This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
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
153.150 g/mol
XLogP3
0.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
153.059 Da
Monoisotopic Mass
153.059 Da
Topological Polar Surface Area
43.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
149.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block in the Product Data. For synthetic use, see Reaction Conditions and Synthetic Utility for general guidance.
Biological Roles
This product is a small aromatic amide intended for laboratory synthesis; no endogenous biological role is associated with 2-(2-fluorophenyl)acetamide.
General biochemistry context (literature, not product-specific)
Aromatic amides can engage in hydrogen bonding (via the carbonyl oxygen and amide NH) and π–π interactions, which is why arylacetamide cores are common in medicinal chemistry scaffolds.
Fluorine substitution on aromatic rings modulates lipophilicity, metabolic stability, and conformational preferences by influencing C–F dipoles and aryl–amide torsion.
Amide hydrolysis enzymes (amidases) can, in principle, convert arylacetamides to their corresponding acids and amines; actual rates vary widely and are substrate-specific.
Research-use note
This material is supplied strictly for research and laboratory use only. It is not intended for diagnostic, therapeutic, or in vivo applications.
Buffer Applications
Not typically applicable. 2-(2-Fluorophenyl)acetamide is a neutral, poorly ionizing aromatic amide and does not function as a buffering agent. For aqueous work it is usually dissolved first in a miscible organic co-solvent (e.g., DMSO) before dilution into buffer if required by an assay. See Solvent Selection for guidance.
Green Alternatives
While the compound itself is a solid building block (not a solvent), greener practices can be applied to its use and transformations.
Solvent choices (general guidance)
Prefer bio-based or lower-toxicity solvents when compatible with the chemistry. For dissolution and coupling steps, consider:
Safer alternatives to DMF/NMP: Cyrene (dihydrolevoglucosenone), propylene carbonate, or dimethyl isosorbide when reagent compatibility allows.
Replace dichloromethane with ethyl acetate or 2-MeTHF for extractions and peptide-type couplings.
Use water/ethanol co-solvent systems for recrystallizations where feasible.
Energy and process considerations
Employ microwaves or flow heating to shorten reaction times and reduce energy consumption for amide transformations.
Catalytic dehydrations and coupling reagents with better E-factors (e.g., T3P, CDI) can reduce waste relative to oxalyl chloride or carbodiimides.
Small comparison (illustrative; not item-specific specs)
DMF vs Cyrene: similar polarity/solvating power; Cyrene is biorenewable and has a better environmental profile but different reactivity with strong bases and acylating agents—screen conditions.
DCM vs EtOAc: EtOAc is less toxic and biodegradable; boiling point is higher, which may require adjustments in workup and concentration steps.
Always verify solubility/reactivity before wholesale substitution to greener media.
Pharmaceutical Uses
Item-specific status
No pharmacopeial grade or excipient designation is provided for this item; refer to CoA/Spec Sheet if regulatory use is contemplated.
General formulation/manufacturing context (not product-specific)
Fluorinated arylacetamide motifs are common synthetic intermediates during drug discovery campaigns. This compound may serve as a starting material or intermediate en route to candidate molecules, salts, or prodrugs.
As a neutral, low-volatility solid, it can be handled in standard dry rooms and purified by crystallization or chromatography. Residual solvent control and impurity profiling are critical for later-stage development, if pursued.
Important limitation
No medical, diagnostic, or therapeutic claims are made. This product is offered strictly for research and laboratory synthesis.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (catalog item): Not specified for this item; refer to CoA/Spec Sheet.
Phase at ambient: typically a crystalline solid for arylacetamides of this class
Solubility profile: generally sparingly soluble in water; readily soluble in polar aprotic solvents (DMSO, DMF) and moderately soluble in alcohols (MeOH, EtOH). Solubility increases with gentle heating.
Acid/base: neutral amide; no titratable groups in physiological pH range; amide pKa (conjugate acid) very low; amide N is weakly basic.
Lipophilicity: arylacetamides with a single F substituent generally show moderate logP; exact value for this item not established here.
UV characteristics: aromatic chromophore exhibits π→π* absorption in near-UV; specific cutoffs/ε not established for this item.
