This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene 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
Not applicable
No tested bioassay or immunoassay application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.
Biological Roles
Item-specific
Intended use: For research use only (per Product Data). No biological role is assigned for this reagent.
General context (literature)
Ethyl 2-(3,4-difluorophenyl)-2,2-difluoroacetate is a small, non-ionic, hydrophobic organic molecule used as a synthetic intermediate. It is not a biological buffer, ligand, or nutrient.
Organofluorine motifs such as aryl–CF2–C(O)– are frequently explored in medicinal chemistry as metabolic stability enhancers or carbonyl bioisosteres, but this does not imply any direct biological activity or clinical utility of the reagent itself.
Practical note
Any studies involving biological systems should treat this compound as an experimental chemical entity. Ensure appropriate containment, dosing, and disposal practices consistent with institutional EHS guidelines. No clinical, diagnostic, or therapeutic uses are intended or permitted.
Buffer Applications
Not typically applicable
This product is an organic building block and is not used as a buffering agent. It lacks acid/base pairs in the physiological pH range and has poor water solubility.
Guidance
For aqueous work involving this compound (e.g., biphasic reactions or extractions), standard laboratory buffers (phosphate, acetate) may be used to control pH of the aqueous phase, but the compound itself does not function as a buffer.
Green Alternatives
Context
This SKU is a synthetic building block, not a process solvent. Greener considerations focus on the choice of reaction and workup solvents and reagents used with it.
Greener solvent choices (literature/general)
Prefer ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or Me-THF:toluene blends over chlorinated solvents where compatible.
For extractions, EtOAc and MTBE can substitute for DCM/chloroform; heptane is a lower-toxicity alternative to hexane for normal-phase chromatography.
Coupling and derivatization
Amide formations: Use carbodiimide alternatives with better EHS profiles (e.g., COMU, EDCI) and catalytic DMAP instead of HATU/HBTU where feasible; employ green solvents (EtOAc, MeCN, 2-MeTHF).
Hydrolysis: Favor aqueous ethanol/2-MeTHF biphasic systems with recyclable bases (K2CO3) over strong mineral bases when kinetics allow.
Reductions: Consider catalytic hydrogenation of intermediate derivatives or borane alternatives instead of stoichiometric LAH; for ester-to-aldehyde, explore catalytic hydrosilylation (e.g., Pt, B(C6F5)3 systems) in safer solvents.
Trade-offs
Replacing DCM with EtOAc or 2-MeTHF may slow certain acylations; temperature or catalyst loading adjustments can compensate.
CPME/2-MeTHF offer better safety and water tolerance but can alter selectivity in reductions.
Waste minimization
Leverage 19F NMR for rapid reaction monitoring to reduce TLC/chromatography runs.
Consolidate fluorinated waste streams; avoid incineration conditions that generate HF without proper scrubbing.
Pharmaceutical Uses
Item-specific
Research Use Only. No pharmacopoeial grade or excipient status is provided for this SKU.
General formulation/manufacturing context (non-clinical; literature)
Fluorinated aryl–CF2–carbonyl motifs are frequently incorporated into discovery-stage compounds to tune lipophilicity, metabolic stability, and binding interactions. This reagent can serve as a precursor to such motifs via hydrolysis/amide coupling or selective reduction.
Typical roles are as a synthetic intermediate in route scouting and SAR exploration; it is not formulated as an active or excipient.
Regulatory note
No clinical, diagnostic, or therapeutic applications are supported. For any cGMP or scale-up activities, separate sourcing with defined pharmacopeial or GMP documentation would be required.
Physical Properties
Item-specific
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Room temperature (per Product Data)
Literature/computed (general guidance; not item specifications)
Physical state: Typically a colorless to pale liquid for related aryl gem-difluoroacetates; exact state for this item not specified.
Expected solubility profile: Low solubility in water; good solubility in common organic solvents (e.g., dichloromethane, ethyl acetate, THF, toluene, acetonitrile) typical for aromatic ethyl esters with multiple fluorines.
