This compound belongs to the class of organic compounds known as benzyl cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
197.180 g/mol
XLogP3
2.100
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Exact Mass
197.065 Da
Monoisotopic Mass
197.065 Da
Topological Polar Surface Area
33.000 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
225.000
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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Application Protocols
Not applicable. No bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.
For synthetic use, see Reaction Conditions and Application notes. When incorporating into screening libraries, follow your lab’s standard compound handling and plating SOPs (dissolution in DMSO/MeCN, plate mapping, storage under inert gas where relevant).
Biological Roles
This product is a synthetic organic building block and is not intended for biological function studies. No item-specific biological roles are provided.
General context (for professional users):
Arylacetonitriles are occasionally encountered as intermediates in the synthesis of bioactive candidates, but the reagent itself is not a biochemical metabolite or cofactor.
The nitrile group can serve as a masked amine/acid functionality in synthetic sequences leading to compounds for biological evaluation; however, any biological activity would arise from downstream molecules, not from this reagent per se.
Research Use Note: For research use only. Not for diagnostic, therapeutic, or clinical applications.
Buffer Applications
Not typically applicable. 3-Ethoxy-2,6-difluorophenylacetonitrile is a hydrophobic organic building block, not a buffering agent. It lacks acid/base pairs suitable for maintaining pH in aqueous media.
For laboratory work, prepare and control pH with conventional buffer systems (e.g., phosphate, acetate, HEPES) and dissolve this reagent in suitable organic solvents for synthetic steps as described in Solvent Selection.
Green Alternatives
Greener choices relate primarily to solvent and base selection, as the reagent itself is a specialty building block. Consider the following literature-based substitutions and tradeoffs:
Replace classical ethers/halogenated solvents:
THF → 2‑MeTHF or CPME: similar solvating power for organometallic and enolate chemistry; lower peroxide formation (CPME), improved hydrophobicity for extractions, often biorenewable (2‑MeTHF). Tradeoff: slightly different low-temperature performance and azeotrope behavior.
DCM/CHCl3 → EtOAc, MTBE, or toluene for workups and chromatography where feasible; reduced halogenated waste.
Swap polar aprotics:
DMF/DMA/DMSO → propylene carbonate, Cyrene, or acetonitrile in compatible transformations (e.g., SN2 alkylations with inorganic bases). Tradeoff: solubility of inorganic salts and base strengths may differ.
Base choices and energy:
Use carbonate bases (K2CO3/K3PO4) in polar aprotic or phase-transfer systems to avoid pyrophoric bases when high basicity is unnecessary. Tradeoff: slower reactions, possible need for heating.
Workup and purification:
Emphasize solvent recycling (toluene/EtOAc/hexanes systems), minimize silica by employing crystallizations or liquid–liquid partitions when possible.
Illustrative comparison (general):
THF vs 2‑MeTHF: similar yields in benzylic alkylations; 2‑MeTHF improves phase separation and EHS profile.
DCM vs EtOAc: comparable elution strength for many aromatics; EtOAc is biodegradable and non-halogenated.
Note: Verify reaction compatibility experimentally; re-optimization may be required when changing solvents/bases.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item. It is supplied for research and development as a synthetic intermediate.
General formulation/manufacturing context (non-clinical):
Arylacetonitriles can serve as intermediates en route to APIs or process development targets, where the nitrile is transformed into amines, amides, acids, or heterocycles. Any such use remains within research/process chemistry until validated under GMP.
If used in route scouting, attention should be paid to purge of residual starting material and potential aromatic impurities; develop robust analytical methods (HPLC/GC/MS) accordingly.
Research Use Note: For research use only. Not for diagnostic, therapeutic, or clinical applications.
Physical Properties
Item-specific measured physical constants are not provided for this catalog entry. The following values and behaviors are general/literature guidance for compounds of this structure; verify with CoA/Spec Sheet for specifications.
Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting/boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Arylacetonitriles with similar substitution are often low-melting solids or high-boiling liquids.)
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature): Expected to be soluble in common organic solvents (e.g., dichloromethane, ethyl acetate, THF, acetone, toluene) and poorly soluble in water due to the aryl/ether/fluoro substitution pattern.