Practical notes
For solution preparation, start with DMSO or DMF stock (e.g., 10–100 mg/mL) and dilute into compatible media. Warm gently and sonicate if needed. Filter through 0.2 µm if particulate persists.
Quantitative physical constants such as melting point, density, and refractive index are not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: None indicated in Product Data.
Guidance on interpreting grades (general)
Research-grade aromatic building blocks are typically suitable for synthesis, screening, and method development. If low metal content, residual solvent limits, or chromatographic purity thresholds (e.g., ≥98% by HPLC/GC/NMR) are required, request the current CoA.
HPLC grade (when applicable for solvents) implies low UV-absorbing impurities; for solids like this amide, “assay by HPLC/NMR” is more relevant than solvent grades.
What to verify for this compound class
Identity confirmation by 1H/13C NMR and MS; optional 19F NMR provides a diagnostic ortho-F resonance and coupling.
Purity profile: check for residual acid/amide isomers, starting aniline derivatives, and dehydration products (nitrile) if exposed to strong dehydrating agents.
Water content (KF), residual solvents, and inorganic residue are application-dependent. For this specific item: Not specified; refer to CoA/Spec Sheet.
Lot-specific documentation
CoA typically provides assay, ID (NMR/IR/MS), and impurity limits. Request NMR reference spectra and chromatograms if your workflow is sensitive to trace aromatic impurities.
Reaction and Applications
2-(2-Fluorophenyl)acetamide is a versatile arylacetamide building block. Its benzylic methylene and amide moiety enable diverse transformations while the ortho-F provides a handle for further arene derivatization.
Transformations centered on the amide/benzylic site (literature, general)
Alpha-functionalization: deprotonation at the methylene (e.g., with LDA, NaHMDS) followed by electrophile trapping affords substituted derivatives (e.g., halogenation, alkylation, acylation), enabling synthesis of arylglycine motifs or benzylated frameworks.
Dehydration to nitrile: SOCl2, POCl3, or T3P can convert the amide to 2-fluorophenylacetonitrile.
Hydrolysis: acidic or basic conditions furnish 2-fluorophenylacetic acid; subsequent activation enables amide reformation with alternate amines or esterification.
Hofmann/Curtius-type rearrangements (from suitable precursors): Hofmann rearrangement of the amide can provide 2-fluorobenzylamine (one-carbon contraction) under halogen/base conditions.
Arene functionalization (literature, general)
Metalation: ortho/ortho′ metalation strategies can be guided by the amide as a weak directing group; the aryl F can persist or be displaced in SNAr if a strong ring activator is installed.
Cross-coupling after halogen exchange: aryl F is robust; installation of Br/I (via directed lithiation then quench with electrophilic halogen) allows Suzuki, Negishi, or Buchwald–Hartwig couplings.
Applications
Medicinal chemistry scaffold elaboration of fluorinated arylacetamide cores.
Intermediate for agrochemical and material monomer synthesis where ortho-F influences conformation and polarity.
Practical tip: Ensure rigorous drying of polar aprotic solvents for strong-base chemistry; 19F NMR is a convenient handle for rapid reaction monitoring.
Reaction Conditions
General literature guidance for common transformations of arylacetamides; adjust based on scale and sensitivity.
Alpha-alkylation
Base: LDA (1.1–1.5 equiv) in THF or THF/DMF at −78 to 0 °C; then add alkyl halide (1.2–2.0 equiv). Typical times: 0.5–4 h; warm to rt as needed.
Notes: Ensure rigorously dry conditions; quench carefully. Monitor by 19F and 1H NMR.
Benzylic halogenation
NBS (1.1 equiv) with AIBN or light initiation in CCl4/MeCN or greener alternatives (MeCN/EtOAc). 0–25 °C, 1–3 h. Provides bromomethyl amide for further substitution.
Hydrolysis to acid
Basic: NaOH (1–3 M) in EtOH/H2O, reflux 2–6 h. Acidify to precipitate 2-fluorophenylacetic acid.
Acidic: HCl (6 M) aqueous, reflux 4–12 h. Choose conditions to minimize dehalogenation.
Dehydration to nitrile
SOCl2 (3–5 equiv) with catalytic DMF, 60–80 °C, 2–6 h; or T3P (50% in EtOAc) with base (DIPEA) in acetonitrile, 50–80 °C.