Volatility: Moderate; anticipated boiling point in the range typical of substituted aromatic ethyl esters; exact BP/MP for this item not specified.
Not specified for this item; refer to CoA/Spec Sheet
Boiling point, melting point, density, refractive index, pKa, logP/logD, UV cutoff/epsilon.
Practical notes (general)
The gem-difluoro motif and aromatic ring increase hydrophobicity relative to non-fluorinated analogs; anticipate higher organic partitioning and lower aqueous miscibility.
Handle under dry conditions if precise stoichiometry is critical; esters can undergo slow hydrolysis in moist conditions over long storage times.
Quality and Grades
Item-specific
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance
Research-use reagent: Supplied for research and laboratory use only (per Product Data). Typical expectations include identity confirmation (e.g., NMR/LC–MS) and assay/purity characterization.
If labeled as “AR,” “Reagent,” or similar on the CoA, this denotes suitability for general synthetic work. HPLC-grade designations are uncommon for building-block esters; when present, they indicate low UV background and minimal nonvolatile residue.
Fluorinated esters are often stable without added stabilizers. If a stabilizer is present (rare for this class), it will be listed on the CoA and may need to be removed before sensitive transformations.
Trace impurity considerations: Water content, residual solvents, and acidity/basicity can influence base- or acid-catalyzed steps (e.g., amidations, transesterifications). For moisture-sensitive steps, consider Karl Fischer and pre-drying protocols.
Verification and documentation
Request and review the batch CoA for: purity/assay, residual solvents, identity (1H/13C/19F NMR), and chromatographic profile. These are the authoritative specifications for this SKU.
Reaction and Applications
Item-specific context
Ethyl 2-(3,4-difluorophenyl)-2,2-difluoroacetate is a fluorinated aryl-alkyl ester building block intended for research use in organic synthesis and medicinal chemistry.
Representative applications (literature/general; expand as appropriate)
Carboxylate derivatization: Hydrolysis to the corresponding acid, followed by conversion to acid chlorides, anhydrides, or amides (including Weinreb amides) enables access to diverse CF2–aryl carbonyl derivatives.
Reductive transformations: Selective reduction of the ester to the aldehyde (DIBAL-H, −78 °C to 0 °C) or to the primary alcohol (LiAlH4, NaBH4/activation) while retaining the gem-difluoro motif. Subsequent oxidation can furnish aryl–CF2–carbonyl scaffolds.
Defluorinative functionalization: Under specialized conditions (e.g., metal-catalyzed or radical pathways), gem-difluoro groups can undergo selective C–F activation to introduce CFH or carbon–carbon linkages; substrate control from the aryl group can influence selectivity.
Transesterification: Exchange of the ethyl group for sterically or electronically tuned alcohols (ROH/base or acid catalysis) to tailor downstream reactivity or lipophilicity.
Cross-coupling downstream: The 3,4-difluorophenyl ring tolerates many cross-coupling conditions; transformations are typically performed on pre-functionalized analogs, but the present scaffold is stable to Pd-catalyzed conditions used after converting the ester to other handles.
Medicinal chemistry utility: The –CF2– adjacent to a carbonyl acts as a polar lipophilic group and carbonyl bioisostere, used to modulate metabolic stability and binding interactions in lead optimization.
Practical tips
Maintain anhydrous conditions for moisture-sensitive steps; monitor by 19F NMR where possible to track CF2 integrity.
Fluorinated aromatics often crystallize poorly; plan for chromatographic purification with fluorine-aware eluents (e.g., hexanes/EtOAc).
Reaction Conditions
General conditions (literature guidance; not item specifications)
Hydrolysis to acid: NaOH (1–2 equiv) in MeOH/H2O (3:1 to 9:1), 0–25 °C to reflux, 1–12 h. Work up by acidification and extraction with EtOAc. Yields commonly high (70–95%) for ethyl aryl esters.
