This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
External Descriptors
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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 as an antibody or assay kit. There are no WB/IHC/IF/FC protocols specific to this item. For synthetic uses, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory procedures and adapt them to your specific substrates and setup.
Biological Roles
Applicability: Difluoropropanedioic acid is a synthetic, fluorinated dicarboxylic acid and is not known as a natural metabolite.
General biochemical context (literature/general)
Non‑endogenous analogue: Fluorination of small carboxylic acids is commonly used to modulate acidity, lipophilicity, and metabolic stability in biochemical tool compounds. The gem‑difluoro motif increases electron withdrawal and can alter interactions with carboxylate‑recognizing enzymes and transporters.
Potential as a probe: Carboxylate salts of fluorinated dicarboxylic acids may serve as surrogates in studies of transporter selectivity, enzyme inhibition kinetics, or 19F NMR‑based binding screens (no claims for this specific compound without supporting data).
19F NMR handle: The CF2 group provides a sensitive, background‑free nucleus for in vitro binding or environment reporting in biochemical assays.
Caveats
No established physiological role is reported for this compound. Any biological testing should be performed under controlled laboratory conditions. For research use only (per Product Data). Avoid extrapolating to clinical or therapeutic contexts.
Buffer Applications
Not typically applicable. Difluoropropanedioic acid is a strong, small dicarboxylic acid but is not a standard biological buffer component with defined buffering ranges and formulations. If a carboxylate buffer is required, consider established systems (e.g., citrate, acetate, MES, MOPS) with well‑characterized pKa values and buffering ranges. Use this product primarily as a synthetic building block rather than a buffering agent.
Green Alternatives
Context: As a solid reagent, difluoropropanedioic acid itself is not a solvent target for substitution. However, greener choices arise in the solvents and activating reagents used with it.
Esterification media: Replace chlorinated solvents with alcohols as both reagent and solvent (MeOH/EtOH/iPrOH) and employ catalytic solid acids (Amberlyst‑15) instead of mineral acids where possible.
Couplings: Favor carbodiimide alternatives with better EHS profiles (e.g., CDI) and catalytic DMAP over large excesses of hazardous reagents; employ greener solvents (2‑MeTHF, CPME, ethyl acetate) when solubility allows.
Acid chloride formation: Consider mixed anhydride methods (isobutyl chloroformate) or CDI activation to avoid SOCl2/(COCl)2, reducing corrosive off‑gassing.
Workup: Minimize halogenated waste; use aqueous ethanol or EtOAc/brine partitions rather than DCM when feasible.
Illustrative comparison (general)
Traditional: SOCl2 in DCM; Pros—high reactivity; Cons—HCl/SO2 emissions, chlorinated waste.
Alternative: CDI in EtOAc or 2‑MeTHF; Pros—milder, less corrosive, greener solvent; Cons—may require optimization and thorough removal of imidazole byproducts.
Process tips
Evaluate solvent replacement through small‑scale solubility screens; the high polarity of diacids often favors protic or polar aprotic media—seek bio‑derived options (2‑MeTHF, Cyrene, propylene carbonate) where compatible.
Apply aqueous ethanol recrystallization to reduce VOC impact compared with acetone/ACN when practical.
Pharmaceutical Uses
Formulation/excipient context
This compound is not a standard pharmacopeial excipient. As a highly acidic, fluorinated dicarboxylic acid, it is more appropriately used as a research intermediate/building block in medicinal chemistry rather than a formulation aid.
Fluorinated dicarboxylic acids and their esters may be used to access difluorinated acyl fragments, amides, and heterocycles for SAR exploration. The gem‑difluoro motif is valued for tuning acidity (pKa), metabolic stability, and dipole moments in APIs.
Salt screening: Carboxylate functionality allows exploration of metal or organic counterion salts (e.g., sodium, potassium, organic amines) for materials or intermediate isolation, but such salts are typically research tools, not dosage‑form excipients.
Compliance
No pharmacopeial monograph is implied. For any cGMP or clinical manufacturing, source specifications, residual solvent limits, elemental impurity controls, and stability data must be established independently. This product is for research use only (per Product Data).
