Dioxo(phenyl)(3-phenyl-2-propenyl)-lambda6-sulfane - ≥95% , CAS No.16212-07-0

CAS: 16212-07-0 Cat. No.: D951030 Fórmula: C₁₅H₁₄O₂S Peso molecular: 258.34 PubChem CID: 1482405

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: C1=CC=C(C=C1)C=CCS(=O)(=O)C2=CC=CC=C2
• IUPAC Name: [(E)-3-(benzenesulfonyl)prop-1-enyl]benzene
• InChIKey: AWOQCRQDXFVJPL-JXMROGBWSA-N
• INCHI: 1S/C15H14O2S/c16-18(17,15-11-5-2-6-12-15)13-7-10-14-8-3-1-4-9-14/h1-12H,13H2/b10-7+
• SMILES isoméricas: C1=CC=C(C=C1)/C=C/CS(=O)(=O)C2=CC=CC=C2
• PubChem CID: 1482405
• Peso molecular: 258.34

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzenesulfonyl compounds

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzenesulfonyl compounds
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzenesulfonyl compounds
• Alternative Parents: Styrenes Sulfones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzenesulfonyl group - Styrene - Sulfonyl - Sulfone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Aromatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
• 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: 258.300 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 258.071 Da
• Monoisotopic Mass: 258.071 Da
• Topological Polar Surface Area: 42.500 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 352.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable for biological assay formats (WB, IHC, IF, FC, etc.). This item is a small-molecule reagent for chemical synthesis. For practical usage, refer to Reaction & Applications and Reaction Conditions for literature-based setups. Any procedural details should be validated and optimized in your laboratory context.

Biological Roles

This product is a small-molecule organic sulfone designed for synthetic chemistry. No biological function is assigned for this catalog item.

General biochemical context for sulfones (literature; not product-specific):

• Sulfone functionality (–SO2–) is metabolically robust and appears in some bioactive molecules and materials due to its strong dipole and oxidative stability. However, the present compound is intended for chemical synthesis rather than biological assays.
• The aryl–allyl architecture is hydrophobic, with low aqueous solubility; nonspecific membrane partitioning could occur, but no defined biological pathway or receptor specificity is implied.

Note: For research use only. Not intended for diagnostic, therapeutic, or in vivo applications.

Buffer Applications

Not typically applicable. This is a non-ionic organic reagent with poor water solubility and no buffering capacity. For experimental work involving this compound, select an appropriate organic solvent and, if necessary, introduce the solution into buffered aqueous systems via cosolvents or emulsification. Refer instead to Solvent Selection and Reaction & Applications.

Green Alternatives

Contextual, literature-based green chemistry considerations (not product specifications):

• Solvent choices:

  • Prefer ethers like 2-MeTHF over THF for base-mediated steps (renewable feedstock, higher boiling point, improved peroxide stability vs THF requires monitoring).
  • CPME offers wide liquid range and low water miscibility, easing workups; it can replace DCM in some cases.
  • Ethyl acetate and dimethyl carbonate can replace chlorinated solvents for extractions and some reactions.

• Leaving group alternatives for allylic substitution:

  • Allyl carbonates/acetates (formed from CO2-derived reagents or bio-based acetic acid) can substitute for allyl sulfones under Pd catalysis, often at milder conditions and with more benign byproducts (CO2/acetate) versus sulfinates.

• Energy efficiency:

  • Conduct reactions at ambient temperature where possible (ligand-accelerated Pd catalysis, phase-transfer conditions for alkylations) to reduce heating/cooling loads.

Tradeoffs (brief comparison):

• Allyl sulfones vs allyl carbonates
  • Pros (sulfones): Greater stability on storage; distinctive reactivity enabling eliminations and anion chemistry; often excellent regioselectivity.
  • Cons (sulfones): Potential generation of sulfinates/aryl sulfinate wastes; may require stronger bases or higher catalyst loadings.

Waste minimization:

• Recover/recycle polar aprotic solvents (MeCN, EtOAc) by fractional distillation.
• Use aqueous carbonate/bicarbonate workups to avoid strong mineral acids where compatible.

Pharmaceutical Uses

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

General context (non-clinical):

• Aryl sulfones can be used as intermediates in the synthesis of drug-like molecules. The sulfone serves as a robust, polarity-enhancing handle that can be removed (desulfonylation) or transformed (e.g., Julia-type olefinations) later in a synthetic sequence.
• Because of their stability and crystalline tendencies, sulfones sometimes facilitate purification and characterization of advanced intermediates.

