This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
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 assay-specific, validated application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent and none are provided in the Product Data. Typical laboratory uses are in synthetic organic chemistry and method development.
General usage notes:
For reaction screening, prepare stock solutions in dry organic solvents (e.g., DCM, THF, MeCN) at known concentrations and monitor by TLC/HPLC.
For hydrolysis or derivatization studies, set up small-scale reactions (0.05–0.2 mmol) to define conditions before scale-up. Use UV detection at 254–280 nm for HPLC where appropriate.
For stability tests, evaluate in selected media (solvent, pH, temperature, light) and analyze at intervals to profile hydrolysis or oxidation.
Refer to your internal SOPs and method validation requirements for quantitative work.
Biological Roles
Item-specific biological data are not provided for this product; it is sold strictly for research use.
General biochemical context (no clinical/therapeutic claims):
Indole-2-acetic acid (IAA) is a well-known plant auxin hormone involved in cell elongation and tropisms. Ethyl indole-2-acetate is the ethyl ester derivative of IAA and is commonly used as a protected or transport form in synthetic and biochemical studies.
In biological systems, esters of carboxylic acids can undergo hydrolysis (chemical or enzymatic) to liberate the parent acid. Thus, ethyl indole-2-acetate can serve as a pro-form for generating IAA under hydrolytic conditions in vitro.
The indole moiety is a key chromophore and structural motif found in tryptophan and many natural products. Its spectroscopic properties (notably UV absorption near 280 nm, literature) facilitate detection in analytical assays.
In enzyme or receptor studies focused on auxin-binding proteins, indole-2-acetate derivatives (including esters) are sometimes used as substrate or ligand analogues to probe binding determinants. Any such use should be validated for the specific system, as esterification alters polarity, hydrogen-bonding capacity, and membrane permeability relative to IAA.
Note: No activity, potency, or target-binding claims are made for this product. Researchers should design appropriate controls to account for potential ester hydrolysis and for the distinct physicochemical profile of the ester vs the free acid.
Buffer Applications
This compound is a neutral organic ester with limited water solubility and is not typically used as a buffering agent or in aqueous buffer preparation.
Practical guidance:
For experiments requiring this compound in aqueous systems, employ co-solvents (e.g., ethanol, DMSO, or acetonitrile) at minimal percentages compatible with your biological or analytical assay, and confirm solubility.
If pH control is needed for hydrolysis or stability studies, use standard buffer systems (e.g., phosphate, acetate, Tris) independent of the compound; the compound itself does not provide buffering capacity.
For buffer recipes and pH ranges, refer to established buffering agents; this product does not serve that role.
Green Alternatives
While ethyl indole-2-acetate itself is a target molecule, greener choices can be made around its synthesis, handling, and purification.
Greener solvent choices (compared to traditional options):
Replace dichloromethane/chloroform with:
2-MeTHF or CPME for extractions and many reactions; water-immiscible, reusable, and derived partly from renewable feedstocks.
Ethyl acetate for work-ups and chromatography; biodegradable and lower toxicity.
Replace DMF/DMSO where feasible with:
Acetonitrile or propylene carbonate for polar aprotic needs; or green-engineered solvents like Cyrene in compatible reactions.
Process considerations:
Fischer esterification of indole-2-acetic acid can be run under solvent-free conditions or in green solvents (e.g., ethanol) using solid acid catalysts (e.g., Amberlyst-15), reducing waste and eliminating halogenated solvents.
Enzymatic esterification (lipase-catalyzed) in 2-MeTHF or solvent-free systems may offer milder conditions and improved selectivity, with easy catalyst recovery (literature, biocatalysis practices).
Use aqueous work-ups optimized to minimize solvent volumes; consider liquid–liquid extraction with EtOAc and brine to reduce emulsions.
Comparison snapshot (general):
Dichloromethane: excellent performance, high E-factor, halogenated waste.
2-MeTHF: comparable solvency for indoles, lower environmental impact, forms peroxides slowly—monitor and stabilize as needed.
Ethyl acetate: benign profile, good for chromatography and extractions; watch for transesterification under strong acid/base.
Always validate reaction rates/selectivity when changing solvents; small screening matrices help balance green metrics and performance.
Pharmaceutical Uses
No pharmacopeial status or excipient designation is provided for this product; it is supplied for research use only.
General formulation/manufacturing context (non-clinical):
As an indole ester intermediate, ethyl indole-2-acetate may be employed in medicinal chemistry campaigns as a scaffold for SAR exploration, where the ester can be retained, hydrolyzed to the acid, or transformed into amides and other bioisosteres.
