3,3,5-Trimethylcyclohexanone - ≥98%(GC) , CAS No.873-94-9

CAS: 873-94-9 Cat. No.: T161473 Formula: C₉H₁₆O Peso molecolare: 140.23 Beilstein Registry Number: 507452 Numero EC: 212-855-9 PubChem CID: 13398

QUALITÀ & PUREZZA ≥98%(GC)

Synonyms

EC 212-855-9 | AKOS016844138 | STL146504 | EN300-19037 | FT-0614017 | 3,5,5-Trimethylcyclohexanone | SCHEMBL24862 | 3,5,5-trimethyl cyclohexanone | 3.3.5-Trimethyl cyclohexanone | AKOS000119271 | NCGC00256179-01 | VS-02938 | EINECS 212-855-9 | (+/-)-DIHYD

Storage

Room temperature

Shipped In

Normal

Specifiche

Sinonimi

EC 212-855-9 | AKOS016844138 | STL146504 | EN300-19037 | FT-0614017 | 3,5,5-Trimethylcyclohexanone | SCHEMBL24862 | 3,5,5-trimethyl cyclohexanone | 3.3.5-Trimethyl cyclohexanone | AKOS000119271 | NCGC00256179-01 | VS-02938 | EINECS 212-855-9 | (+/-)-DIHYD

Specifiche e purezza

≥98%(GC)

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥98%(GC)

Nomi e identificatori

Pubchem Sid

488181845

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488181845

Sorrisi canonici

CC1CC(=O)CC(C1)(C)C

IUPAC Name

3,3,5-trimethylcyclohexan-1-one

InChIKey

POSWICCRDBKBMH-UHFFFAOYSA-N

INCHI

1S/C9H16O/c1-7-4-8(10)6-9(2,3)5-7/h7H,4-6H2,1-3H3

Isomeri SMILES

CC1CC(=O)CC(C1)(C)C

WGK Germania

1

RTECS

GW2185000

PubChem CID

13398

Peso molecolare

140.23

Beilstein

507452

Reaxy-Rn

507452

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones
• Direct Parent: Cyclic ketones
• Alternative Parents: Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclic ketone - Organic oxide - Hydrocarbon derivative - Aliphatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
• 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

• Indice di rifrazione: 1.445
• Punto di infiammabilità (°F): 150.8 °F
• Punto di infiammabilità (°C): 68°C(lit.)
• Punto di ebollizione (°C): 188-192 °C (lit.)
• Punto di fusione (°C): −10 °C (lit.)
• Peso molecolare: 140.220 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 140.12 Da
• Monoisotopic Mass: 140.12 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 147.000
• 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

No assay/application protocols are specified for this SKU. Not specified for this item; refer to CoA/Spec Sheet.

General lab protocol examples (non-binding, literature-based) for method development with alicyclic ketones:

• Enolate alkylation (screening): Dry a 50 mL Schlenk flask; charge substrate (1.0 mmol) in dry THF (10 mL). Cool to −78 °C under N2. Add 1.1 mmol LDA (1.5 M in THF/heptane) dropwise. Stir 30 min, then add alkyl halide (1.2 mmol). Warm to −20 °C over 1 h. Quench with sat. NH4Cl, extract, dry, and purify by flash chromatography.
• Baeyer–Villiger (screening): Dissolve substrate (1.0 mmol) in CH2Cl2 (10 mL), cool to 0 °C. Add mCPBA (1.2 mmol, pre-dried). Stir 2–16 h from 0 to 25 °C. Wash with Na2CO3, then Na2S2O3, water; dry and concentrate. Analyze regioisomer ratio by NMR.

These examples are provided for research planning only and are not validated conditions for this specific lot/material.

Biological Roles

This compound is an industrial/academic organic intermediate and does not have a known endogenous biological role. It is not a buffer, enzyme cofactor, or metabolite in standard biochemical pathways (general knowledge).

