Ethyl 2-cyano-2-(2-fluorophenyl)acetate - ≥95% , CAS No.102276-85-7

CAS: 102276-85-7 Cat. No.: E974659 Fórmula: C₁₁H₁₀NO₂F Peso molecular: 207.2 PubChem CID: 13432078

GRAU & PUREZA ≥95%

Storage

Room temperature

Especificações

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CCOC(=O)C(C#N)C1=CC=CC=C1F

IUPAC Name

ethyl 2-cyano-2-(2-fluorophenyl)acetate

InChIKey

CSTOKYOKTOJYOX-UHFFFAOYSA-N

INCHI

1S/C11H10FNO2/c1-2-15-11(14)9(7-13)8-5-3-4-6-10(8)12/h3-6,9H,2H2,1H3

SMILES isoméricas

CCOC(=O)C(C#N)C1=CC=CC=C1F

PubChem CID

13432078

Peso molecular

207.2

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Fluorobenzenes
• Alternative Parents: Aryl fluorides Carboxylic acid esters Nitriles Monocarboxylic acids and derivatives Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Fluorobenzene - Aryl fluoride - Aryl halide - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Carbonitrile - Nitrile - Organohalogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Cyanide - Organofluoride - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descrição: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriedades químicas e físicas

• Peso molecular: 207.200 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 207.07 Da
• Monoisotopic Mass: 207.07 Da
• Topological Polar Surface Area: 50.100 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 271.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No biological assay protocols are associated with this chemical reagent in the Product Data.

• Synthetic use protocols should be adapted from the Reaction Conditions and Synthetic Utility sections. For example, a general Knoevenagel protocol: combine aldehyde (1.0 eq), ethyl 2‑cyano‑2‑(2‑fluorophenyl)acetate (1.1 eq), piperidine (10 mol%) in EtOH, stir at 50 C with 3 Å MS until completion, then work up and purify by silica gel. Optimize equivalents and temperatures per substrate.

For chromatographic method development, begin with hexanes/EtOAc (7:3 to 5:5) and adjust based on TLC/LC data. Always confirm identity and purity by NMR, LC–MS, and HRMS as needed.

Biological Roles

This product is a synthetic small-molecule building block and is not a known natural metabolite or cofactor.

• No inherent biological role is established for ethyl 2‑cyano‑2‑(2‑fluorophenyl)acetate. Its utility is in chemical synthesis, including preparation of probe molecules and intermediates for SAR campaigns.
• The nitrile and ester functionalities can modulate physicochemical properties (lipophilicity, H‑bond acceptor count) of derivatives, which is relevant to medicinal chemistry optimization, but these are design considerations rather than intrinsic biological functions.

For any biological testing, ensure appropriate purification and analytical characterization of the final compounds synthesized from this building block. This product is intended for research use only.

Buffer Applications

Not typically applicable. Ethyl 2‑cyano‑2‑(2‑fluorophenyl)acetate is a hydrophobic organic reagent with poor aqueous solubility and no buffering capacity.

• If used in biochemistry experiments, dissolve in a compatible organic co‑solvent (e.g., DMSO, MeCN, EtOH) and add to buffers at low percentages while monitoring precipitation and pH drift.
• For true buffering needs, select established systems (e.g., phosphate, HEPES, Tris) appropriate to your pH range; this reagent does not substitute for a buffer.

Green Alternatives

Greener choices relate primarily to solvent/base systems and processing rather than the core reagent (which is required for its unique reactivity). Consider the following substitutions and tradeoffs (literature/general guidance):

• Replace chlorinated solvents (DCM, CHCl3) with EtOAc, MeTHF/2‑MeTHF, CPME, or toluene when solubility and selectivity permit.
• Use ethanol or isopropanol as condensation media for Knoevenagel reactions with catalytic amines; apply water removal (azeotrope or molecular sieves) to drive conversion.
• Favor carbonate bases (K2CO3, Cs2CO3) or organic superbases (DBU) over strong inorganic hydroxides to reduce saponification risk.
• Continuous flow for exothermic base additions can reduce solvent volumes and improve safety.

Comparison (general):

• DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; may require longer reaction times or higher temperatures.
• THF vs 2‑MeTHF: 2‑MeTHF is bio‑derived, higher bp (80 C) beneficial for reflux and extractions; THF offers lower viscosity and broader literature precedence.
• DMF/DMSO vs MeCN/MeTHF: MeCN and 2‑MeTHF are easier to remove and often adequate for condensations; DMF/DMSO enable difficult deprotonations but are higher boiling and less green.

