This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with 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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Revisões
Avaliações dos Clientes
Application Protocols
Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) are relevant for this small-molecule reagent. For synthetic use, see the Reaction Conditions and Application notes provided in the corresponding sections.
Biological Roles
This product is intended for research and laboratory chemical synthesis; it is not a biochemical metabolite or buffer component.
Biological/functionality context (general):
Aryl ethers and aryl fluorides are common motifs in medicinal and materials chemistry due to their metabolic stability and modulated lipophilicity. The acetal group serves as a protecting group for an aldehyde functionality rather than conferring specific biological activity.
Upon acid hydrolysis, the diethoxyacetal can yield an aldehyde-bearing aryl ether that may be used to install biomolecular conjugation handles (e.g., oxime/hydrazone linkage formation) in chemical biology workflows; such uses remain strictly in vitro/analytical.
Metabolism/toxicity (general literature):
Aryl fluorides often resist oxidative metabolism at the C–F site; ethers undergo typical oxidative O-dealkylation in vivo, but such outcomes are context-dependent and not claims for this specific compound.
No biological role, target, or pathway is specified for this item. For any biological experimentation, ensure appropriate approvals and handle solely for research use as stated: For research use only.
Buffer Applications
Not typically applicable. 1-(2,2-Diethoxyethoxy)-2-fluorobenzene is a neutral, hydrophobic organic reagent and is not used to prepare aqueous laboratory buffers.
Practical guidance:
If used in bioconjugation workflows after acetal deprotection to an aldehyde, conduct reactions in compatible aqueous-organic mixtures (e.g., acetate buffer pH 4–5 with MeCN/MeOH cosolvent) appropriate for oxime/hydrazone formations. Select buffers that do not catalyze unwanted acetal cleavage unless that is the intended step.
Item-specific buffer-use parameters: Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
Greener choices usually pertain to solvents and reagents used with this compound rather than replacing the compound itself.
Solvent choices (literature-level comparison):
2-MeTHF vs THF: 2-MeTHF is biorenewable, higher boiling (bp ~80 °C vs ~66 °C for THF), lower peroxide tendency, and often allows phase separations. Trade-off: broader UV background and occasional solubility differences.
CPME vs DCM/toluene: Cyclopentyl methyl ether offers low peroxide formation and good hydrophobicity, replacing DCM or toluene in many extractions and reactions. Trade-off: odor and cost.
EtOAc/IPA vs chlorinated solvents: Ethyl acetate and isopropanol can substitute for DCM in workups and crystallizations where polarity permits.
Reagent considerations:
Acid catalysts for acetal deprotection: Use aqueous organic acids (e.g., acetic acid) or solid acids (Amberlyst-15) to minimize corrosive mineral acids; aqueous workups reduce waste of halogenated media.
Bases: Choose carbonate bases in alcohol/ester media when feasible instead of strong inorganic bases to reduce salt load.
Process-intensification ideas:
Telescoping: Perform acetal deprotection followed by capture (e.g., oxime formation) in one pot to reduce solvent exchanges.
Solvent recycling: Toluene/EtOAc recovery is straightforward; design with distillable, lower-toxicity solvents.
Item-specific environmental metrics (e.g., E-factor, solvent selection guide rating): Not specified for this item; refer to CoA/Spec Sheet.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is offered for research use only.
General, non-clinical context:
Structural motif relevance: Aryl fluorides and aryl ethers are common in medicinal chemistry to modulate potency, lipophilicity, and metabolic stability. The diethoxyacetal serves as a protecting group for an aldehyde synthon during library synthesis or lead derivatization.
Process/formulation perspective: If used as a synthetic intermediate en route to APIs, control of residual ethanol (from acetal hydrolysis) and aromatic impurities is typically required at later stages; such considerations are project-specific and not specifications for this product.
No therapeutic claims are made. This product is not intended for human or veterinary use and has no approved pharmaceutical application details provided by the manufacturer.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for compounds of this class (aryl ether with a diethoxyacetal side chain; provided for planning only, not as product specifications):
Physical state/appearance: Typically a colorless to pale yellow liquid for similar aryl diethoxyacetals at ambient conditions; viscosity modest; characteristic aromatic odor.
