3-[(Ethanesulfonyl)methyl]benzonitrile - ≥97% , CAS No.1267212-27-0

CAS: 1267212-27-0 Cat. No.: E971389 Summenformel: C₁₀H₁₁NO₂S Molekulargewicht: 209.265 PubChem CID: 21030988

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Reinheit

≥97%

Namen und Kennungen

Kanonisches Lächeln

CCS(=O)(=O)CC1=CC(=CC=C1)C#N

IUPAC Name

3-(ethylsulfonylmethyl)benzonitrile

InChIKey

VAOSJHQNSGVYRK-UHFFFAOYSA-N

INCHI

1S/C10H11NO2S/c1-2-14(12,13)8-10-5-3-4-9(6-10)7-11/h3-6H,2,8H2,1H3

Isomere SMILES

CCS(=O)(=O)CC1=CC(=CC=C1)C#N

PubChem CID

21030988

Molekulargewicht

209.265

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzonitriles
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzonitriles
• Alternative Parents: Sulfones Nitriles Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzonitrile - Sulfonyl - Sulfone - Nitrile - Carbonitrile - Organic nitrogen compound - Organic oxygen compound - Cyanide - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
• 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: 209.270 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 209.051 Da
• Monoisotopic Mass: 209.051 Da
• Topological Polar Surface Area: 66.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 320.000
• 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

Application Protocols

• Not applicable. No immunoassay or bioassay protocols are associated with this small-molecule building block.
• For synthetic applications, see the Reaction & Applications and Reaction Conditions sections for general literature guidance.

Biological Roles

• This compound is a synthetic aromatic nitrile containing a sulfone and is not known as a natural metabolite or cofactor. It is intended for research and chemical synthesis use only.
• General considerations (literature-based): Aromatic nitriles and sulfones do not typically participate in primary metabolic pathways. If used in biological assays as a small-molecule intermediate or probe precursor, ensure full characterization and purity, and verify DMSO stock stability.
• No endogenous biological role or pathway association is established for this specific structure.

Note: No medical or clinical claims are made; for research use only.

Buffer Applications

• Not typically applicable. 3-[(Ethanesulfonyl)methyl]benzonitrile is a neutral organic building block, not a buffering agent.
• If preparing analytical stock solutions (e.g., for bioassays), dissolve in suitable organic cosolvents (DMSO, DMF) before diluting into assay media, and verify solubility and nonspecific binding experimentally.

Green Alternatives

Context

• This product is a benchtop building block rather than a solvent or reagent used in bulk. Green considerations focus on solvent choice, base/reductant selection, and workup.

Greener choices (general guidance)

• Solvents for reactions and workup:
  • Prefer 2‑MeTHF, CPME, EtOAc, or propylene carbonate over chlorinated solvents when compatible with base and reactivity.
  • For strong-base deprotonations, 2‑MeTHF or CPME can sometimes replace THF; confirm stability and solubility.
• Bases/reductants:
  • Use less hazardous bases (e.g., K2CO3 for SN2 of pre-formed sulfone anions when possible) instead of pyrophoric LDA.
  • Reductive transformations of sulfones may be accomplished with catalytic hydrogenation or silane-based methods as alternatives to stoichiometric metal hydrides, where compatible.
• Workup/purification:
  • Minimize silica usage via crystallization or telescoping steps. Employ aqueous ethanol or EtOAc for extractions instead of DCM when feasible.

Trade-offs

• Replacing THF with 2‑MeTHF/CPME can alter anion stability and reaction rates; optimization is often required.
• Avoiding chlorinated solvents may increase solvent volumes due to solubility limitations; balance EHS gains against process efficiency.

Pharmaceutical Uses

• No pharmacopeial monograph or excipient designation is indicated for this item. It is not listed as an approved excipient per the Product Data.
• Potential role is as a synthetic intermediate in discovery chemistry or process route scouting where a benzylic sulfone and nitrile serve as orthogonal handles.
• If used in medicinal chemistry workflows, control residual solvents and impurities to internal specifications; consult the CoA for lot-specific purity and impurity profile.

