similar cryogenic performance but better renewability; CPME can allow higher reflux temperatures and water tolerance.
  • Alcohols: Prefer ethanol over methanol for hydrogenolysis when compatible, due to lower toxicity and bio-based sourcing options.

• Oxidants and reductants

  • Baeyer–Villiger: Consider hydrogen peroxide with catalytic systems (e.g., Sn-beta zeolite, organocatalysts) as alternatives to mCPBA, reducing chlorinated waste.
  • Debenzylation: Transfer hydrogenation using HCO2NH4 or cyclohexene with Pd/C can avoid high-pressure H2 cylinders on small scale.

• Energy and workup

  • Leverage flow hydrogenolysis for efficient H2 usage and enhanced safety.
  • Replace brine/DCM extractions with EtOAc/MTBE systems and minimal aqueous washes when possible.

Comparison snapshot (general)

• THF vs 2-MeTHF: Similar performance; 2-MeTHF is bio-derived, less miscible with water, facilitates phase separations.
• DCM vs EtOAc: EtOAc has lower toxicity and better biodegradability; may require larger volumes for equivalent solubility.

Ensure that any alternative maintains chemoselectivity (e.g., preserve benzyl ether until intended cleavage). Validate on small scale before implementation.

Pharmaceutical Uses

No pharmacopeial or excipient status is indicated for this item.

• Item-specific

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

• General formulation context (literature)

  • As a small-molecule intermediate, 2-(benzyloxy)cyclohexanone may serve as a starting material or protected synthon toward drug-like scaffolds containing 1,2-oxygenation patterns, lactones, or benzylic aryl motifs. It is not used as an active ingredient or approved excipient.
  • Hydrogenolysis can unmask 2-hydroxycyclohexanone for subsequent derivatization (e.g., carbamate, carbonate, or ester formation) during route scouting.

All uses are strictly for research and process development; no clinical or therapeutic claims are made or implied.

Physical Properties

Item-specific specifications for this catalog lot are not provided. Where values are useful for planning, indicative literature/computational information is summarized and explicitly labeled.

• Item-specific specs (this product)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
  • Water, peroxides, metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Typical physical data (literature/estimates; non-spec)

  • Physical state: Generally reported as a colorless to pale yellow liquid or low-melting solid depending on sample history and purity (literature).
  • Molecular weight (from formula C13H16O2, literature/inference): ~204.27 g/mol.
  • Density: Often near 1.05–1.12 g/mL at 20–25 °C for similar benzyloxycyclohexanones; specific value for this item not established (literature trend only).
  • Boiling behavior: Distills at elevated temperature; reported bp values vary widely with pressure for benzylic ethers. Use short-path or Kugelrohr under reduced pressure to minimize thermal decomposition (literature guidance).
  • Melting point: Often below ambient; specific value not compiled (literature trend only).
  • Solubility: Low in water; miscible with common organic solvents (Et2O, DCM, THF, acetone, EtOAc, toluene, alcohols) (literature).
  • Refractive index: Typical nD for related benzylic ethers ~1.50–1.54 (literature trend).
  • LogP: Expected moderate hydrophobicity due to benzyl group (cLogP in the ~2–3 range for analogs; literature/computation trend).

Always treat the above as planning guidance only; confirm with your own measurements or primary literature for critical work.

Quality and Grades

• Item-specific (Product Data)

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

• Guidance on interpreting grades (general)

  • Research-grade organics are typically suitable for synthesis and method development. If offered in HPLC or LC–MS grade, those denote stringent controls on UV background, particulates, and often water/volatile impurities—useful when this molecule is a mobile-phase modifier or reference standard (not the typical role here).
  • For synthetic building blocks, supplier specifications may include assay (GC/GC–MS/NMR), residual solvents, and limits on common impurities (e.g., benzylic alcohol, anisole, unfunctionalized cyclohexanone). When stereochemistry is relevant, enantiomeric/diastereomeric ratios may be specified.