Boiling point: Aromatic ethers of comparable size often boil in the 230–300 °C range at 1 atm; acetal groups can modestly elevate b.p. due to polarity (literature trend; not item-specific).
Melting point: Usually below room temperature for analogous structures (literature trend).
Density: Aryl ethers with C–F substitution commonly show ρ ~1.05–1.20 g/mL (literature range for guidance only).
Refractive index: Similar aryl ethers/acetal derivatives often exhibit nD20 ~1.48–1.53 (literature range).
Solubility: Low in water; high miscibility with common organic solvents (EtOAc, DCM, THF, toluene, alcohols). Acetal increases organic polarity but does not confer aqueous solubility.
LogP: Expected to be moderately lipophilic (estimated logP 2–3.5 for comparable aryl ethers with one F and one acetal side chain; literature-level estimate).
UV characteristics: Aryl chromophore absorbs in near-UV (λmax ~205–215 nm, tailing to 260–280 nm; literature-level for substituted benzenes). Not specified for this item; refer to CoA/Spec Sheet for any HPLC-grade UV cutoffs.
Always verify exact physical constants from the CoA/SDS for the specific lot.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for compounds of this type (general/literature context):
Research grade: Suitable for most synthetic applications. Typical assays reported by GC or 1H NMR. Trace water, residual ethanol, and acetal stability are common QC concerns.
Low-water or anhydrous variants: Beneficial if subsequent steps are moisture-sensitive (e.g., organometallics) because acetals can hydrolyze in wet environments under acid catalysis. Absence of water specifications here means users should dry as needed and verify by KF if critical.
Stabilizers: Not commonly added to such ethers; if present in other suppliers, acid scavengers may be used to suppress acetal hydrolysis. For this item, stabilizers are Not specified for this item; refer to CoA/Spec Sheet.
Analytical characterization typically employed (general):
Identity: 1H/13C NMR (acetal methine ~4.5–5.0 ppm, ethoxy CH3 ~1.1–1.3 ppm), 19F NMR (aryl F, typically −110 to −125 ppm range), IR (C–O–C stretches ~1050–1150 cm−1), HRMS.
Purity: GC or HPLC area %, residual solvents (ethanol may appear), and water by Karl Fischer as applicable.
For chromatography-sensitive work (e.g., UV detection), consider verifying UV background; specific UV-cutoff for this item is Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
This aryl ether bearing an ortho-fluoro substituent and a terminal diethoxyacetal is a versatile intermediate in aromatic synthesis and aldehyde chemistry.
Strategic roles (literature/general):
Latent aldehyde: The 2,2-diethoxy group is an acetal protecting group. Acidic hydrolysis unmasks the corresponding aldehyde at the benzyloxyethyl terminus (–O–CH2–CHO), enabling downstream condensations (Wittig, HWE, oxime/hydrazone formation, reductive amination after oxidation/reduction sequences).
Ortho-fluoro handle: While aryl fluorides are less prone to oxidative addition than iodide/bromide, they enable selective transformations under specialized catalytic systems (e.g., Ni, Pd with tailored ligands) or SNAr on activated rings; the adjacent electron-donating ether typically deactivates SNAr, aiding F-retention when desired.
Aryl ether platform: The phenoxy linkage can direct ortho-lithiation on the ring in the presence of strong bases (s-BuLi, TMEDA) for further functionalization (literature strategy; temperature control critical to prevent acetal cleavage).
Example application ideas (non-item-specific):
Build masked-aldehyde linkers from an activated aryl platform, then deprotect late-stage to install formyl-derived motifs (Schiff bases, crotonylations).
Sequential functionalization: (1) Directed ortho-metalation to install a new substituent; (2) Acetal deprotection to reveal –CHO; (3) Condensation to elaborate side chains while retaining the aryl fluoride for later C–F functionalization if required.
Practical notes:
Maintain neutral to basic conditions to preserve the acetal during non-acidic transformations.
Minimize protic acids and prolonged silica exposure; neutralized silica or rapid chromatography is recommended.
