This compound belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
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.
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Application Protocols
Not applicable.
No validated bioassay or immunoassay protocols are associated with this small-molecule building block. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general procedural guidance.
Biological Roles
Scope
This catalog item is intended strictly for research and laboratory synthesis. It is not a biological reagent and has no assigned physiological role.
General context (literature)
Small aliphatic β-ketonitriles are not endogenous metabolites. When used in chemical biology or medicinal chemistry, they serve as synthetic intermediates to access heterocycles, advanced building blocks, or probes after further functionalization (e.g., conversion of the nitrile to amide/amine).
Reactivity considerations: The activated methylene can react with biological nucleophiles under strong basic conditions, but under physiological conditions the molecule is largely unreactive aside from hydrophobic interactions; it lacks specific receptor/enzymatic targets.
Compliance note
No medical, diagnostic, or therapeutic uses are claimed. For any experiments involving biological systems, ensure appropriate solvent vehicles (e.g., DMSO) and conduct preliminary compatibility/toxicity assessments.
Buffer Applications
Not typically applicable.
4,4-Dimethyl-3-oxohexanenitrile is a neutral organic building block and does not function as a buffering agent. It lacks a conjugate acid/base pair suitable for maintaining pH in aqueous systems.
For work in aqueous media, select standard biological buffers (e.g., phosphate, HEPES, Tris) and dissolve this compound in a compatible co-solvent (e.g., DMSO, MeCN) if needed.
Green Alternatives
Context
This product is a specialized β-ketonitrile building block. Greener choices focus on solvent/process selection and, where feasible, use of functionally equivalent but lower-hazard reagents.
Greener process choices (literature-informed)
Solvents: Prefer 2-MeTHF or CPME over THF/Et2O for enolate chemistry (better safety, water immiscibility, renewable sourcing for 2-MeTHF). For condensations, use bio-based EtOH or water/EtOH mixtures with organocatalysts; apply Dean–Stark in toluene only when necessary.
Bases: Consider carbonate or organic base catalysis (DBU, piperidine) for Knoevenagel-type couplings in solvent-minimized or solvent-free conditions to reduce strong-base waste.
Energy: Microwave-assisted condensations in green solvents can cut time/energy use significantly.
Functionally related alternatives (trade-offs)
Cyanoacetates (e.g., ethyl cyanoacetate) can replace β-ketonitriles in many C–C bond-forming reactions, offering milder handling and often lower vapor hazard; however, they introduce an ester that must later be manipulated (hydrolyzed/reduced), adding steps.
1,3-Dicarbonyls (e.g., acetylacetone, dimedone) are widely available, benign, and effective nucleophiles but lack a nitrile handle for later diversification.
Comparison snapshot (general)
4,4-Dimethyl-3-oxohexanenitrile: High nucleophilicity at C2; nitrile enables downstream amide/acid/amine chemistry; somewhat higher hazard classification typical of nitriles.
Cyanoacetates: Greener profile in some guides; extra functional-group manipulations required.
1,3-Dicarbonyls: Greener/tox profiles favorable; reduced structural flexibility versus nitrile-containing intermediates.
Implement waste minimization via telescoped steps and in-line solvent recovery where possible.
Pharmaceutical Uses
Scope
This product is supplied for research use only. It is not an API, excipient, or GMP-grade material.
Formulation/manufacturing context (general)
As a β-ketonitrile, it can serve as a versatile intermediate in medicinal chemistry programs to build heterocyclic cores or to introduce a nitrile handle that can later be transformed to amides, acids, or amines. Typical roles include:
Scaffold assembly for small-molecule libraries via condensations and cyclizations.
Late-stage diversification through nitrile interconversions (hydrolysis, reduction) after C–C bond construction.
Pharmacopeial status: No compendial monograph is known for this specific structure. If a regulated path is envisioned, a defined impurity profile, residual solvent control, and stability indicating methods will be required.
Process considerations
Protect the ketone as a ketal if selective nitrile chemistry is planned. Where possible, telescope steps to reduce solvent exchanges and minimize exposure to strong bases/acids.
