3-Methanesulfonylcyclohexan-1-one - ≥95% , CAS No.1495492-84-6

CAS: 1495492-84-6 Cat. No.: M955256 Fórmula: C₇H₁₂O₃S Peso molecular: 176.240 Número CE: 890-673-4

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: CS(=O)(=O)C1CCCC(=O)C1
• IUPAC Name: 3-methylsulfonylcyclohexan-1-one
• InChIKey: YACQHBDYAZSZMW-UHFFFAOYSA-N
• INCHI: 1S/C7H12O3S/c1-11(9,10)7-4-2-3-6(8)5-7/h7H,2-5H2,1H3
• Peso molecular: 176.240

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organosulfur compounds
    • Classe Sulfonyls
      • Subclass Sulfones

• Kingdom: Organic compounds
• Superclass: Organosulfur compounds
• Classe: Sulfonyls
• Subclass: Sulfones
• Intermediate Tree Nodes: Not available
• Direct Parent: Sulfones
• Alternative Parents: Cyclic ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Sulfone - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as sulfones. These are compounds containing a sulfonyl group( which as the general structure RS(=O)2R' (R,R' =alkyl, aryl)) attached to two carbon atoms.
• 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: 176.240 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 176.051 Da
• Monoisotopic Mass: 176.051 Da
• Topological Polar Surface Area: 59.600 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 247.000
• 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 tested bioassay or immunoassay application protocols (e.g., WB, IHC, IF, FC) are associated with this synthetic intermediate. For synthetic usage, see Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

This product is a synthetic organic intermediate (β-sulfonyl ketone) and is not typically studied for intrinsic biological function.

• Applicability

  • Not commonly associated with natural metabolic pathways or signaling roles.
  • Any bioactivity reports for related sulfones/ketones are context-specific and not generalizable.

• Research Use Note (from Product Data)

  • For research use only.

For biological assays or cellular work, ensure solvent and concentration compatibility and perform appropriate toxicology and control experiments; no item-specific biological role data are provided.

Buffer Applications

Not typically applicable. 3-Methanesulfonylcyclohexan-1-one is a neutral, non-ionic organic building block and is not used to prepare aqueous buffer systems. For experimental work involving this compound, see Solvent Selection and Reaction & Applications for relevant handling in organic media.

Green Alternatives

• Greener solvent choices for handling this substrate (general)

  • Prefer 2-MeTHF or CPME over THF/Et2O to reduce peroxide hazard and improve sustainability; both often dissolve β-sulfonyl ketones adequately.
  • Replace DCM with EtOAc or Me-THF for workups and chromatography when feasible.

• Greener reagents/routes (literature guidance)

  • Desulfonylation: SmI2 is effective but generates iodine-containing waste; alternative photoredox methods using organic dyes and benign reductants (e.g., Hantzsch ester, ascorbate) can lower environmental impact.
  • Elimination to enones: Use catalytic base with azeotropic water removal (where compatible) or phase-transfer conditions to minimize strong base loadings and salts.

• Comparison snapshot (general)

  • Operation | Conventional choice | Greener alternative | Trade-offs
  • Solvent for base-induced elimination | THF/DMF | 2-MeTHF/MeCN | Rate/solubility may decrease; optimize temperature
  • Extraction/workup | DCM | EtOAc/MTBE | Slightly larger volumes, but lower toxicity
  • Reductive desulfonylation | SmI2, Na/Hg | Photoredox + organohydride | Requires light setup; scope-dependent

Note: The substrate itself is a stable, bench-handled solid/liquid; the main green impact levers are solvent selection, reagent choice, and waste minimization. Validate greener options on small scale before scale-up.

Pharmaceutical Uses

No item-specific pharmacopeial status or excipient role is provided. This compound is primarily a synthetic intermediate for research and process development.

• General context (non-clinical)
  • β-Sulfonyl ketones can appear as masked enone precursors or as handles for late-stage diversification in medicinal chemistry campaigns.
  • They are not typical formulation excipients.

Research-only notice: For research use only (as provided). Not for human or veterinary use, diagnostic procedures, or clinical applications.