LogP (qualitative, literature): Likely moderate lipophilicity owing to aryl ether and difluoro substitution; exact value not established here.
pKa (literature, of benzylic CH as C–H acidity in DMSO): Benzylic nitriles typically have pKa ≈ 21–25 (DMSO), enabling deprotonation with strong bases (e.g., LDA, NaH, KOtBu) under anhydrous conditions.
UV characteristics (qualitative): Aromatic chromophore present; no item-specific UV cutoffs are provided.
Always corroborate critical parameters (mp/bp, density, purity, UV cutoffs) with the CoA/SDS for the supplied lot.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for purity, residual solvents, and analytical limits.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance):
When purity is reported (e.g., ≥95%, ≥98%), this typically reflects assay by NMR, HPLC/GC, or elemental analysis. For sensitive applications (e.g., base-mediated alkylations of the benzylic nitrile), trace protic/ionic impurities can be detrimental; verify water content and acidity/basicity if available.
If an HPLC or GC assay is provided, check for closely eluting aromatic byproducts (e.g., regioisomers or over-alkylated species). 1H/13C NMR should confirm: benzylic –CH2– (~3.3–3.6 ppm), ethoxy –CH3 (~1.2–1.4 ppm) and –CH2–O (~3.9–4.2 ppm), aromatic region reflecting 2,6-difluoro pattern, and CN carbon (~115–120 ppm in 13C).
UV specifications (if HPLC-grade solvents are involved) are not applicable to this neat reagent; any UV cutoffs would pertain to solvents, not this compound.
Stabilizers: None are stated for this item. If present in other lots to prevent degradation, they should be disclosed on the CoA.
Suggested QC checks before critical use:
Confirm identity by NMR and HRMS (calc. [M+H]+ ≈ 198.19 for C10H10F2NO; literature/computed).
Assess residual water by KF if using strong bases.
Run a small-scale test reaction to benchmark reactivity.
Reaction and Applications
As a 3-ethoxy-2,6-difluorophenylacetonitrile, this molecule is a versatile benzylic-nitrile building block for aryl–alkyl frameworks. The nitrile activates the benzylic position toward anion chemistry while the aryl substituents tune electronics and sterics.
Key application families (literature guidance):
Benzylic deprotonation/alkylation: Generate the benzyl anion/enolate with LDA, NaH, KOtBu, or KHMDS (–78 to 0 °C in THF/2‑MeTHF). Trap with alkyl halides, Michael acceptors, or carbonyls (via aldol-like additions). Control over mono- vs di-alkylation requires stoichiometry and temperature management.
Condensation chemistry: Knoevenagel-type coupling with aldehydes/ketones (piperidine or ammonium acetate catalysis) affords arylidenemalononitrile analogs or styrylnitriles after elimination.
Functional group interconversions of –CN: Hydrolysis to acid (acidic or basic conditions), amidation via intermediate imidates, or reduction to primary amine (LiAlH4, BH3·THF) or to aldehyde (DIBAL-H, carefully controlled).
Benzylic oxidations/reductions: Selective benzylic transformations while preserving the nitrile (e.g., catalytic hydrogenation of double bonds if present after condensation; transfer hydrogenations under mild conditions).
Aryl-ring diversification: While C–F activation is challenging, strongly activated SNAr at aryl fluorides can occur only under forcing conditions and with powerful nucleophiles. Alternatively, directed metallation strategies may enable further ring functionalization depending on conditions.
Use cases in synthesis:
Precursor to substituted phenethylamines (via nitrile reduction) for material/ligand libraries (research only).
Intermediate toward substituted benzoic acids/amides after nitrile hydrolysis.
Scaffold for elaborating difluorinated, ether-containing aromatic motifs relevant in agro/material chemistry.
Reaction Conditions
General literature conditions for benzylic nitriles; optimize per substrate and scale:
Benzylic deprotonation/alkylation:
Base: LDA (1.1–1.5 equiv) or NaH (60% dispersion, 1.2–2.0 equiv).
