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
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
214.280 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
214.066 Da
Monoisotopic Mass
214.066 Da
Topological Polar Surface Area
62.800 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
245.000
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
Lösungsrechner
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Application Protocols
No standardized biological assay protocols apply to this small-molecule intermediate.
Item-specific (from Product Data):
Manufacturer Applications: Not specified for this item.
General lab protocols (chemistry-focused, literature/general):
Representative oxidation of the alcohol to aldehyde: Dissolve substrate (1.0 equiv) in dry DCM (0.1–0.2 M), add Dess–Martin periodinane (1.3 equiv) at 0 °C, stir to RT 1–2 h, monitor by TLC/LC-MS. Quench with sat. NaHCO3 and aq. Na2S2O3, extract, dry, and purify by silica gel chromatography (EtOAc/hexanes).
Representative mesylation then SN2: In dry DCM, cool to 0 °C, add Et3N (2.0 equiv) and MsCl (1.5 equiv) to the alcohol solution; warm to RT 1 h. Concentrate, dissolve crude mesylate in MeCN, add amine nucleophile (2–3 equiv), heat 50–80 °C until completion, then work up and purify.
Representative alpha-alkylation: Suspend NaH (60% in oil, 1.2 equiv) in dry THF under N2, cool to 0–5 °C, add solution of the sulfone slowly; after gas evolution subsides and clear solution forms, add alkyl halide (1.5–2.0 equiv) at 0–25 °C; quench with NH4Cl, extract, and purify.
These are illustrative protocols only; optimize for scale, safety, and regulatory constraints.
Biological Roles
This product is a synthetic organic intermediate and is not a biological molecule per se.
Item-specific (from Product Data):
Research Use Note: For research use only.
Literature/general context:
Sulfones in biology: While sulfones appear in some bioactive molecules and metabolites, aryl sulfones like the 4-ethylphenyl variant are typically xenobiotic in biological systems and used primarily as synthetic building blocks rather than as endogenous components.
Functional group behavior: The sulfone moiety is metabolically robust and polar; primary alcohols can undergo enzymatic oxidation in biological systems, but there is no established physiological role for this specific compound.
Applications in chemical biology: Bifunctional small molecules bearing alcohol and sulfone groups can serve as handles for immobilization, probe development, or conjugation after derivatization; such uses are investigational and assay-dependent.
No claims of therapeutic activity are made or implied. Any biological testing should be conducted under appropriate institutional approvals and safety protocols.
Buffer Applications
This compound is not a buffering agent and does not form a defined conjugate acid/base pair suitable for pH control in aqueous systems.
Practical note:
If aqueous handling is necessary (e.g., extractions or crystallizations), the compound may partition into organic phases due to its aromatic core; modest aqueous solubility may arise from the alcohol and sulfone but is formulation-dependent.
For pH-sensitive transformations of derived species, standard buffer systems (phosphate, acetate, TRIS, etc.) should be selected based on the reaction chemistry, not on this compound’s properties.
Green Alternatives
Solvent choices (literature/general):
Favor greener solvents where feasible. For many transformations of sulfone–alcohols, the following substitutions can reduce environmental impact:
Comparison (general guidance):
Traditional: DCM for oxidations/extractions
Greener alternative: Ethyl acetate or 2-methyltetrahydrofuran (2-MeTHF) when compatible with reagent solubility and selectivity.
Traditional: DMF/DMSO for SN2 and base-mediated steps
Greener alternative: Cyrene, propylene carbonate, N-butylpyrrolidone (NBP), or 2-MeTHF; note that strong bases’ solubility and rates may differ—pilot tests advised.
Traditional: THF (petroleum-derived)
Greener alternative: 2-MeTHF (biomass-derived) or CPME; both offer improved safety profiles (higher peroxide stability than ethers like THF) but still require peroxide monitoring.
Traditional: Acetonitrile
Greener alternative: MeOH/EtOH or ethyl acetate depending on reaction; check for competing transesterification or nucleophilicity of alcohol solvents.
Reagent choices:
Alcohol oxidations: Replace chromium(VI) reagents with catalytic TEMPO/bleach or O2/NOx systems; Dess–Martin or PIFA are chromium-free but still require careful waste handling.
Activations of the alcohol: Use green coupling reagents (e.g., CDI for carbonate/urea formation) and avoid halogenated activating agents where possible.
Process tips:
Solvent minimization via telescoping alcohol activation and substitution can reduce waste.
Choose aqueous workups that allow phase splits without chlorinated solvents; design crystallizations from greener solvent pairs (e.g., EtOAc/hexane or IPA/water) when physical properties allow.