This product is supplied strictly For research use only and is not intended for human or veterinary use.

Physical Properties

Item-specific specifications:

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

Literature/general properties for cinnamyl phenyl sulfones (for context only; not product specifications):

• Physical state: Typically a low-melting solid or high-boiling liquid depending on substitution pattern; aryl/allyl sulfones are often crystalline solids.
• Polarity: Polar aprotic due to the highly polar S(=O)2 group; strong dipole (~4–5 D typical for sulfones, literature).
• Solubility profile: Generally low solubility in water; good solubility in polar organic solvents (e.g., DCM, THF, EtOAc, acetonitrile, DMF, DMSO); variable in nonpolar hydrocarbons.
• Acid/base behavior: No Brønsted basicity; α-CH2 next to SO2 is acidic relative to simple hydrocarbons (pKa often ~28–31 in DMSO for benzylic/allylic sulfones, literature). This facilitates carbanion formation under strong base.
• Partitioning: Moderate hydrophobicity balanced by sulfone polarity (logP commonly in the 2–3 range for diaryl/allyl sulfones, literature).
• Thermal stability: Sulfones are generally thermally robust; decompose only at elevated temperatures; exact MP/BP not cited here.

Note: For authoritative numeric values (mp, bp, density, refractive index, UV cutoff, metal/peroxide/water specs), consult the item’s CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting grades (general guidance):
  • Research/technical grade: Suitable for most synthetic applications; typical residual solvents, water, and UV-absorbing impurities are controlled but not to chromatographic standards.
  • HPLC/UV grade (if applicable): Emphasizes low UV background and low particulate/metal content for analytical use; not indicated for this item unless explicitly stated on CoA.
  • “Assay” vs. “Area%/GC%”: Sulfone purity is frequently expressed by NMR or GC/HPLC area%; check the CoA for analytical method, assay basis, and impurity profile.
• Stabilizers/inhibitors: None specified for this item. Sulfones are typically inhibitor-free and shelf-stable; any stabilizer would be declared on the CoA.
• Trace specifications: Water, peroxide, metal limits, residual solvents, and UV cutoffs are Not specified for this item; refer to CoA/Spec Sheet.

Recommendation: For moisture-/base-sensitive transformations (e.g., strong-base α-deprotonation), verify Karl Fischer water and residual solvent content on the CoA, and consider brief drying (vacuum, mild heat) if compatible.

Reaction and Applications

This compound is a cinnamyl phenyl sulfone, combining an allylic unit with a strong electron-withdrawing sulfone. That duality underpins several useful transformations (literature/general guidance):

• Allylic electrophile chemistry (Tsuji–Trost-type): Allyl sulfones can serve as allylic leaving groups under Pd(0) catalysis, enabling SN2′ additions by soft nucleophiles (malonates, enolates, thiols, amines). The phenylsulfonyl group acts as a leaving group after π-allyl palladium formation, often affording high regioselectivity toward the substituted terminus.
• Anion chemistry (α to SO2): The benzylic/allylic CH2 adjacent to SO2 is significantly acidified (pKa ~28–31 in DMSO, literature). Strong bases (e.g., LDA, NaHMDS, KHMDS, t-BuOK under phase-transfer) generate sulfone-stabilized carbanions for:
  • Alkylation (C–C bond formation) with primary halides or Michael acceptors.
  • Julia- or modified Julia-type olefinations when appropriately configured (installation of alkenes with predictable geometry).
• Elimination reactions: β-Elimination or reductive pathways can convert allyl sulfones to alkenes, leveraging the sulfone as a traceless activating group.
• Radical chemistry: Under photoredox or tin hydride conditions, sulfones can participate as radical precursors or undergo desulfonylation to access hydrocarbon frameworks.
• Reductive desulfonylation: Raney Ni or dissolving-metal conditions can remove the phenylsulfonyl unit to unveil the corresponding hydrocarbon skeleton, useful for protecting/activating group strategies.

Practical notes:

• For Pd-catalyzed allylic substitution, rigorously exclude air/moisture and use freshly prepared Pd(0) sources (e.g., Pd2(dba)3 with phosphine ligands).
• For base-mediated anion chemistry, pre-cool bases and add substrate slowly to control exotherm; quench carefully to avoid over-alkylation.
• Monitor by TLC or LC–MS; sulfones exhibit strong UV absorbance (Ar–SO2–) aiding detection.

