5,5-Diethylhydantoin - ≥95% , CAS No.5455-34-5

CAS: 5455-34-5 Cat. No.: D1068518 Fórmula: C₇H₁₂N₂O₂ Peso molecular: 156.18 Número CE: 864-128-6 PubChem CID: 21600

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CCC1(C(=O)NC(=O)N1)CC

IUPAC Name

5,5-diethylimidazolidine-2,4-dione

InChIKey

GWTZZUPJEUZZLU-UHFFFAOYSA-N

INCHI

1S/C7H12N2O2/c1-3-7(4-2)5(10)8-6(11)9-7/h3-4H2,1-2H3,(H2,8,9,10,11)

SMILES isoméricas

CCC1(C(=O)NC(=O)N1)CC

PubChem CID

21600

Peso molecular

156.18

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Azolidines
      • Subclass Imidazolidines
        • Level5 Imidazolidinones
          • Level6 Imidazolidinediones
            • Level7 Hydantoins

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Azolidines
• Subclass: Imidazolidines
• Intermediate Tree Nodes: Imidazolidinones - Imidazolidinediones
• Direct Parent: Hydantoins
• Alternative Parents: Alpha amino acids and derivatives 5-monosubstituted hydantoins N-acyl ureas Dicarboximides Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Hydantoin - Alpha-amino acid or derivatives - 5-monosubstituted hydantoin - N-acyl urea - Ureide - Dicarboximide - Carbonic acid derivative - Urea - Carboxylic acid derivative - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organic nitrogen compound - Aliphatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
• 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

Propriedades químicas e físicas

• Peso molecular: 156.180 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 156.09 Da
• Monoisotopic Mass: 156.09 Da
• Topological Polar Surface Area: 58.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 197.000
• 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

No biological assay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For synthetic use, see the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

• Item is supplied strictly for research use. No clinical or diagnostic use is implied.
• Hydantoin core (general biochemistry):
  • Hydantoins can arise in metabolic or degradative pathways (e.g., via Bucherer–Bergs-type chemistry in vitro), and hydantoinases convert certain hydantoins to amino acids in microbial biocatalysis.
  • The 5,5-dialkyl substitution increases lipophilicity and decreases aqueous solubility versus unsubstituted hydantoin, typically reducing direct bioavailability in aqueous systems.
• 5,5-Diethylhydantoin specifically:
  • No established endogenous biological role is described in the literature. It serves primarily as a synthetic intermediate/precursor to N-halo reagents or as a hydantoin scaffold for structure–activity exploration in research.
• Protein/ligand interactions (conceptual):
  • The imide carbonyls act as H-bond acceptors and the ring NHs as donors, enabling potential binding motifs; C-5 dialkylation modulates logP and sterics, which are useful parameters in medicinal chemistry optimization studies.

Note: Any biological testing should be performed under appropriate institutional approvals. Avoid extrapolation of scaffold-level literature to this specific compound without generating item-specific data.

Buffer Applications

This compound is not a buffer reagent and is not typically used to prepare defined pH buffer systems. If dissolution in aqueous media is required for assays, consider:

• Using co-solvents (e.g., DMSO, ethanol) to make concentrated stocks followed by dilution into buffered aqueous solutions.
• Selecting biologically compatible buffers (e.g., phosphate, HEPES) appropriate to your assay pH range and ionic strength. For true buffering applications, refer to dedicated buffering agents rather than 5,5-diethylhydantoin.

Green Alternatives

Context: 5,5-Diethylhydantoin is an organic solid used as a building block/precursor to N-halo reagents. Greener considerations focus on solvent selection and halogenation methods rather than replacing the core substrate.

• Greener solvent choices (literature/general):
  • Prefer MeCN, EtOAc, or 2-MeTHF over chlorinated solvents (e.g., CCl4, CH2Cl2) for halogenation or N-alkylation when compatible with selectivity.
  • Use ethanol or isopropanol for recrystallization instead of higher-toxicity solvents when solubility permits.
• Greener halogen sources/processes:
  • Employ NCS/NBS or electrochemical halogenation to form N-halo derivatives, reducing direct handling of Cl2/Br2 gas. Hypohalite salts (e.g., NaOCl/NaOBr) under biphasic or solvent-minimized conditions can also be effective.
• Energy/material efficiency:
  • Conduct reactions at ambient temperature where feasible; leverage solvent recycling and crystallization-based purifications to avoid chromatography.