Physical Properties
Item-specific (Product Data)
Appearance: 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/computed (general guidance, not specifications)
Calculated molecular formula (from structure): C8H13NO
Calculated molecular weight: ~139.20 g/mol
Expected physical state: low-viscosity liquid at ambient temperature is typical for C8 β-ketonitriles, but this item’s state is not specified; confirm on CoA.
Volatility: moderate to low relative to small ketones; presence of both nitrile and carbonyl increases boiling point versus hydrocarbons of similar size (literature trend).
Polarity: polar aprotic; capable of enolization, but lacks H-bond donors; moderate dipole due to C≡N and C=O.
Solubility (qualitative, literature expectation): miscible with many polar aprotic solvents (MeCN, THF, EtOAc, acetone, DMF, DMSO); limited solubility in water is expected for C8 ketonitriles.
Refractive index, density, bp/mp, UV cutoff: Not readily found in major reference compilations for this exact structure at time of writing; verify experimentally or consult CoA/Spec Sheet.
Notes
All numerical specifications for this catalog item should be verified on the CoA/Spec Sheet for your lot.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general)
Research-use chemical (per Research Use Note). In the absence of a specified grade (e.g., AR, HPLC, anhydrous), assume standard research grade suited for organic synthesis and method development; verify impurity limits and residual solvents on the lot-specific CoA.
If low UV background or chromatographic purity is critical (e.g., LC-UV method development), request HPLC or LC-MS grade specifications (low non-volatile residue, low UV absorbance). If water sensitivity is a concern for base-mediated enolate chemistry, request Karl Fischer moisture data and ensure appropriate packaging.
Stabilizer considerations: This class typically does not require polymerization inhibitors; however, basic impurities can catalyze self-condensation. Where ultra-high purity is required, pass through a short plug of neutral alumina/silica under inert atmosphere immediately prior to use and confirm by GC/LC.
Documentation: For regulated workflows, retain CoA, SDS, and any impurity profiling (GC/LC, NMR). For quantitative synthesis, verify assay (wt%) and main impurity identities to set appropriate specs.
Reaction and Applications
Use profile (general for β-ketonitriles; expand from building-block role)
Enolate chemistry: The C2 methylene between –C≡N and C=O is strongly activated (pKa in DMSO typically ~9–11 for β-ketonitriles, literature). Clean deprotonation with LDA/LiHMDS enables alkylation, acylation, and Michael additions. Gem-dimethyl substitution at C4 can direct regioselectivity and block overreaction.
Heterocycle synthesis:
Pyridines via cyclocondensation with 1,3-dicarbonyls or enamines (e.g., Hantzsch-type variants) and ammonia/amine sources.
Pyrazoles/isoxazoles from condensation with hydrazines or hydroxylamines, exploiting the 1,3-dielectrophile character (C=O and activated methylene).
Pyrimidines/quinazolines via coupling with amidines/guanidines under basic or Lewis acid conditions.
Knoevenagel/Doebner-type condensations: Reaction with aldehydes/ketones under amine catalysis to form α,β-unsaturated nitrile–ketone adducts; subsequent Michael/cyclization elaborations are common.
Michael donor/acceptor chemistry: Acts as a soft carbon nucleophile upon enolate formation; the nitrile can be retained or transformed downstream (e.g., to amide, acid, amine).
Functional group interconversions: Nitrile hydrolysis (acidic/basic) to amide/carboxylic acid; reduction (e.g., DIBAL-H, LiAlH4, catalytic hydrogenation) to aldehyde or amine. Chemoselectivity is key versus the ketone—protect as ketal if needed.
Practical tips
Ensure rigorously anhydrous conditions for strong-base steps; pre-dry glassware and solvents. Titrate base (e.g., BuLi) and use cryogenic temperatures to control enolate geometry and reactivity.
Monitor by TLC/GC; β-ketonitriles often show characteristic downfield 1H NMR methylene (~3.2–3.6 ppm) and strong IR bands near 2250 cm−1 (C≡N) and 1710–1730 cm−1 (C=O) (literature).