Research context (literature):

• Toxicology studies: Alicyclic ketones are sometimes used as model substrates to study carbonyl metabolism (e.g., reduction by alcohol dehydrogenases) or phase I oxidation. However, 3,3,5-trimethyl substitution can hinder enzymatic turnover relative to cyclohexanone.
• Material science: Substituted cyclohexanones serve as precursors to functionalized polymers, UV-curable resins, or fragrances after downstream transformations; such uses relate to materials rather than biology.

For laboratory use: This product is supplied strictly for research use only (per product data). No clinical, diagnostic, or therapeutic applications are intended or supported.

Buffer Applications

Not applicable. 3,3,5-Trimethylcyclohexanone is a hydrophobic ketone reagent and is not used as a buffering agent or pH control component. For experimental planning involving this substrate, refer instead to the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections.

Green Alternatives

As a reagent/building block, 3,3,5-trimethylcyclohexanone is not typically used as a process solvent; “green alternative” considerations therefore focus on the solvents and oxidants/reductants employed with it (literature guidance).

Greener choices when designing transformations:

• Solvent selection:
  • Prefer 2-MeTHF, CPME, or EtOAc over THF/toluene/DMF where feasible (biogenic sources, better safety/air stability).
  • Use MeOH/EtOH or water/MeOH mixtures for NaBH4 reductions when compatible.
• Oxidants:
  • Replace mCPBA with H2O2 systems (e.g., urea–H2O2, H2O2/formic acid) for Baeyer–Villiger, minimizing halogenated waste.
• Bases:
  • Consider KHMDS or tBuOK in greener ethers (CPME, 2-MeTHF) vs LDA in THF when the reactivity window allows.
• Workup/waste:
  • Implement in situ quenches that reduce halogenated solvent usage; prioritize solvent recovery.

Illustrative comparison (general):

• THF (petro, peroxide former) → 2-MeTHF (biomass-derived, slower peroxide formation, similar polarity).
• CH2Cl2 (halogenated, high E-factor) → EtOAc or Me-THF when reaction compatibility allows.

Note: Selection must balance EHS improvements with chemoselectivity; verify performance by small-scale screens.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.

Context (general, non-clinical):

• Substituted cyclohexanones can be synthetic intermediates en route to APIs or performance chemicals, but this product is offered for research use only (per product data).
• In formulation science, ketones may serve as processing solvents or reaction intermediates during API synthesis; however, 3,3,5-trimethylcyclohexanone itself is not typically used as an excipient.

Any application in cGMP or regulated manufacturing would require separate qualification and specification development beyond the scope of this research-grade listing.

Physical Properties

Item-specific physicochemical specifications (e.g., exact density, refractive index, UV cutoff) are not provided for this SKU.

Representative literature values for 3,3,5-trimethylcyclohexanone (for method development/reference only; not product specifications):

• Appearance: Colorless to pale yellow liquid (literature; item-specific appearance: Not specified for this item; refer to CoA/Spec Sheet.)
• Molecular weight: 140.23 g/mol (literature)
• Formula: C9H16O (literature)
• Boiling point: Typically reported in the upper ~190–210 °C range at 1 atm (literature; consult primary sources for exact value and pressure conditions).
• Melting point: Often below room temperature (liquid at ambient) (literature).
• Density (20–25 °C): Commonly around 0.89–0.92 g/mL for similar alicyclic ketones (comparative literature; exact value not specified for this item).
• Refractive index (nD20): Typical of alicyclic ketones ca. 1.43–1.45 (comparative literature; not item-specific).
• Solubility: Low in water; miscible with common organic solvents (ethers, alcohols, chlorinated and aromatic hydrocarbons) (literature trend for aliphatic ketones).
• pKa (enolization): Enol content low; α-C–H acidity similar to hindered cyclohexanones (literature qualitative).

Notes:

• Values above are for general guidance in planning experiments and should not be used as acceptance criteria. For procurement decisions and QC, use the lot-specific CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity, stabilizers, and metal/peroxide/water limits are not provided for this SKU. Not specified for this item; refer to CoA/Spec Sheet.

