This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
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 application protocols are specified or validated for this item. Not applicable to immunoassays or bioanalytical kits. For chemical use, see Reaction Conditions for general laboratory procedures (hydrolysis, transesterification, reduction, and activation) relevant to this class of esters.
Biological Roles
This compound is a synthetic aryl alkyl ester intended for laboratory use. It is not a natural metabolite or a commonly cited biochemical probe.
Endogenous role: None known (not a biomolecule).
Biotransformation (general): In biological systems, esters can undergo enzymatic hydrolysis to the corresponding acid and alcohol by carboxylesterases; however, no specific kinetic or pathway data are established for this exact structure in the literature.
Physicochemical implications: The para‑fluoro substituent and tert‑alkyl group increase hydrophobicity, which typically reduces aqueous solubility and can influence partitioning behavior in biological matrices (general observation for aryl‑fluoro esters).
Research Use Note: For research use only. Not for diagnostic or therapeutic use.
Buffer Applications
Not typically applicable. This product is a hydrophobic organic ester and is not used as a buffering agent. If your work involves aqueous manipulations (e.g., hydrolysis), select an appropriate buffer or aqueous base/acid system based on your reaction kinetics rather than expecting intrinsic buffering from this compound. See Reaction & Applications and Reaction Conditions for practical guidance.
Green Alternatives
While this product is a building block rather than a solvent, greener strategy choices can reduce EHS footprint during its synthesis and use.
Greener media and reagents (literature/general):
Solvents: Prefer 2‑MeTHF or CPME over THF/Et2O for reductions and organometallic steps; replace DCM with EtOAc or toluene where feasible. For hydrolysis/transesterification, use ethanol or propylene carbonate as greener protic/polar media.
Catalysis: Employ solid acid catalysts (Amberlyst-15, sulfonated silica) for transesterification to simplify workup and minimize mineral acid waste. Enzymatic ester exchange (lipases) in 2‑MeTHF or solvent-free systems can proceed under mild conditions.
Energy: Conduct reactions at ambient temperature/pressure when possible; apply microwave or flow methods to shorten cycle times and reduce energy demand.
Workup: Use brine-free or low-salt workups; replace MgSO4 with reusable molecular sieves for drying organic phases when compatible.
Illustrative comparison (general guidance):
THF vs 2‑MeTHF: similar polarity; 2‑MeTHF is biorenewable, has higher boiling point (improved reflux control), and better phase separation from water; may improve safety profile.
DCM vs EtOAc: EtOAc offers lower toxicity and environmental burden and often dissolves aryl esters effectively; evaporation energy is slightly higher due to higher bp.
Note: The choice of green alternatives must be validated against reaction performance and impurity profiles for your system.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. Not specified for this item; refer to CoA/Spec Sheet.
Contextual information (general; not a claim for this product):
Aryl‑alkyl esters are often used as synthetic intermediates en route to carboxylic acids, amides, or alcohols during active pharmaceutical ingredient (API) development. The ester can serve as a protecting/activating group for carboxyl functions during multi‑step sequences.
The para‑fluoroaryl and tert‑alkyl motifs are common steric/hydrophobic elements in medicinal chemistry SAR exploration; this ester may be leveraged in route scouting to such targets.
Compliance note: For research use only. Not for human or veterinary use. This listing makes no therapeutic or clinical performance claims.
Physical Properties
Item-specific specifications (this lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Water, peroxides, metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values (for contextual reference; not item specifications):
Molecular formula (computed from name/structure): C12H15FO2
Molecular weight (computed): ~210.25 g/mol
Physical state: typically a colorless to pale liquid for closely related ethyl aryl‑neopentanoates; solidification near or below ambient is possible depending on purity and isomers (literature/general).
Solubility: expected low solubility in water; good solubility in common organic solvents (EtOAc, THF, toluene, hexanes, DCM, alcohols) (literature/general for aryl tert‑alkyl esters).