If cross-coupling is needed at C–F, consider high-temperature Ni catalysis or modern ligand sets; otherwise, use F as a metabolically stabilizing group in materials/medchem explorations.
Reaction Conditions
General literature-level conditions relevant to this scaffold (not product specifications):
Acetal deprotection to aldehyde:
Typical: 0.5–2 M in MeOH/H2O (9:1 to 4:1) or THF/H2O with catalytic HCl, H2SO4, or p-TsOH (1–10 mol%).
Temperature: 0–25 °C for sensitive substrates; 40–60 °C for robust systems.
Time: 0.5–6 h depending on acidity and solvent.
Workup: Neutralize, extract with EtOAc, wash brine, dry, and purify rapidly to avoid aldehyde hydration/polymerization.
Directed ortho-lithiation (DoM) on aryl ether ring (if desired):
Reagents: s-BuLi (1.1–1.5 eq) with TMEDA in THF or 2-MeTHF.
Temperature: −78 to −40 °C; brief contact times (10–60 min) to limit side reactions and acetal cleavage.
Catalysts: Ni(cod)2 or Pd with specialized ligands (e.g., bulky NHCs) under high temperature (120–160 °C) in dioxane/toluene; yields vary widely.
Alternative: Halogenate via DoM and then perform standard Suzuki/Negishi at the new C–X site.
Oxime/hydrazone formation from the unveiled aldehyde:
Conditions: Aldehyde (1.0 eq) with hydroxylamine·HCl or hydrazine derivatives (1.1–1.5 eq) in MeOH/AcOH or acetate buffer pH 4–5; rt to 40 °C, 1–3 h.
Note: Monitor acetal integrity by 1H NMR (acetal methine) and TLC (anisaldehyde stain responsive after deprotection). These are general guidelines; optimize per substrate.
Safety and Handling
Item-specific hazard data:
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
Hazard (H-) statements and pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl ethers bearing acetal functionality (literature/general guidance):
Likely hazards: Combustible liquid; may cause skin/eye irritation; harmful if swallowed or inhaled for analogous compounds. Avoid aerosol generation.
Special chemical risks: The acetal moiety is acid-labile; avoid contact with strong acids to prevent hydrolysis that may release ethanol and an aldehyde (irritants). Aryl ethers do not typically form peroxides, but storage with oxidizers should be avoided.
PPE: Lab coat, safety glasses or splash goggles, nitrile gloves. Use in a fume hood.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical attention for irritation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire-fighting: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and irritating fumes.
Spill response: Absorb on inert material, collect for disposal. Prevent entry into drains.
Always consult the SDS for authoritative, lot-specific hazard information and disposal guidance.
Solvent Selection
This molecule is a neutral, moderately polar organic liquid (aryl ether plus acetal). It is largely hydrophobic yet highly soluble in common organic solvents.
Dielectric context: Effective solvation in medium-polarity ethers/esters (THF, EtOAc) and chlorinated solvents; aromatic solvents (toluene) support elevated-temperature reactions.
Selection tips by task (general):
Acetal protection/deprotection studies: Use aprotic solvents (DCM, MeCN) for acetal formation; for deprotection, aqueous acetone, THF/H2O, or MeOH with catalytic acid are common.
Cross-coupling or metalation on the aryl ring: Toluene, dioxane, CPME, or 2-MeTHF can balance solubility and temperature tolerance; ensure low water content.
Purification: Normal-phase silica typically effective; gradient from hexanes to EtOAc or MTBE. Avoid strongly acidic silica if acetal lability is a concern; neutralized silica/alumina can help.
Comparison to alternatives (general):
THF vs 2-MeTHF: 2-MeTHF often provides similar solubility with greener profile and higher boiling point (fewer solvent exchanges).
DCM vs EtOAc: DCM offers rapid workups and excellent solubility but is less green; EtOAc is a viable alternative for many steps if kinetics permit.
Item-specific solvent compatibility data: Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Item-specific storage: Room temperature (per Product Data).
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling recommendations for this class of compounds:
Store tightly capped under inert atmosphere (e.g., nitrogen) if long-term storage is anticipated, to minimize moisture ingress and oxidative degradation.
