This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
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
No validated bioassay or immunoassay application protocols are provided for this small-molecule reagent. Typical laboratory uses involve chemical synthesis.
General preparation tips for solution handling (informational):
Prepare stock solutions in DMSO or ethanol (e.g., 10–100 mM), vortex to dissolve, and, if needed, warm gently to 30–40°C.
For aqueous use, dilute organic stock into buffer with vigorous mixing; monitor for precipitation. Adjust pH only if enolate formation is desired and compatible with your system.
For detailed, application-specific procedures, consult the primary literature relevant to your transformation (e.g., Knoevenagel or multicomponent reactions).
Biological Roles
Item-specific biological/clinical information: Not specified for this item; research use only (Product Data). No medical or clinical claims are made.
General biochemistry context (literature/informational):
Origin: 1,3-Diethylbarbituric acid is a synthetic derivative of barbituric acid (a pyrimidine-2,4,6-trione). It is not known to occur naturally.
Scaffold relevance: Barbituric acid cores are privileged motifs in medicinal chemistry and chemical biology screening libraries due to their hydrogen-bonding topology and ability to present conjugated acceptor systems after condensation at C5.
Probe design: The N,N-dialkyl substitution reduces acidity at N1/N3, focusing reactivity at C5; this can be advantageous when designing reporter conjugates or affinity ligands where a single point of diversification is desired.
Assay considerations: Solutions are typically prepared in DMSO and diluted into assay media; the tricarbonyl motif can chelate or hydrogen-bond to protein residues in a non-specific manner, which should be considered during hit validation.
Note: Any biological activity should be determined empirically under controlled laboratory conditions; consult institutional biosafety guidance.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare biological or analytical buffer systems. If solutions are needed for assays or reactions, prepare in suitable organic solvents (e.g., DMSO, ethanol) and dilute into the working medium while monitoring pH and solubility.
For buffering needs, select established systems (e.g., phosphate, Tris, HEPES) appropriate to the pH range of your experiment.
Green Alternatives
Perspective: As a solid building block, the greener considerations focus on solvent/base choice and reaction energy input rather than replacing the compound itself.
Greener practice options (literature/general):
Solvent swaps: Use ethanol or water/ethanol mixtures instead of DMF/DMSO where feasible for Knoevenagel and multicomponent reactions.
Catalysis: Employ organocatalysts (L-proline, ammonium acetate) or heterogeneous bases (basic alumina, hydrotalcites) to enable milder, recyclable conditions.
Energy efficiency: Microwave or ultrasound can shorten reaction times and lower temperatures; mechanochemical milling (solvent-free) is reported for related condensations.
Base minimization: Catalytic amounts of piperidine or ammonium acetate often suffice; avoid strong bases unless required.
Greener alternative: EtOH/H2O (or neat), catalytic ammonium acetate, 50–80°C or ultrasound, 0.5–2 h; product precipitates and is isolated by filtration.
Trade-offs:
Solvent-free/mechanochemical routes can face scale-up and heat removal challenges.
Aqueous ethanol may limit solubility of some substrates, requiring higher temperatures or surfactants.
Always validate greener conditions with small-scale trials to ensure equivalent selectivity and purity.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical; for formulation/process R&D):
Role: 1,3-Diethylbarbituric acid is primarily a synthetic intermediate/scaffold in medicinal chemistry rather than a standard excipient.
Process utility: The solid can be recrystallized from alcohols to high purity and may serve as an intermediate in the synthesis of barbiturate-derived candidates for structure–activity studies.
Analytical characterization in pharma settings: Assay by HPLC/UV, identity by NMR and MS; residual solvents and elemental impurities per ICH Q3C/Q3D as applicable when used in regulated development.
No therapeutic claims are made. Use is limited to research and development under appropriate controls.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, refractive index, UV cutoff, residuals/metals: Not specified for this item; refer to CoA/Spec Sheet.
General/literature context for N,N-dialkylbarbituric acids (informational only):
Physical state: typically crystalline solids due to strong intermolecular hydrogen-bond acceptor carbonyls forming organized lattices.
Solubility profile: low to moderate solubility in water; readily soluble in polar aprotic solvents (DMSO, DMF) and moderately soluble in polar protic organics (ethanol, methanol). Solubility increases with base due to enolate formation at C5.
Acid/base behavior: the C5 methylene is activated by adjacent carbonyls and can be deprotonated by mild bases (e.g., amines, carbonates) to form a resonance-stabilized enolate (literature/general).
Tautomerism: keto–enol tautomerism at C5; the tricarbonyl system favors the keto form in neutral conditions (literature/general).
Important: Where exact numeric values are required for your process validation, please consult the item’s CoA/Spec Sheet and SDS.
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 (general):
Research grade: adequate for most synthesis and screening; impurities typically controlled to standard assay levels, but detailed trace specifications may not be assigned.
High-purity/analytical grade: tighter assay; may include limits for water, residual solvents, and UV-absorbing impurities suitable for photochemical or analytical workflows.