Note: No therapeutic or clinical claims are made. For research and manufacturing development use only.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed (for general guidance; not product specifications)

• Estimated molecular formula: C10H11NO2S (see Structure & Identity)
• Estimated molecular weight: ~209.27 g/mol
• Polarity/functional profile: Neutral, moderately polar aromatic containing a strongly electron-withdrawing nitrile and a sulfone; expected to be non-protic and moderately polarizable.
• Solubility tendencies (literature-based expectations):
  • Likely soluble in polar aprotic organic solvents (e.g., DMSO, DMF, acetonitrile) due to the sulfone and nitrile groups.
  • Moderately soluble in chlorinated solvents and ethyl acetate; lower solubility expected in hexanes/heptane.
  • Aqueous solubility expected to be low.
• pKa: Benzylic C–H alpha to sulfone typically has pKa ~27–30 (literature, varies with substitution); nitrile is non-ionizable under neutral conditions.
• LogP: Not located in common references for this exact structure; expect moderate logP due to aromatic ring balanced by sulfone polarity.
• Melting/boiling points, density, refractive index: Not located in standard literature sources for this specific compound.

Note: For regulatory or process-critical parameters (mp/bp, water content, residual solvents, metal content, UV cutoff), consult the item-specific CoA/SDS.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/additives: None indicated in the Product Data; if present, they will be listed on the CoA/SDS.

Interpreting common grades (general guidance)

• Research or laboratory grade materials are fit for synthetic and analytical lab use. If HPLC/LCMS suitability is required, verify UV cutoffs, residual solvent levels, and trace metals on the CoA.
• For reaction development, impurity profiles (water, peroxides, residual metals) can influence outcomes; confirm specifications on the lot-specific CoA.

What is specific to this item

• Storage at room temperature is indicated in the Product Data, consistent with typical stability of benzylic sulfones and aromatic nitriles. For long-term integrity and to limit hydrolysis or base-catalyzed side reactions, protect from moisture and strong bases.

Documentation

• For definitive grade, assay, and impurity limits, consult the lot-specific Certificate of Analysis (CoA) and Specification Sheet.

Reaction and Applications

Role in synthesis (general/literature)

• Benzylic sulfone handle: The –CH2–SO2Et group renders the benzylic position relatively acidic. Deprotonation (e.g., with strong bases such as LDA, NaHMDS, KHMDS, or t‑BuOK under appropriate conditions) generates a carbanion that can participate in:
  • Alkylation/acylation at the benzylic carbon.
  • Conjugate (Michael) additions to activated alkenes.
  • Formation of α-halosulfones and subsequent Ramberg–Bäcklund reactions to generate alkenes.
• Nitrile handle: The –C≡N group enables orthogonal transformations:
  • Reduction to primary amine (e.g., catalytic hydrogenation, borane, or metal hydrides—selectivity considerations required due to sulfone stability).
  • Partial reduction to imine/aldehyde equivalents; or hydrolysis to amide/carboxylic acid under controlled conditions.
  • Nitrile anion chemistry is not applicable here (no α‑H on nitrile carbon), but the nitrile is a strong ring deactivator/director for electrophilic aromatic substitution patterns.

Applications in target synthesis

• Useful intermediate in constructing meta‑substituted biphasic pharmacophores or materials precursors where a benzylic linker and nitrile are needed.
• The benzylic sulfone can serve as a masked carbanion for installing side chains, then be removed (reductive desulfonylation) after elaboration, enabling net benzylic substitution with defined stereoelectronic control.

Practical tips

• Strictly anhydrous, oxygen‑free conditions are recommended for strong-base operations; quench carefully to avoid retro-elimination or over-alkylation.
• Monitor reactions by LCMS; the sulfone typically shows strong [M–CH3] or characteristic SO2-related fragments.