Protect from strong acids to prevent unintended acetal hydrolysis; keep away from acid vapors and acidic drying agents.
If solid residues form upon cooling (unlikely for this class but possible as impurities crystallize), gently warm to redissolve before use; verify integrity by NMR/GC.
Do not freeze aqueous mixtures; store the neat material in amber glass if prolonged light exposure is a concern for aromatic ethers.
Reconstitution:
If received as a neat liquid, use as supplied. If a concentrate or solution is required, dissolve in a dry organic solvent such as DCM, THF, EtOAc, toluene, or MeCN to the desired molarity. Filter through a PTFE syringe filter (0.45 µm) if particulate is observed.
Always refer to the lot-specific CoA and SDS for definitive storage guidance and stability information.
Structure and Identity
A fluorinated aryl ether bearing a protected 2-hydroxyethyl equivalent via a 2,2-diethoxy (acetal) motif.
Item-specific (Product Data):
CAS: 1313712-61-6
PubChem CID: 57361148
InChIKey: 306489 (as provided; atypical length for an InChIKey — verify against database entry)
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 interpretation from name; literature-level):
Aromatic core: substituted benzene ring with fluorine at the 2-position (ortho to the ether substituent).
Aryl–O–(alkyl) ether linkage at the 1-position.
Pendant chain: “(2,2-diethoxy)ethoxy” corresponds to an acetal-protected hydroxyethyl fragment, i.e., –O–CH2–CH(OC2H5)2. The central carbon is an acetal center bearing two ethoxy groups.
Functional groups: aryl fluoride (C–F), aryl ether (Ar–O–), acetal (ketal-like) carbon bound to two –OEt substituents.
Stereochemistry: none specified; the acetal center is prochiral but typically isolated as a racemic mixture if chiral.
2D description in words (literature-level):
A benzene ring bearing two ortho substituents: fluorine at C-2 and an ether oxygen at C-1 that connects to a –CH2–CH(OC2H5)2 unit. The terminal carbon bears two ethoxy groups, characteristic of an acetal protecting a formyl-equivalent that can be revealed by hydrolysis.
Synthetic Utility
Key functional groups and their use in synthesis (literature/general):
Diethoxyacetal (–CH(OC2H5)2): A classic protecting group for aldehydes. In this scaffold, it masks a 2-formylethoxy unit that can be unveiled under mild acid. Advantages include stability to many bases, nucleophiles, and reducing agents; sensitivity to protic/Brønsted acids enables chemoselective unmasking.
Aryl fluoride (Ar–F): Serves as a persistent handle. While less reactive than Ar–Br/I in cross-coupling, modern Ni/Pd catalysis enables C–F activation. Alternatively, the group modulates electronics and can direct ortho-metalation via an adjacent phenoxy oxygen.
Aryl ether (Ar–O–): Provides directing effects and stability; can be a leaving group under strong conditions (e.g., demethylation analogs) but is generally inert.
Transformations enabled:
Acetal hydrolysis → aldehyde → condensations (Wittig/HWE/aldol with prior oxidation), reductive amination (via oxime/hydrazone → reduction), or cyanation (Strecker-type on imines derived from –CHO).
Directed ortho-metalation on the aromatic ring for installation of electrophiles (D2O quench, halogenation, formylation via DMF) while preserving the acetal.
Late-stage diversification that retains Ar–F as a metabolic and conformational modulator in medchem.
Practical tips:
Keep acid exposure minimal until deprotection is desired; neutral silica or quick chromatography helps maintain acetal integrity.
If attempting C–F cross-coupling, consider elevated temperatures, strong σ-donor ligands, or nickel catalysts; alternatively, convert F to a more labile handle earlier if needed.
Target Specificity
Not applicable. This product is a small-molecule synthetic intermediate, not a biological macromolecule or affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
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 1313712-61-6, the molecular formula is C12H17FO3, and the molecular weight is 228.26 g/mol. InChIKey QUAGZJIIKHPNPN-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.
Usamos cookies para garantir o funcionamento adequado do site e, quando permitido, para melhorar a sua experiência. Você pode gerenciar suas preferências a qualquer momento nas Configurações. Saiba mais em nossa Política de Cookies.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