General guidance on grades for ketone building blocks (context; not this item’s spec):

• Reagent/AR grade: Suitable for most synthetic procedures; impurities controlled to typical reagent limits.
• High-purity/assay-stated: Useful when impurity profiles (e.g., enones, residual solvents) can affect selectivity or catalyst tolerance.
• GC/HPLC tested: When trace UV-active or volatile impurities must be minimized (e.g., analytical or kinetic studies).

Practical considerations:

• Carbonyl integrity: Alicyclic ketones can form minor enone impurities by dehydrogenation on storage in air/light. Review GC area% on CoA and consider a brief distillation if required for sensitive catalysis.
• Water content: While many ketone reactions tolerate modest water, water-sensitive steps (e.g., strong base enolate chemistry) may benefit from Karl Fischer data or drying over molecular sieves. Item-specific water content: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: Typically not used for this class; if present, will be listed on the CoA.

Accept/reject decisions should be based on the lot-specific CoA (assay, GC purity, residual solvents, and any stated trace-metal/UV specs).

Reaction and Applications

3,3,5-Trimethylcyclohexanone is a sterically hindered cyclohexanone useful for probing selectivity in carbonyl transformations and as a precursor to highly substituted cyclohexyl frameworks (literature/general use cases).

Key applications:

• Selective reductions:
  • Catalytic hydrogenation to the corresponding alcohol using Raney Ni, Pd/C, or Pt (solvent: alcohols, ethers; monitor to avoid ring hydrogenolysis).
  • Hydride reductions (NaBH4 in MeOH/EtOH or NaBH(OAc)3 in aprotic media) give tertiary alcohols with minimal overreduction due to sterics.
• Enolate formation and α-functionalization:
  • Use strong, non-nucleophilic bases (LDA, LiHMDS) at −78 to −20 °C to form the kinetic enolate; electrophiles: alkyl halides, silyl chlorides, or acylating agents. Steric hindrance suppresses over-alkylation.
• Baeyer–Villiger oxidation:
  • Conversion to a substituted ε-caprolactone using mCPBA or peracetic acid; regioselectivity favors migration of the more substituted carbon (tertiary migration trend).
• Oxime/hydrazone formation:
  • For protection/derivatization; subsequent Beckmann rearrangement can access amide scaffolds.
• Wittig/olefination on derived aldehyde:
  • Via reduction to alcohol then oxidation to aldehyde, followed by Wittig/HWE to install exocyclic double bonds on the ring.
• Cross-coupling via enol triflates:
  • Enolization then triflation (e.g., Tf2O, base) to give vinyl triflates suitable for Suzuki/Negishi/Stille to elaborate substituted cyclohexenes.

Practical notes:

• The gem-dimethyl (C3) and 5-methyl groups impart conformational bias and suppress undesired side reactions (e.g., poly-alkylation in enolate chemistry), often improving regio/control relative to cyclohexanone.

Reaction Conditions

The following conditions are generalized from literature precedent for alicyclic, hindered ketones; they are not specifications for this product and should be optimized per application.