Stabilizers: N,N-disubstituted barbituric acids generally do not require stabilizers; any use of stabilizers or anti-caking agents would be disclosed on the CoA/Spec Sheet.
Quality considerations for this scaffold (general best practice):
Identity confirmation: 1H/13C NMR should show ethyl resonances (triplet–quartet pattern), barbiturate ring carbons (carbonyls ~160–170 ppm), and the C5 methylene.
Purity assessment: HPLC/UPLC with UV at ~210–230 nm typically gives strong responses due to the tricarbonyl chromophore; LC–MS provides rapid confirmation of [M+H]+.
Residual inorganic base: if the material has been neutralized after enolate chemistry, verify absence of residual carbonate/amine salts (conductivity or ion chromatography if critical).
Always refer to the item’s CoA/Spec Sheet for the definitive grade, assay, and any stabilizer present.
Reaction and Applications
Scope (general chemistry/literature for N,N-dialkylbarbituric acids):
Active-methylene donor: The C5 methylene, flanked by two carbonyls, participates readily in base-catalyzed Knoevenagel condensations with aldehydes/ketones to form barbiturate-derived alkenes (push–pull chromophores), often isolating as E-alkenes with high yields.
Multicomponent reactions: Combines with aldehydes and activated nitriles (e.g., malononitrile, ethyl cyanoacetate) to furnish fused heterocycles (e.g., pyrano[2,3-d]pyrimidinones) under mild conditions.
Michael additions and conjugate additions: The stabilized enolate adds to electron-deficient alkenes/alkynes; subsequent cyclizations can elaborate molecular diversity.
Electrophilic substitution at C5: Halogenation or sulfenylation at the activated methine of preformed Knoevenagel adducts allows further functionalization.
Photophysical materials: Barbiturate-based donor–acceptor systems are explored as nonlinear optical materials and organic dyes due to strong intramolecular charge transfer (literature reports).
Practical tips:
Base selection: Mild bases (secondary amines, ammonium acetate, K2CO3) are typically sufficient. Strong bases (NaH, t-BuOK) generate enolates rapidly but may induce side reactions.
Solvent: Ethanol or acetonitrile commonly balance rate and workup convenience; DMSO/DMF accelerate but complicate isolation.
Water tolerance: Many condensations proceed in EtOH/H2O and can benefit from product precipitation for simple filtration.
Workup: Neutralize residual base; wash with water/brine; recrystallize from alcohols or alcohol/ether mixtures.
Manufacturer Applications: Not specified in Product Data; the above reflect general literature uses of 1,3-disubstituted barbituric acids.
Reaction Conditions
General literature guidance for reactions of 1,3-disubstituted barbituric acids (not item-specific):
Solvent: ethanol, acetonitrile, or toluene; greener variants use EtOH/H2O.
Temperature/time: rt to reflux; 0.5–6 h depending on substrate.
Workup: dilute with cold solvent; product often crystallizes; filter and wash; recrystallize from ethanol.
Reported outcomes: moderate to high conversions and isolated yields (often 60–95%) in literature for analogous N,N-dialkylbarbiturates.
Multicomponent synthesis of pyranopyrimidinones (barbiturate + aldehyde + malononitrile):
Catalyst: ammonium acetate, piperidine, or basic alumina (catalytic).
Solvent: EtOH/H2O (1:1) or neat under grinding/ultrasound.
Temperature/time: 50–80°C or ultrasound at ambient; 0.5–3 h.
Notes: product typically precipitates; simple filtration and washing suffice.
Enolate alkylation at C5:
Base: NaH or t-BuOK (1.1–1.5 equiv.) in dry THF/DMF under N2.
Electrophiles: benzyl or allyl halides; acyl chlorides for acylation.
Temperature: 0°C to rt (exothermic upon base addition); 1–3 h.
Quench: aqueous NH4Cl; extract with EtOAc; purify by crystallization or column chromatography.
Always optimize on small scale and consult current literature for your exact substrates.
Safety and Handling
GHS classification and hazard statements (item-specific):
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 laboratory safety guidance (informational; defer to SDS):
PPE: wear lab coat, safety glasses, and appropriate chemical-resistant gloves. Handle solids in a fume hood to avoid dust inhalation.
Incompatibilities: strong bases (can generate enolates; vigorous reactions in protic media), strong acids (possible ring hydrolysis under forcing conditions), strong oxidizers.
Handling: avoid creating dust; weigh with care. If preparing basic solutions (enolate), add base slowly with cooling and inert atmosphere when needed.
First aid (overview; consult SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention for irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: use CO2, dry chemical, or foam extinguishers. Combustion may release nitrogen oxides and CO/CO2 (general for nitrogenous organics).
Waste: collect solid and solutions as organic laboratory waste; neutralize basic enolate solutions before disposal per institutional and regulatory guidance.
Storage per Product Data:
Store at room temperature. Keep container tightly closed, dry, and protected from direct light and reactive chemicals. Label and segregate from strong oxidizers and strong acids/bases.