• Stabilizers/inhibitors

  • No stabilizer is indicated for this item. If present in a particular lot, that will be disclosed on the CoA and may impact certain reactions (e.g., hydrogenolysis or oxidative steps). Always check the CoA.

• Acceptance testing suggestions (practitioner tips)

  • Verify identity by 1H/13C NMR (distinct benzylic –CH2– at ~4.5–5.2 ppm; carbonyl at ~δC 208–212), IR (C=O ~1715–1730 cm−1; Ar C–H), and GC–MS/LC–MS (M+•/MH+ consistent with ~204 Da).
  • Assess residual cyclohexanone and benzyl alcohol; both are common process-related impurities.

Reaction and Applications

As a benzyloxylated α-keto building block, 2-(benzyloxy)cyclohexanone is a versatile intermediate for accessing oxygenated cyclohexane motifs and lactones.

• Debenzylation to 2-hydroxycyclohexanone (literature)

  • Hydrogenolysis: Pd/C, H2 (1–3 atm), MeOH/EtOH, rt–40 °C, providing the α-hydroxy ketone. This unmasking enables downstream aldolizations, acylations, and cyclic hemiacetal equilibria.
  • Alternative cleavage: Lewis-acid-assisted transfer hydrogenation or dissolving metal/hydrogenolytic systems; avoid strong acids that may prompt carbocationic rearrangements.

• Enolate and α-functionalization chemistry (literature)

  • The α-alkoxy substituent modulates enolate geometry and electrophile approach (Felkin–Anh and Cram-type considerations). Typical transformations include α-alkylation, α-azidation, α-fluorination, and nitrosation.
  • Chelation-controlled additions (e.g., with Mg2+, TiCl4) can impart diastereoselectivity.

• Oxidation and rearrangements (literature)

  • Baeyer–Villiger oxidation gives δ-lactones bearing benzyloxy substituents, which can be further manipulated and/or debenzylated to diols.
  • α,β-Unsaturation can be introduced via selenoxide or bromination–elimination sequences (then exploited in Michael additions).

• Reductive elaborations (literature)

  • NaBH4 or catalytic hydrogenation can reduce the carbonyl to give 1,2-diol frameworks (after subsequent debenzylation) or 2-(benzyloxy)cyclohexanol as an intermediate.

• Protecting-group relay (literature)

  • The benzyl ether serves as a temporary protecting group for a 2-hydroxyl, surviving many base-mediated steps and removable under mild H2/Pd conditions—useful in cascade or telescoped sequences.

Practical tips: Use anhydrous conditions for base-driven steps; monitor for benzyl cation–derived side products under strong acid. Silica containing residual acid may slowly cleave benzyl ethers; neutralize or use basic alumina for chromatography when needed.

Reaction Conditions

The following are literature-style, non-binding conditions commonly employed with α-alkoxy cyclohexanones; optimize for your system.

• Debenzylation (hydrogenolysis)

  • Catalyst: 5–10 wt% Pd/C (5–20 mol% Pd relative to substrate for small scale)
  • Solvent: MeOH or EtOH (EtOAc or AcOEt/EtOH mixtures also effective)
  • H2 pressure: 1–3 atm; Temperature: 20–40 °C; Time: 1–8 h
  • Notes: Degas solvent; filter over celite to remove Pd; avoid sulfur/amine poisons. For acid-sensitive substrates, add small amounts of base (e.g., Et3N) to suppress acetalization.

• Enolate formation and α-alkylation

  • Base: LDA or LHMDS (1.1–1.5 equiv)
  • Solvent: Dry THF, 2-MeTHF, or toluene; Temperature: −78→0 °C
  • Electrophiles: MeI, BnBr, allyl/benzyl halides, aldehydes (for aldol after TiCl4 mediation)
  • Notes: The α-alkoxy group can favor E-enolate; control geometry via base/temperature. Quench at low temperature to limit O- vs C-alkylation.