Reaction Conditions

General literature guidance (non-binding; optimize per system):

• α-Deprotonation/alkylation:

  • Base: LDA, NaHMDS, KHMDS (1.0–1.5 equiv).
  • Solvent: Dry THF or 2-MeTHF; −78 to 0 °C for deprotonation, then 0 to rt upon electrophile addition.
  • Electrophiles: Primary alkyl bromides/iodides, benzylic halides, activated secondary halides; typical times 0.5–4 h; workup with NH4Cl.

• Pd-catalyzed allylic substitution (allyl sulfone as electrophile):

  • Catalyst: 1–5 mol% Pd(0) (e.g., Pd2(dba)3) with 2–10 mol% phosphine ligand (PPh3, XPhos, DPPF).
  • Nucleophiles: Malonates, enolates, amines, thiols, boron enolates; 1.2–2.0 equiv.
  • Solvent: MeCN, THF, dioxane; temperature 0–50 °C; 1–12 h.
  • Notes: Add base (e.g., Cs2CO3, NaH) as needed to generate the nucleophile; inert atmosphere improves reproducibility.

• Reductive desulfonylation:

  • Raney Ni (slurry) in EtOH/MeOH under H2 or transfer hydrogen conditions; ambient to 60 °C.
  • Alternatives: SmI2 in THF with HMPA or amine donors; photoredox with HAT catalysts (conditions substrate-dependent).

• Elimination/olefination (Julia-type, general):

  • Strong base (NaHMDS, KHMDS) in THF; add carbonyl partner at low temperature; allow to warm; E/Z selectivity depends on reagent set (e.g., Kocienski variants typically favor E-alkenes).

Expected outcomes (illustrative): High regioselectivity in SN2′ allylic substitutions; clean alkylations at α-CH2; desulfonylation furnishing hydrocarbons. Yields vary widely with substrate and conditions; consult primary literature for close analogs.

Safety and Handling

Item-specific hazard data 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 aryl/allyl sulfones (literature; not a substitute for the SDS):

• Expected hazards: May cause skin/eye irritation and respiratory irritation if dust or vapors are generated. Handle as a laboratory chemical of unknown acute toxicity, For research use only.
• PPE: Use gloves (nitrile recommended), lab coat, and splash-resistant eye protection. Handle in a fume hood to avoid inhalation of dust or aerosols.
• Incompatibilities: Strong reducing agents (can reduce sulfone to sulfide/sulfoxide); very strong bases (can generate carbanions at α-CH2); powerful electrophiles (may react with sulfone-stabilized anions). Avoid contact with strong oxidizers for general best practice, although the sulfone is already at a high oxidation state.
• Stability/reactivity: Sulfones are air-stable, non-peroxidizable (unlike ethers). Avoid excessive heating above decomposition temperature.
• 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 and seek medical advice. Always follow institutional SOPs and consult the SDS.
• Fire safety: Combustible organic; use CO2, dry chemical, or foam. Combustion may release SOx; firefighters should wear self-contained breathing apparatus.

Always defer to the product’s SDS and institutional risk assessment before use.

Solvent Selection

• Polarity class: Polar aprotic substrate; dissolves best in moderately polar organic solvents.
• Miscibility/solubility (general):
  • Good: DCM, chloroform, THF, EtOAc, acetonitrile, toluene (warm), DMF, DMSO.
  • Limited: Hexanes/heptane (unless heated or with cosolvent).
  • Poor: Water.
• Selection by application:
  • Nucleophilic/allylic substitution (Tsuji–Trost using allyl sulfones as electrophiles): Polar aprotic solvents (THF, MeCN, dioxane) facilitate Pd(0) catalysis; DMF/DMSO can be used but may complicate workup.
  • Anion chemistry at α-CH2 (deprotonation/alkylation): Ethers (THF, MTBE) or hydrocarbons with cosolvent under cryogenic to ambient temperatures; ensure stringent dryness.
  • Thermal processes/eliminations: High-boiling aromatics (toluene, xylene) or sulfolane when elevated temperatures are needed.
• Comparison to alternatives:
  • Versus allyl halides: Allyl sulfones can offer cleaner SN2′ selectivity and are less volatile; however, they generally require catalysts or stronger conditions.
  • Versus sulfonates (allyl carbonates/acetates): Carbonates often react under milder Pd catalysis; allyl sulfones can be advantageous for chemoselectivity and stability in storage.