Physical Properties

• Item-specific specs (Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature estimate ~176.23 g/mol; see below.)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature: C7H12O3S.)

• Literature/computed values (non-spec; for context only)

  • Approx. formula: C7H12O3S (β-sulfonyl cyclohexanone bearing –SO2Me at C3)
  • Approx. formula mass: ~176.23 g/mol (C 7 × 12.011 = 84.08; H 12 × 1.008 = 12.10; O 3 × 15.999 = 48.00; S 32.06)
  • Physical state: typically a crystalline solid or low-melting solid for analogous β-sulfonyl ketones; exact MP/appearance not established here.
  • Melting point, boiling point, density, refractive index, UV cutoff, solubility data: Not specified for this item; consult CoA/SDS or measure.

• General physicochemical expectations for β-sulfonyl ketones (literature)

  • Polarity: high dipole due to carbonyl and sulfone; often soluble in moderately polar aprotic solvents (e.g., EtOAc, MeCN, acetone, DCM, THF) and sparingly soluble in nonpolar hydrocarbons; low aqueous solubility.
  • Acidic sites: activated α-C–H positions (to the ketone and to the sulfone) exhibit increased acidity, enabling base-promoted reactions.

Note: Where exact, item-specific values are required for QC or method development, please refer to the CoA/Spec Sheet or determine experimentally.

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.

• Interpreting common grades (general guidance)

  • Research-grade: Suitable for most synthetic and method-development work. Purity typically >95% by NMR/HPLC/GC; actual value must be confirmed on the CoA.
  • Analytical/HPLC grade solvents (context): Low UV absorbance and low non-volatile residue, used when this material is analyzed chromatographically. Not directly applicable to this solid but relevant to associated solvent choices.
  • Trace metal/low-water specifications: Critical if using strong bases or organometallics that are moisture-sensitive. For this item, specific ppm limits are Not specified for this item; refer to CoA/Spec Sheet.

• Practical QC considerations for β-sulfonyl ketones (general)

  • Identity: 1H/13C NMR (diagnostic sulfone methyl singlet ~2.9–3.2 ppm, carbonyl ~δC 200–210 ppm), IR (strong SO2 stretches ~1310–1150 cm−1; C=O ~1715 cm−1), HRMS (M+ or [M+Na]+ ~176/199 Da).
  • Purity: HPLC or GC (if thermally stable); TLC in EtOAc/hexanes or DCM/MeOH systems. Check for β-elimination product (enone) as a potential impurity after base exposure.
  • Residual solvents/water/peroxides/metals: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As a β-sulfonyl ketone, 3-methanesulfonylcyclohexan-1-one serves as a versatile intermediate in synthesis. The juxtaposition of a ketone and a sulfone enables eliminations, desulfonylations, and radical chemistries.

• Elimination to enones (literature)

  • Base-promoted E1cB: Strong bases (e.g., t-BuOK, LDA) can induce β-elimination of sulfinic acid to generate the corresponding α,β-unsaturated cyclohexanone. Reaction selectivity is influenced by base strength, temperature, and solvent (THF/DMF). Proton shuttling and anti-periplanar alignment govern rates.

• Desulfonylative transformations (literature)

  • Reductive: SmI2, Mg/MeOH, or Na(Hg) can remove the sulfone, effectively accessing the parent cyclohexanone skeleton or enabling net deoxygenative coupling sequences.
  • Radical cross-couplings: Photoredox or nickel-catalyzed desulfonylative alkylations may leverage alkyl sulfones as radical precursors, releasing sulfinate under single-electron transfer.

• Functionalization adjacent to carbonyl (literature)

  • The β-sulfone activates the ring toward enolate formation at C2/C4; subsequent trapping (acylation, alkylation) followed by elimination can install defined olefin geometries.

• Protection/activation logic (general)

  • The sulfone functions as a traceless, strongly electron-withdrawing “leaving group” surrogate. After strategic C–C bond formation, it can be removed to unmask an enone or saturated framework.

• Practical tips

  • Control base strength and temperature to avoid over-elimination.
  • Monitor for formation of the enone by TLC/LC-MS (λmax often increases upon conjugation).
  • Exclude moisture and protic additives when elimination is undesired.

