Ethyl 2-(1-Imidazolyl)acetate - ≥95% , CAS No.17450-34-9

CAS: 17450-34-9 Cat. No.: E708902 Formule: C₇H₁₀N₂O₂ Poids moléculaire: 154.17 Numéro CE: 834-626-8 PubChem CID: 3798501

GRADE & PURITY ≥95%

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Store at 2-8°C,Protected from light

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥95%

Noms et identifiants

Sourires canoniques

CCOC(=O)CN1C=CN=C1

IUPAC Name

ethyl 2-imidazol-1-ylacetate

InChIKey

OITZNDMCFHYWLX-UHFFFAOYSA-N

INCHI

1S/C7H10N2O2/c1-2-11-7(10)5-9-4-3-8-6-9/h3-4,6H,2,5H2,1H3

Isomères SMILES

CCOC(=O)CN1C=CN=C1

PubChem CID

3798501

Poids moléculaire

154.17

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alpha amino acid esters
• Alternative Parents: Imidazolyl carboxylic acids and derivatives N-substituted imidazoles Heteroaromatic compounds Carboxylic acid esters Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-amino acid ester - Imidazolyl carboxylic acid derivative - N-substituted imidazole - Azole - Imidazole - Heteroaromatic compound - Carboxylic acid ester - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Azacycle - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Carbonyl group - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
• 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

Mécanismes d'action

Propriétés chimiques et physiques

• Poids moléculaire: 154.170 g/mol
• XLogP3: 0.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 154.074 Da
• Monoisotopic Mass: 154.074 Da
• Topological Polar Surface Area: 44.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 138.000
• 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 assay or bioanalytical protocols are specified for this catalog item.

• Tested applications, recommended dilutions, and positive controls: Not specified for this item; refer to any project-specific SOPs.

General laboratory use suggestions (literature/general):

• For synthetic use, verify identity by 1H/13C NMR and LC–MS prior to scale-up.
• For library synthesis, standard parallel hydrolysis/coupling workflows apply; include light protection and moisture control in protocols per Product Data storage notes.

Biological Roles

This product is a synthetic imidazole-containing ester intended for research and laboratory use; it is not a biological reagent per se.

General context (literature/general):

• Imidazole motif: Found in histidine and many biomolecules; participates in metal coordination and acid–base catalysis around physiological pH due to its amphoteric character.
• Derivatization potential: Hydrolysis to imidazol-1-ylacetic acid or conversion to amides/esters can furnish probes or linkers for biochemical studies, e.g., tethering imidazole to peptides, surfaces, or chelating frameworks.
• Metal binding: The imidazole ring can weakly bind transition metals, which is leveraged in biomimetic catalysis and material interfaces (though binding strength depends on substitution and medium).

What does not apply:

• No inherent role as a buffer or nutrient. Any biological activity would be context-dependent and requires dedicated evaluation. No claims are made for clinical or therapeutic use.

Practical guidance:

• For biochemical experiments (e.g., ligand screening), confirm purity and residual solvent profile via LC–MS/1H NMR.
• Consider converting to the free acid or amide for improved aqueous compatibility before interfacing with biological systems.

Buffer Applications

This compound is an ethyl ester of imidazolylacetic acid and is not typically used as a buffering agent. The imidazole ring can confer weak basicity, but the ester lacks the acid/base pair and pKa profile needed for robust buffering in aqueous media.

• If a buffer with imidazole character is required, use imidazole or histidine buffers (pH range ~6.2–7.8; literature) instead.
• For aqueous work involving this ester, consider hydrolyzing to the corresponding acid (imidazol-1-ylacetic acid) or forming a water-soluble salt/amide to improve compatibility.

Item-specific buffer recipes, pKa values, and ionic strength data: Not applicable and not specified for this item.

Green Alternatives

Green chemistry considerations for using and transforming Ethyl 2-(1-imidazolyl)acetate center on solvent choice, coupling reagents, and protection/deprotection strategy.

• Solvent choices (greener vs. conventional; literature/general):

  • Prefer EtOAc, MeCN, 2-MeTHF, propylene carbonate over chlorinated solvents (DCM, CHCl3) when feasible.
  • For hydrolysis or amidation, aqueous ethanol or MeCN/H2O systems can reduce hazardous solvent use.

• Coupling chemistry:

  • Avoid benzotriazole-based additives (e.g., HOBt) where safety is a concern; consider ethyl chloroformate alternatives, CDI, DMTMM, or green carbodiimides with OxymaPure.

• Energy and process:

  • Perform saponifications at ambient temperature with catalytic phase-transfer/base when possible; use microwave only when justified by rate/atom economy improvements.

• Waste minimization:

  • Use catalytic transesterification with solid acids/bases (e.g., Amberlyst) to simplify workup and enable solvent recycling.