Pharmaceutical Uses
Item-specific (from Product Data):
No pharmacopeial grade or excipient designation is provided. Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general (non-clinical):
Role: Potential synthetic intermediate in the preparation of drug substance candidates or analog libraries, leveraging the sulfone’s stability and the alcohol’s versatility (ester/ether/halide formation).
Process chemistry considerations: Sulfone-containing intermediates often exhibit good thermal stability and crystalline tendencies, aiding purification. Conversion of the primary alcohol to more process-friendly derivatives (e.g., carbonate) can improve handling.
Regulatory note: If used in GMP settings, material would require full characterization, impurity profiling, and trace-residual assessments; none of these parameters are specified here.
No therapeutic or clinical claims are made. This product is intended for research and development use only.
Physical Properties
Item-specific (from 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/general (non-spec, for context):
Estimated molecular formula and weight (from structure inference): C10H14O3S; MW ~214.28 g/mol.
Physical state: Many arylsulfone–alcohols are low-melting solids or viscous oils at ambient temperature; exact MP/BP for this CAS are not readily available in standard compilations. Use CoA for definitive values.
Polarity: Moderately high polarity due to one sulfone (strongly polar S=O bonds) and one primary alcohol; capable of hydrogen bonding (HBD/HBA).
Solubility (qualitative, literature expectation):
Good solubility in polar aprotic solvents (DMSO, DMF, acetonitrile) and polar protic solvents (MeOH, EtOH).
Limited solubility expected in nonpolar hydrocarbons (hexanes, heptane); improved in ethyl acetate and dichloromethane.
LogP: Aryl sulfones bearing a C2 alcohol side chain typically exhibit moderate logP (approx. 1–2.5), but exact logP for this specific compound is not confirmed.
pKa: No titratable basic centers; primary alcohol pKa (ROH) typically ~15–16 (water, literature). Alpha C–H to sulfone is relatively acidic in nonaqueous media (pKa ~29 in DMSO, literature for sulfones in general), facilitating carbanion chemistry; specific pKa not confirmed for this molecule.
Refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific (from 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 quality considerations (general):
Structural integrity: For sulfone–alcohols, NMR (1H, 13C) provides clear diagnostics: deshielded methylene adjacent to sulfone (typically 3.0–3.5 ppm), and primary alcohol methylene (3.5–3.7 ppm) with OH signal depending on solvent.
Purity metrics: HPLC or GC area % and 1H NMR integration are standard. Residual solvents and water content may influence reactivity in base-promoted transformations; Karl Fischer and headspace GC are typical controls. For chromatography-sensitive applications (e.g., method development), low UV background is advantageous; sulfones show strong absorption below ~230 nm (literature), so HPLC-grade solvent selection is important during analysis.
Trace metals/ions: Not typically limiting for this class unless used in metal-catalyzed coupling. If required, request ICP or metals screen on CoA.
Stabilizers: None are typically required for arylsulfones; if any stabilizer is present in a specific lot, it will be declared on the CoA as it can influence downstream reactions.
Recommendation: For reproducible reactivity (e.g., base-mediated alkylations or oxidations), verify assay purity and water content on receipt; consult the CoA/Spec Sheet for the exact specifications of this item.
Reaction and Applications
Synthetic roles (literature/general):
Bifunctional intermediate: The primary alcohol enables derivatization (esterification, carbonate/urethane formation, halide/tosylate/mesylate generation), while the benzylic-adjacent sulfone imparts acidity to alpha C–H enabling carbanion chemistry.
Alpha-functionalization: Deprotonation at the carbon alpha to the sulfone (–SO2–CH2–) with strong base (e.g., NaH, LDA, KHMDS) allows alkylation, acylation, or condensation to build complexity; subsequent eliminations can form vinyl sulfones.
Oxidation state manipulations: Primary alcohol oxidation to aldehyde (e.g., Dess–Martin, Swern, TEMPO) or carboxylic acid (e.g., Jones, TEMPO/NaClO2). The resulting aldehyde/acid can undergo further transformations (e.g., Wittig, amidation).
Leaving group chemistry: Conversion of the terminal alcohol to bromide/iodide (PBr3/PI3 or Appel) or to sulfonates (MsCl/TsCl) provides handles for SN2 reactions forming C–N, C–O, C–S bonds.
Sulfone as a masked functionality: Reductive desulfonylation (e.g., with Mg/MeOH or SmI2 under specific conditions) can ultimately remove the sulfone after its directing/stabilizing role, enabling temporary activation strategies.
