Ethyl 2-(3-iodophenyl)acetate , CAS No.90888-00-9

CAS: 90888-00-9 Cat. No.: E972355 Fórmula: C₁₀H₁₁IO₂ Peso molecular: 290.100

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: CCOC(=O)CC1=CC(=CC=C1)I
• IUPAC Name: ethyl 2-(3-iodophenyl)acetate
• InChIKey: AFIJJIQLANZBQG-UHFFFAOYSA-N
• INCHI: 1S/C10H11IO2/c1-2-13-10(12)7-8-4-3-5-9(11)6-8/h3-6H,2,7H2,1H3
• Peso molecular: 290.100

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Iodobenzenes
• Alternative Parents: Aryl iodides Carboxylic acid esters Monocarboxylic acids and derivatives Organoiodides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Iodobenzene - Aryl iodide - Aryl halide - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organoiodide - Organohalogen compound - Carbonyl group - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.
• 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

Propiedades químicas y físicas

• Peso molecular: 290.100 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 289.98 Da
• Monoisotopic Mass: 289.98 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 170.000
• 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 validated bioassay or analytical application protocols are provided for this item. As a synthetic building block, usage protocols are reaction-specific (e.g., Pd-catalyzed cross-coupling, enolate alkylation). Refer to the Reaction Conditions and Synthetic Utility sections for practical starting points and adjust to your substrates, catalysts, and scale.

Biological Roles

This product is a synthetic organic building block (aryl iodide ester) without inherent biological role or function. It is not a metabolite, cofactor, or signaling molecule in standard biochemical pathways.

• No endogenous biological activity is associated with ethyl 2-(3-iodophenyl)acetate in literature beyond incidental interactions expected for hydrophobic aromatic esters.
• In life-science research, such compounds are typically used as chemical precursors to prepare probe molecules, ligands, or labeled scaffolds via cross-coupling rather than as bioactive agents themselves.

For cellular or biochemical studies, any use would be as a synthetic intermediate toward a target structure. Handle strictly for research use in chemical synthesis; it is not intended for in vivo or clinical applications.

Buffer Applications

Not applicable. Ethyl 2-(3-iodophenyl)acetate is not a buffering reagent and does not form controlled pH systems. For biochemical work requiring buffers, select appropriate buffer systems (e.g., phosphate, HEPES, Tris) and use this compound, if relevant, only as a synthetic intermediate upstream of the biological study.

Green Alternatives

Although the molecule itself is fixed, greener choices can be made in its use (solvents, bases, and catalysts). Below are literature-based considerations.

Greener solvent options for couplings and functionalizations:

• Prefer 2-MeTHF or CPME over THF/dioxane when feasible (biorenewable feedstock, better safety profile). Both dissolve aryl iodides and support Pd catalysis.
• Use EtOH/H2O or MeOH/H2O mixtures for Suzuki–Miyaura with water-tolerant ligands and inorganic bases (e.g., K2CO3, K3PO4).
• Replace DMF/DMA/NMP (reproductive tox concerns) with propyl/ethyl carbonates or polar green ethers where catalyst systems allow.

Base and catalyst choices:

• Employ aqueous carbonate or phosphate bases instead of strong amines where applicable.
• Use ligand-precatalysts that are effective at low loadings (ppm–0.1 mol% Pd), and consider nickel catalysis for certain cross-couplings to reduce precious metal usage (substrate-dependent).

Waste minimization:

• Maximize atom economy via one-pot sequences (e.g., in situ hydrolysis/alkylation-hydrolysis) to reduce solvent swaps.
• Apply microwave or flow to shorten reaction times and lower energy demand.

Trade-offs:

• Water-rich media can reduce solubility and require phase-transfer strategies.
• 2-MeTHF/CPME may change selectivity or rate; optimization needed.

Small comparison (literature):

• THF vs 2-MeTHF: similar coupling performance; 2-MeTHF offers lower peroxide tendency and greener sourcing.
• 1,4-Dioxane vs Toluene: dioxane aids miscibility with water but has higher chronic toxicity; toluene less polar, better EHS profile with proper controls.

Pharmaceutical Uses

No pharmacopeial excipient role or formulation use is specified for this item. As an aryl iodide ester, its primary relevance in the pharmaceutical context is as a synthetic intermediate in medicinal chemistry and process development.