Amidation (via acid): Convert acid to acid chloride with SOCl2 (catalytic DMF) in DCM or toluene, 0–25 °C, 1–3 h; then couple with amine (1–2 equiv) and base (Et3N, DIPEA) at 0–25 °C. Alternatively, EDCI/HOBt or COMU/DIPEA in DCM/DMF at 0–25 °C affords amides directly from the acid.
Reduction to aldehyde: DIBAL-H (1.1–1.5 equiv) in toluene or DCM, −78 °C to −20 °C, 0.5–2 h; quench with MeOH then Rochelle’s salt. Aldehyde can be sensitive; isolate at low temperature if needed.
Reduction to alcohol: LiAlH4 (2–3 equiv) in THF, 0–25 °C to reflux, 1–3 h; careful quench sequence (H2O/NaOH/H2O).
Transesterification: ROH (excess) with catalytic acid (TsOH) or base (NaOMe/ROMe), 25–60 °C, 2–16 h; remove alcohol under reduced pressure to drive equilibrium.
Defluorinative functionalization (advanced): Transition-metal-catalyzed or radical-mediated protocols may enable selective C–F activation; conditions are substrate- and method-specific and often require photoredox or Ni/Cu catalysis.
Monitoring and analytics
19F NMR: CF2 typically appears as a characteristic signal distinct from aryl-F; track for conversion and side reactions.
LC–MS/GC–MS: The fluorinated mass signature aids confirmation; choose APCI/ESI depending on derivative.
Notes
The 3,4-difluorophenyl ring resists electrophilic substitution; choose cross-couplings on pre-installed handles if aryl diversification is desired.
Safety and Handling
Item-specific
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
Storage: Room temperature (per Product Data)
General safety guidance for aromatic gem-difluoro ethyl esters (literature/analog-based; defer to SDS)
Likely hazards: Combustible liquid, skin/eye irritant, and harmful if swallowed or inhaled are common for comparable aryl esters. Avoid inhalation of vapors and contact with skin/eyes.
PPE: Safety glasses or goggles, lab coat, and suitable chemically resistant gloves (e.g., nitrile). Work in a fume hood to control vapor and prevent inhalation.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse thoroughly with water for 15 minutes; remove contaminated clothing; seek medical attention if irritation develops.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire response: Use CO2, dry chemical, or foam. Combustion may generate irritating/toxic fumes (HF may form in fires involving organofluorine compounds); firefighters should use SCBA.
Spills: Absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains.
Always consult the product-specific SDS for authoritative hazard classification and response measures.
Solvent Selection
Applicability
This product is a fluorinated aromatic ethyl ester building block, not a solvent. Solvent selection guidance below is for using this compound in synthesis, workup, and purification.
General solvent behavior (literature/experience)
Polarity/miscibility: Hydrophobic; low water solubility. Readily soluble in common organic solvents such as dichloromethane (DCM), chloroform, ethyl acetate (EtOAc), THF, acetone, acetonitrile (MeCN), and aromatics (toluene).
Dielectric/polarity preference: The ester and aryl CF2 unit favor moderately polar aprotic media for acyl substitution and coupling; nonpolar aromatics are preferred for high-temperature stability or when minimizing ester exchange.
Use-case guidance
Nucleophilic acyl substitutions (to amides, hydrazides): DCM, THF, or MeCN with coupling reagents; for base-catalyzed transesterification, choose anhydrous alcohol solvent (MeOH, EtOH) with catalytic base.
Hydrolysis: Aqueous MeOH/THF with NaOH or K2CO3; phase-transfer options exist for biphasic conditions (toluene/aqueous base).
Reductions (e.g., DIBAL-H): Non-protic, low-temperature solvents such as toluene, DCM, or THF.
Purification: Normal-phase silica with hexanes/EtOAc or hexanes/DCM gradients; 19F-containing aromatics often show strong UV absorbance for detection at 210–254 nm.