Solvent: Anhydrous THF or 2‑MeTHF; inert atmosphere.
Temperature: –78 to 0 °C for deprotonation; 0 to rt for electrophile addition.
Time: 0.5–3 h typical; monitor by TLC/LC–MS.
Notes: Control di-alkylation by limiting base and electrophile; quench at low temperature.
Knoevenagel condensation:
Catalyst: Piperidine (5–20 mol%) or ammonium acetate.
Solvent: Toluene (Dean–Stark) or EtOH; removal of water drives equilibrium.
Temperature: Reflux; 2–8 h.
Nitrile hydrolysis:
Acidic: conc. H2SO4 or HCl, H2O, 80–110 °C; hours to overnight; affords acid (via amide).
Basic: KOH (3–5 equiv) in EtOH/H2O (1:1), reflux; amide/acid depending on workup.
Reductions:
To aldehyde: DIBAL-H (1.2–1.5 equiv) in toluene/THF, –78 to –20 °C; careful quench to avoid over-reduction.
To amine: LiAlH4 (2–3 equiv) in THF/Et2O, 0 °C to reflux; or BH3·THF under reflux.
Workup/purification:
Neutralize carefully after hydrides; use Rochelle salt or saturated ammonium chloride for complexation/quench.
Silica gel chromatography typically effective; eluents: hexanes/EtOAc or toluene/EtOAc.
The difluoro/ethoxy substitution may influence rates and selectivity; run small-scale screens to refine conditions.
Safety and Handling
Safety classifications specific to this item are not provided; consult the SDS for authoritative guidance. The notes below reflect typical hazards of arylacetonitriles and aryl ethers and are intended for research planning only.
GHS/Signal word/pictograms/H-statements: Not specified for this item; refer to SDS.
Likely hazard profile (general): May cause irritation to skin/eyes/respiratory tract. Harmful if swallowed or inhaled. Combustible organic compound. Nitriles are not cyanide salts, but some may liberate toxic gases upon thermal decomposition.
PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of vapors or dust.
Storage conditions: Room temperature (per Product Data). Keep tightly closed in a dry, well-ventilated place. Protect from moisture and heat sources. Segregate from strong oxidizers and strong bases/acids.
Incompatibilities (general): Strong oxidizing agents; strong bases can deprotonate the benzylic position; reactive metals.
Handling tips:
Avoid prolonged exposure to air and light if performing anionic chemistry (use dry, inert atmosphere).
Prevent skin contact; wash thoroughly after handling.
Use secondary containment for spill control; absorb small spills with inert material (vermiculite) and collect for disposal.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation develops.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always defer to the SDS for the supplied lot before use.
Solvent Selection
This reagent behaves as a moderately lipophilic aromatic nitrile with an ether substituent; it dissolves well in many organic media used for anion chemistry and condensations.
Poor solubility: Water and highly aqueous buffers.
Choosing a solvent by transformation:
Base-mediated benzylic deprotonation/alkylation: anhydrous ethers (THF, 2‑MeTHF) or toluene with strong bases (LDA, NaH, KOtBu). Polar aprotics (DMF/DMSO) enable milder bases (K2CO3/K3PO4) but complicate workup.
Condensations (Knoevenagel-type) with aldehydes: toluene, EtOH/amine catalysis, or greener ethers (2‑MeTHF) under Dean–Stark if water removal is needed.
Reductions (to amines/aldehydes): etheral solvents for hydrides (Et2O/THF); protic solvents for catalytic hydrogenation.
Hydrolysis to acid/amides: aqueous alcohols or dioxane/H2O mixtures under acid/base catalysis.
Practical tips:
For strong-base chemistry, rigorously dry solvent (molecular sieves or distillation) and maintain inert atmosphere.
Avoid DMF/DMSO when downstream purification is by silica, as high-boiling residues complicate isolation; consider MTBE/EtOAc/toluene for easier removal.
Quick comparison (literature-based):
THF: excellent for LDA/NaH deprotonation; peroxide-forming; dry required.
2‑MeTHF/CPME: greener, hydrophobic, easier phase separation; tolerate water traces better.
