6-(4-Methoxyphenyl)-6-oxohexanenitrile , CAS No.29395-08-2

CAS: 29395-08-2 Cat. No.: M975055 Formula: C₁₃H₁₅NO₂ Peso molecolare: 217.268 PubChem CID: 24726801

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

COC1=CC=C(C=C1)C(=O)CCCCC#N

IUPAC Name

6-(4-methoxyphenyl)-6-oxohexanenitrile

InChIKey

BMKMHMPWYIQLKG-UHFFFAOYSA-N

INCHI

1S/C13H15NO2/c1-16-12-8-6-11(7-9-12)13(15)5-3-2-4-10-14/h6-9H,2-5H2,1H3

Isomeri SMILES

COC1=CC=C(C=C1)C(=O)CCCCC#N

PubChem CID

24726801

Peso molecolare

217.268

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Butyrophenones Phenoxy compounds Methoxybenzenes Benzoyl derivatives Aryl alkyl ketones Anisoles Alkyl aryl ethers Nitriles Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Butyrophenone - Phenoxy compound - Anisole - Benzoyl - Phenol ether - Aryl alkyl ketone - Methoxybenzene - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - Nitrile - Carbonitrile - Ether - Organonitrogen compound - Hydrocarbon derivative - Organic nitrogen compound - Organic oxide - Cyanide - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl 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

Proprietà chimiche e fisiche

• Peso molecolare: 217.260 g/mol
• XLogP3: 1.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 217.11 Da
• Monoisotopic Mass: 217.11 Da
• Topological Polar Surface Area: 50.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 258.000
• 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 tested biological assay formats (e.g., WB, IHC, IF, FC) are relevant to this small-molecule reagent. For practical usage, refer to the Reaction & Applications and Reaction Conditions sections for synthetic procedures.

Biological Roles

This product is intended for research and synthetic chemistry use. No specific biological role is established for 6-(4-methoxyphenyl)-6-oxohexanenitrile.

General considerations (informational):

• Aryl ketones and nitriles are common motifs in bioactive molecules, but the presence in a structure does not imply biological activity.
• The para-methoxybenzoyl group is a photophore in some contexts; however, any photochemical properties here are relevant to materials/synthetic chemistry rather than biology.

Summary: There are no known endogenous roles or metabolic pathways specific to this compound. Any use in biological studies would be as a synthetic intermediate or probe precursor, not as a buffer component or nutrient. For biological testing, appropriate safety review and institutional approvals are required.

Buffer Applications

Not typically applicable. 6-(4-Methoxyphenyl)-6-oxohexanenitrile is a neutral organic building block, not a buffering agent. It does not form defined conjugate acid/base pairs in aqueous media across physiological pH and is poorly water-soluble.

Recommendation: For aqueous work, focus on extraction/partitioning strategies and the solvent selection, reaction, and synthetic utility sections for guidance on handling and transformations.

Green Alternatives

While the compound itself is a fixed structure, greener choices arise in the way it is handled and transformed.

• Solvent choices (comparative, literature-informed):
  • Replace dichloromethane with ethyl acetate or 2-MeTHF for workups and chromatography when resolution permits.
  • For enolate chemistry or reductions, 2-MeTHF can substitute for THF, offering renewable sourcing and better phase-splitting.
  • Use ethanol or isopropanol instead of methanol where compatible (lower toxicity, bio-based availability).
• Reagent choices:
  • Nitrile hydrolysis: Consider catalytic hydration (e.g., metal-organic frameworks, nitrilase enzymes in aqueous media) instead of stoichiometric mineral acids/bases when feasible.
  • Carbonyl reductions: Catalytic hydrogenation (H2/Pd, H2/Ni) in green solvents may replace stoichiometric borohydrides; or use aqueous formate transfer hydrogenation (e.g., Ru- or Fe-catalyzed) when chemoselectivity allows.
  • O-Demethylation: Oxidative demethylation using benign Lewis acids or electrochemical methods can reduce halogenated waste vs BBr3.

Small comparison table (process choices):

• Task: Column chromatography
  • Conventional: DCM/hexanes
  • Greener: EtOAc/heptane or cyclopentyl methyl ether (CPME)/heptane
• Task: Ketone reduction
  • Conventional: NaBH4 in MeOH
  • Greener: H2 (1–3 bar) over Pd/C in EtOH or 2-MeTHF
• Task: Nitrile → amide
  • Conventional: 6 M H2SO4, reflux
  • Greener: Aqueous biocatalysis (nitrilase) near ambient conditions

Note: Validate chemoselectivity with small-scale screens when substituting greener conditions.

Pharmaceutical Uses

No pharmacopeial excipient status or formulation role is specified for this item. It is offered for research use only.