Contextual applications:
Linker/scaffold in medicinal chemistry and chemical biology programs where a polar handle (–OH) coexists with a metabolically robust sulfone.
Precursor to para-ethylphenethyl derivatives after appropriate transformations (e.g., reduction of sulfone to sulfide then further manipulation; or displacement after converting the alcohol to a better leaving group).
Practical notes:
Maintain anhydrous conditions for base-mediated alpha-deprotonation.
The sulfone strongly deactivates adjacent carbons toward elimination; design conditions to favor SN2 on derived leaving groups rather than E2 unless vinyl sulfones are the goal.
Monitor reactions by LC-MS; sulfones typically ionize well in ESI positive and negative modes.
Reaction Conditions
Literature/general guidance for common transformations of arylsulfone–alcohols; adjust to this substrate by small-scale trials.
Alpha-deprotonation and alkylation (at –SO2–CH2–):
Base: NaH (60% dispersion), LDA, KHMDS.
Solvent: Dry THF, DME, or toluene/THF; DMF/DMSO for enhanced solubility when using alkyl halides.
Temperature: 0 to –78 °C for metallation; 0 to room temp for alkylation.
Notes: Avoid protic impurities; quench carefully with NH4Cl at low temperature.
Oxidation of the primary alcohol:
Dess–Martin: DCM, 0–25 °C, 1.3–1.5 equiv, 1–3 h; work up with NaHCO3 and Na2S2O3.
Swern: DMSO/Oxalyl chloride, –78 °C, then add base (Et3N); volatile byproducts simplify purification.
TEMPO/NaOCl: Biphasic CH2Cl2/H2O with NaHCO3 buffer, 0–10 °C; catalytic TEMPO and KBr; greener alternative to chromium reagents.
Alcohol activation and substitution:
Mesylation/Tosylation: MsCl or TsCl, Et3N, catalytic DMAP, DCM, 0–25 °C; then SN2 with amines/thiols/azide in DMF or MeCN.
Appel halogenation: PPh3/CBr4 (or CCl4) in DCM, 0–25 °C; or PPh3/NBS for bromides.
Formation of vinyl sulfones:
After alpha-alkylation, base-induced elimination (e.g., t-BuOK, DMSO, 60–80 °C) affords alkenyl sulfones; conditions vary with substituents.
Expected outcomes:
Yields commonly 60–90% for clean oxidations and mesylations; alpha-alkylations are substrate- and base-dependent (40–80% typical in literature). Optimize for this specific compound.
All values above are general literature guidance and not specifications for this product.
Safety and Handling
Item-specific (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Normal.
GHS Classification / Pictograms / Signal Word / H-Statements: Not specified for this item; refer to SDS.
General safety guidance (literature/general; consult SDS for authoritative information):
Likely hazards: Sulfone–alcohols are generally of low volatility; potential for eye/skin irritation. Avoid inhalation of aerosols or dust if solid. Handle as a laboratory chemical of unknown toxicity.
PPE: Safety glasses, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid exposure to vapors or aerosols during heating or reaction work.
Incompatibilities: Strong oxidizers may over-oxidize organic functionality; strong reducing agents may affect the sulfone under forcing conditions; dehydrating agents/acyl halides react with the alcohol. Avoid strong bases in the presence of moisture unless intended (deprotonation alpha to sulfone can occur under strong base in aprotic media).
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation develops.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Nonvolatile organic; use standard extinguishing media (CO2, dry chemical, foam). Combustion may produce SOx and COx—firefighters should wear SCBA.
Waste: Dispose according to local regulations for organic laboratory chemicals; segregate halogen-free organic waste where applicable.
Always refer to the product’s SDS for definitive hazard classification and response measures.
Solvent Selection
Polarity and solvation profile (literature/general):
The combination of a sulfone and a primary alcohol imparts significant polarity and hydrogen-bonding capability.
Moderate/limited solubility: Toluene (often improved on warming), MTBE, CPME.
Poor solubility: Aliphatic hydrocarbons (hexanes/heptane) at room temperature.
When to choose particular solvents:
Base-mediated transformations (alpha-deprotonation/alkylation at the methylene next to sulfone): dry polar aprotics (THF, DME, DMSO, DMF) are common; THF for organolithium/sodium hydride work; DMSO/DMF for KHMDS/NaH.
Oxidations of the primary alcohol: DCM or MeCN with Dess–Martin or Swern; acetone/EtOAc for TEMPO/bleach; toluene/MeCN for PDC/PCC (if used).
Esterifications/carbonate formation: DCM, MeCN, or THF with coupling reagents; remove water azeotropically if needed.