• Potential roles (general, non-clinical):
  • Entry point for rapid SAR via Suzuki/Sonogashira/Buchwald–Hartwig diversification on the aryl ring.
  • Benzylic ester handle for homologation, installation of heterocycles, or conversion to acids/amides.
• Regulatory note: This product is labeled For research use only and is not intended for use in humans or as a drug substance/excipient.

For GMP or clinical routes, any usage would require qualification of suppliers, full impurity profiles, and process-specific specifications beyond the scope of this catalog listing.

Physical Properties

Item-specific specifications are not provided in the product data. The following are literature/computed values for the neat compound and should be treated as general guidance for method development only.

• Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet. (Literature: aryl-iodide esters are typically colorless to pale yellow liquids or low-melting solids.)
• Molecular weight: ~290.10 g/mol (literature, from C10H11IO2)
• Density: Not specified for this item; refer to CoA/Spec Sheet. (Literature: aryl iodides often 1.5–1.8 g/mL; ester functionality can lower this modestly.)
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Literature: related ethyl iodophenylacetates distill in the ~150–180 °C range at reduced pressure; thermal sensitivity suggests using vacuum.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Literature: often liquid at ambient temperature.)
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• LogP (octanol/water): Not specified for this item; refer to CoA/Spec Sheet. (Literature expectation: moderately lipophilic due to aryl iodide and ester.)
• Solubility: Not specified for this item; refer to CoA/Spec Sheet. (General: soluble in common organic solvents such as dichloromethane, THF, ethyl acetate, toluene; low solubility in water.)

Always verify critical physical constants experimentally for your batch before scale-up. Use the SDS/CoA for authoritative specifications.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff, metal content, residual solvents, water, and peroxide content: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and implications (general guidance for this compound class):

• For cross-coupling chemistry (Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig), trace metal impurities and halide identity affect catalytic performance. When grade is unspecified, we recommend checking the CoA for assay, GC purity, and halide content to ensure reproducibility in Pd- or Cu-catalyzed reactions.
• Acid/base impurities can promote ester cleavage or transesterification; evaluate acidity/alkalinity on receipt if your route is base-sensitive.
• If a stabilizer is present (none specified here), understand its impact: amine stabilizers can poison Pd catalysts; acidic stabilizers may affect enolization at the benzylic position.
• Chromatography: for photochemical or analytical work, low-UV-absorbing grades are not relevant here; instead, ensure absence of non-volatile residues for accurate mass balance.

Recommendation: For demanding synthetic sequences, request the latest CoA and, if needed, an extended specification (assay by qNMR/GC, residual metals by ICP-MS, water by KF, and detailed impurity profile).

Reaction and Applications

Ethyl 2-(3-iodophenyl)acetate is a dual-purpose building block: the aryl iodide enables cross-coupling, and the benzylic position alpha to the ester enables C–H functionalization.

Cross-coupling (literature examples):

• Suzuki–Miyaura: couples with boronic acids/esters to install diverse aryl/alkenyl groups at the 3-position. Aryl iodides typically react under mild conditions (e.g., Pd(PPh3)4 or Pd-PEPPSI, K2CO3/K3PO4, toluene/EtOH/H2O or dioxane, 25–80 °C).
• Sonogashira: terminal alkynes added to the aryl iodide (Pd/Cu co-catalysis or Cu-free systems) to provide 3-alkynyl derivatives, useful for further cyclizations.
• Buchwald–Hartwig: amination to 3-anilines using dialkylbiaryl phosphine ligands; aryl iodides lower the activation barrier vs bromides/chlorides.
• Heck: aryl–alkenyl C–C formation to introduce styrenyl motifs at the meta position.

Benzylic/ester chemistry:

• Enolate formation at the benzylic methylene (Ar–CH2–CO2Et) allows alkylation, acylation, or Michael additions (LDA/LHMDS, −78 to 0 °C; THF).
• Hydrolysis to the corresponding acid followed by decarboxylation gives 3-iodotoluene derivatives; conversely, oxidation (e.g., SeO2/oxidants) can access benzylidene/ketone motifs.
• Nucleophilic substitution at the benzylic position after activation (e.g., bromination then displacement) enables elaboration of side chains.

Strategic applications:

• Late-stage diversification via fast oxidative addition of Ar–I.
• Precursor for biaryl, aryl-alkyne, and arylamine libraries where the benzylic ester serves as a masked handle for further transformations or for installing heterocycles by cyclization.