Context (informational; not a medical claim):

• Structural motif: Aryl ketone plus nitrile is encountered in medicinal chemistry scaffolds; this compound may serve as a synthetic intermediate en route to APIs or probes after functional group interconversions (e.g., nitrile → amide/acid/amine; ketone → alcohol/imine).
• Process considerations: When used in drug discovery campaigns, attention to residual solvents, trace metals, and polymorphism is important for downstream evaluation. For this SKU, specific impurity limits or grades are not specified—consult CoA.

Regulatory note: This product is not intended for human or veterinary use, clinical diagnostics, or as a drug substance/excipient. For any GMP-related development, source material under appropriate quality systems and specifications.

Physical Properties

Item-specific specifications for this SKU (BP/MP, density, UV cutoff, water/peroxide/metals, refractive index, etc.): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for compounds of this class (aryl–alkyl ketone bearing a terminal nitrile; informational only):

• Physical state/appearance: Often low-melting solid or pale oil for similar aryl acyl–alkyl nitriles, depending on purity and crystallinity.
• Polarity: Polar aprotic; both nitrile and ketone contribute to dipole moment; aromatic ring increases hydrophobic surface area.
• Solubility profile (typical):
  • Good solubility in moderately polar organics: dichloromethane, ethyl acetate, acetone, acetonitrile, THF.
  • Limited solubility in alkanes and alcohols; negligible in water.
• Boiling/melting behavior: Aryl ketone nitriles of comparable MW (≈200–240 g/mol) frequently show decomposition before distillation under ambient pressure; purification commonly by column chromatography or recrystallization.
• LogP: Expected moderate logP (literature: often 2–3.5 for p-anisoyl aliphatic nitriles), facilitating organic-phase handling.

Important: The above are general/literature trends for structurally related compounds and are not product specifications. Always consult the item’s CoA/SDS for exact physical property data prior to process design.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on typical grades for organic building blocks (contextual):

• Research grade: Suitable for general synthesis and method development; may have broader impurity profile. Verify by NMR/LC before scale-up.
• ≥95–98% assay (common for fine chemicals): Supports most synthetic applications; residual solvents and UV-absorbing impurities can matter for photochemistry or analytics.
• HPLC/GC assay reporting: When provided, implies quantitative purity determination. Low-UV grade is relevant primarily for chromatographic solvents, not typically for solids/building blocks.

Stabilizers/inhibitors:

• Not specified for this item; refer to CoA/Spec Sheet. Aryl ketones/nitriles usually do not require polymerization inhibitors; no peroxide inhibitors are expected.

Batch quality considerations for this structure:

• Potential impurities: Unreacted anisoyl precursors, homologous nitriles, reduced/oxidized carbonyl species, O-demethylated phenols. Monitor by 1H/13C NMR (diagnostic: methoxy singlet ~3.7–3.9 ppm; carbonyl ~195–198 ppm; nitrile carbon ~115–120 ppm), LC–MS (M+H+ ~218 for computed MW 217.27), and HPLC purity.
• Water content, residual solvents, metals: Not specified for this item; consult CoA for limits if critical to your application.

Reaction and Applications

This bifunctional building block offers a para-methoxy aryl ketone and a terminal nitrile, enabling divergent synthesis and late-stage diversification.

• Transformations of the nitrile:
  • Hydrolysis to amide or acid (–CONH2/–CO2H) under acidic (H2SO4, HCl) or basic (KOH) conditions; lactamization is possible after reduction/functionalization of the carbonyl end.
  • Reduction to primary amine (–CH2NH2) via catalytic hydrogenation (Raney Ni, Pd/C) or metal hydrides (BH3•THF, DIBAL-H followed by hydrolysis).
  • Nucleophilic additions under strong base (anionic α-deprotonation next to the carbonyl, then trapping; or addition to the nitrile with organometallics to form imines/ketimines).
• Transformations of the ketone:
  • Oxime/hydrazone formation; subsequent reduction to the amine (e.g., via NaBH3CN after imine formation—chemoselectivity planning needed to avoid nitrile reduction).
  • Selective carbonyl reduction to secondary alcohol using NaBH4 or catalytic hydrogenation; tuning solvent and catalyst can preserve the nitrile.
  • α-Functionalization (enolate chemistry): Aldol, Claisen-type condensations; Michael donor behavior after enolization.
• Aryl modifications:
  • O-Demethylation (e.g., BBr3) to p-hydroxy analogue for further etherification/esterification.
  • Electrophilic aromatic substitution is deactivated by the acyl group but directed outcomes are achievable with strong activators.

