This compound belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the 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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
202.150 g/mol
XLogP3
2.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
3
Exact Mass
202.044 Da
Monoisotopic Mass
202.044 Da
Topological Polar Surface Area
46.500 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
210.000
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
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Recensioni
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Application Protocols
No application protocols are specified for this item. As a synthetic intermediate, its use depends on the chosen transformation (e.g., amide coupling, esterification, decarboxylative coupling). Refer to the Reaction & Applications and Reaction Conditions sections for general laboratory guidance and adjust to your substrates and scale.
Biological Roles
No item-specific biological data are provided. The following are general considerations for this class of compounds and should not be construed as clinical or therapeutic claims.
Benzoic acid derivatives occur in nature (e.g., p‑hydroxybenzoates) as metabolic intermediates; however, 3,5‑difluoro/2‑ethoxy substitution yields a xenobiotic structure not expected in primary metabolism (literature).
Fluorination often modulates lipophilicity, pKa, and metabolic stability. Two aryl–F substituents can reduce oxidative metabolism on the ring and adjust binding interactions in enzyme/receptor studies (general medicinal chemistry principle).
The free acid can serve as a carboxylate handle for conjugation to biomolecules (e.g., forming amide/ester linkages to amino alcohols or peptides) to produce research probes or tags.
In biophysical assays, aryl carboxylates can bind to hydrophobic pockets with ionic interaction at the carboxylate site; the 19F nuclei can be leveraged for 19F NMR binding studies when incorporated into ligands (literature concept).
Research Use Note: For research use only.
Buffer Applications
This compound is not typically used as a laboratory buffer. As an aromatic carboxylic acid, it has a single acidic proton with an expected pKa in the benzoic acid range (literature estimate ~3.6–4.2), which does not provide strong buffering capacity near physiological pH.
If ionization control is desired (e.g., during extraction or crystallization), adjust to basic pH (NaHCO3/Na2CO3) to form the carboxylate salt and to acidic pH (HCl) to regenerate the free acid.
For true buffering needs, select established systems (e.g., acetate pH 3.6–5.6, citrate pH 3.0–6.2, phosphate pH 6.0–8.0) rather than this compound.
Green Alternatives
While the product itself is a solid building block (not a solvent), greener choices can be made for its typical transformations.
Solvent substitutions (literature guidance):
Replace dichloromethane/toluene with EtOAc or 2‑MeTHF where feasible (e.g., Steglich or EDC couplings often run well in EtOAc/MeCN).
For polar aprotic needs, consider CPME or cyclopentyl methyl ether instead of THF/MTBE when water tolerance and peroxide resistance are desired.
For amide couplings, MeCN or green dipolar solvents (e.g., propylene carbonate) can substitute DMF/NMP in some protocols.
Reagent choices:
Use T3P (in EtOAc) or water-compatible EDC·HCl systems to minimize urea waste from DCC. Enzymatic esterifications in green solvents or solvent-free can be explored.
Oxalyl chloride alternatives: Ghosez’s reagent or mixed anhydrides can reduce exposure to corrosive chlorinating agents; or use acid fluorides via Deoxo‑Fluor followed by amidation (balance hazards vs benefits).
Workup/waste minimization:
Exploit acid/base partitioning to avoid extensive silica; crystallize products when possible.
Employ in-line scavengers (amine or acid scavenger resins) to reduce aqueous waste.
Comparison (general):
THF vs 2‑MeTHF: similar polarity; 2‑MeTHF offers partial bio-sourcing, easier phase splits, higher bp; may impact selectivity.
DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; DCM often provides faster reactions/cleaner separations but with higher environmental/health burden.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item.
Role in development (general): fluorinated benzoic acids are frequently employed as intermediates in the synthesis of drug candidates and radiolabeling precursors. The carboxyl group facilitates rapid generation of amides/esters for SAR campaigns, and the 3,5‑difluoro pattern is a common motif to modulate metabolic stability (literature/general practice).