Comparison (illustrative, literature-based):

• Traditional: Halogenation in CCl4 with elemental halogens; non-renewable, high EHS footprint.
• Greener: Halogenation in MeCN or EtOAc using NCS/NBS or in situ hypohalite, with minimized chlorinated solvent use and improved operator safety.

Trade-offs:

• Greener solvents may alter solubility and reaction rates; re-optimization of temperature and reagent stoichiometry can be required to maintain yields/selectivity.

Pharmaceutical Uses

• Regulatory/excipient status: Not specified for this item; no pharmacopeial grade is indicated. Supplied for research use only.
• Context (general):
  • The hydantoin scaffold is historically important in medicinal chemistry (e.g., anticonvulsant class), but 5,5-diethylhydantoin itself is not presented here as an active or excipient. Do not use in human or veterinary formulations.
• Process/research utility:
  • May be employed as a synthetic intermediate when exploring hydantoin-containing libraries or as a precursor to N-halo reagents sometimes used for process sanitation studies (research scale only).
• Quality considerations for formulation research (if applicable):
  • If exploring solid-state behavior (polymorphism, co-crystals), request detailed characterization (XRPD/DSC/TGA) from the lot-specific CoA; otherwise such attributes are Not specified for this item.

Physical Properties

Item-specific physico-chemical specifications (mp, bp, density, UV cut-off, residual metals, water/peroxide content, refractive index) are Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for the 5,5-dialkylhydantoin class and 5,5-diethylhydantoin specifically:

• Phase at ambient conditions: crystalline solid (literature, typical for 5,5-dialkylhydantoins).
• Acid–base: weakly acidic imide NHs; pKa (hydantoin family, literature) ~8–10 depending on substitution; 5,5-dialkyl substitution often slightly lowers acidity compared to parent hydantoin due to inductive effects.
• Polarity/H-bonding: dual H-bond donor (two NH) and acceptor (two carbonyls); however, 5,5-dialkylation increases hydrophobic surface, reducing water solubility relative to hydantoin/dimethyl analogs.
• Solubility (qualitative, literature): readily soluble in strong polar aprotic solvents (DMSO, DMF); moderately soluble in lower alcohols; limited in nonpolar hydrocarbons; water solubility tends to be low-to-moderate for 5,5-diethyl vs hydantoin.
• Thermal behavior: cyclic imides typically exhibit sharp melting transitions and good thermal stability prior to decomposition; precise melting point for this item is not provided here.

Note: For quantitative values and acceptance ranges relevant to this specific SKU, consult the product CoA/SDS or request the Specification Sheet.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay method and acceptance criteria.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: None indicated in Product Data; if stabilizers are critical to your application, confirm via CoA.
• Storage conditions (item-specific): Room temperature (per Product Data). This is consistent with typical stability of cyclic imides stored dry and protected from moisture.

Context and guidance (general):

• Hydantoin derivatives supplied for research use are commonly assayed by HPLC or GC with supporting spectroscopic identity (NMR/IR/MS). If you require specific impurities control (e.g., residual halogen, inorganic salts, or solvent content), request the detailed specification.
• For chromatographic or trace analysis applications, consider requesting low-residue solvent content and tighter metal limits. Unless explicitly stated on the CoA for this lot, assume these attributes are Not specified for this item.
• If using as a precursor to N-halo-5,5-diethylhydantoin, note that residual base or moisture can affect halogenation yields. Selecting material with documented water content can improve reproducibility; otherwise, dry prior to use.

Reaction and Applications

Literature/general applications of 5,5-dialkylhydantoins and 5,5-diethylhydantoin:

• Precursor to N-halo reagents:
  • N,N-dihalo-5,5-dialkylhydantoins (e.g., DBDMH/DCDMH analogs) are versatile halogenating/biocidal agents. 5,5-Diethylhydantoin can be converted to N,N-dichloro- or N,N-dibromo-5,5-diethylhydantoin by halogenation of the two imide nitrogens under controlled conditions.
  • Resulting reagents are used for selective halogen transfer in radical brominations/chlorinations, water treatment, and as oxidative halogen sources in synthesis.
• N-functionalization chemistry:
  • The imide NH positions can undergo N-alkylation, N-acylation, and N-sulfonylation after base activation (e.g., K2CO3, NaH). Regioselectivity between N1/N3 may be substrate- and condition-dependent.
• Ring transformations:
  • Hydantoin rings can participate in ring-opening hydrolysis to amino acid derivatives; substitution at C-5 with dialkyl groups modulates reactivity and stability.
• As a masked urea/ureide motif:
  • The cyclic imide functions as a constrained urea surrogate in medicinal chemistry scaffolds and materials, providing H-bonding and dipolar interactions while increasing lipophilicity via 5,5-diethyl substitution.
• Practical notes:
  • Drying prior to strong-base-mediated transformations improves reproducibility.
  • For halogenations, exclude water and control exotherms; halogenation efficiency can be monitored by halogen consumption and NMR of N–X formation.