Applications:

• Intermediate toward ω-amino ketones/acids, lactams, and arylated nylon precursors.
• Precursor to photophysical scaffolds (aryl ketone chromophore) and linkers in materials synthesis.

Practical tips:

• For chemoselective ketone reduction in the presence of nitrile, prefer NaBH4 in protic solvents at 0–25 °C; avoid LiAlH4 unless reduction of the nitrile is desired.
• Control enolization with non-nucleophilic bases (LDA, KHMDS) at −78 to 0 °C.

Reaction Conditions

General, literature-informed conditions for common transformations of aryl ketone nitriles like 6-(4-methoxyphenyl)-6-oxohexanenitrile (guidance only; optimize per lab):

• Selective ketone reduction (retain nitrile):
  • NaBH4 (1.5–3.0 equiv) in MeOH, EtOH, or THF/MeOH at 0–25 °C, 0.5–3 h → secondary alcohol (good to excellent yields reported for analogous substrates).
  • Catalytic hydrogenation (H2, 1–3 bar) over Pd/C in EtOH may also reduce ketone selectively; monitor to avoid nitrile hydrogenation.
• Nitrile reduction to amine:
  • BH3•THF (1–3 M, 3–6 equiv), 0–25 °C then reflux as needed, quench with MeOH/H2O → primary amine; ketone may also reduce—use protecting strategies if needed.
  • H2 (10–50 bar) over Raney Ni at 25–80 °C in EtOH/THF → primary amine; carbonyl reduction likely; sequence planning advised.
• Nitrile hydrolysis:
  • Acidic: 6 M HCl or H2SO4, 80–110 °C, 6–24 h → amide/acid depending on time; co-solvent dioxane/MeCN improves solubility.
  • Basic: KOH (2–6 equiv) in EtOH/H2O or dioxane/H2O, reflux 6–24 h → carboxylate then acid upon workup.
• Oxime formation:
  • NH2OH·HCl (1.2–2.0 equiv), pyridine/EtOH or AcOH/MeOH, 25–60 °C, 1–6 h → oxime; follow with reduction (NaBH3CN) to amine if desired.
• Enolate chemistry:
  • LDA (1.1–1.5 equiv) in THF at −78 to −20 °C, then electrophile (alkyl halide, acyl chloride). Quench at low temp to curb side reactions.

These are representative conditions from general organic synthesis literature; verify chemoselectivity against both the nitrile and ketone in pilot trials.

Safety and Handling

Item-specific hazard classifications (GHS signal word, H-statements, pictograms): Not specified for this item; refer to SDS.

General laboratory safety guidance for aryl ketone nitriles (informational; defer to SDS):

• Likely hazards: May cause skin/eye irritation and respiratory tract irritation upon dust/vapor exposure. Nitriles and ketones can be harmful if ingested or absorbed; avoid exposure.
• PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize inhalation.
• Handling:
  • Avoid heat, sparks, and open flame during operations such as solvent removal or distillation.
  • Prevent contact with strong bases (can cause aldol/self-condensation at the carbonyl alpha position) and strong oxidizers.
  • Avoid strong reducing agents unless intentionally performing nitrile/ketone reductions.
• First aid (overview; consult SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Storage incompatibilities: Keep away from strong oxidizers, strong bases, and reactive metals/hydrides. Store tightly closed, protected from moisture.

Always consult and follow the official SDS for authoritative hazard, exposure controls, and emergency measures for this product.

Solvent Selection

Applicability: As a moderately polar, non-ionic aryl ketone–nitrile, this compound dissolves well in common organic solvents. Selection depends on the transformation and workup.

• Polarity/miscibility (literature expectations):
  • Good: DCM, chloroform, ethyl acetate, acetone, acetonitrile, THF, toluene (warm), DMF/DMSO (excellent).
  • Poor: Alkanes (hexanes/heptane) and water.
• Choosing solvents by task:
  • Reaction medium (carbonyl or nitrile chemistry):
    • Reductions (NaBH4, catalytic hydrogenation): MeOH/EtOH for ketone reductions; for chemoselectivity vs nitrile, use aprotic solvents (THF/EtOAc) with milder hydride donors (e.g., NaBH(OAc)3 for iminium).
    • Nitrile hydrolysis: Aqueous alcohols, dioxane/water, or acetonitrile/water under acid/base catalysis.
    • Oxime formation/reductive amination: MeOH, EtOH, or AcOH/MeOH mixtures.
  • Purification: Normal-phase silica chromatography with hexanes/EtOAc (start 7:3 to 1:1) or DCM/MeOH (if polar). Reverse-phase (C18) for high-polarity impurity resolution.
  • Crystallization (if solid): EtOAc/hexanes or toluene/hexanes screens.
• Small comparison (literature-based):
  • DCM vs EtOAc: DCM gives fast kinetics and sharp bands; EtOAc is greener and often adequate for workups and chromatography.
  • THF vs 2-MeTHF: Similar solvation; 2-MeTHF offers greener profile and easier phase separations.