DCM: good solubility and chromatography eluent; limited for strong-base steps.
Storage and Reconstitution
Storage: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated area. Protect from moisture and direct sunlight. Store away from strong oxidizers and strong acids/bases.
Shipping: Normal (ambient) per Product Data.
Reconstitution: Not applicable; supplied as a neat organic compound. For stock solutions, dissolve in a suitable anhydrous solvent (e.g., THF, DCM, toluene, acetonitrile) at the desired concentration.
Stock solution handling (general):
Prepare and store under inert atmosphere (N2/Ar) for moisture-/base-sensitive applications.
For DMSO or MeCN solutions intended for screening, aliquot to minimize freeze–thaw cycles; store chilled or at –20 °C as appropriate for solvent and project SOPs.
Stability considerations (general): Aromatic nitriles are typically stable under ambient conditions; avoid prolonged exposure to strong base, and minimize heating with strong acids to prevent hydrolysis. Confirm lot-specific stability on the CoA/SDS.
Always consult the CoA and SDS accompanying the lot for definitive storage and handling instructions.
Structure and Identity
An arylacetonitrile building block featuring a benzylic nitrile (–CH2–CN) attached to a 2,6-difluoro-3-ethoxy-substituted phenyl ring; combines an electron-withdrawing nitrile with an aryl ether and two ortho fluorides.
Substitution pattern (verbal 2D description): A benzyl cyanide core where the phenyl ring bears fluorine atoms at the 2- and 6-positions (both ortho to the benzylic side chain) and an ethoxy substituent at the 3-position (meta to the side chain). The benzylic methylene links the ring to the nitrile carbon.
Structural features of interest:
Acidic benzylic methylene (activated by –CN) suitable for base-mediated enolate/anion chemistry.
Ortho-difluoro pattern provides steric congestion near the benzylic site and modulates ring electronics.
Aryl ether (–OEt) donates electron density to the ring, influencing reactivity and directing effects.
Note: Where exact identifiers (e.g., canonical SMILES, standardized InChIKey) are required for registration or informatics, consult the CoA/Spec Sheet or generate from a verified structure file.
Synthetic Utility
Functional elements governing reactivity:
Benzylic –CH2–CN: Acidified methylene (pKa ~21–25 in DMSO, literature) supports anion formation for C–C bond construction via alkylation, conjugate addition, and aldol-type couplings.
Nitrile: Convertible into amides/acids (hydrolysis), aldehydes (partial reduction), or primary amines (full reduction), enabling late-stage diversification.
Aryl ether (–OEt) and difluoro substitution: Modulate electron density and sterics on the ring; may affect regioselectivity and stability of intermediates.
Mono-alkylation at benzylic carbon with primary alkyl halides using LDA or NaH in dry THF (–78 to 0 °C), followed by quench and purification.
Michael addition to acrylates or nitroalkenes using KOtBu or phase-transfer catalysis to form extended nitrile frameworks.
Knoevenagel condensation with aldehydes (piperidine, toluene or EtOH, reflux) to generate styrylnitriles, followed by hydrogenation or further elaboration.
Hydrolysis: Acidic (H2SO4/aq. reflux) to carboxylic acid; basic (KOH/EtOH/H2O reflux) to amide/acid depending on conditions.
Reductions: DIBAL-H (–78 to –20 °C, toluene/THF) to aldehyde; LiAlH4 or BH3·THF to primary amine.
Cycloaddition: [3+2] with azide (Cu-catalyzed or thermal, where applicable) to tetrazole derivatives after suitable activation.
Strategic value: Acts as a linchpin for installing a difluorinated, ether-substituted aryl unit onto aliphatic frameworks through the benzylic position, allowing orthogonal manipulation of the nitrile and aryl substituents.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, inhibitor with validated target panel). No target, epitope, isotype, or species reactivity information is provided or expected.
Foire aux questions
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
How should this product be stored?
Store at room temperature.
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.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 1092461-33-0, the molecular formula is C10H9F2NO, and the molecular weight is 197.18 g/mol. InChIKey SNFOWHHWCGVXTQ-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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