Reaction Conditions
General conditions (literature guidance; optimize per substrate)
Enolate generation/alkylation:
Base: LDA (1.1–1.5 equiv) or LiHMDS in dry THF/2-MeTHF under N2/Ar.
Temperature: −78 to 0 °C for deprotonation; add electrophile at −78 to −20 °C, then warm to 0–25 °C.
Time: 0.5–2 h for deprotonation/addition; quench with NH4Cl or AcOH.
Typical yields: 60–90% for primary alkyl halides (literature) with careful exclusion of moisture.
Knoevenagel condensation:
Catalyst: Piperidine (5–20 mol%) or ammonium acetate (0.5–1.0 equiv) with ald./ketone partner.
Solvent: EtOH, i-PrOH, toluene (Dean–Stark), or solvent-free with grinding/microwave.
Temp/Time: 25–110 °C, 0.5–8 h depending on partner and solvent; remove water (azeotrope or sieves) to drive equilibrium.
Heterocycle formation:
Pyrazoles: Hydrazine or arylhydrazines (1.0–1.2 equiv) in EtOH/AcOH or DMF, 25–80 °C, 1–12 h.
Isoxazoles: Hydroxylamine hydrochloride with base (NaOAc, Et3N) in EtOH/MeOH, 25–60 °C.
Nitrile interconversions:
Hydrolysis: Aqueous acid (6 M HCl) reflux to amide/acid (longer times); or base (NaOH) reflux. Protect ketone if needed.
Reduction: DIBAL-H (−78 to −20 °C) to aldehyde; LiAlH4 or catalytic hydrogenation (Raney Ni, Pd/C) to amine—control for ketone reduction via protection or chemoselective conditions.
Always run small-scale trials, monitor by TLC/LC–MS, and dry solvents/reagents rigorously for base-mediated steps.
Safety and Handling
Item-specific (Product Data)
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
General safety considerations (literature/analogous compounds)
Hazard profile: β-Ketonitriles are generally classified as combustible liquids and can be harmful if swallowed, inhaled, or in contact with skin; they are irritants to eyes/skin. Treat as harmful; avoid inhalation of vapors and contact with skin/eyes.
PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to control vapors and to avoid exposure.
Incompatibilities: Strong bases (risk of rapid enolate formation and self-condensation), strong acids (hydrolysis of nitrile/ketone under forcing conditions), strong oxidizers. Avoid moisture ingress if using strong bases during handling.
Stability: Typically stable under ambient conditions when kept dry and sealed. Avoid prolonged exposure to heat, light, or air if high purity is essential for enolate chemistry.
First aid (overview): Eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; do not induce vomiting. Seek medical attention in all cases.
Spill/Fire: Absorb small spills with inert material; for fires use CO2, dry chemical, or alcohol-resistant foam. Vapors may form flammable mixtures with air if heated.
Always consult the Aladdin SDS for authoritative safety, handling, and disposal instructions for this specific SKU.
Solvent Selection
Applicability
This compound is a polar, aprotic β-ketonitrile used as a building block, not as a solvent. Solvent selection pertains to its use in synthesis, purification, and analysis.
Guidance (literature/practice)
Polarity class: Moderately polar, aprotic. Compatible with ethers (THF, MTBE), esters (EtOAc), ketones (acetone, MEK), chlorinateds (DCM), aromatics (toluene), and nitriles (MeCN). Sparingly soluble in water is expected for C8 ketonitriles.
Enolate chemistry: For strong-base deprotonation at C2, use dry, oxygen-free ethers (THF, 2-MeTHF) or hydrocarbons with co-solvent (THF) at −78 to 0 °C (LDA, LiHMDS). Avoid protic media which will quench enolates.
Condensations (Knoevenagel-type): Protic solvents (MeOH, EtOH, i-PrOH) or toluene with Dean–Stark can be effective in the presence of amine catalysts (piperidine, pyrrolidine) or ammonium salts; choice balances rate vs. reversibility and water removal.
N-heterocycle assembly (e.g., pyridines, pyrazoles): Polar aprotic solvents (DMF, DMSO, DMAc, NMP, MeCN) often enhance rates; consider azeotropic removal of water or molecular sieves when needed.