Refractive index, density, melting/boiling point, logP, pKa: Not broadly reported for this exact structure in standard compilations; do not rely on estimates. Refer to CoA/SDS or measure as needed for your process.
Practical notes for method development (general guidance):
Volatility: Esters of this size commonly show moderate volatility; use closed systems for accurate massing.
Chromatography: Normal-phase silica elution generally between toluene/EtOAc or hexanes/EtOAc (gradient). Para‑F increases ring polarity slightly, aiding UV detection at 210–254 nm (general/literature).
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grade meaning and selection (general):
Research grade materials are appropriate for synthetic and analytical R&D, method development, and screening. Where chromatographic sensitivity is critical (e.g., UV detection at 210–254 nm), HPLC-grade solvents/reagents or additional purification may be warranted to minimize baseline drift.
If your application is moisture or base sensitive (e.g., kinetic studies on transesterification), verify water content and residual base/acid levels on the specific lot via Karl Fischer and acid/base number, respectively.
Metal content: For catalytic studies susceptible to ppm-level metals, request ICP data or purify by silica/alumina where compatible. For this item, specific metal limits are Not specified for this item; refer to CoA/Spec Sheet.
Impurity profile: Aryl-alkyl esters may contain minor amounts of the corresponding acid, alcohol (ethanol), and transesterification byproducts. If needed, polish by short-path distillation or flash chromatography.
Batch documentation:
CoA will typically include identity confirmation (1H/13C NMR and/or HRMS), purity, and appearance. Where regulatory submission or GLP requires, request a detailed Spec Sheet and QC data for your lot.
Reaction and Applications
As an aryl‑substituted tertiary alkyl ethyl ester, this compound is a versatile intermediate. Key reactivity patterns (literature/general):
Hydrolysis/saponification: Base- or acid-catalyzed hydrolysis affords 2-(4-fluorophenyl)-2-methylpropanoic acid. The adjacent quaternary center precludes enolization, simplifying reaction pathways. Typical conditions: NaOH or KOH (1–2 equiv) in MeOH/H2O or EtOH/H2O, 0–50 °C; or catalytic mineral acid in aqueous alcohol with heat.
Transesterification: Acidic (p-TsOH) or basic (NaOMe/MeONa) catalysis to exchange the ethyl group for another alcohol; azeotropic removal of ethanol drives equilibrium. Molecular sieves can aid under acid catalysis.
Reduction: LiAlH4 or Red-Al in THF/Et2O reduces the ester to the corresponding primary alcohol (2-(4-fluorophenyl)-2-methylpropanemethanol). DIBAL-H at low temperature may be tuned toward the aldehyde, though sterics demand careful control.
Conversion to acid chloride and amides: After hydrolysis, SOCl2 or (COCl)2 forms the acid chloride; subsequent coupling with amines (e.g., via Schotten–Baumann or peptide coupling reagents such as EDCI/HOBt) yields amides bearing the sterically hindered tert-alkyl–aryl motif.
Cross-coupling on the aryl fluoride: The para‑F position is typically unreactive in Pd-catalyzed cross-couplings; however, directed metalation on the ring (e.g., ortho to F) can be exploited on appropriately protected derivatives (advanced; literature-dependent).
Applications in synthesis:
Use as a protected/carboxyl-activated synthon for generating hindered carboxamides, acid derivatives, and neopentyl benzyl alcohols.
The quaternary center serves as a steric element in SAR libraries and materials where bulk and hydrophobicity are required.
Reaction Conditions
General literature guidance for common transformations of aryl tert‑alkyl ethyl esters. Values are typical ranges, not specifications for this item; optimize for your system.
Base hydrolysis (saponification): 1.0–2.0 equiv NaOH or KOH in MeOH/H2O (3:1 to 9:1 v/v), 0–50 °C, 1–16 h. Work up by solvent removal, acidify aqueous layer (pH ~2), extract with EtOAc, wash, dry, and concentrate to obtain the acid.
Acid hydrolysis: 1–3 M HCl or H2SO4 in MeOH/H2O or dioxane/H2O, reflux 2–12 h. Neutralize, extract, and isolate acid.