Physical Properties
Item-specific specifications
Appearance: 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.
Other specs (bp/mp/density/UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values (non-spec)
Empirical formula (literature): C3H2F2O4
Formula weight (literature): ~140.04 g/mol
Physical state: Typically a crystalline solid (literature reports for related malonic acids)
Acidity: Enhanced vs malonic acid due to –CF2– inductive effect; pKa values for gem‑difluoro dicarboxylic acids are generally lower than malonic acid (pKa1 2.83, pKa2 5.69 for malonic acid; difluoro analogue expected lower; check primary literature).
Solubility (general behavior): Expected good solubility in polar protic solvents (water, alcohols) and in basic aqueous media as the di- or mono‑carboxylate salts; limited solubility in nonpolar solvents.
Hygroscopicity: Many low‑molecular dicarboxylic acids exhibit some moisture affinity; confirm on receipt (not item‑specific).
Notes
The above values are for context and experimental planning only. For lot-specific properties and analytical limits (water, metals, residual solvents, etc.), consult the CoA/Spec Sheet for this item.
Quality and Grades
Item-specific details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, titration value, or chromatographic purity.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research grade dicarboxylic acids are typically supplied with assay by acidimetric titration and/or chromatographic purity (HPLC/GC). Low water content may be important for stoichiometric reactions or anhydride/ester formation; verify Karl Fischer values on the CoA if relevant.
If offered as “ACS/AR grade,” it generally indicates compliance with analytical reagent specifications for heavy metals and assay; “High-purity” or “99%+” indicates chromatographic purity and low nonvolatile residue. HPLC grade is not usually applicable to solids unless specified for LC compatibility (low UV‑absorbing impurities).
Quality considerations specific to difluoro analogues (general)
Halogenated dicarboxylic acids may show increased acidity; residual inorganic fluoride or halide content can be critical for certain catalyses and metal-sensitive reactions. Check the Spec Sheet for halide/metal content if your application is catalyst‑sensitive (e.g., Pd, Ni catalysis).
If performing quantitative acid–base titrations or materials synthesis, confirm water content and crystallization solvent history to ensure reproducibility.
Reaction and Applications
Overview (general/literature)
Difluoropropanedioic acid (difluoromalonic acid) serves as a fluorinated malonic‑acid analogue and a versatile building block for introducing a gem‑difluoro (–CF2–) motif adjacent to carbonyls.
Representative application families
Esterification/Protection: Formation of diesters (e.g., dimethyl/dietyl difluoromalonate) via Fischer esterification. These esters are convenient intermediates for further transformations.
Decarboxylation pathways: Thermally or catalytically promoted decarboxylation can generate difluoroacetic derivatives. Sequential activation (e.g., formation of half‑esters/anhydrides) may facilitate controlled mono‑decarboxylation (literature reports for malonate analogues).
Activation to acid chlorides/anhydrides: Conversion with SOCl2, (COCl)2, or carbodiimide/DMAP protocols enables amide, imide, or mixed anhydride formation.
Nucleophilic substitution at the CF2‑center: While the CF2 group is strongly deactivating, gem‑difluoro centers adjacent to carbonyls can undergo selective transformations (e.g., deoxyfluorination/reduction or fluorine–carbonyl interconversions under specialized conditions), enabling access to CHF‑ or CF3‑containing motifs after further steps.
Coordination/Materials: Carboxylate salts can coordinate metals, offering routes to fluorinated metal–organic materials (MOFs/coordination polymers) with distinctive polarity and hydrophobicity contrasts.
Practical tips
Control acidity: Strong acidity can quench bases and catalysts; stage additions and buffering may be necessary.
Use dry conditions for acyl chloride or ester synthesis; remove residual SOCl2/(COCl)2 thoroughly.
Monitor by 19F NMR when applicable; the CF2 resonance provides a sensitive handle for conversion tracking.
For decarboxylation studies, use small‑volume vented setups to safely release CO2 and maintain temperature control.
Note: The above are literature/general applications; adapt to your system and consult primary sources.
Reaction Conditions
General literature guidance (not item specifications)
Solvent/reagent: Neat ROH (MeOH/EtOH) or ROH with catalytic H2SO4 or p‑TsOH.