Reaction Conditions

The following are literature/general guidelines; adapt to your specific substrates and scale. Item-specific specifications are not implied.

• N-Halogenation to N,N-dihalo derivative:
  • Solvent: MeCN or EtOAc (greener) or historically CCl4.
  • Reagents: Cl2/Br2 gas or in situ hypohalite (NaOCl/NaOBr); catalytic acid may facilitate; maintain 0–25°C to control exotherm.
  • Procedure note: add halogen gradually to a stirred suspension/solution of 5,5-diethylhydantoin; monitor by 1H NMR (loss of NH) and iodometric titration (active halogen content).
• N-Alkylation (mono-):
  • Base: K2CO3 or Cs2CO3 (1.1–1.5 equiv) in DMF or MeCN; electrophile: alkyl halide (1.1–1.3 equiv).
  • Temperature: 20–50°C; Time: 2–16 h; Monitor by TLC/LC-MS. For di-alkylation increase base/electrophile equivalents and reaction time/temperature.
• Ring opening (to ureido/amino acid derivatives):
  • Conditions: aqueous base (e.g., NaOH) or acid (HCl), reflux; outcome depends on substitution and workup.
• Purification:
  • Crystallization from alcohols/EtOAc or trituration to remove salts. If chromatography is needed, use polar eluents (EtOAc/MeOH/CH2Cl2) mindful of strong adsorption.

Note: Expected yields and kinetics vary with substituents and electrophiles; small-scale screening is recommended to optimize selectivity (N1 vs N3). Always assess compatibility with the ethyl-substituted, more hydrophobic C-5 environment.

Safety and Handling

• GHS/CLP classification, Signal Word, H/P statements, and pictograms: Not specified for this item; refer to SDS.
• General hazards (literature/general for hydantoin derivatives): may cause skin and eye irritation; dust may cause respiratory irritation. Avoid inhalation of dust and contact with skin/eyes.
• PPE recommendations (good laboratory practice):
  • Wear safety glasses or goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile).
  • Use in a well-ventilated area or fume hood to minimize dust exposure.
• Handling notes:
  • Prevent generation of dust; avoid contact with strong oxidizers and strong bases that can deprotonate imide nitrogens and enhance reactivity.
  • Although N-halo-5,5-dialkylhydantoins are oxidizing/halogenating agents, the parent 5,5-diethylhydantoin is not an oxidizer; keep separate from halogenating reagents unless intended for synthesis.
• First aid (overview; defer to SDS for authoritative detail):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for several minutes; remove contaminated clothing; seek medical attention if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Combustible organic solid; use water fog, dry chemical, CO2, or foam. Thermal decomposition may produce nitrogen oxides and carbon oxides.
• Spill response: Avoid dust; collect mechanically; place in suitable container for disposal per local regulations.

Solvent Selection

This product is a solid building block, not a solvent. Solvent choice concerns its dissolution and use in synthesis/processing.