Comparison notes (literature/general)
DCM vs EtOAc: DCM provides better solubility and chromatographic control; EtOAc is greener and useful for extractions.
THF vs MeCN: THF offers broad solubility and low-temperature performance; MeCN provides higher polarity, faster couplings, and easy removal but can be less benign for certain bases.
Storage and Reconstitution
Item-specific
Storage conditions: Room temperature (per Product Data)
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Physical form/appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance
Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and prolonged exposure to strong light.
If long-term storage is planned, consider storing under inert gas after purging headspace, especially if frequent opening is expected.
No reconstitution is typically required; use as supplied. If solidification occurs upon cold storage, gently warm to ambient and, if necessary, sonicate to ensure homogeneity before use.
For moisture-sensitive transformations, pre-dry by azeotropic removal (co-evaporate with dry toluene or heptane) or hold over activated molecular sieves in an appropriate solvent.
Stability
Esters are generally stable at room temperature. Avoid strong acids/bases and nucleophiles during storage. Review the CoA for any lot-specific stability or inhibitor notes.
Disposal
Dispose of contents/container in accordance with local/regional regulations for organic fluorinated waste. Segregate from aqueous corrosive waste streams.
Functional groups: aromatic ring (1,3,4-trisubstituted phenyl), geminal difluoromethylene (–CF2–) adjacent to carbonyl, ethyl ester (–CO2CH2CH3).
2D structural description (in words): A 3,4-difluorophenyl ring is bonded at the ipso carbon to a quaternary carbon bearing two fluorine atoms (–CF2–), which is carbonyl-adjacent; the carbonyl is esterified with ethanol (–CO2Et). Substitution pattern on the arene is 1-(CF2CO2Et),3-F,4-F (overall 1,3,4-trisubstituted).
Notes
The provided InChIKey is non-standard in length; consult the CoA/SDS for definitive identifiers used for regulatory and inventory control.
Synthetic Utility
Key reactive elements (literature/general)
Ethyl ester (–CO2Et): Undergoes nucleophilic acyl substitution (hydrolysis, aminolysis, transesterification), reductions (to aldehyde/alcohol), and activation (acid chloride via hydrolysis then SOCl2/Oxalyl chloride).
Gem-difluoromethylene (–CF2–): Electron-withdrawing and sterically compact. It can stabilize adjacent carbanions poorly; typically inert to many bases at ambient temperature but can participate in selective defluorinative or radical chemistry under specialized conditions.
Aryl ring (3,4-difluoro): Deactivated toward electrophilic aromatic substitution; resilient under many cross-coupling conditions performed on appropriately functionalized derivatives.
Retrosynthetic value
Enables introduction of an aryl–CF2–carbonyl fragment. After hydrolysis and amide coupling, provides aryl–CF2–CONR2 scaffolds. DIBAL-H reduction affords aryl–CF2–CHO, a versatile handle for further elaboration (e.g., Wittig, reductive amination after conversion).
Named/typical transformations (examples)
DIBAL-H partial reduction of esters to aldehydes (−78 to 0 °C).
LAH reduction to primary alcohols.
EDCI/COMU-mediated amidations following hydrolysis to the acid.
Acid- or base-catalyzed transesterification to tailor protecting group strategy or solubility.
Practical considerations
Monitor reactions by 19F NMR to observe distinct CF2 and aryl-F resonances for conversion and integrity.
Avoid strong, prolonged basic conditions that can lead to ester saponification and potential side reactions at C–F under harsh conditions.
Target Specificity
Not applicable
This product is a small-molecule chemical reagent and does not have biological target specificity data (e.g., antigen/epitope, clone, isotype). No such information is provided in the Product Data.
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 73789-95-4, the molecular formula is C10H8F4O2, and the molecular weight is 236.16 g/mol. InChIKey GUAAKHWBEHBVKT-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.
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