Conditions: Reflux 4–24 h; remove water by azeotrope or molecular sieves for higher conversion.
Workup: Neutralize acid, evaporate alcohol, extract into EtOAc; purify by distillation/crystallization.
Acid chloride formation
Reagents: SOCl2 (2–4 equiv) or oxalyl chloride, catalytic DMF.
Solvent: Anhydrous DCM or toluene.
Temperature: 0 °C to reflux until gas evolution ceases (HCl/SO2 or CO/CO2).
Notes: Thoroughly remove excess reagent; minimize exposure to moisture.
Amide coupling (mono‑ or di‑acylation)
Reagents: EDC·HCl or DIC with HOBt/HOAt or DMAP; or CDI for greener profile.
Solvent: DMF, DCM, or 2‑MeTHF.
Base: DIPEA/Et3N to manage acidity.
Temperature/time: 0–25 °C (activation), then 25–50 °C for 2–18 h.
Decarboxylation (to difluoroacetic derivatives)
Strategy: Prepare mono‑ester/anhydride, then heat.
Conditions: 150–200 °C (neat or high‑boiling solvent such as DMSO, sulfolane) or catalytic decarboxylation under microwave; CO2 release observed.
Caution: Conduct in vented apparatus; monitor by 19F NMR.
Salt formation/crystallization
Base: NaOH/KOH (aqueous) or organic amines.
pH control: Target pH near pKa1 for mono‑salt; >pKa2 for di‑salt; isolate by evaporation/cooling.
Expected outcomes
Yields: Highly procedure‑dependent; esterifications commonly 60–90% after optimization; couplings 50–85% for mono‑acylation due to competing di‑acylation.
Always consult primary literature and conduct small‑scale optimizations before scale‑up.
Safety and Handling
Item-specific hazard data
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / Hazard Statements / Pictograms: Not specified for this item; refer to SDS.
General safety guidance for difluoro-dicarboxylic acids (literature/analog-based; defer to SDS)
Likely hazards: Organic acids may cause skin/eye irritation and respiratory tract irritation. The gem‑difluoro group does not inherently impart volatility but can increase acidity; handle as a corrosive/irritant precaution.
PPE: Lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or aerosols.
Handling: Avoid creating dust. Do not breathe dust. Prevent contact with bases or reactive metals that can evolve heat/CO2 upon neutralization. Keep away from strong oxidizers and strong reducing agents.
Storage: Room temperature per Product Data. Store tightly closed in a dry, well‑ventilated area. Protect from moisture; keep container tightly sealed to prevent caking or deliquescence if hygroscopic.
Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Thermal decomposition: Carboxylic acids can decarboxylate at elevated temperatures; heat can evolve CO2. Avoid heating in closed systems.
Always consult the item’s SDS for authoritative hazard classification and response measures.
Solvent Selection
Relevance: Difluoropropanedioic acid is a polar, diacidic solid rather than a solvent. Solvent selection pertains to dissolving/processing it in synthesis or purification.
General solvent behavior (literature/general)
Polarity: High polarity due to two carboxylic acids; forms extensive hydrogen bonding.
Miscibility/solubility: Typically readily soluble in water upon neutralization (formation of mono-/di‑carboxylate salts). Solubility in alcohols (MeOH, EtOH) is generally good; limited in aprotic nonpolar media (hexanes, toluene).
Acid‑catalyzed transformations (esterification): Use anhydrous ROH (MeOH/EtOH) with catalytic H2SO4 or HCl(g); Dean–Stark in toluene/xylene is less effective with strong polyfunctional acids.
Amide formation: Conduct in polar aprotic solvents (DMF, DMAc, NMP, DMSO) with coupling reagents; ensure base selection is compatible with strong acidity.
Selection tips
For salt formation and aqueous workup: Water, then adjust pH with NaOH/K2CO3 to target mono- or di‑salt.
For isolation/crystallization: Aqueous alcohols or acetone/water mixtures can aid crystallization; check small-scale trials.
For moisture‑sensitive downstream steps (acid chloride formation): Dry solvents (DCM, THF) and low water content are important; use standard drying/degassing protocols.