For optimization, control base strength to avoid undesired saponification and monitor for deiodination under strongly reducing conditions.

Reaction Conditions

General literature guidance for this substrate class; optimize for your system and scale.

• Suzuki–Miyaura arylation: Pd(PPh3)4 (1–2 mol%) or precatalysts with dialkylbiaryl phosphines; base K3PO4 or K2CO3 (2–3 equiv). Solvent toluene/EtOH/H2O or 1,4-dioxane/H2O, 50–80 °C, 2–12 h. Aryl iodide enables lower temperatures or reduced catalyst loadings. Typical isolated yields for well-matched partners: 70–95% (literature).
• Sonogashira coupling: PdCl2(PPh3)2 (0.5–1 mol%), CuI (2–5 mol%), Et3N or iPr2NEt as base, solvent THF, DMF, or toluene/amine; 25–60 °C, 2–16 h. Copper-free variants with bulky ligands mitigate Glaser homocoupling.
• Buchwald–Hartwig amination: Pd2(dba)3 (0.5–1 mol%) with BrettPhos/SPhos/XPhos (1–3 mol% ligand), base NaOtBu or Cs2CO3, solvent toluene or dioxane, 60–100 °C. Aryl iodides generally give higher rates.
• Heck reaction: Pd(OAc)2 (1–2 mol%), PPh3 (5–10 mol%), base Et3N or DIPEA, solvent DMF or NMP alternative (e.g., propylene carbonate), 80–120 °C.
• Benzylic enolate alkylation: LDA or LHMDS (1.1–1.5 equiv) in THF at −78 to −20 °C; electrophiles: allyl, benzyl, alkyl halides; quench and warm slowly to minimize retro-aldol or over-alkylation. Competing ester cleavage under strong base/heat should be monitored.

Notes:

• Protect from strong base/long heat to avoid saponification.
• Deiodination can occur under hydrogenation or with active metal reductants; adjust conditions/ligands accordingly.
• Always degas and use dry solvents for moisture-sensitive couplings.

Safety and Handling

Hazard classification details (GHS, signal word, pictograms) are not specified for this item in the product data; consult the SDS for authoritative information.

General safety guidance for aryl iodide esters (literature-based):

• Likely hazards: may cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid dusts/aerosols and vapors. Handle in a fume hood.
• PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use splash protection when charging or transferring.
• Incompatibilities: strong bases (risk of saponification), strong nucleophiles (transesterification), strong oxidizers (iodoarene oxidation), and prolonged exposure to light/heat (possible decomposition of C–I bond). Store away from alkali metals and reducing agents.
• Handling tips: keep containers tightly closed; purge headspace with inert gas for sensitive cross-coupling campaigns. Minimize exposure to light to reduce potential iodide degradation.
• First aid (overview; follow 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 easy; get medical advice.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: carbon oxides and hydrogen iodide/iodine may form upon combustion. Use CO2, dry chemical, or foam; avoid water streams on solvent fires.

Always defer to the SDS for the specific GHS classification and emergency procedures for this SKU.

Solvent Selection

This product is a synthetic building block (aryl iodide ester), not a solvent. Solvent choice relates to its use in reactions or purifications.

General solvent compatibility (literature):

• Likely soluble in: DCM/CH2Cl2, THF, EtOAc, acetone, acetonitrile, toluene, DMF, DMSO.
• Poorly soluble in: water.

Choosing solvents by application:

• Pd-catalyzed couplings (Suzuki/Heck/Buchwald–Hartwig): toluene, 1,4-dioxane, THF, DMA/DMF, 2-MeTHF, CPME. Water/EtOH mixtures are possible for Suzuki with appropriate ligation/bases.
• Sonogashira: THF, Et3N or iPr2NEt as base; alternative solvents include DMF or toluene/amine mixtures.
• Benzylic functionalization (enolate alkylation): polar aprotic media such as THF, DME, or DMF at low temperature with LDA/LHMDS.
• Purification: normal-phase silica using hexane/EtOAc or toluene/EtOAc gradients; aryl iodides often elute slower than non-halogenated analogs.

Small comparison (literature):

• THF vs 2-MeTHF: 2-MeTHF offers greener profile and better water tolerance; both dissolve this substrate well.
• Toluene vs dioxane: toluene is less polar, higher bp; dioxane is miscible with water and may aid biphasic Suzuki systems but has safety concerns.