• Hydride reduction to alcohol:
  • Reagents: NaBH4 (1.1–1.5 eq) in MeOH/EtOH or THF/MeOH (0–25 °C, 0.5–2 h); work up with NH4Cl(aq). Typical isolated yields for analogous cyclohexanones: 80–95% (literature).
  • Catalytic hydrogenation: 5–10 wt% Pd/C or Raney Ni, 1–5 bar H2, EtOH or iPrOH, 20–40 °C; monitor to avoid over-reduction.
• Enolate alkylation/acylation:
  • Base: LDA (1.1–1.5 eq) generated in situ in dry THF or 2-MeTHF at −78 to −20 °C; electrophile added slowly. Quench with NH4Cl or HOAc. Reaction times: 0.5–3 h after addition.
• Silyl enol ether formation:
  • Base: Et3N or pyridine with TMSCl under catalytic DMAP, or via enolate (LDA) then TMSCl in THF at −78 to 0 °C. Useful for Mukaiyama aldol.
• Baeyer–Villiger oxidation:
  • Oxidant: mCPBA (1.2–1.5 eq, 77% grade dried) in CH2Cl2, 0–25 °C, 2–16 h, Na2CO3 wash. Alternative: H2O2/formic acid in MeCN at 20–40 °C.
• Oxime formation/Beckmann:
  • Hydroxylamine·HCl (1.2–1.5 eq), pyridine/EtOH or AcOH, 50–80 °C; rearrangement with SOCl2 or P2O5 in MeCN/CH2Cl2.
• Enol triflation and coupling:
  • Enolate (LDA, −78 °C), quench with Tf2O, then Pd-catalyzed cross-coupling (e.g., Pd(dppf)Cl2, K3PO4) in dioxane/H2O at 80–100 °C with boronic acids (Suzuki).

Notes:

• The gem-dimethyl substitution reduces acidity; stronger bases or lower temperatures with longer times may be required vs cyclohexanone.
• Ensure dry, oxygen-free conditions for base-mediated steps; rigorously exclude moisture when targeting high enolate selectivity.

Safety and Handling

GHS classification, pictograms, signal word, and H-statements are not provided for this SKU. Always consult the product SDS for authoritative safety information.

General safety guidance for alicyclic ketones (literature/industry practice):

• Hazards: Many ketones are combustible liquids and can cause eye/skin irritation and CNS effects upon high vapor exposure. Low water solubility and moderate vapor pressure warrant good ventilation.
• PPE: Use appropriate gloves (e.g., nitrile), lab coat, and splash goggles. Employ in a fume hood to minimize inhalation exposure.
• First aid (overview):
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if easy; continue rinsing.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Handling: Avoid sources of ignition. Prevent aerosol/mist formation. Ground/bond containers during transfer if handling bulk liquid.
• Incompatibilities: Strong oxidizers, strong bases (which can promote aldol/self-condensation under forcing conditions), strong reducing agents for carbonyls (manage exotherm).
• Spill response: Contain with inert absorbent (vermiculite, sand), collect for disposal. Ventilate area.
• Waste: Dispose in accordance with local regulations for organic solvents/ketones; segregate from oxidizers.

Storage per product data: Room temperature in well-closed container; shipped under normal conditions. Protect from heat/ignition and moisture ingress. Defer to SDS for detailed storage class and thresholds.

Solvent Selection

This product is a ketone reagent/intermediate rather than a routine reaction solvent. Solvent selection thus pertains to using 3,3,5-trimethylcyclohexanone as a substrate in synthesis.

General solubility and handling (literature):

• Polarity: Moderately polar aprotic (carbonyl dipole), but overall hydrophobic due to the alicyclic and alkyl substituents.
• Solubility profile:
  • Miscible with common organic solvents (ethers, esters, chlorinated, aromatic hydrocarbons, alcohols).
  • Poorly soluble in water.
• Typical media for reactions:
  • Enolate chemistry: Dry THF, MTBE, toluene, or hexanes/THF mixtures with LDA/LHMDS.
  • Reductions/oxidations: Alcohols, ethers, or toluene under catalytic hydrogenation, NaBH4 (in alcohol), or DIBAL/metal hydrides (aprotic).
  • Baeyer–Villiger: Halogenated solvents (e.g., CH2Cl2) or acetonitrile with peracids/H2O2 systems.

Comparison notes (literature trends):

• Versus less substituted cyclohexanone, this substrate is more hydrophobic and may show lower miscibility in polar protics, but dissolves readily in ethers and aromatics.
• When acting as a cosubstrate in catalysis, avoid solvent combinations that promote self-condensation under basic conditions; include acid scavengers or milder bases where needed.