Practical tips:

• If solubility is marginal, warm gently or add a small percentage of DMSO/DMF as cosolvent.
• For moisture-sensitive base chemistry, dry solvents thoroughly (molecular sieves, distillation).

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Keep tightly closed in a dry, well-ventilated place. Protect from excessive heat and direct sunlight.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Form/appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Solution preparation (general guidance):
  • Solubility: Readily soluble in common organic solvents such as DCM, THF, EtOAc, MeCN, DMF, and DMSO (literature). Poorly soluble in water.
  • To prepare stock solutions, dissolve in a dry, oxygen-free solvent if the downstream chemistry is air/moisture sensitive. Typical lab stocks: 0.1–1.0 M in dry THF, MeCN, or DMSO, stored under inert gas.
• Stability of solutions: Sulfones are generally stable in neutral, anhydrous organic media for days to weeks at room temperature; for extended storage, keep solutions sealed under inert gas at 2–8 °C. Always check for precipitation or discoloration before use.
• Freeze–thaw: Not typically relevant to solids; if storing solutions, avoid repeated freeze–thaw cycles by aliquoting.

Always consult the product’s CoA/SDS for definitive handling and storage guidance.

Structure and Identity

Brief overview: Dioxo(phenyl)(3-phenyl-2-propenyl)-lambda6-sulfane is the systematic name for a diaryl/allyl sulfone in which a hexavalent sulfur (S(VI)) bears two oxo groups and is bonded to a phenyl ring and a 3-phenyl-2-propenyl (cinnamyl) group. Functionally, it is a cinnamyl phenyl sulfone (Ph–SO2–CH2–CH=CH–Ph).

• Item-specific identifiers from Product Data:

  • CAS: 16212-07-0
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/structure description (for general reference; not product specification):

  • Common structural class: Aryl–allyl sulfone (S(VI), sulfone, R–SO2–R′)
  • Representative (non-spec) SMILES (literature): O=S(=O)(c1ccccc1)CC=Cc2ccccc2
  • Representative (non-spec) formula/MW (literature): C15H14O2S; ~258.34 g/mol
  • Key functional groups: sulfone (SO2), aryl ring (phenyl), allylic chain conjugated to phenyl (cinnamyl)
  • 2D structural features in words: A central tetra-coordinated sulfur with two S=O bonds, one S–phenyl bond, and one S–CH2–CH=CH–phenyl substituent; the C=C is conjugated with the terminal phenyl ring; no stereocenters; C=C geometry may exist as E/Z but is not specified here.

• Stereochemistry: None at sulfur (sulfone), and the allylic double bond may exhibit geometric isomerism in principle; specific isomer ratio not provided for this item.

Synthetic Utility

Key reactivity elements:

• Sulfone group (–SO2–): Strong electron withdrawal stabilizes adjacent carbanions and supports eliminations; excellent handle for Julia/modified-Julia olefinations and for traceless activation strategies.
• Allylic system (CH2–CH=CH–Ph): Readily engages in Pd-catalyzed allylic substitutions (via π-allyl intermediates) and SN2′ reactions with soft nucleophiles.
• Dual activation: The α-CH2 to SO2 is allylic and benzylic, maximizing anion stability and enabling selective C–C bond formations.

Representative synthetic maneuvers (literature):

• α-Deprotonation/alkylation: LDA or NaHMDS in THF at −78 to 0 °C, then electrophile (R–X) to extend the carbon chain with high control.
• Allylic substitution: Pd(0) catalysts (e.g., Pd2(dba)3/PPh3 or Buchwald phosphines) in MeCN/THF at 0–40 °C with nucleophiles (malonates, amines, thiols) to forge C–C or C–X bonds.
• Reductive removal: Raney Ni hydrogenolysis or SmI2/donor systems to delete the sulfone as a traceless activating group, revealing the hydrocarbon framework.
• Olefination strategies: With suitable aldehydes/ketones and base, sulfone-derived anions participate in Julia-type couplings to deliver defined alkene geometry.

Operational tips:

• Use rigorously dry glassware/solvents; sulfone anions are quenched by moisture/CO2.
• Control temperature to manage E/Z outcomes in olefination and regioselectivity in allylic substitution.
• The arylsulfonyl byproducts (e.g., sodium phenylsulfinate) can be water-soluble, aiding separations.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent (no antigen/epitope, clone, isotype, or species reactivity). No item-specific targeting data are provided.