Reaction Conditions

General literature guidance for β-sulfonyl ketones; optimize for your substrate and scale.

• Base-induced elimination to enone

  • Typical conditions: t-BuOK (1.1–1.5 equiv) in dry THF or t-BuOH, 0–25 °C to reflux, 0.5–4 h.
  • Alternative bases: LDA in THF at −78 to 0 °C; K2CO3/DBU in polar aprotics (DMF, MeCN) for milder eliminations.
  • Workup: Quench with NH4Cl, extract with EtOAc, wash, dry, and purify. Monitor by TLC/LC-MS; UV λmax increase indicates enone formation.

• Reductive desulfonylation

  • SmI2 (0.2–0.5 M in THF), 2–6 equiv SmI2, 0 °C to rt, 0.5–2 h; additives (HMPA alternatives like TPPA) may accelerate, but consider EHS aspects.
  • Alternative SET approaches: Photoredox (blue LEDs), organocatalysts (eosin Y, 4CzIPN) with Hantzsch ester or ascorbate; Ni catalysts for C–C coupling variants.

• Enolate generation/functionalization

  • LDA (1.1–1.5 equiv) in THF/hexanes at −78 °C, then electrophile (R–X, R–CHO). The β-sulfone influences regioselectivity; study conditions.

• Expected outcomes (scope-dependent)

  • Eliminations often proceed in good yields to the corresponding cyclohexenone; reductive desulfonylation yields vary with method and substitution.

All parameters above are literature-style guidance, not item-specific specifications. Conduct small-scale trials, and ensure anhydrous, oxygen-free techniques where required.

Safety and Handling

• Item-specific hazard data (Product Data)

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

• General safety considerations for ketones and sulfones (literature/good practice)

  • Likely hazards: May cause skin/eye irritation and respiratory irritation upon dust or vapor exposure; avoid inhalation and contact. Handle under a fume hood.
  • PPE: Use lab coat, nitrile gloves, and splash goggles as a baseline. Upgrade to chemical-resistant gloves and face protection for scale-up or splash risk.
  • Engineering controls: Work in a functioning chemical fume hood; use local exhaust if weighing fine powders.
  • Incompatibilities/instabilities: Strong bases can promote β-elimination to enones; strong reducing agents (e.g., LiAlH4, dissolving metals) may effect desulfonylation; strong acids may cause decomposition. Avoid strong oxidizers and reductants unless intended.
  • Storage compatibility: Keep away from alkali metals, strong bases, and strong reducing agents. Segregate from oxidizers.
  • First-aid overview: If on skin/eyes, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow SDS instructions.
  • Spill/cleanup: Contain solids with inert absorbent, avoid dust formation, collect for disposal per institutional guidelines. For solutions, absorb with vermiculite or pads and ventilate area.

Defer to the product SDS for authoritative hazard classification, exposure limits, and emergency measures.

Solvent Selection

This compound is a moderately polar, aprotic organic molecule with a ketone and a sulfone, favoring solvents capable of solvating polar functionalities.

• Solubility/miscibility profile (literature expectations)

  • Good: DCM, chloroform, acetone, acetonitrile, THF, ethyl acetate, DMF/DMSO.
  • Moderate: Toluene, MTBE, CPME, 2-MeTHF (often upon gentle warming).
  • Poor: Aliphatic hydrocarbons (hexanes, heptane) and water.

• Choosing a solvent for common operations

  • Crystallization: EtOAc/hexanes or toluene/EtOAc mixtures can provide useful crystallization windows; confirm experimentally.
  • Reactions under basic conditions: Use dry, aprotic media (THF, DMF, DME, 2-MeTHF) and rigorously exclude moisture to control E1cB-type eliminations.
  • Reductive chemistry: Ethereal solvents (THF, DME) for SmI2 or dissolving-metal variants; avoid protic solvents unless mechanistically intended.
  • Purification: Flash chromatography using silica, eluting with EtOAc/hexanes or DCM/MeOH; the sulfone increases polarity relative to the parent ketone.