Formulation context: the free acid is not commonly used directly as an excipient due to limited aqueous solubility and potential irritancy; its derivatives (esters, salts, amides) may be explored in preclinical research formulations as part of prodrug or conjugate strategies (research only).
Regulatory note: Any clinical or GMP application would require dedicated qualification, impurity control, and stability programs. This listing is for research use only.
Item-specific notes:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Residual solvent/metals/elemental impurities: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific specifications are not provided; consult CoA/Spec Sheet for exact values.
Molecular weight: 202.16 g/mol (calculated from inferred formula C9H8F2O3; literature/computed)
Exact mass/monoisotopic mass: ~202.0459 Da (computed; literature)
Predicted lipophilicity: aromatic, moderately lipophilic due to aryl ring and two F atoms; carboxyl group confers acidity and polarity (qualitative, literature/analogy)
Acid–base: weak aromatic carboxylic acid; pKa expected in the benzoic acid range and modulated by F (electron-withdrawing) vs ethoxy (electron-donating) substituents; estimated pKa ~3.6–4.2 (literature, by analogy; not a specification)
Solubility (qualitative, literature):
Low in neutral water; increased in basic aqueous media as the carboxylate salt.
Soluble in common organic solvents such as dichloromethane, ethyl acetate, THF, acetone; sparingly to moderately soluble in alcohols; highly soluble in polar aprotic solvents (DMF/DMSO).
Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Note: All non-specified values above are general literature expectations for substituted benzoic acids and should not be used as product specifications.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvents, and impurity profile.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: None indicated; if present, they will be listed on the CoA/SDS.
Guidance on typical grades for this compound class (general information):
Research grade aromatic carboxylic acids are commonly supplied at ≥95–98% purity for routine synthesis. Higher-purity material (>99%) may be preferred for SAR/medchem or materials applications.
For chromatography-sensitive work, low-UV-absorbing solvent residuals and tightly controlled inorganic residues are advantageous. If HPLC/GC area% is critical, request the latest CoA.
Batch-to-batch consistency: For multi-gram synthesis, confirm water content (Karl Fischer), residual mineral acids (for acid chloride preparations), and halogen content if required by downstream specifications. Not specified for this item; refer to CoA/Spec Sheet.
Quality control recommendations (general):
Identity confirmation by 1H/13C NMR, 19F NMR (distinct aryl-F signals), IR (broad O–H and strong C=O ~1680–1720 cm−1), and HRMS.
Purity assessment by HPLC/UPLC with diode array detection; 254 nm response expected due to aromatic chromophore.
Reaction and Applications
As a fluorinated aryl carboxylic acid, this compound is a versatile building block for medicinal and materials chemistry.
Carboxylate derivatization:
Esterification: Fischer (acid-catalyzed in ROH), Steglich (DCC/DMAP in DCM), or Mitsunobu to invert an alcohol partner (literature). Methyl/ethyl esters aid volatility and chromatographic behavior.
Amide formation: EDC·HCl/HOBt, HATU, T3P, or CDI-mediated couplings in DMF/DCM/MeCN. The ortho-ethoxy and difluoro pattern can modulate amide electronics for SAR libraries.
Acid chloride (SOCl2/oxalyl chloride, catalytic DMF), followed by acylation of amines/alcohols.
Decarboxylative transformations (literature):
Formation of N‑hydroxyphthalimide (NHPI) esters enables Ni/photoredox-catalyzed decarboxylative arylations, vinylations, and borylations.
Classical Hunsdiecker/Simonini routes are less common for aryls but modern Ag/Cu/photoredox decarboxylative couplings are effective.
Aromatic substitution/cross-coupling context:
The 3,5‑difluoro pattern imparts inductive withdrawal; however, the 2‑ethoxy group donates by resonance, so SNAr on the F sites may require strong nucleophiles and elevated temperatures. Lithium/amide bases or cesium fluoride activation can assist in some cases (literature).