Comparison (general)
Water: Best for neutralization/ion‑exchange work.
Alcohols: Enable Fischer esterification and offer moderate solubility.
Polar aprotics (DMF/DMSO): Maximize solubility for coupling; harder to remove.
Chlorinated solvents (DCM): Useful after converting acids to acid chlorides/esters; limited direct solubility as the free diacid.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (from Product Data). Store in a tightly closed container in a dry place, away from incompatible materials.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice)
Solid handling: Minimize exposure to ambient moisture to prevent clumping or partial neutralization. If material cakes, gently break up under dry atmosphere before weighing.
Stock solutions: Prepare solutions freshly in appropriate solvents (water with base, alcohols, or polar aprotics). Filter if necessary. For water-based solutions, adjust pH carefully; cool if exotherm is observed during neutralization.
Stability: Carboxylic acids are generally stable at ambient temperature when dry and protected from light; avoid prolonged heating which can promote decarboxylation.
Freeze–thaw: Not typically relevant to the solid. If preparing aqueous stocks, store aliquots at 2–8 °C and avoid repeated freeze–thaw; check for precipitation upon warming.
Always consult the product CoA/SDS for definitive storage, stability, and compatibility information.
Structure and Identity
Brief description: Difluoropropanedioic acid is the gem-difluoro analogue of malonic acid (often referred to in the literature as difluoromalonic acid), bearing two carboxylic acids flanking a geminal CF2 center.
Item-specific (from Product Data)
SKU: D1068342
Product Name: Difluoropropanedioic acid
CAS: 1514-85-8
InChIKey: 200214 (as provided)
Storage: Room temperature
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed identifiers and features (for reference only; not item specifications)
Synonym: Difluoromalonic acid
Molecular formula (literature): C3H2F2O4
Molecular weight (literature): ~140.04 g/mol
SMILES (literature): O=C(O)C(F)(F)C(=O)O
2D structural description: A three‑carbon backbone with terminal carboxyl groups at C1 and C3; the central carbon (C2) bears two fluorine substituents (gem‑difluoro). No stereocenters; planar carboxylate groups capable of hydrogen bonding.
Functional groups and structural motifs (general chemistry)
Strong inductive –I effect from CF2 increases acidity and deactivates the central carbon toward enolization compared with malonic acid.
Synthetic Utility
Key reactivity elements (general/literature)
Dual carboxylic acids: Enable formation of diesters, diacyl derivatives, mixed anhydrides, and amides. Stepwise protection/activation allows selective mono‑functionalization.
Gem‑difluoro center: Strong –I effect lowers pKa and suppresses enolization vs malonic acid, impacting condensation chemistry. Serves as a masked difluoroacyl fragment after decarboxylation or activation.
Representative transformations
Fischer esterification → dialkyl difluoromalonates (building blocks for further C–C or C–X formation).
Conversion to acid chlorides (SOCl2/(COCl)2) → difluoromalonyl dichloride for acylation or polymer‑forming reactions with diols/diamines.
Curtius/Schmidt pathways from activated derivatives → access to difluoroacyl azides/isocyanates (specialized, handle with extreme care; literature procedures only).
Thermal/catalytic decarboxylation of mono‑esters or half‑amides → difluoroacetate/difluoroacetamide derivatives; useful entries to CHF2/CF2‑containing fragments after further manipulations.
Formation of metal carboxylates → coordination polymers/MOF precursors incorporating a polar CF2‑bridged linker.
Retrosynthetic value
Serves as a convergent synthon for installing a –C(=O)–CF2–C(=O)– motif or, after stepwise decarboxylation, a –CF2–CO2H fragment. Retrosynthetic disconnections often proceed via ester intermediates to manage acidity and enable selective activation.
Practical notes
Use protecting groups or stepwise esterification to control chemoselectivity.
Monitor reactions by 19F NMR/IR (C=O stretches) to track activation and conversion.
Neutralize carefully; CO2 evolution and exotherm can occur with bases/carbonates.
Target Specificity
Not applicable. This product is a small‑molecule reagent, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies.
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