Waste minimization:

• Design telescoped sequences (condensation → cyclization) to avoid isolations.
• Use in situ base-neutralization and solvent swaps to reduce aqueous waste.

Note: Verify solvent compatibility to avoid transesterification or hydrolysis.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided in the Product Data. Do not use for human or veterinary applications.

• Role in R&D (general): serves as a versatile intermediate in medicinal chemistry for assembling α‑cyanoacrylates, β‑arylcarbonyls, and heterocyclic cores. The ortho‑fluoro substituent is often leveraged to tune metabolic stability or act as a synthetic handle.
• Process considerations: for route scouting, the reagent’s remaining α‑hydrogen allows late‑stage diversification (alkylation/condensation), then optional functional-group interconversions (nitrile reduction/hydrolysis, ester hydrolysis). Residual reagent and byproducts should be purged to acceptable research specifications.

No therapeutic claims are made. For research use only.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are literature/computed descriptors to aid experimental planning; they are not product specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (literature/computed): C11H10FNO2
• Molecular weight (literature/computed): ~207.20 g/mol
• Boiling point, melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• pKa of the α-methine (literature): active methylene/methine adjacent to –CN and –CO2Et typically shows pKa ≈ 9–11 in water and ≈ 13–16 in DMSO, depending on aryl substitution. Ortho‑fluoro aryl stabilization may slightly lower the pKa relative to ethyl cyanoacetate (lit. ~9.0 aqueous; ~13.5 in DMSO).
• LogP (predicted, literature): cyanoaryl ethyl acetates often fall in logP ≈ 1.5–2.5; substituent and isomerism dependent.
• Solubility (general): expected to be soluble in common organic solvents (EtOAc, MeCN, acetone, THF, DCM, toluene) and poorly soluble in water due to ester and aryl content. Verify experimentally.

Always verify properties relevant to your process (bp, mp, density, UV cutoff, water/peroxide content) on the CoA/SDS for the shipped lot.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance:

• In the absence of a declared grade, users should verify assay, residual solvents, and key impurities on the lot-specific CoA. For use in sensitive reactions (e.g., organometallic, photoredox), consider pre-purification or drying.
• Typical grade definitions (general):
  • Research/technical grade: suitable for routine synthesis; may have higher residual volatiles or UV background.
  • AR/reagent grade: tighter impurity controls suitable for analytical or reproducible synthesis.
  • HPLC grade (for solvents): low UV absorbance and stringent particulate control; not generally applicable to non-solvent reagents.
• Stabilizers/inhibitors: None are listed. If required by your protocol, evaluate need for acid/base scavengers or antioxidants; however, do not assume presence of any additive in this product.
• Documentation: For batch-specific purity, water content, inorganic residue/metals, and chromatographic profile, consult the CoA/Spec Sheet. Where ultra-low metal content is required (e.g., for cross-coupling screening), consider additional purification steps or metal scavenging resins.

Reaction and Applications

Ethyl 2-cyano-2-(2-fluorophenyl)acetate is an activated methine reagent combining –CN and –CO2Et stabilization with an electron‑withdrawing o‑fluorophenyl group. It serves as a versatile synthon for building densely functionalized arylacrylonitriles, heterocycles, and β‑aryl carbonyl frameworks.

Representative application families (literature/general):

• Knoevenagel condensations with aldehydes/ketones to furnish (E/Z)-arylidenes (α‑cyano‑cinnamates). The o‑fluoro motif can direct subsequent cyclizations or cross-couplings.
• Michael additions: the resulting arylidenes serve as Michael acceptors for amines, thiols, or carbon nucleophiles enabling step‑economic assembly of β‑functionalized products.
• α‑Alkylation/acylation: deprotonation at the α‑methine followed by SN2 coupling introduces additional substituents; subsequent decyanation or ester manipulation reveals diverse motifs.
• Cyclizations to heterocycles: with nucleophiles (e.g., amidines/guanidines) to form pyridines/pyrimidines; with hydrazines affording pyrazoles after prior condensation.
• Nitrile transformations: reduction to primary amine, hydrolysis to amide/acid (via amide), or imidate formation, enabling entry to peptidomimetics.

Practical tips:

• Base selection tunes chemoselectivity: secondary amine catalysts (piperidine) for Knoevenagel; non-nucleophilic bases (DBU, DBN) for clean condensations; strong bases (LDA/LHMDS) for α‑alkylation at low temperature.
• Water removal (Dean–Stark or 3Å MS) accelerates equilibrating condensations.
• The ortho‑F substituent can influence E/Z ratios and facilitate subsequent metalation or cross‑coupling after conversion to aryl boron/metal species.