Workup/purification: EtOAc/hexane, DCM/MeOH, or toluene/EtOAc gradients frequently give clean separations on silica. The ketonitrile absorbs in UV; monitor by TLC at 254 nm.
Analytical: MeCN/H2O or MeOH/H2O with 0.1% formic acid for LC–MS; add weak base (e.g., 2 mM NH4OAc) for negative ESI if enolate/anion detection is desired.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Room temperature.
General guidance for this class of compounds
Container: Store in a tightly sealed, chemical-resistant bottle with minimal headspace. If frequent enolate chemistry is planned, consider storing under inert gas to minimize adventitious moisture uptake.
Light/moisture: Protect from moisture during handling, especially before strong-base steps; ambient light is generally acceptable, but opaque/amber containers minimize any photochemical risk.
Stability: β-Ketonitriles are typically stable for many months at RT when sealed. Avoid prolonged exposure to strong bases/acids. If purity-sensitive applications are planned, check by GC/LC-NMR before use.
Reconstitution: Not applicable (neat liquid/soluble solid). For stock solutions, prepare in dry THF, 2-MeTHF, MeCN, DCM, or EtOAc as needed. Filter through 0.2 µm PTFE if particulate is present.
Shipping: No specific shipping condition provided; default ambient shipping is typical unless otherwise stated on the SDS.
Note
For definitive storage limits, retest intervals, and any stabilizer information, consult the SDS and lot-specific CoA/Spec Sheet. Research use only.
Proposed SMILES: N#CCC(=O)C(C)(C)CC (derived from IUPAC name)
Core functional groups: a β-ketonitrile motif consisting of a nitrile (–C≡N) at C1 and a ketone (3-oxo) at C3; tertiary carbon at C4 bearing two methyl substituents (gem-dimethyl).
2D structure (described): a six-carbon chain numbered from the nitrile carbon (C1). C3 is a carbonyl carbon (ketone), C4 is quaternary with two methyl groups, followed by an ethyl terminus (C5–C6). There is no stereocenter; the molecule is achiral.
Notes
The β-ketonitrile framework places an acidic methylene (C2) between the nitrile and the carbonyl, enabling enolate formation and broad synthetic utility. Refer to the CoA/SDS for definitive identifiers used for this catalog item.
Synthetic Utility
Key functional elements
β-Ketonitrile synthon: Combines a strong electron-withdrawing nitrile and a carbonyl, conferring high acidity at C2 and enabling robust enolate chemistry with excellent chemo- and regioselective control.
Gem-dimethyl effect: The 4,4-dimethyl substitution increases steric bulk, often steering alkylation to less-hindered electrophiles, influencing cyclization regiochemistry, and improving stability of intermediates.
Transformations (literature)
Alkylation/acylation: LDA/LiHMDS-mediated enolates alkylate efficiently with primary halides/tosylates; acylation with acid chlorides or anhydrides yields 1,3-dicarbonyl–nitrile adducts.
Condensations: Knoevenagel reactions with aldehydes/ketones (amine catalysis) to form conjugated enones bearing a nitrile handle for further elaboration (Michael, Diels–Alder as dienophiles after activation).
Heterocycle assembly: Cyclocondensation with hydrazines or hydroxylamines to give pyrazoles/isoxazoles; with amidines/guanidines to deliver pyrimidines/quinazolines; with sulfur/amines (Gewald-type) to access substituted thiophenes when the carbonyl is sufficiently activated.
Functional group interconversions: Nitrile → amide/acid/amine; ketone → alcohol (NaBH4) or protected ketal; chemoselective sequences can be designed by temporary protection.
Analytical handles
IR: ~2250 cm−1 (C≡N), 1710–1730 cm−1 (C=O).
NMR: Activated methylene at ~3.2–3.6 ppm (1H), carbonyl carbon ~200 ppm (13C), nitrile carbon ~115–120 ppm (13C) (literature ranges). These aid in rapid reaction tracking and purity assessment.
Target Specificity
Not applicable.
This product is a small-molecule building block and is not an antibody, enzyme, or targeted biological reagent. No antigen/epitope, clone, isotype, or species reactivity applies.
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