Directed ortho metalation adjacent to the ethoxy or carboxyl group is possible under strong base (s‑BuLi/TMEDA) to install additional substituents (quench with electrophiles).
Applications (general):
Fluorinated benzoate motifs serve as precursors to probes, agrochemical intermediates, monomers for specialty polymers, and enzyme-binding fragments in fragment-based discovery.
Manufacturer Applications: Not specified for this item; typical uses include synthesis of esters/amides and decarboxylative cross-couplings.
Reaction Conditions
General literature guidance for typical transformations of aryl benzoic acids; optimize per substrate and scale.
Amide coupling (EDC/HOBt or HATU):
Solvent: DMF or MeCN (or DCM for HATU).
Base: DIPEA (2–3 equiv).
Temperature: 0 °C to rt (often 2–16 h).
Typical isolated yields: 70–95% for unhindered amines.
Reagents: SOCl2 (2–5 equiv), catalytic DMF; reflux 1–3 h.
Subsequent acylation in DCM/THF with amine/alcohol and base (pyridine/Et3N).
Redox-active ester formation and decarboxylative coupling (literature):
NHPI (1.1 equiv), DIC or EDC, DMAP in DCM/DMF; then Ni-catalyzed cross-coupling with organozinc/boron partners or photoredox (Ir/Ru) with alkyl radicals in MeCN/DMF, rt to 50 °C, 4–24 h.
SNAr at aryl‑F (substrate dependent):
Nucleophile: amines/alkoxides (2–5 equiv), solvent DMSO/DMF, 80–140 °C, 4–24 h; monitor by LC–MS and 19F NMR.
DoM (directed ortho‑metalation):
Base: s‑BuLi (1.1–1.5 equiv) with TMEDA in THF, −78 to −20 °C, 0.5–2 h; quench with electrophile (CO2, MeI, B(OR)3). Carefully assess compatibility with aryl‑F.
These conditions are representative literature ranges and not product specifications.
Safety and Handling
GHS classification, pictograms, signal word, and H-statements: Not specified for this item; consult the product SDS for authoritative hazard information.
Likely hazards (general for aromatic carboxylic acids and fluorinated aromatics; literature): may cause skin/eye irritation; harmful if swallowed or inhaled as dust; avoid aerosol/dust generation.
Personal protective equipment (PPE): laboratory coat, safety glasses or goggles, appropriate chemical-resistant gloves (e.g., nitrile), and use in a fume hood to control vapors/dust.
Handling guidance:
Avoid contact with bases and oxidizers during storage/handling unless intended for reaction.
Prevent moisture ingress only if working with reactive derivatives (e.g., acid chloride); the acid itself is generally stable under ambient humidity.
For weighing, minimize dust; use antistatic tools and weigh paper/boats.
First-aid overview (general):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Organic solids can burn; use CO2, dry chemical, or foam. Thermal decomposition may release irritating fumes (including HF in extreme conditions for fluorinated aromatics; literature caution).
Spill response: Avoid dust; collect mechanically or with inert absorbent; dispose according to local regulations.
Storage incompatibilities: Strong bases (will form carboxylates), strong oxidizers, and reactive acid derivatives.
Always defer to the SDS and institutional EHS guidelines.
Solvent Selection
This product is a solid aryl carboxylic acid; solvent choice depends on task (reaction, purification, or formulation).
Polarity and miscibility (general, literature):
Neutral form: low aqueous solubility; good solubility in moderately polar organics (EtOAc, acetone, MeCN, THF, DCM). Highly soluble in DMSO/DMF.
As the carboxylate salt: soluble in basic aqueous media (e.g., Na2CO3/NaOH solutions) enabling biphasic extractions.
Selection by use case:
Esterification (Fischer): anhydrous alcohols (MeOH/EtOH/i-PrOH) with catalytic acid; remove water azeotropically (Dean–Stark with toluene or use molecular sieves).