Always validate solubility and reaction compatibility on your scale; adjust solvent polarity to balance substrate solubility, catalyst stability, and byproduct removal.

Storage and Reconstitution

• Storage: Room temperature (as specified in product data). Store tightly closed in a dry, well-ventilated place. For long-term stability in sensitive synthetic campaigns, consider storing under inert gas and protecting from light as general good practice for aryl iodides.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable; supplied as a neat organic compound. If preparing stock solutions, use dry, oxygen-free solvents (e.g., toluene, THF, DCM) and store in sealed amber vials at 2–8 °C or room temperature as compatible with solvent volatility.
• Freeze–thaw: Not relevant to solids/liquids without aqueous matrices; avoid repeated heating/cooling cycles that can promote ester hydrolysis or iodide degradation.
• Stability considerations (general): Avoid prolonged exposure to strong bases, moisture (to limit saponification), and intense light/heat that may promote deiodination. Verify integrity by NMR/GC before critical reactions.

Always consult the product’s CoA/SDS for batch-specific handling and storage recommendations.

Structure and Identity

Ethyl 2-(3-iodophenyl)acetate is an aryl iodide ester combining a benzylic acetate motif with a meta-iodinated phenyl ring, making it a versatile cross-coupling substrate and benzylic building block.

• Preferred name: Ethyl 2-(3-iodophenyl)acetate
• CAS: 90888-00-9 (literature)
• Molecular formula: C10H11IO2 (literature calculation from structure)
• Molecular weight: ~290.10 g/mol (literature, calculated)
• InChIKey: As provided in product data: "4057" (appears truncated; full InChIKey not specified for this item; refer to CoA/Spec Sheet.)
• SMILES: CCOC(=O)Cc1cccc(I)c1 (literature depiction)

Structural features (descriptive):

• Functional groups: ethyl ester (–CO2Et) tethered to a benzylic methylene (–CH2–) attached to a 3-iodophenyl ring.
• Aryl iodide: highly reactive carbon–iodine bond at the meta position facilitates Pd- or Cu-catalyzed cross-couplings.
• Benzylic position alpha to carbonyl** (Ar–CH2–CO2Et) amenable to base-mediated functionalization (alkylation, halogenation, oxidation).
• 2D arrangement in words: An ethyl acetate unit (EtO–C(=O)–) is connected to a methylene linker (–CH2–) that is bonded to a phenyl ring bearing an iodine substituent at the position meta to the benzylic attachment.

Note: Exact identifiers for this catalog item not specified where indicated; consult the product CoA/Spec Sheet for definitive identity data.

Synthetic Utility

Key reactivity elements of ethyl 2-(3-iodophenyl)acetate (literature/general):

• Aryl iodide (Ar–I): fastest oxidative addition among aryl halides → ideal for Pd-catalyzed cross-couplings at low temperature and low catalyst loadings. Tolerates diverse partners (boron, tin, zinc, silanes, alkynes, amines).
• Benzylic methylene alpha to carbonyl: deprotonation to an enolate/enamine equivalent enables C–C bond formation (alkylation, acylation). The ester can be carried through and unmasked later.
• Ester as a masked acid: hydrolysis (acidic or basic) affords 2-(3-iodophenyl)acetic acid, which can be coupled (amide formation), decarboxylated, or transformed via Curtius/Hunsdiecker-type chemistry.

Representative transformations:

• Suzuki–Miyaura to 3-aryl-phenylacetate derivatives; subsequent saponification → amide coupling to give substituted phenylacetamides.
• Sonogashira to 3-alkynyl derivatives followed by hydrogenation or cycloaddition to heterocycles.
• Buchwald–Hartwig amination to 3-anilines; then electrophilic cyclization leveraging the benzylic acetate.
• Benzylic bromination (NBS/AIBN, hv) → SN2 with N/O/S nucleophiles to diversify side chains.
• Asymmetric alkylation of the enolate with chiral auxiliaries or phase-transfer catalysis to access enantioenriched phenylacetic frameworks.

Strategic value: orthogonal handles (Ar–I and –CH2–CO2Et) permit convergent, late-stage diversification with minimized protecting-group gymnastics.

Target Specificity

Not applicable. This product is a small-molecule synthetic intermediate and is not an antibody, enzyme, or bioassay reagent with defined biological targets. No target specificity is provided in the product data.