• Baeyer–Villiger oxidation

  • Reagent: mCPBA (1.2–2.0 equiv, buffered) in DCM at 0–25 °C; Time: 2–16 h
  • Greener variant: H2O2 (30%) with catalytic systems (e.g., Sn-beta) in MeCN or alcohols
  • Notes: Control acidity to protect the benzyl ether. Work up with Na2S2O3/NaHCO3.

• Carbonyl reduction

  • NaBH4 (1.2–2.0 equiv) in MeOH/EtOH at 0–25 °C; or catalytic hydrogenation (Pd/C) in alcohols
  • Provides 2-(benzyloxy)cyclohexanol; subsequent hydrogenolysis yields 1,2-diol motifs.

Yields and selectivities depend on substitution and scale; run small-scale trials and monitor by TLC/GC–MS/LC–MS.

Safety and Handling

Safety classifications specific to this item are not provided by the supplier in the Product Data.

• Item-specific (from Product Data)

  • GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to the SDS.
  • Storage conditions: Room temperature.

• General hazards (literature/analog-based; not a specification)

  • Organic ketone/benzyl ether: May cause skin/eye irritation and respiratory irritation upon vapor or aerosol exposure. Avoid inhalation and contact. Some ketones and benzylic ethers can form sensitizing or irritating peroxides upon prolonged air exposure, though benzyl ethers are generally less prone than dialkyl ethers.
  • Flammability: Many benzylic ethers and ketones are combustible liquids; keep away from ignition sources. Determine flash point from SDS before scale-up.

• Handling and PPE (good laboratory practice)

  • Use in a fume hood; wear safety glasses, lab coat, and chemical-resistant gloves (e.g., nitrile). For extended contact, verify glove compatibility.
  • Prevent contact with strong oxidizers and strong acids/bases that could promote cleavage or side reactions.
  • Avoid heating to decomposition; distill under reduced pressure if purification is required.

• First aid (overview; defer to SDS)

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation develops.
  • Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.

Consult the product’s SDS for authoritative hazard, exposure limit, flash point, and disposal instructions.

Solvent Selection

This product is an organic building block, not a solvent. The following guidance focuses on dissolving and reacting it efficiently.

• Polarity and solubility (literature trends)

  • Poorly soluble in water; readily soluble in moderately polar and nonpolar organics: DCM, chloroform, THF, EtOAc, acetone, toluene, diethyl ether, and alcohols.
  • As an α-alkoxy ketone, it is compatible with many aprotic media used for enolate chemistry.

• Choosing a solvent by operation

  • Hydrogenolysis (debenzylation): MeOH, EtOH, or EtOAc under H2/Pd–C are common; avoid sulfur-containing solvents that poison Pd.
  • Enolate generation/α-functionalization: Anhydrous THF, MTBE, or toluene with LDA/LHMDS at −78 to 0 °C.
  • Oxidation (Baeyer–Villiger): DCM or chlorinated solvents with peracids (e.g., mCPBA) at 0–25 °C.
  • Reductions (NaBH4, catalytic hydrogenation): Alcohols (MeOH/EtOH) or protic/aprotic mixtures.

• Quick comparison (general)

  • THF vs 2-MeTHF: 2-MeTHF offers similar solubility with improved sustainability and water partitioning; consider for scale.
  • DCM vs EtOAc: EtOAc is greener and often sufficient for workup/extractions; DCM may be favored for low-temperature control and faster phase separation.

Always dry solvents for strong base chemistry; trace water promotes retro-additions and undesired cleavage.

Storage and Reconstitution

• Item-specific (Product Data)

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

• General storage guidance (good practice)

  • Store tightly capped under inert gas (N2/Ar) when possible to minimize oxidative byproducts and moisture uptake.
  • Keep away from strong acids/bases and oxidizers. Protect from prolonged light exposure to limit benzylic oxidation.
  • If long-term storage is anticipated, refrigeration (2–8 °C) can further slow degradation, though not required per Product Data.

• Reconstitution/handling

  • Supplied neat. Warm gently to dissolve if crystallized; sonication or addition of a small volume of a compatible solvent (e.g., DCM, THF, EtOAc) can assist in weighing/transfer.
  • For air- or moisture-sensitive steps, dispense by syringe or under inert atmosphere into dry solvent.