Illustrative comparison (general):

• DCM vs. EtOAc in workup/purification:
  • EHS profile: EtOAc preferred (biodegradable, lower toxicity).
  • Performance: DCM may yield sharper separations; test EtOAc/hexanes first, reserve DCM for challenging separations.
• DMF/DMAc vs. MeCN/2-MeTHF for coupling:
  • MeCN/2-MeTHF are easier to remove and have better EHS scores; if high polarity is required, consider Cyrene or propylene carbonate as exploratory greener options.

Note: These are general best practices; adapt to reaction needs and safety constraints.

Pharmaceutical Uses

Item-specific pharmacopeial status, excipient grade, or GMP suitability: Not specified for this item; refer to CoA/Spec Sheet.

General context (literature/general):

• Role in discovery: Imidazole-containing esters like Ethyl 2-(1-imidazolyl)acetate are commonly used as intermediates in medicinal chemistry campaigns to access amide-linked imidazole analogs, SAR probes, and heteroaromatic fragments.
• Formulation relevance: The compound itself is not a standard excipient. If used in a pharmaceutical R&D setting, it would be as a synthetic intermediate en route to an API candidate or as a building block for prodrug exploration after transesterification/aminolysis.
• Analytical considerations: For regulatory studies, residual solvent and impurity profiles must be controlled for any downstream intermediates or final compounds derived from this ester; none of these are specified for this catalog item.

Compliance reminder: This product is supplied for research use only and is not intended for human or veterinary use, clinical diagnostics, or as an active pharmaceutical ingredient.

Physical Properties

Item-specific specifications (this lot):

• Boiling point, melting point, density, refractive index, water/peroxide/metal limits, and UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

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

• Molecular weight: ~154.17 g/mol (C7H10N2O2; literature)
• Physical state: Often obtained as a low-melting solid or liquid oil depending on purity/form (literature observation across sources); confirm appearance on CoA.
• Qualitative solubility: Typically soluble in polar organic solvents (methanol, ethanol, acetonitrile, acetone, ethyl acetate, DMSO). Moderate water solubility may be observed due to the imidazole ring, but the ethyl ester reduces hydrophilicity relative to the free acid (literature/general chemistry).
• Acid–base behavior: The imidazole ring contains a pyridine-like nitrogen (weak base); the ester is not ionizable under neutral conditions. Hydrolysis yields the corresponding carboxylic acid with significantly increased water solubility (general chemistry).

Notes for method development (general):

• For GC: Presence of an imidazole may increase tailing on untreated columns; derivatization or use of base-deactivated liners can help (literature practice).
• For HPLC: Reversed-phase methods with low-moderate % organic and volatile modifiers (e.g., 0.1% formic acid or 10–20 mM ammonium acetate) typically provide good peak shape; the imidazole’s basic site can interact with silanols—endcapped or polar-embedded phases mitigate this (general guidance).

Quality and Grades

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

Guidance on typical grades for heteroaromatic esters (general information):

• Research-grade vs. higher-purity: For most synthetic applications, standard research-grade material is adequate. For analytical or medicinal chemistry campaigns, a higher-purity grade (e.g., ≥98–99%) helps minimize byproducts in coupling and alkylation steps.
• Water content: Esters can hydrolyze under basic or acidic conditions; low moisture content is helpful for long-term stability and for moisture-sensitive reactions. If Karl Fischer (KF) moisture is critical, request CoA.
• Residual solvents and metals: For catalytic applications or where trace metals interfere (e.g., Suzuki or NHC generation from imidazoles), low metal background is desirable. Trace metal specs are item-specific; check CoA.
• Stabilizers: Not commonly stabilized; if present, stabilizers would be disclosed on the label/CoA. Stabilizer details for this item: Not specified for this item; refer to CoA/Spec Sheet.

Practical recommendations:

• On receipt, record appearance and any odor; compare to CoA.
• For sensitive applications (e.g., LC–MS bioanalytical method development), consider a quick purity check (1H NMR and LC) before use.
• If necessary, purify by flash chromatography under subdued light to align with the “protect from light” storage instruction.

Reaction and Applications

Ethyl 2-(1-imidazolyl)acetate is a versatile building block combining an imidazole heteroaromatic with a latent carboxyl group (as an ethyl ester). This enables a variety of downstream transformations (literature/general chemistry):

• Access to imidazol-1-ylacetic acid and amides:

  • Base- or acid-catalyzed hydrolysis to imidazol-1-ylacetic acid, then coupling (e.g., EDCI/HOBt, HATU, PyBOP) to generate amides and peptidomimetics linking imidazole to diverse amines.
  • Direct aminolysis under forcing conditions (neat amine or catalytic), though ester aminolysis is often less selective than carboxylate activation from the acid.