Manufacturer Applications: None listed in the Product Data; the above reflect common literature uses of 2‑cyano‑2‑arylacetate esters.

Reaction Conditions

General, literature-based guidance for 2‑cyano‑2‑arylacetate chemistry (adapt as needed; verify on small scale):

• Knoevenagel condensations:
  • Conditions: aldehyde (1.0 eq), this reagent (1.0–1.2 eq), catalytic piperidine (5–20 mol%) or ammonium acetate (0.5 eq); solvent EtOH, toluene, or MeCN; 25–80 C.
  • Water removal: 3 Å molecular sieves or Dean–Stark in toluene improves rates and E/Z selectivity.
  • Times/yields: 1–12 h; literature yields commonly 70–95% depending on substrate electronics.
• α‑Alkylation:
  • Base: LDA or LiHMDS (1.1–1.5 eq) in dry THF/2‑MeTHF at −78 to 0 C; add alkyl bromide/iodide (1.2–2.0 eq). Alternatively, Cs2CO3/K2CO3 in DMF or MeCN at 20–60 C for activated electrophiles.
  • Notes: control temperature to avoid O‑alkylation/transesterification; quench with NH4Cl.
• Nitrile reduction:
  • H2 (1–5 bar) with Raney Ni or Pd/C in MeOH/EtOH at 25–60 C; or BH3·THF (1–3 eq) at 0–25 C; typical 2–16 h.
• Ester hydrolysis/reduction:
  • Saponification: NaOH or K2CO3 in MeOH/H2O (pH ≥ 12), 0–25 C; monitor to prevent nitrile hydrolysis if undesired.
  • DIBAL‑H (1.5–2.0 eq) in toluene/THF at −78 to −20 C for partial reduction to aldehyde.

Workup/purification:

• Avoid prolonged basic aqueous exposure to limit transesterification and nitrile hydrolysis.
• Silica gel chromatography with hexanes/EtOAc or toluene/EtOAc gradients typically separates starting material from E/Z products.

All conditions are literature/general guidance and should be optimized per substrate.

Safety and Handling

Hazard classifications are not provided in the Product Data. Handle as an organic nitrile/ester of unknown hazard profile until SDS review.

• GHS classification, signal word, pictograms, H‑statements: Not specified for this item; refer to SDS.
• Likely hazards (general for cyanoaryl esters): eye/skin irritation, combustible liquid, harmful if swallowed/inhaled. Avoid dust/vapors and prolonged exposure.
• Special risks: contains a nitrile group; while aliphatic/aromatic nitriles are generally stable, avoid strong acids/bases that may hydrolyze to amide/acid or cause transesterification. No known tendency to form peroxides.
• Incompatibilities: strong bases/nucleophiles (can deprotonate at α-position; transesterification with alkoxides), strong acids (hydrolysis), strong oxidizers, reducing agents for nitrile.
• PPE: lab coat, nitrile gloves, splash goggles; use in a fume hood. For scale-up, consider face shield and appropriate respirator per risk assessment.
• First aid (general):
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contacts if present and easy.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire: use CO2, dry chemical, or foam. Combustion may produce COx, NOx, HF from aryl fluoride—firefighters should wear SCBA.

Always consult the product SDS for authoritative safety data and local regulatory compliance.

Solvent Selection

This molecule is a moderately polar, aprotic organic reagent with good solubility in common organic solvents and poor aqueous solubility.

• Polarity/miscibility (general):
  • Expected to dissolve well in EtOAc, MeCN, acetone, DCM, chloroform, THF, dioxane, toluene; limited solubility in alcohols increases with heating.
  • Poorly soluble in water; use co-solvents for biphasic systems.
• Dielectric environment: Reactions involving α-deprotonation (enolate/carbanion formation) benefit from polar aprotic media (DMF, DMSO, NMP, MeCN) or ethereal solvents (THF, 2-MeTHF) with soluble bases.
• When to choose which solvent:
  • Base-promoted condensations (Knoevenagel): ethanol, toluene, or acetonitrile with catalytic amine base (piperidine, morpholine) or secondary amines under Dean–Stark where water removal is desired.
  • Alkylation at the α-position: THF/2-MeTHF with LDA/LHMDS at 0 to −78 C, or DMF/DMSO with weaker bases (Cs2CO3, K2CO3) for SN2 electrophiles.
  • Nitrile transformations (hydrolysis, reduction): aqueous-organic mixtures (MeOH/H2O, dioxane/H2O) under acid/base or catalytic hydrogenation conditions.
• Small comparison (general guidance):
  • THF vs 2‑MeTHF: similar solvating power for organolithiums; 2‑MeTHF offers greener profile and higher bp (safer reflux).
  • DCM vs EtOAc: DCM offers greater substrate solubility and low bp for extractions; EtOAc is greener and often sufficient for workups.