• Polarity and miscibility (literature/general):
  • Expected to dissolve well in polar aprotic media such as DMSO and DMF; often soluble in hot ethanol/isopropanol; limited solubility in nonpolar hydrocarbons (hexanes, toluene) due to polar imide core.
  • Water solubility is reduced relative to hydantoin due to the two ethyl substituents; if aqueous work is required, use co-solvents (e.g., EtOH, MeCN) or gentle heating.
• Selection tips by task:
  • N-alkylation/acylation: use dry polar aprotic solvents (DMF, DMSO, MeCN) with a non-nucleophilic base (e.g., K2CO3, Cs2CO3) to deprotonate the imide NH.
  • Preparation of N-halo derivatives: perform halogenation in inert, anhydrous solvents (e.g., CCl4 historically; greener options include MeCN or EtOAc) under temperature control.
  • Crystallization/purification: alcohols (EtOH/IPA) or EtOAc/hexanes mixtures can be screened; increased hydrophobicity vs hydantoin may enable anti-solvent crystallizations.
• Comparison (general):
  • 5,5-Dimethylhydantoin (more polar) often dissolves better in water/alcohols; 5,5-diethylhydantoin favors less polar organic media, which may benefit moisture-sensitive transformations.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Store in a tightly closed container, in a dry place, away from strong oxidizers and strong bases. Protect from prolonged exposure to moisture.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/solution preparation (general):
  • Prepare stock solutions in dry DMSO, DMF, MeCN, or alcohols depending on downstream use. Filter if particulates are present.
  • For biological assays requiring aqueous media, dissolve first in a suitable organic co-solvent (e.g., DMSO or ethanol) and dilute into buffer with vigorous mixing; verify solubility and avoid precipitation.
• Stability of solutions (general):
  • DMSO/DMF stocks are typically stable for days to weeks at 2–8°C under inert atmosphere; prepare fresh if discoloration or precipitation occurs. Aqueous stability is lower due to potential hydrolysis under extreme pH.
• Freeze–thaw: For solution stocks, aliquot to minimize freeze–thaw cycles. Solid material tolerates ambient storage when kept dry.
• Research Use Note: For research use only.

Structure and Identity

Research-use hydantoin derivative bearing two ethyl substituents at the C-5 position of the imidazolidine-2,4-dione ring.

• Item-specific identifiers from Product Data:
  • CAS: 5455-34-5
  • CID: 21600 (literature identifier for reference)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Composition (literature/general):
  • Preferred name: 5,5-Diethylhydantoin
  • Synonym class: 5,5-dialkylhydantoin (hydantoin = imidazolidine-2,4-dione)
  • Molecular formula (literature): C7H12N2O2
  • Molecular weight (literature): ~156.18 g/mol
• Structural features (general description):
  • Core ring: five-membered imidazolidine with two carbonyls at C-2 and C-4 (cyclic imide). Two ring nitrogens (N-1, N-3) are ureide-type NHs capable of H-bonding and weak acidity.
  • Substitution: the C-5 ring carbon is quaternized by two ethyl groups (–CH2CH3), yielding a 5,5-dialkyl pattern that increases hydrophobicity vs parent hydantoin.
  • 2D description: a planar urea-like N–C(=O)–N–C(=O) motif embedded in a saturated five-membered ring, with two pendant ethyl chains projecting from C-5 above and below the ring plane; no stereogenic centers (C-5 is quaternary, not chiral).

Synthetic Utility

• Functional group profile:
  • Cyclic imide (two carbonyls) with two N–H sites offers ambident nucleophilicity upon deprotonation. The 5,5-diethyl quaternary carbon blocks C-5 functionalization, focusing reactivity at N-1/N-3 and at carbonyls.
• Transformations (literature/general):
  • N-Halogenation: formation of N,N-dihalo-5,5-diethylhydantoin (chlorinated/brominated) as halogen-transfer reagents.
  • N-Alkylation/Acylation: selective mono- vs di-substitution controlled by base strength, temperature, and stoichiometry.
  • Carbonyl chemistry: activation (e.g., with CDI or POCl3) can enable further derivatization; ring opening under strong basic/acidic hydrolysis can furnish ureido/amino acid derivatives.
  • Metalation: strong bases (NaH, LDA) can generate N-centered anions for subsequent electrophile capture; care with temperature and exclusion of moisture is advised.
• Retrosynthetic value:
  • Serves as a robust, readily handled hydantoin core for rapid exploration of N1/N3 substitution patterns without the need to install C-5 substituents de novo.
• Practical points:
  • Use dry, polar aprotic solvents and non-nucleophilic bases to favor clean N-functionalization.
  • Monitor reactions by 1H NMR (NH disappearance/shift) and IR (N–H/C=O changes). Workups benefit from acid–base partitioning to remove inorganic salts.

Target Specificity

Not applicable. This product is a small-molecule hydantoin, not an antibody, enzyme, or targeted biological reagent. No antigen/epitope, clone, isotype, or species reactivity data apply.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 5455-34-5, the molecular formula is C7H12N2O2, and the molecular weight is 156.18 g/mol. InChIKey GWTZZUPJEUZZLU-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.