Reaction Conditions

General literature guidance (not product specifications; optimize per substrate)

• Benzylic deprotonation/alkylation:
  • Base: LDA, LiTMP, NaHMDS, or KHMDS (0.9–1.2 equiv) at −78 to 0 °C in dry THF, ether, or 2‑MeTHF; then add electrophile (alkyl halide, Michael acceptor). Typical times 0.5–2 h for deprotonation, 1–4 h for trapping. Quench with NH4Cl.
  • Alternative: t‑BuOK in DMSO/THF at 0 to rt for less hindered electrophiles.
• Ramberg–Bäcklund alkene formation:
  • α‑Halogenate the sulfone (e.g., NBS or NCS with base), then treat with strong base to induce rearrangement to alkene with loss of SO2. Solvents: THF, DME, or DMF; temperatures 0–rt. Yields vary widely (40–80%).
• Nitrile transformations:
  • Hydrolysis: Acidic (H2SO4, HCl) or basic (NaOH, KOH) aqueous-organic systems, 50–120 °C; amide formation at shorter times/temperatures, full acid upon extended conditions.
  • Reduction to amine: H2/Pd, Raney Ni, or BH3·THF can reduce nitriles; note that sulfones are generally stable to hydrogenation but verify to avoid undesired desulfonylation.
• Workup/purification:
  • Standard aqueous quench followed by extraction with EtOAc; charcoal treatment can improve color. Silica gel chromatography with EtOAc/hexanes or DCM/MeOH as needed.

Always conduct small-scale trials to determine compatibility of chosen reagents with both the nitrile and sulfone motifs.

Safety and Handling

Item-specific hazard information

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• Hazard (H) Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety considerations for aromatic nitriles and sulfones (literature/general guidance)

• Avoid inhalation of dust/vapors and skin/eye contact. Use appropriate PPE: lab coat, nitrile gloves, splash goggles. Handle in a fume hood.
• While many benzylic sulfones have low volatility, nitrile-bearing aromatics can be irritants. Wash thoroughly after handling.
• Incompatibilities: Strong bases can deprotonate the benzylic position alpha to the sulfone; strong reducing agents may affect the sulfone; strong oxidizers may over-oxidize organic substrates.
• Thermal stability: Sulfones are generally thermally robust; avoid excessive heating until substance-specific data are reviewed.
• Spills: Absorb with inert material, avoid dust generation, and dispose per local regulations.
• First aid (overview; follow SDS):
  • Inhalation: Move to fresh air; seek medical advice if symptoms persist.
  • Skin/eyes: Rinse with water for 15 minutes; remove contaminated clothing; seek medical advice as needed.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product’s SDS for authoritative, item-specific hazard classification and response guidance.

Solvent Selection

Applicability

• This product is a small-molecule building block, not a solvent. Nevertheless, solvent choice is critical for its handling, dissolution, and use in synthesis and purification.

General solvent behavior (literature-based expectations)

• Polarity class: Moderately polar, non-protic substrate with polar functional groups (nitrile, sulfone).
• Likely miscibility/solubility: Good solubility in polar aprotics (DMSO, DMF, NMP, acetonitrile), moderate in ethyl acetate and CH2Cl2/CHCl3, limited in alkanes and water.
• Crystallization/recrystallization: Ethyl acetate/hexanes or toluene/hexanes mixtures may be effective; DCM/hexanes may oil out—test on small scale.

Selection guidance by use-case

• NMR: DMSO‑d6 or CDCl3 typically dissolve sulfone-containing aromatics well; confirm solubility experimentally.
• Chromatography: Normal-phase silica with EtOAc/hexanes or DCM/MeOH gradients; the sulfone increases polarity, so higher EtOAc content may be needed compared to simple benzonitriles.
• Strong-base chemistry (alpha-deprotonation next to SO2): Use dry, polar aprotic solvents (THF, DME, DMPU, DME/THF, or THF/DMF blends) under inert atmosphere.