Solvent Selection
Applicability: as a crystalline organic building block, solvent choice is dictated by intended use (e.g., dissolution for reaction, recrystallization, or analytical prep).
General solvent compatibility (literature/general):
Highly suitable: DMSO, DMF, NMP — excellent solubilization of the polar tricarbonyl framework and its enolate.
Moderately suitable: ethanol, methanol, acetonitrile, acetone — often adequate for reactions (e.g., Knoevenagel condensations) and recrystallization.
Limited solubility: water (neutral pH). Solubility increases in basic aqueous media via enolate formation.
Nonpolar solvents (toluene, hexanes): typically poor solubility unless used in biphasic systems or with phase-transfer catalysis.
When to choose what (practical tips):
For base-promoted condensations: ethanol or isopropanol with a catalytic secondary amine (e.g., piperidine) provides good rates and crystallization-driven workups.
For catalyst-free, greener protocols: EtOH/H2O mixtures at reflux or under ultrasound often suffice for multicomponent assemblies.
For moisture/air-sensitive couplings involving the enolate: use dry acetonitrile or THF under inert gas; consider non-nucleophilic bases (DIPEA, DBU).
For analytical stock solutions: DMSO at 10–100 mM, then dilute into assay buffer/organic mobile phase as required.
Note: Verify actual solubility for your batch/temperature; consult the CoA for any item-specific solubility data if provided.
Storage and Reconstitution
Storage (Product Data):
Store at room temperature. Keep container tightly closed in a dry, well-ventilated place. Protect from strong acids/bases and oxidizers.
Stability (general):
Solid is typically stable under ambient laboratory conditions when dry. Prolonged exposure to moisture or strong base can lead to enolate formation and potential degradation.
Reconstitution/preparation of solutions (general guidance):
Solvents: DMSO or DMF for concentrated stocks; ethanol or acetonitrile for reaction solutions. Water solubility is limited at neutral pH.
Concentrations: Prepare 10–100 mM stocks as appropriate for screening or synthesis. Filter (0.22 µm) if particulate matter is present.
Handling: If making basic solutions (for enolate chemistry), prepare fresh under inert atmosphere; avoid prolonged storage of basic solutions.
Freeze–thaw:
Not typically necessary for the dry solid. If storing solutions, aliquot to minimize freeze–thaw cycles; DMSO solutions are commonly stored at −20°C for short to medium term.
Always refer to the item’s CoA/Spec Sheet and SDS for authoritative storage and handling instructions.
Structure and Identity
Brief description: 1,3-Diethylbarbituric acid is an N,N-disubstituted barbituric acid (pyrimidine-2,4,6-trione) bearing ethyl groups on both ring nitrogens (N1 and N3). The core is a six-membered uracil-like ring with three carbonyls at C2, C4, and C6; there are no stereocenters.
SKU: D1339101
Product name: 1,3-Diethylbarbituric acid
CAS: 32479-73-5 (Product Data)
PubChem CID: 122889 (Product Data)
InChIKey: 427320 (Product Data; note: format appears non-standard; defer to CoA/SDS for definitive identifier)
SMILES: 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.
Structural features (general chemistry/literature):
Substitution: ethyl groups at N1 and N3 (N,N-dialkylation)
Functional groups: three amide-like carbonyls (imide), one acidic methylene at C5 (flanked by two carbonyls; “active methylene”)
2D description: a six-membered ring with alternating N–C units; carbonyls at positions 2, 4, 6; ethyl substituents bound to both ring nitrogens; the C5 methylene lies between the two carbonyl-bearing carbons, enabling enolization.
Notes:
Research use only (Product Data).
Synthetic Utility
Functional group reactivity (literature/general):
Active methylene at C5: readily deprotonated to an enolate that undergoes Knoevenagel condensation with aldehydes/ketones, affording conjugated alkenes anchored on the barbiturate ring.
Enolate chemistry: Alkylation or acylation at C5 can proceed under strong base with suitable electrophiles; selectivity and over-alkylation must be managed.
Cycloadditions/annulations: In multicomponent assemblies with activated nitriles and aldehydes, delivers fused heterocycles (e.g., pyrano[2,3-d]pyrimidin-4-ones) with useful substitution patterns.
Electrophile trapping: Halogenation (NBS/NCS) or sulfenylation at the C5 position of derived alkenes introduces handles for cross-coupling or further elaboration.
Retrosynthetic value:
The N,N-diethyl protection suppresses N-deprotonation and directs chemistry to C5, offering a controlled single diversification site – beneficial in library synthesis.
Deprotection or transalkylation at nitrogen is generally disfavored; plan routes assuming the N-ethyls are retained.
Practical notes:
Choose bases judiciously (DIPEA/DBU for mild, NaH/t-BuOK for strong). Monitor by TLC/HPLC; C5-functionalized products often crystallize and simplify purification.
Avoid protic nucleophiles when strong base is present to prevent undesired N- or O-alkylation side reactions.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies.
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