Amide coupling: DMF, MeCN, DCM, or NMP commonly used; add base (DIPEA) and coupling reagents (EDC/HOBt, HATU, COMU).
Acid chloride formation: refluxing toluene or neat SOCl2/Oxalyl chloride with catalytic DMF; subsequent reactions in DCM/THF.
Decarboxylative cross-coupling (via NHPI redox-active esters): MeCN/DMF/DMA under Ni/photoredox conditions.
Purification: silica gel chromatography with hexanes/EtOAc or DCM/MeOH gradients; acid can tail—pre-treat silica with 1–2% AcOH or elute as methyl/tert-butyl ester, then hydrolyze.
Practical notes:
For extractions, exploit acid/base partitioning: wash organic with NaHCO3 to transfer acid to aqueous; re-acidify to pH ~2 and back-extract with EtOAc.
For NMR, DMSO‑d6 or CD3OD dissolve the acid well; CDCl3 may require warming or addition of a drop of TFA.
Shipped in: Not specified for this item; refer to product label.
Container: Store tightly closed in a clean, dry, chemically compatible container (glass recommended). Protect from strong light and heat sources.
Stability: Aromatic carboxylic acids are generally stable at ambient conditions. Avoid prolonged exposure to strong bases or oxidants.
Reconstitution/preparation of solutions:
Not required for use as a solid reagent. For stock solutions, dissolve in a suitable organic solvent (e.g., DMSO, DMF, MeCN, DCM, EtOAc) at the desired concentration.
For aqueous work, prepare salts by neutralization with base (e.g., NaOH) to enhance solubility; re-acidify after use if the free acid is needed.
Freeze–thaw guidance: Not applicable to the solid. If preparing solutions for storage, aliquot and store according to solvent stability (e.g., DMSO solutions at 2–8 °C or −20 °C, protected from moisture) and avoid repeated freeze–thaw cycles.
Shelf-life and specifications: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only.
Structure and Identity
A fluorinated, ether-substituted benzoic acid designed for use as an aryl carboxylic building block.
The 2-ethoxy group is electron-donating by resonance; fluorines are inductively electron-withdrawing, giving a tunable electronic profile across the ring.
2D description in words: a benzoic acid ring with –CO2H at position 1; adjacent (ortho) is an –OCH2CH3 substituent; the carbons meta to the carboxyl (positions 3 and 5) each carry a fluorine atom; the remaining ring positions are unsubstituted C–H.
Synthetic Utility
Key reactivity arises from the carboxylic acid handle and the electronically tuned aryl ring.
Carboxyl group transformations:
Amide coupling using EDC/HOBt, HATU, T3P, or CDI to access anilides/benzamides rapidly.
Esterification (Fischer/Steglich) to modulate lipophilicity or introduce protecting groups (e.g., tert‑butyl, benzyl) for downstream steps.
Activation to acid chlorides (SOCl2, oxalyl chloride) or mixed anhydrides for acylation chemistry.
Redox-active esters (NHPI/TCNHPI) enabling decarboxylative C–C, C–B, and C–S bond constructions under Ni/photoredox catalysis (literature).
Aryl ring elaboration:
3,5‑Difluoro substitution imparts inductive withdrawal; SNAr at F positions is possible with strong nucleophiles (e.g., alkoxides, amines) and heat, though the 2‑ethoxy donor may partially offset activation—optimize base/solvent (DMSO/DMF) and temperature.
Directed ortho‑metalation (DoM) adjacent to ethoxy or carboxyl functions (s‑BuLi/TMEDA, −78 to 0 °C) followed by electrophile quench introduces additional substituents.
Electrophilic aromatic substitution is deactivated by F and modulated by ethoxy; halogenation/nitration may be sluggish—consider metalated pathways.
Retrosynthetic value:
Serves as a convergent node connecting aryl fluoride chemistry with carboxylate diversification, enabling rapid library synthesis for medchem and materials applications.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, inhibitor with defined target). No antigen/epitope or species reactivity information is associated with this item.
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