Transesterification (acid-catalyzed): 1–10 mol% p‑TsOH in the target alcohol, azeotropic removal of EtOH (Dean–Stark with toluene or neat if feasible), 60–110 °C, 2–24 h.
Transesterification (base-catalyzed): 5–20 mol% NaOMe in MeOH (or corresponding alkoxide/alcohol), 20–40 °C, 0.5–6 h; quench with acid, extract.
Reduction to primary alcohol: LiAlH4 (1.5–2.5 equiv) in dry THF or Et2O, 0 °C to rt, 1–4 h; careful aqueous quench (NH4Cl). DIBAL‑H (1.1–1.5 equiv) in toluene/hexane, −78 to −40 °C, 1–3 h may afford the aldehyde with strict temperature control; sterics can reduce conversion—monitor by TLC/GC/MS.
Activation to acid chloride (after hydrolysis): SOCl2 (2–4 equiv) with a catalytic DMF drop, 0–70 °C, 0.5–3 h under inert atmosphere; distill off excess reagent before coupling.
Analytical monitoring:
TLC UV at 254 nm; stains (KMnO4, p‑anisaldehyde) reveal ester/acid.
19F NMR offers clean, sensitive tracking of aryl fluoride environment.
Safety: Conduct reductions and acid chloride formations under inert atmosphere in a fume hood; follow SDS and institutional SOPs.
Safety and Handling
Authoritative safety information must be taken from the product SDS.
Item-specific hazard information (from Product Data):
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl alkyl esters (literature/general):
Likely hazards: Combustible organic liquid; may cause irritation on contact with skin/eyes or if inhaled as mist/vapor.
PPE: Use lab coat, safety glasses or splash goggles, and nitrile gloves. Employ in a chemical fume hood to avoid inhalation of vapors.
Storage incompatibilities: Keep away from strong oxidizing agents and strong bases/acids that promote hydrolysis. Avoid prolonged exposure to moisture if maintaining exact composition is important (transesterification/hydrolysis risk under strong conditions).
Fire safety: Keep away from ignition sources. Use CO2, dry chemical, or foam to extinguish. Ground/earth containers when transferring larger volumes.
First aid (overview, not a substitute for SDS):
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Stability: Esters do not form peroxides like ethers; however, they can slowly hydrolyze under basic or acidic conditions. Avoid strong nucleophiles if integrity must be preserved.
Solvent Selection
This product is an organic ester building block rather than a solvent, but solvent choice is central to its handling, purification, and transformation.
General solvent compatibility and polarity (literature/general):
Polarity class: low-to-moderate polarity, aprotic; expected logP > 2 due to aryl + tert-alkyl features.
Miscibility: insoluble to sparingly soluble in water; freely soluble in EtOAc, DCM, chloroform, toluene, THF, MTBE, hexanes mixtures, and alcohols.
Dielectric environment: reactions involving ionics (e.g., saponification) favor polar protic solvents (MeOH/EtOH/H2O) or polar aprotics (DMF/DMSO) with base; reductions and transesterifications often run in Et2O, THF, toluene, or alcohols.
Practical choices by task:
Weighing/transfer and storage: toluene or heptane for rinses; avoid prolonged contact with strong alcoholic KOH/NaOMe unless saponification/transesterification is intended.
Flash chromatography: start 0–20% EtOAc in hexanes; para‑F ring affords strong UV at 254 nm for tracking.
Kinetics of hydrolysis: use aqueous MeOH/EtOH with NaOH or HCl; buffer ionic strength to control rates and minimize ester exchange.
Comparison (general):
THF vs toluene: THF accelerates nucleophilic processes and metal hydride reductions; toluene minimizes solvolysis and is advantageous for thermal robustness.
EtOAc vs DCM: EtOAc is a greener, higher-boiling alternative and frequently dissolves aryl esters well; DCM offers faster evaporation but higher EHS burdens.