• Stability notes (general)

  • Benzyl ethers are generally stable; monitor for hydrolysis or oxidation upon extended storage. Test purity by NMR/GC–MS prior to critical applications.

Refer to the product CoA/SDS for any lot-specific storage and stability statements.

Structure and Identity

A benzyloxylated cyclic ketone useful as a masked 2-hydroxycyclohexanone building block and a handle for α-functionalization chemistry.

• Item-specific (Product Data)

  • SKU: C978370
  • Product name: Cyclohexanone, 2-(phenylmethoxy)- (also known as 2-(benzyloxy)cyclohexanone)
  • CAS: 36713-55-0
  • InChIKey: 58046 (as provided)
  • Storage conditions: Room temperature
  • Research use: For research use only

• Structure (literature/structural inference)

  • Common name: 2-(Benzyloxy)cyclohexanone
  • Functional groups: cyclic ketone (cyclohexanone), benzylic ether (–O–CH2–C6H5) at the α-position to the carbonyl
  • Molecular formula (inferred): C13H16O2
  • Molecular weight (inferred): ~204.27 g/mol
  • Proposed SMILES (structural inference): O=C1CC(OCH2c2ccccc2)CCC1
  • Stereochemistry: Typically supplied as a racemic mixture at C2 unless otherwise specified (no stereochemical information provided for this item)

• 2D structure description (words; general)

  • A six-membered ring bearing a ketone at C1. At the adjacent carbon (C2), an ether oxygen links to a benzylic –CH2– that is para- to ortho protons on a monosubstituted phenyl ring. The α-carbon (C2) is stereogenic in the absence of rapid enolization, giving potential for enantiomeric or diastereomeric contexts in chiral environments.

Note: Exact identifiers (e.g., InChI, definitive SMILES, stereochemistry) for this catalog item are not specified by the supplier beyond what is listed above; consult the CoA/SDS for definitive identity data.

Synthetic Utility

Key reactivity arises from the juxtaposition of a carbonyl and an α-alkoxy (benzyloxy) substituent.

• Functional group synopsis

  • Ketone: amenable to reductions (NaBH4, catalytic hydrogenation), oxidations (Baeyer–Villiger), condensations (aldol, Claisen–Schmidt with prior enolization), and enamine chemistry.
  • Benzylic ether: robust to many bases and nucleophiles; removable by hydrogenolysis to reveal an α-hydroxy ketone—unlocking 1,2-diol and acetal chemistry after further manipulation.

• Strategic roles (literature)

  • Protected α-hydroxy motif: Serves as a relay protecting group for C2–OH during enolate-driven C–C bond formation. After α-alkylation or acylation, benzyl deprotection affords stereodefined α-hydroxy ketones.
  • Stereocontrol: Under chelating conditions (e.g., TiCl4-mediated additions), the α-alkoxy can direct approach of nucleophiles (Cram/chelation control), enabling diastereoselective synthesis of substituted cyclohexanones.
  • Lactone access: Baeyer–Villiger introduces oxygen adjacent to the carbonyl, yielding δ-lactones that retain or translate the benzyloxy handle for further diversification.

• Representative transformations (literature)

  • α-Alkylation: LDA, THF, −78→0 °C; electrophiles: MeI, benzyl bromides, allyl bromides.
  • α-Halogenation/fluorination: NFSI or Selectfluor under mild conditions.
  • Debenzylation: H2 (1–3 atm), Pd/C, MeOH/EtOH, rt–40 °C, furnishing 2-hydroxycyclohexanone.
  • Reductive routes to 1,2-diols: Carbonyl reduction followed by O-debenzylation.

These features make the compound a compact, high-information synthon for assembling oxygen-rich cyclohexane frameworks and bicyclic derivatives.

Target Specificity

Not applicable. This product is a small-molecule organic intermediate, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined target, or affinity ligand). No antigen, epitope, or species reactivity data are associated with this catalog item.