• Transesterification and alcohol conjugation:

  • Exchange the ethyl group for other alcohols (Fischer or catalytic transesterification) to tailor solubility or for prodrug-like masking in medicinal chemistry exploration.

• Quaternization/alkylation at the ring nitrogen:

  • The remaining pyridine-like nitrogen can be alkylated to form imidazolium salts—useful ionic liquid precursors or ligands. Subsequent deprotonation can lead to N-heterocyclic carbene (NHC) complexes after suitable modification (advanced organometallic applications).

• Electrophilic substitution on the imidazole ring:

  • Directed functionalization (e.g., at C4/C5) using halogenation or metalation strategies enables further diversification.

• Coordination/ligand uses:

  • The imidazole nitrogen can weakly coordinate to transition metals, offering opportunities in catalyst-ligand discovery when combined with tethering via the acetate handle.

Applications span heterocycle diversification, linker installation onto imidazole scaffolds, and synthesis of materials precursors (e.g., imidazolium ionic liquids) after N-alkylation (all literature/general).

Reaction Conditions

The following are literature-style, general conditions for common transformations of Ethyl 2-(1-imidazolyl)acetate; they are guidance only and not product specifications.

• Saponification to acid:

  • Typical: 1–2 M NaOH in MeOH/H2O (4:1 to 1:1), 0–25°C, 1–4 h. Quench with dilute acid, extract if needed. Yields: often high (70–95%) after acidification and crystallization.
  • Alternative: LiOH in THF/H2O for base-sensitive substrates.

• Amide formation from the acid:

  • HATU (1.1–1.5 equiv), DIPEA (2–3 equiv), amine (1.1–1.5 equiv), DMF/MeCN, 0–25°C, 1–12 h. Typical yields 60–90% depending on amine sterics.
  • EDCI (1.2 equiv) + Oxyma (1.2 equiv), NMM or DIPEA base, DCM/DMF, 0–25°C, 2–16 h.

• Transesterification:

  • Catalytic p-TsOH (1–10 mol%) in the target alcohol, Dean–Stark or reduced pressure removal of EtOH, 50–100°C, 2–16 h. Or NaOMe (5–20 mol%) at 25–60°C.

• N-alkylation to imidazolium salts:

  • Alkyl halide (1.2–2 equiv), K2CO3 or Cs2CO3 (1.5–2 equiv), MeCN or DMF, 25–80°C, 4–24 h. Monitor by LC–MS. Workup includes counterion exchange if desired (e.g., PF6− via NH4PF6).

• Electrophilic ring functionalization:

  • NBS (1.0–1.2 equiv) in DMF/DCM, 0–25°C for bromination at activated positions; follow with cross-coupling (Suzuki/Negishi) under Pd catalysis.

Notes:

• Keep moisture controlled to avoid unintended hydrolysis.
• Protect from light per Product Data; amber glass and minimized exposure recommended.
• Drying: If needed, dry over molecular sieves (3Å/4Å) after confirming compatibility.

Safety and Handling

Item-specific hazard classifications and statements:

• Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.

General safety guidance for imidazole-containing esters (not a substitute for SDS):

• Likely hazards: May cause skin/eye irritation and respiratory irritation. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
• Personal protective equipment (PPE): Lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and avoid exposure.
• Handling notes:
  • Avoid moisture and strong bases/acids that can catalyze ester hydrolysis.
  • Keep away from strong oxidizers.
  • Protect from light (per Product Data) to minimize potential degradation.
• First-aid overview (consult SDS for details):
  • Skin/eye contact: Rinse immediately with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; keep at rest; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; get medical attention.
• Spill/cleanup: Absorb small spills with inert material (e.g., vermiculite), collect in chemical waste. Prevent entry to drains. Decontaminate surfaces with appropriate solvent and detergent.
• Fire safety: Use CO2, dry chemical, or foam. Combustion may produce COx and nitrogen oxides. Ensure proper grounding if transferring flammable liquids.

Always defer to the product’s SDS for authoritative hazard and response information.

Solvent Selection

As a moderately polar heteroaromatic ester, Ethyl 2-(1-imidazolyl)acetate dissolves well in many organic media and is compatible with standard synthetic conditions.

• Polarity/miscibility (literature/general):

  • Polar aprotic solvents (recommended): DMSO, DMF, DMAc, acetonitrile—enhance solubility and support SN2, amidation, and coupling chemistry.
  • Protic solvents: Methanol, ethanol—useful for transesterification or solvolysis; monitor for unintended ester exchange.
  • Esters/ethers: Ethyl acetate, MTBE, THF—good for workups and extractions; THF supports base-mediated steps but monitor for peroxide formation (solvent-specific risk).
  • Hydrocarbons: Limited solubility expected; often used as antisolvents during crystallization of downstream products.