In pre-formulation research, esterification is sometimes used to modulate lipophilicity and permeability for in vitro assays; subsequent hydrolysis or further derivatization can furnish libraries of analogs.
No claims are made regarding use as an API or excipient. Any progression beyond bench research would require comprehensive quality, safety, and regulatory evaluation under appropriate GMP frameworks.
For any regulated application, consult your QA/QC team and request detailed CoA and impurity/residual solvent data, and establish validated analytical methods (HPLC-UV/LC–MS) suitable for your matrices.
Physical Properties
Item-specific specifications (this product):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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/computational expectations for the class (indole-2-alkyl esters):
Physical state: typically colorless to pale yellow oils or low-melting solids depending on purity and crystallinity (literature, compound-class trend).
Volatility: low to moderate; esters of this size often distill under reduced pressure if thermally stable (literature).
Solubility profile: generally sparingly soluble in water; freely soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, THF, toluene, alcohols) due to aromatic and ester functionality (literature/general).
Polarity/logP: expected moderate lipophilicity owing to indole ring and ethyl ester; capable of H-bond donation via indole NH and H-bond acceptance via the ester carbonyl (general/estimated behavior).
UV absorbance: indole chromophore shows strong absorption in the near-UV (~220–290 nm) with a band near 280 nm (literature, indole chromophore), useful for HPLC-UV tracking.
Notes and guidance:
Refractive index, density, mp/bp, UV cutoff, water content, and residual solvents are not specified for this item; refer to CoA/Spec Sheet.
For analytical method development, monitor at 254–280 nm to leverage the indole chromophore (general practice). Validate extinction coefficients experimentally for quantitative work.
Quality & Grades
Item-specific grade/purity for SKU E183801: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
If provided as “research grade,” typical intent is suitability for synthetic and analytical research, without certification for clinical or GMP uses.
For chromatographic or spectroscopic applications, an “HPLC grade” or “GC grade” designation (if supplied) would imply lower UV background and minimized volatile/nonvolatile residues; absent such designation, pre-test solvent blank baselines and consider simple polish (e.g., bulb-to-bulb distillation or recrystallization) if your method is particularly sensitive.
Stabilizers: None are specified for this item. If a stabilizer were used (e.g., acid inhibitor), it would be listed on the CoA; presence of stabilizers can affect some reactions (e.g., basic hydrolyses). Always check the CoA for any additives.
Impurity profile: For indole esters, common related impurities include hydrolyzed acid (indole-2-acetic acid), transesterification byproducts, N-acylated or O-acyl migrated species, and trace solvents. If your application is sensitive, request or review the CoA for residual solvent and impurity data.
Recommendations:
Verify purity by 1H/13C NMR and HPLC-UV at ~254–280 nm leveraging the indole chromophore.
If trace acid/base impacts your process, perform a brief silica plug or preparative recrystallization prior to use. Document any further purification if regulatory filings are anticipated.
Reaction & Applications
Ethyl indole-2-acetate is a versatile indole building block and protected form of indole-2-acetic acid. Typical research uses include:
Ester as a protecting/transport form of IAA: readily hydrolyzed to indole-2-acetic acid under acidic, basic, or enzymatic conditions, enabling late-stage deprotection.
Functionalization at indole C-3: electrophilic substitution (e.g., Vilsmeier–Haack formylation, Mannich reactions, halogenation) proceeds predominantly at C-3, generally without disturbing the 2-acetate side chain.
Benzylic methylene chemistry: the –CH2– adjacent to the indole ring can be deprotonated with strong, non-nucleophilic bases (e.g., LDA) at low temperature to effect alkylation/acylation, enabling side-chain elaboration before or after ester manipulation.
N-Protection/modification: N-acylation or N-alkylation to tune electronics/solubility; Boc or sulfonyl protections help direct regioselectivity in subsequent steps.
Cross-coupling after pre-functionalization: introduction of halogens at C-3 (or other positions) allows Suzuki, Heck, or Sonogashira couplings to diversify the scaffold.
Oxidations/reductions: chemoselective transformations on the side chain (e.g., reduction of the ester to alcohol with DIBAL-H; oxidation to amide via Curtius after conversion to acid/acid chloride), while managing indole sensitivity to strong oxidants.
Heterocycle fusion and cyclizations: the side chain can engage in intramolecular condensations or amidations to create fused indole frameworks common in natural product analogs.
Practical tips:
Maintain anhydrous conditions for base-mediated steps to avoid ester hydrolysis.