Comparison (general)

• Versus simple benzonitrile, the sulfone elevates polarity and HBA count, improving solubility in polar aprotic media and retention on silica. Water miscibility remains poor.

Storage and Reconstitution

Item-specific storage

• Storage Conditions: Room temperature (per Product Data). Keep tightly closed in a dry, well-ventilated place. Protect from moisture and prolonged exposure to strong bases or acids.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

General handling

• Store in original container or compatible amber glass. If long-term storage is anticipated, consider desiccation and inert atmosphere to minimize hydrolysis or base-catalyzed side reactions.
• Reconstitution/solution preparation: For stock solutions, dissolve in dry DMSO, DMF, acetonitrile, or other suitable anhydrous solvent. Filter through PTFE syringe filter if particulate is present. Record concentration and date; for DMSO stocks, typical storage at −20 °C is common practice in discovery labs.
• Freeze–thaw: Not typically applicable to neat solids or liquids; for solution stocks, aliquot to avoid repeated freeze–thaw cycles.

Research use note

• For research use only. Consult the SDS for stability and incompatibility details before scale-up.

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: E971389
• Product Name: 3-[(Ethanesulfonyl)methyl]benzonitrile
• CAS: 1267212-27-0
• PubChem CID: 21030988
• InChIKey: 374080 (as provided)
• Storage Conditions: Room temperature

Computed/literature structural information (for context; not product specifications)

• Systematic description: meta-substituted benzonitrile bearing a benzylic sulfone side-chain of the form Ar–CH2–SO2–CH2CH3 (ethanesulfonylmethyl group) positioned at the 3-position relative to the nitrile.
• Likely molecular formula (literature/computed): C10H11NO2S
• Approximate molecular weight (literature/computed): ~209.27 g/mol
• Representative SMILES (literature/computed): N#Cc1cccc(CS(=O)(=O)CC)c1
• Functional groups: aromatic nitrile (–C≡N), benzylic methylene, sulfone (–SO2–) linked to ethyl.
• 2D structure in words: A benzene ring bearing a nitrile group and, meta to it, a –CH2–SO2–CH2CH3 substituent; the benzylic CH2 connects the ring to the sulfone sulfur, which in turn is bound to an ethyl group.

Notes

• No stereocenters are present. The sulfone renders the benzylic CH2 relatively acidic compared with unsubstituted toluene derivatives.

Synthetic Utility

Key functional elements and their reactivity (literature)

• Benzylic sulfone (Ar–CH2–SO2Et):
  • α‑Deprotonation forms a stabilized carbanion suitable for C–C bond formation (alkylation, acylation, Michael addition).
  • α‑Halogenation followed by Ramberg–Bäcklund affords alkenes (net one‑carbon extrusion from sulfones bearing appropriate substituents).
  • Reductive desulfonylation (e.g., with sodium amalgam variants, SmI2, or catalytic hydrogenation under select conditions) can unmask the benzylic methylene.
• Aromatic nitrile (–C≡N):
  • Hydrolysis to amide or acid; reduction to primary amine; partial reduction to aldehyde via imidate pathways.
  • Strongly meta‑directing/deactivating for EAS; facilitates nucleophilic aromatic substitution if additional leaving groups are present elsewhere on the ring.

Retrosynthetic value

• Functions as a bifunctional synthon: nitrile serves as a transformable nitrogen/one‑carbon unit, while the benzylic sulfone serves as a masked carbanion for installing substituents before removal or conversion.

Selectivity notes

• Sulfone is generally robust to many oxidants and hydrogenation conditions that would reduce nitriles; plan sequences to exploit differential stability.
• Protecting-group logic: The sulfone can act as a temporary activating group at benzylic position; nitrile can be carried through basic conditions but avoid strong acids during prolonged heating.

Target Specificity

• Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, or species reactivity applies.