Storage and Reconstitution

• Storage conditions (product data): Store at room temperature. Ship under normal conditions.
• Container recommendations: Keep tightly closed in a dry, well-ventilated area. Use amber glass where possible to minimize light exposure that can promote slow oxidative byproduct formation.
• Inerting: For long-term storage or when ultra-low impurity levels are required, consider storing under nitrogen/argon headspace.
• Moisture control: While ketones are generally stable, maintain desiccation to support moisture-sensitive downstream chemistry (e.g., enolate formation). If needed, dry over 3 Å molecular sieves (compatible glass contact only).
• Freeze–thaw: Not applicable; material is typically a liquid at ambient temperature. Avoid freezing to prevent container stress and phase separation of minor components.
• Stability/retention samples: Periodically verify by GC or 1H NMR for formation of enone impurities during prolonged storage.

Note: No reconstitution is required. For critical applications, confirm suitability by small-scale test and consult the lot-specific CoA/Spec Sheet for any additional storage notes.

Structure and Identity

A hindered alicyclic ketone featuring a cyclohexanone core with three methyl substituents, giving a sterically encumbered carbonyl environment useful for selectivity studies and enolate chemistry.

• Preferred name: 3,3,5-Trimethylcyclohexanone
• CAS: 873-94-9 (product data)
• PubChem CID: 13398 (product data)
• Molecular formula: C9H16O (literature)
• Molecular weight: 140.23 g/mol (literature)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural description (general):

• Core ring system: Cyclohexanone (six-membered carbocycle with a C=O at C1).
• Substitution pattern: Two methyl groups geminal at C3 (3,3-dimethyl) and one methyl at C5, leading to a total of three methyl substituents on the ring.
• Functional groups: One saturated ketone (cyclohexanone); no additional heteroatoms.
• Stereochemistry: None required at the carbonyl carbon; ring conformations (chair/boat) possible; substitution pattern can bias conformational preferences and axial/equatorial orientations.
• Electronic features: A polarized carbonyl with reduced enolization rate relative to less hindered cyclohexanones due to α-substitution, useful for controlled enolate generation.

Synthetic Utility

Functional group and reactivity profile (literature):

• Carbonyl electrophile: Undergoes nucleophilic addition (hydrides, organometallics) to give tertiary alcohols. Steric bulk modulates rates and can improve selectivity vs less substituted ketones.
• Enolate chemistry: Strong, non-nucleophilic bases (LDA/LiHMDS) generate enolates for α-alkylation, acylation, and silylation. Substitution at C3 reduces polyalkylation and can influence axial/equatorial delivery.
• Oxidation/rearrangement: Amenable to Baeyer–Villiger oxidation producing lactones; migration selectivity typically favors more substituted carbons, yielding defined regioisomers for further ring-opening chemistry.
• Derivatization: Oxime/hydrazone formation, ketalization for protection, and subsequent rearrangements (e.g., Beckmann) expand accessible scaffolds.
• Vinylation handles: Enol triflation enables cross-coupling (Suzuki–Miyaura, Negishi), converting the saturated ketone to elaborated alkenes while preserving substitution pattern.

Strategic value:

• The 3,3,5-trimethyl substitution imparts conformational and steric control, making this ketone a valuable probe for:
  • Stereochemical outcome studies in reductions (hydride vs catalytic hydrogenation).
  • Regioselectivity in α-functionalization.
  • Migratory aptitude mapping in Baeyer–Villiger/Beckmann sequences.

Downstream opportunities include access to substituted cyclohexanols, ε-caprolactones, and tertiary carbinols, useful in materials, fragrance intermediates, and complex molecule fragments.

Target Specificity

Not applicable. This product is a small-molecule ketone and not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information is relevant or provided.

Domande frequenti

What is the purity of this product, and how is it determined?

This product is supplied at ≥98% purity, determined by gas chromatography (GC). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

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

The CAS Number is 873-94-9, the molecular formula is C9H16O, and the molecular weight is 140.23 g/mol. InChIKey POSWICCRDBKBMH-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.