Small comparison (literature/general):
THF vs DMSO: THF facilitates low-temperature metallation with strong bases; DMSO/DMF provide higher solubility for salts and may accelerate SN2 steps but complicate workup.
MeOH/EtOH: useful for solubility and benign workup; avoid in reactions sensitive to transesterification or where alcohol acts as a nucleophile.
Practical tips:
Dry solvents are recommended for base-sensitive steps; water will quench carbanions at the alpha-sulfone position and suppress desired reactivity.
If crystallization is desired for purification, EtOAc/hexanes or toluene/hexanes systems may be explored depending on physical form.
Storage and Reconstitution
Item-specific (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Normal.
General handling (literature/general):
Store tightly capped in a dry, well-ventilated area away from strong oxidizers or strong bases unless in use. Protect from prolonged moisture exposure to preserve reactivity in base-mediated steps.
If hygroscopicity is observed (varies by lot and physical form), consider storing under inert gas and/or with desiccant.
No reconstitution is required; use as supplied. If a solution is desired (e.g., analytical standard), prepare in a suitable solvent (e.g., acetonitrile, methanol, DMSO) at known concentration and store at 2–8 °C for short term, protected from light; verify stability by LC before extended storage.
Stability notes:
Sulfones are generally robust thermally and oxidatively; the primary alcohol may undergo slow oxidation on extended air exposure. For long-term storage, keep container well sealed and minimize headspace.
Freeze–thaw: Not applicable to solids; for prepared solutions, avoid repeated freeze–thaw cycles by aliquoting.
Refer to the CoA/Spec Sheet for any lot-specific storage or stability instructions.
Structure and Identity
Brief description: 4-Ethylphenylsulfonylethanol is a bifunctional small molecule combining a para-ethyl arylsulfone with a terminal primary alcohol, useful as a synthetic intermediate.
Structural features: benzene ring bearing a para-ethyl substituent and a para-sulfonyl-ethyl chain; the sulfone sulfur is tetra-coordinate (S(VI)) with two S=O bonds and sigma bonds to aryl and carbon; linear –CH2–CH2–OH side chain attached to sulfur.
2D description in words: A benzene ring with an ethyl group at the para position relative to a sulfonyl substituent; the sulfonyl connects to a two-carbon chain terminating in a hydroxyl group (Ar–SO2–CH2–CH2–OH). No stereocenters are present.
Notes:
Where exact identifiers (SMILES/InChI) are needed for informatics workflows, please refer to the CoA/Spec Sheet for this specific lot.
Synthetic Utility
Key functional groups and reactivity (literature/general):
Primary alcohol (–CH2CH2–OH): amenable to oxidation (aldehyde/acid), activation (halides, sulfonates), Mitsunobu inversion, and carbamate/carbonate formation.
Aryl sulfone (Ar–SO2–): strongly electron-withdrawing; activates alpha-methylene toward deprotonation/alkylation; participates in eliminations to vinyl sulfones; can be used as a temporary activating group.
Named/typical transformations:
Alpha-alkylation of sulfones (e.g., with NaH/KHMDS in THF/DMF), followed by elimination to install alkenes (Julia-type tactics using non-heteroaryl sulfones require additional steps; heteroaryl variants are more classical for Julia–Kocienski).
Oxidation of primary alcohol to aldehyde: Dess–Martin periodinane, Swern, TEMPO/bleach.
Conversion to leaving groups: Appel halogenation (PPh3/CX4), PBr3/PI3, or sulfonylation (MsCl/TsCl) enabling SN2 with amines/thiols/alkoxides.
Reductive manipulations: Desulfonylation under dissolving-metal or metal-hydride conditions in select cases, enabling traceless activation strategies.
Retrosynthetic value:
The ethanol side chain can be installed by alkylation of an arylsulfinate or via sulfonylation of a haloethanol derivative followed by coupling to the para-ethyl arene.
The para-ethyl aryl core serves as a handle for further diversification via electrophilic aromatic substitution on other positions (if accessible in precursors) before sulfonylation.
Practical points:
Rigorously dry conditions improve efficiency in base-mediated alpha-functionalizations.
The sulfone increases polarity; plan chromatographic systems accordingly (e.g., add 1–2% MeOH in DCM or switch to EtOAc/hexanes).
Monitor for over-oxidation of the alcohol during strong oxidative conditions.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting reagent.
Item-specific (from Product Data):
No antigen/epitope, species reactivity, clone, or isotype information is provided for this item.
For biochemical targeting reagents (e.g., antibodies, ligands), see product-specific pages with validated specificity data.
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