• Selection guidance:

  • For saponification/amidation: MeOH/THF/H2O mixtures for base hydrolysis; DMF/DCM or EtOAc for coupling after generating the acid.
  • For N-alkylation of the ring nitrogen (to imidazolium salts): Use polar aprotic solvents (MeCN, DMF) to improve rates; ensure anhydrous conditions.
  • For chromatographic purification: Start with EtOAc/hexanes or DCM/MeOH gradients; imidazole functionality can cause tailing—add a few drops of Et3N to eluents if needed.

• Small comparison (general):

  • MeCN vs. DMF: MeCN is easier to remove and cleaner in downstream analytics; DMF offers higher solubility for polar substrates.
  • EtOAc vs. DCM: EtOAc is greener and less dense; DCM may give sharper separations but with higher EHS burden.

Storage and Reconstitution

• Storage conditions (item-specific, from Product Data): Store at 2–8°C, protected from light. Shipped on wet ice.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Handling and stability (general guidance):

• Keep tightly closed under inert headspace if possible to minimize moisture ingress and oxidative degradation.
• Protect from light using amber vials or foil wrapping, consistent with Product Data.
• Allow cold shipments to equilibrate to room temperature before opening to reduce condensation.

Reconstitution/solubility:

• Reconstitution instructions: Not applicable; this is supplied neat unless otherwise specified. If preparing stock solutions, use dry solvents (e.g., DMSO, MeCN, EtOAc) and record concentration/date.
• Example stock solution solubility (literature/general): Readily prepares ≥10–100 mg/mL solutions in DMSO, DMF, MeCN, MeOH. Aqueous solubility is limited; consider co-solvent or convert to the acid/amide for aqueous work.

Shelf life:

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

Disposal:

• Dispose of contents/container in accordance with institutional and local regulations for organic chemical waste.

Structure and Identity

Ethyl 2-(1-imidazolyl)acetate is an imidazole N1-substituted acetate ester, serving as a heteroaromatic ester building block.

• Item-specific identifiers (from Product Data):

  • CAS: 17450-34-9
  • SKU: E708902
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a truncated value.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/typical identifiers (for reference only; verify before use):

  • Synonym: Ethyl (imidazol-1-yl)acetate; Ethyl imidazole-1-acetate
  • Molecular formula (literature): C7H10N2O2
  • Molecular weight (literature): ~154.17 g/mol
  • Example SMILES (literature): CCOC(=O)Cn1ccnc1 (represents an N1-substituted imidazole linked via –CH2–COOEt)

• Structural features (general description):

  • Ring system: 5-membered aromatic imidazole containing two nitrogens (one pyridine-like sp2 N and one amide-like sp2 N that is substituted at N1).
  • Functional groups: Ethyl ester (–COOEt) attached through a methylene spacer (–CH2–) to the imidazole N1 atom.
  • Structural topology in 2D: Ethyl ester tail (Et–O–C(=O)–) connected to a methylene linker (–CH2–) which is bound to the N1 of the imidazole ring; the remaining ring N is pyridine-like and can act as a weak base/ligand.

• Stereochemistry: None (achiral, no stereocenters).

Synthetic Utility

Key functional elements and their reactivity (literature/general):

• Ethyl ester as a latent carboxyl group: Enables saponification to the acid, aminolysis to amides, transesterification to alternate esters, or activation (e.g., acid chloride, mixed anhydride) for coupling.
• Imidazole heteroaromatic: Provides a basic/ligating site (pyridine-like N) for coordination or quaternization to imidazolium salts; positions C4/C5 are amenable to electrophilic substitution and metalation strategies for diversification.

Typical transformations:

• Hydrolysis: NaOH/MeOH/H2O at rt–reflux to give imidazol-1-ylacetic acid.
• Coupling: HATU/DIPEA or EDCI/Oxyma to furnish amides with high chemoselectivity; DCM/DMF or MeCN as solvents.
• Transesterification: Acidic (p-TsOH) or basic (NaOMe) catalysts to introduce alcohol-derived variants.
• N-alkylation: Alkyl halides or sulfates in MeCN/DMF with base to form imidazolium salts; counterion exchange as needed.
• Halogenation/metalation of ring carbons: NBS or directed lithiation (t−BuLi at low temperature) followed by electrophile trapping to build libraries.

Retrosynthetic value:

• Serves as an imidazole-linker synthon where the N1–CH2–CO fragment anchors the heterocycle to carboxyl-derived functionality, simplifying access to imidazole–amide conjugates and materials linkers.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, nucleic acid, or biological that would have target/epitope specificity.

Item-specific biological target, clone, isotype, or species reactivity: Not specified for this item.