Note: Verify actual solubility with a small-scale test; adjust solvent strength to maintain homogeneous conditions during reaction.

Storage and Reconstitution

• Item-specific storage: Room temperature (as provided). Store tightly closed in a dry, well-ventilated place.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable; use as received. If solid and recrystallization is desired, typical solvent systems include EtOAc/hexanes or toluene/hexanes. If viscous, dissolve in a suitable organic solvent (e.g., DCM, EtOAc, THF) to prepare stock solutions.
• Stability considerations (general):
  • Aryl ketone nitriles are generally stable at ambient conditions. Protect from strong light/UV to minimize potential photoreactions of the aryl ketone chromophore.
  • Avoid prolonged exposure to strong acids/bases unless performing intended reactions (hydrolysis, aldol, etc.).
  • Moisture sensitivity: low; however, keep container tightly closed to prevent hydrolysis during long-term storage.
• Inventory control: Record opening date; for long projects, consider retesting purity by NMR/LC after 12–24 months at RT.

Always consult the product’s CoA and SDS for definitive storage guidance and stability information for your specific lot.

Research Use Note: For research use only.

Structure and Identity

Brief overview: 6-(4-Methoxyphenyl)-6-oxohexanenitrile is an aryl–alkyl ketone bearing a terminal nitrile; it combines a p-anisoyl moiety with a pentanenitrile chain. Two orthogonal handles (ketone and nitrile) enable diverse downstream transformations.

• Item-specific (from Product Data):
  • Product name: 6-(4-Methoxyphenyl)-6-oxohexanenitrile
  • CAS: 29395-08-2
  • PubChem CID: 24726801
  • InChIKey: 28688 (as provided)
  • Storage: Room temperature
• Computed/literature structural details (informational; not item specifications):
  • Preferred 2D connectivity: p-anisoyl–(CH2)4–C≡N, i.e., p-MeO-Ph–C(=O)–(CH2)4–C≡N
  • Functional groups: aryl ketone (benzoyl), para-methoxy aryl ether, terminal nitrile
  • Putative molecular formula: C13H15NO2 (computed from name)
  • Putative molecular weight: ~217.27 g/mol (computed)
  • SMILES (derived from name): COc1ccc(cc1)C(=O)CCCCC#N
  • Stereochemistry: none (acyclic, achiral as named)
• Described 2D structure in words:
  • A para-methoxyphenyl ring is bonded to a carbonyl carbon (benzoyl). The carbonyl is connected to a linear tetramethylene spacer ending in a nitrile (–C≡N). The ring bears a methoxy substituent para to the acyl linkage. No stereocenters are present.

Note: Structural strings and formula are provided for reference (literature/computed). For definitive identifiers specific to this lot, refer to the CoA/Spec Sheet.

Synthetic Utility

Key functional elements and reactivity:

• Terminal nitrile (–C≡N):
  • Hydrolysis ladder: nitrile → amide → acid (acidic or basic conditions; control by time/temperature/catalyst).
  • Reductions: to primary amine (BH3•THF, DIBAL-H then hydrolysis, or H2/Raney Ni). Chemoselectivity vs ketone must be managed.
  • Nucleophile umpolung: Organometallic addition to nitrile gives imine/ketimine that can be trapped/reduced to form tertiary amines.
• Aryl ketone (Ar–CO–):
  • Enolization allows α-alkylation/acylation; aldol additions to electrophiles.
  • Imine/oxime/hydrazone formation; reductive transformations to secondary amines.
  • Selective reduction to benzylic secondary alcohol while retaining nitrile under mild conditions.
• Para-methoxy group:
  • O-Demethylation to phenol (BBr3, AlCl3/thiols, or oxidative protocols) enabling subsequent etherification, carbonate/urethane formation, or cross-coupling after activation.

Strategic roles:

• Bifunctional linchpin enabling divergence: one branch manipulates the nitrile to an amine/acid while orthogonally elaborating the carbonyl center.
• Linker chemistry: The (CH2)4 spacer supports macrocyclization or conjugation strategies after end-group transformations.

Analytical handles:

• UV-active aromatic chromophore; monitor by HPLC-UV at 254–280 nm.
• Distinctive NMR: methoxy singlet ~3.7–3.9 ppm; benzylic carbonyl region ~195–198 ppm; nitrile carbon ~115–120 ppm (weak).

All values and conditions are general/literature guidance.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or isotype information applies.