Monitor by TLC/HPLC at 254–280 nm to exploit the indole chromophore.
For electrophilic substitutions, protect the indole N if required to enhance regioselectivity and yield.
Reaction Conditions
General literature guidance for common operations on indole-2-acetate esters (not item-specific specifications):
Hydrolysis (saponification):
Conditions: MeOH/H2O, NaOH or K2CO3, 0–25 °C to reflux depending on base strength.
Notes: Monitor by TLC/HPLC; acidify aqueous phase to pH ~2 to precipitate the free acid for isolation. Avoid over-heating to protect indole.
Acidic hydrolysis (Fischer-type):
Conditions: Aqueous mineral acid (e.g., HCl), reflux; or catalytic acid in wet alcohol followed by aqueous work-up.
Notes: Indole can be acid-sensitive; milder acid (AcOH) under longer times can be preferable.
DIBAL-H reduction to alcohol:
Conditions: DIBAL-H in toluene or THF, −78 to 0 °C; quench carefully with MeOH then aqueous buffer.
Notes: Control stoichiometry and temperature to suppress over-reduction.
Electrophilic substitution at C-3:
Halogenation: NBS/NCS in DMF/MeCN/CHCl3 at 0–25 °C; catalytic acids may accelerate.
Formylation: POCl3/DMF (Vilsmeier), 0–25 °C then quench into ice/water; neutralize cautiously.
Benzylic deprotonation/alkylation:
Conditions: LDA or NaHMDS in THF or 2-MeTHF at −78 to −20 °C, then add electrophile (alkyl halide, acyl chloride).
Notes: Exclude moisture/CO2; quench at low temperature to minimize side reactions.
Cross-coupling (post-halogenation):
Conditions: Pd catalysts (e.g., Pd(PPh3)4), bases (K2CO3, Cs2CO3), solvents (toluene/EtOH/H2O or dioxane), 60–100 °C.
Notes: Protect indole N to improve yields and reduce protodehalogenation.
Always pilot small-scale trials and optimize; indole substrates can undergo side reactions under strongly oxidizing or acidic conditions.
Safety & Handling
Item-specific hazard data:
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / Pictograms / H-Statements: Not specified for this item; refer to SDS.
General laboratory safety guidance for indole esters (informational, not a substitute for the SDS):
Likely hazards: Organic esters and indole derivatives commonly present eye/skin irritation risks and may cause respiratory irritation if aerosolized. Avoid inhalation, ingestion, and contact. Handle in a well-ventilated fume hood.
Personal protective equipment: lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use splash protection when handling larger quantities.
Incompatibilities: Strong bases and aqueous acids can hydrolyze the ester; strong oxidizers may react with the indole ring; potent electrophiles (e.g., acylating agents) may react at the indole nitrogen.
Stability considerations: Esters may undergo slow hydrolysis under moist or basic conditions. Keep containers tightly closed and minimize exposure to moisture. Protect from prolonged light to limit potential indole photo-oxidation.
First aid (overview): In case of skin/eye contact, rinse with plenty of water; remove contaminated clothing. If inhaled, move to fresh air. If swallowed, rinse mouth; seek medical advice. Always follow site-specific emergency procedures and consult the SDS.
Waste disposal: Collect organic residues as hazardous chemical waste. Avoid release to drains. Follow institutional and regulatory guidelines.
Always consult the product’s SDS for authoritative hazard classification and response measures.
Solvent Selection
Compound class behavior (indole ethyl ester): moderately lipophilic, weakly hydrogen-bond donating (indole NH), hydrogen-bond accepting at the ester carbonyl. Not expected to be water-miscible.
Preferred solvents (general):
Aromatic/aprotic: toluene, xylene for thermal transformations (Friedel–Crafts, cyclizations) where higher bp is helpful.
Chlorinated: dichloromethane or chloroform for workups and electrophilic substitutions; excellent solubility and UV transparency; consider greener alternatives when possible.
Ethers: THF, 2-MeTHF, MTBE for base-mediated steps (alkylations, reductions) and organometallics; ensure dryness to avoid ester hydrolysis.
Esters/alcohols: ethyl acetate, isopropanol/methanol for crystallization and transesterification contexts; be mindful of exchange under acidic/basic conditions.
Polar aprotics: acetonitrile, DMF, DMSO for nucleophilic substitutions or coupling chemistry; assess stability vs basic media.
Miscibility profile (general/literature):
Poorly soluble in water; freely soluble in most organic solvents listed above.
Selection tips:
For monitoring and purification, ethyl acetate/hexanes or toluene/EtOAc systems typically provide good TLC separation from polar impurities (e.g., hydrolyzed acid).