Always pilot solubility and base compatibility at small scale before process execution.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Form: Not specified for this item; refer to CoA/Spec Sheet. Many 2‑cyano‑2‑arylacetates are stable oils or low‑melting solids; confirm for the received lot.

Handling and stability (general guidance):

• Keep container tightly closed in a dry, well‑ventilated place. Protect from moisture, strong acids/bases, and prolonged light/heat.
• If long-term storage is anticipated, consider an inert atmosphere (nitrogen/argon) and amber glass to minimize hydrolysis and photolysis.
• Drying: If moisture is suspected, dry under high vacuum at ambient temperature. Avoid elevated temperatures that may promote transesterification or decomposition.

Solution preparation:

• Prepare stock solutions in dry solvents (e.g., MeCN, DMSO, THF, EtOH) immediately before use. For sensitive base-mediated steps, pre-dry solvents over molecular sieves.
• Store solutions at 2–8 C when necessary and use within a few days; stability will depend on solvent and base content.

Research Use Note: For research use only.

Structure and Identity

A 2-cyano-activated aryl acetate building block suited for C–C bond formation and heterocycle synthesis.

• SKU: E974659
• Product name: Ethyl 2-cyano-2-(2-fluorophenyl)acetate
• CAS: 102276-85-7; PubChem CID: 13432078
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (computed from name, literature): C11H10FNO2
• Molecular weight (computed): ~207.20 g/mol

Structural features (descriptive):

• Core is an ethyl acetate ester bearing an α-cyano substituent and an α-(2-fluorophenyl) substituent; the α-carbon is a methine (one acidic H) substituted by –CN and o-fluorophenyl.
• Functional groups: ethyl ester (–CO2Et), nitrile (–C≡N), aryl fluoride (o-F–C6H4–).
• Aromatic ring: monosubstituted phenyl (ortho-fluoro) enhancing inductive withdrawal and influencing conformation via o-F interactions.
• The 2D structure can be viewed as EtO2C–C*(H)(CN)–C6H4–F (F at ortho position). No stereocenters are present in the free acid/ester tautomer; the α-carbon is prochiral prior to substitution.

Notes:

• Identity elements above are provided as general/literature descriptors for this chemical name. For definitive batch-specific identifiers, consult the product CoA.

Synthetic Utility

Key reactivity elements:

• Activated α‑position: the –CN and –CO2Et groups strongly stabilize the carbanion formed upon deprotonation at the α‑methine, enabling alkylation, acylation, and aldol/Knoevenagel-type condensations.
• Dual handles for diversification: the nitrile can be reduced (→ amine), hydrolyzed (→ amide/acid), or converted to imidates; the ester can be hydrolyzed (→ acid), reduced (→ alcohol), or transesterified.
• Aryl fluoride effects: the o‑F substituent exerts −I effect, slightly increasing acidity and influencing conformation/reactivity; it also provides a potential site for metal–halogen exchange or SNAr in suitably activated systems.

Typical transformations (literature/general):

• Knoevenagel with aromatic aldehydes → α‑cyano‑cinnamates; subsequent Michael additions or cycloadditions build complexity.
• α‑Alkylation with alkyl halides (NaH, K2CO3, Cs2CO3, or LDA) → quaternary carbon centers after further elaboration.
• Reductive decyanation (Ni/RANEY, catalytic hydrogenation with formic acid or silanes) to unveil simple α‑aryl esters.
• Nitrile reduction (Raney Ni/H2 or BH3/THF) to primary amine; intramolecular cyclizations with amidines/hydrazines to N‑heterocycles.
• Ester manipulations: saponification (NaOH, MeOH/H2O) to the acid; DIBAL‑H reduction to aldehyde/alcohols for further coupling.

These features make it a convergent synthon for installing α‑aryl quaternary/tertiary centers and for heterocycle assembly.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and has no antibody/biological target specificity.

• Antigen/epitope/species reactivity/clone/isotype: Not applicable.

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 102276-85-7, the molecular formula is C11H10NO2F, and the molecular weight is 207.2 g/mol. InChIKey CSTOKYOKTOJYOX-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.