Storage and Reconstitution
Item-specific conditions from Product Data:
Storage Conditions: Room temperature
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (for esters of this class; not product specifications):
Storage: Keep container tightly closed in a dry, well-ventilated place at ambient temperature. Protect from moisture and strong light if long-term storage is anticipated. Use amber glass for extended storage to minimize photolysis of aromatic systems.
Inerting: Not required, but headspace nitrogen or argon can help preserve material during long storage, particularly after multiple openings.
Stability: Esters are generally stable at room temperature. Avoid prolonged exposure to strong acids/bases or nucleophiles that can induce hydrolysis/transesterification.
Reconstitution: Not applicable—supplied neat. If crystallization or viscosity impedes handling, gently warm (e.g., 30–40 °C) and sonicate to homogenize before use.
Packaging/handling: Use PTFE-lined caps to avoid extractables. Reseal promptly after dispensing to limit ethanol loss or uptake of moisture from the atmosphere.
Research Use Note: For research use only.
Structure and Identity
Brief description: Ethyl 2-(4-fluorophenyl)-2-methylpropanoate is an aryl-substituted, sterically hindered tertiary alkyl carboxylate (ethyl ester). The molecule features a para‑fluorophenyl ring attached to a quaternary carbon that also bears two methyl groups and a carbonyl carbon of an ethyl ester.
Item-specific identifiers from Product Data:
CAS: 1035261-07-4
CID: 62393957
InChIKey: 18863 (as supplied; note: typical InChIKeys are 27-character hashes)
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.
Literature/typical identifiers and descriptors (for reference only; not item specifications):
Common (non-IUPAC) name: Ethyl p-(fluorophenyl)neopentanoate (descriptive)
Functional groups: aromatic aryl fluoride (para-F), tertiary α-quaternary center [C(Ph)(Me)2], and ethyl carboxylate ester.
Ring systems: one para-substituted benzene ring.
Stereochemistry: none (tetra-substituted center is not stereogenic because two substituents are identical methyl groups).
2D structure in words: an ethyl ester carbonyl is bonded to a quaternary carbon bearing two methyl groups and a 4‑fluorophenyl ring (para F on the ring).
Synthetic Utility
Functional-group profile and reactivity (literature/general):
Carboxylate ester (ethyl): amenable to hydrolysis (acid/base), alcohol exchange (transesterification), reduction (hydrides to primary alcohol or aldehyde under controlled conditions), and activation to acid chloride or mixed anhydride after hydrolysis.
Aryl fluoride (para): robust to many conditions, mildly directing in metalation chemistry; rarely a first-choice leaving group in cross-coupling but can be exploited under specialized catalysis.
α-Quaternary center [C(Ph)(Me)2–C(=O)OEt]: blocks enolization and classical Claisen-type condensations; confers steric bulk, which can be harnessed to modulate reactivity and selectivity in downstream steps.
Typical synthetic maneuvers:
Saponify → acid → (i) acid chloride (SOCl2) → amide/ester diversification; (ii) coupling via EDCI/HATU/DIC.
Reduce with LiAlH4 (THF, 0–25 °C) to 2-(4-fluorophenyl)-2-methylpropanemethanol; subsequent oxidation (e.g., Dess–Martin) yields the corresponding benzyl‑neopentyl aldehyde.
Transesterify under p‑TsOH (Dean–Stark in toluene) or NaOMe (MeOH) to tailor protecting group properties.
Orthogonal manipulation of the aryl ring (e.g., directed ortho‑metalation adjacent to F on suitably protected derivatives) enables installation of additional functionality for library build‑outs.
Purification/analysis tips:
Strong UV chromophore at 254 nm aids HPLC/flash tracking; para‑F facilitates 19F NMR monitoring (singlet, compound‑specific shift) for reaction progress without chromophoric interference.
Target Specificity
Not applicable. This product is a small-molecule organic building block and is not an antibody, enzyme, or biological targeting agent. No antigen/epitope specificity, clone, isotype, or species reactivity data apply.
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