For base-catalyzed steps (e.g., Knoevenagel on the methylene), use anhydrous ether or THF and non-nucleophilic bases to avoid ester cleavage.
For electrophilic aromatic substitution at C-3, dichloromethane or acetic acid media are common; control temperature to protect the ester.
When water or biocompatible systems are required, consider converting to a salt or employing a co-solvent strategy; however, this class is generally handled in organic media.
Storage & Reconstitution
Item-specific instructions from Product Data:
Storage Conditions: Room temperature.
Shipped In: Normal.
General guidance for this class of compounds:
Store tightly sealed in a dry, inert atmosphere (e.g., with desiccant). Although stable at ambient conditions, prolonged exposure to moisture can promote slow ester hydrolysis; limiting humidity is beneficial.
Protect from direct light to minimize potential indole photo-oxidation; amber glass recommended.
If long-term storage is anticipated, consider refrigeration (2–8 °C) as a precaution to slow hydrolytic/oxidative processes, while ensuring the container is dry. Allow to equilibrate to room temperature before opening to avoid condensation.
Reconstitution/handling:
The product is typically used neat or dissolved directly in anhydrous organic solvents (e.g., dichloromethane, THF, ethyl acetate, toluene, acetonitrile). Choose solvent based on downstream chemistry and solubility.
For analytical stock solutions, prepare at known concentration under dry conditions; filter if particulates are present. Record solvent, lot, and preparation date; store stocks in sealed vials away from moisture.
Avoid repeated freeze–thaw cycles of solutions; prepare single-use aliquots if necessary.
For definitive stability, impurity limits, and any additives, consult the lot-specific CoA and SDS. This product is for research use only.
Structure & Identity
Ethyl indole-2-acetate is the ethyl ester of indole-2-acetic acid, comprising an indole ring substituted at C-2 by a –CH2–CO2Et side chain.
SMILES: 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.
Structural features (general chemistry description):
Core scaffold: bicyclic aromatic heteroaromatic indole (benzene fused to pyrrole).
Functional groups: indole NH (weakly acidic), benzylic methylene at C-2, and an ethyl ester (carboxylic ester) appended via –CH2–.
2D description: The indole nitrogen (N–H) is part of a five-membered ring fused to a benzene; at the 2-position of the indole, a –CH2–CO2Et chain extends, terminating in an ethyl ester (–COOCH2CH3). No stereocenters are present; molecule is achiral.
Notes:
The 2-position benzylic methylene is activated toward deprotonation/alkylation relative to simple alkyl aromatics due to indole stabilization.
The indole 3-position remains the most electrophile-reactive site under typical EAS conditions, enabling further functionalization while retaining the 2-acetate side chain.
Synthetic Utility
Key functional elements and their synthetic leverage:
Indole nucleus: highly versatile in electrophilic aromatic substitution at C-3 (e.g., halogenation, acylation, formylation), enabling rapid diversification. N-protection (Boc, tosyl) can tune regioselectivity and stabilize against side reactions.
Ethyl ester: serves as a carboxyl protecting group for indole-2-acetic acid; compatible with many conditions and removable under acidic, basic, or enzymatic hydrolysis. The ester can be chemoselectively reduced (e.g., DIBAL-H to the corresponding alcohol) or transformed via standard carboxylate chemistry after hydrolysis.
Benzylic methylene (–CH2–): acidic relative to simple benzylic positions; deprotonation with strong bases (e.g., LDA, NaHMDS) allows alkylation/acylation, enabling construction of quaternary centers or β-functionalization before final deprotection.
Vilsmeier–Haack formylation at C-3 followed by reductive amination or Wittig olefination.
Halogenation (NBS/NCS) at C-3 enabling cross-couplings (Suzuki, Sonogashira) to append aryl/alkynyl units.
Hydrolysis to indole-2-acetic acid followed by amide coupling (EDC/HATU) to access indole-2-acetamides.
Curtius/Schmidt pathways after conversion to acid chloride to reach amines or ureas on the side chain (via acid intermediate).
Practical notes:
Protect the indole nitrogen when subjecting the scaffold to strong electrophiles or oxidants.
Control moisture in base-mediated steps to avoid saponification; if hydrolysis occurs, the resulting acid can often be recycled via re-esterification.
Target Specificity
Not applicable to this small-molecule reagent. No antibody/biological target specifications (antigen, epitope, clone, isotype, species reactivity) are provided or relevant for this item. For biochemical context regarding auxin-related research, see the Biological Roles section.
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