• Brief comparison (general)

  • THF vs 2-MeTHF: 2-MeTHF offers greener credentials and higher boiling point; both dissolve β-sulfonyl ketones well.
  • DCM vs EtOAc: DCM provides strong elution and solubility; EtOAc is safer/greener but may require larger volumes.

Note: No item-specific solubility specifications are provided; verify experimentally for your process.

Storage and Reconstitution

• Item-specific storage (from Product Data)

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

• General storage guidance (good practice)

  • Keep tightly closed in a dry, inert environment (desiccator or with desiccant). Minimize exposure to moisture and strong light.
  • Segregate from strong bases, strong reducing agents, and strong oxidizers.
  • If long-term storage is planned, consider amber glass and an inert headspace (N2/Ar).

• Reconstitution/solution preparation (general)

  • Solvents: DCM, THF, EtOAc, MeCN, acetone, or DMSO (analytical grade). Filter if particulates are present.
  • Concentration: Prepare stock solutions appropriate for your workflow (e.g., 10–100 mM); store aliquots at 2–8 °C if using moisture-sensitive media, and warm to rt before opening to avoid condensation.
  • Stability in solution: β-Sulfonyl ketones are generally stable in dry, aprotic solvents; avoid strong bases or acids in stock solutions to prevent elimination or decomposition.

Always consult the CoA/SDS for product-specific instructions and stability ranges.

Structure and Identity

Brief overview: 3-Methanesulfonylcyclohexan-1-one is a β-sulfonyl ketone building block featuring a cyclohexanone ring (C=O at C1) bearing a methanesulfonyl (–SO2–CH3) substituent at C3. The sulfone strongly withdraws electron density, enabling eliminations and desulfonylative transformations.

• Item-specific (from Product Data)

  • SKU: M955256
  • Product name: 3-Methanesulfonylcyclohexan-1-one
  • CAS: 1495492-84-6
  • CID: 64716295
  • InChIKey: 431912 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identifiers and descriptors (non-spec)

  • Typical molecular formula (literature): C7H12O3S
  • Typical molecular weight (literature): ~176.23 g/mol
  • Representative SMILES (literature, for the constitutional isomer described): O=S(=O)(C)C1CCC(=O)CC1 with sulfone at the 3-position relative to the ketone. Note: positional numbering is ring-convention dependent; structural intent is β-sulfonyl ketone.

• Structural features (general description)

  • Ring system: saturated six-membered carbocycle with a ketone at C1 (cyclohexanone).
  • Functional groups: ketone (C=O), sulfone (–SO2–) bound to a methyl (methanesulfonyl) at C3.
  • Stereochemistry: none specified; the molecule is achiral but exists in chair conformations; the C3 substituent can adopt axial/equatorial conformers.
  • 2D description in words: a cyclohexanone ring with a carbonyl at the top (C1) and a methanesulfonyl substituent two carbons away (C3), placing the sulfone β to the carbonyl.

Synthetic Utility

Key reactivity derives from the juxtaposed ketone and sulfone.

• Functional group behavior (literature)

  • Sulfone as a leaving group: Under basic conditions, E1cB elimination of sulfinate produces α,β-unsaturated ketones with predictable geometry.
  • Enolate chemistry: The ketone enables regioselective enolate formation; the β-sulfone can direct subsequent functionalization and facilitate downstream eliminations.
  • Reductive chemistry: SmI2 and related single-electron reagents enable desulfonylation, radical cyclizations, or fragmentations.

• Named/related transformations (general)

  • E1cB eliminations to enones.
  • Desulfonylative couplings (Ni/photoredox) from alkyl sulfones as radical precursors.
  • Ramberg–Bäcklund-type logic applies to α-halosulfones (not this substrate directly) to form alkenes; the current substrate can be a stepping stone to such motifs.

• Retrosynthetic value

  • Treat the –SO2Me group as a traceless activator: install it to control reactivity and stereochemistry, then remove or eliminate it to reveal the target enone/saturated scaffold.

• Practical notes

  • Protect from strong base if the sulfone must be retained through steps.
  • Monitor for sulfinic by-products during eliminations; scavengers (amine bases, carbonate) and temperature control improve selectivity.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, protein, or ligand with defined biological target specificity. No item-specific target data are provided.