Hofmann rearrangement (to 2-fluorobenzylamine)
NaOH (2–4 equiv) and Br2 (1.1–1.3 equiv) in aqueous/MeOH, 0–25 °C, then warm. Gas evolution; control exotherm. Work up to isolate amine (often as HCl salt).
Yields vary by substrate and conditions; optimize on small scale. All conditions are literature-style guidelines and not item-specific specifications.
Safety and Handling
Item-specific hazard statements and GHS: Not specified for this item; refer to the SDS for authoritative safety information.
General hazards for aromatic amides (contextual, not product-specific)
Low volatility; dust may cause mechanical irritation to eyes/respiratory tract.
Prolonged skin contact may cause irritation or sensitization in susceptible individuals.
Recommended PPE and controls
Wear lab coat, appropriate gloves (e.g., nitrile), and safety glasses or goggles.
Handle powders in a fume hood or with local exhaust to minimize dust inhalation.
Incompatibilities and reactivity
Avoid strong oxidizers and strong bases during storage. Under strong dehydrating conditions, amides can convert to nitriles.
Thermal decomposition may release hazardous fumes (e.g., HF traces from aryl fluorides at high temperature); avoid excessive heating.
First-aid overview (refer to SDS for full guidance)
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 contact lenses if easy.
Ingestion: rinse mouth; seek medical attention.
Handling tips
Minimize dust generation; use spatulas and weigh boats. Cap containers promptly to avoid moisture uptake and contamination.
Waste: collect organic solid waste per institutional guidelines; do not discharge to drain.
Solvent Selection
This product is a neutral, aromatic amide solid. Solvent choice is driven by dissolution needs and downstream reaction compatibility.
Polarity and miscibility (general expectations)
Best solvents: DMSO, DMF, NMP (high-boiling polar aprotic) for concentrated stock solutions.
Useful solvents: methanol, ethanol, acetone, acetonitrile for moderate solubility and easy removal.
Water: typically low solubility; co-solvent strategy or pH adjustment is usually ineffective due to amide neutrality.
Selection guidance
For biochemistry screening or stock solutions: dissolve first at 10–100 mg/mL in DMSO, then dilute into assay buffer with vigorous mixing to avoid precipitation.
For synthetic transformations: choose solvent to match transformation—e.g., polar aprotics for base-mediated alpha-functionalization; toluene/xylene for high-temperature dehydrations; mixed THF/DMF for coupling.
Small comparison (general)
DMSO vs DMF: DMSO offers higher solvating power and easier handling; DMF may be advantageous for some coupling reagents; both are hygroscopic.
Alcohols vs acetonitrile: alcohols can participate in H-bonding and sometimes in side reactions under strong activation; MeCN is more inert but may offer lower solubility.
Note: No item-specific solubility numbers are provided; consult the CoA/Spec Sheet or measure empirically for your system.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (per Product Data).
Shipping: Normal ambient shipping.
General storage practices for aromatic amide solids
Keep tightly closed in a dry, well-ventilated place. Protect from prolonged light and excessive heat. Use desiccant if ambient humidity is high.
Avoid contamination; dispense with clean, dry tools. Record open date for internal change-control.
Reconstitution and solution handling (guidance)
Prepare concentrated stocks in DMSO or DMF (e.g., 10–100 mg/mL). Warm gently (30–40 °C) and sonicate if needed. Filter (0.2 µm PTFE) for particulate removal.
For aqueous assays, add DMSO stock slowly to buffer with vigorous mixing to prevent precipitation; keep final DMSO ≤1–2% v/v when possible.
Short-term solution storage: 4 °C, protected from light; use within days. Long-term: prefer aliquoted frozen stocks (−20 °C) to minimize freeze–thaw.
Stability notes
Aromatic amides are generally stable at room temperature. Avoid strong acids/bases and dehydrating agents during storage to prevent hydrolysis/dehydration.
For any item-specific stability data (assay over time, impurity profile), consult the CoA/Spec Sheet.
Structure and Identity
Research-use aromatic amide building block featuring an ortho-fluoro substituent on a phenyl ring and a phenylacetamide linkage.
Item-specific (from Product Data)
Product name: 2-(2-Fluorophenyl)acetamide
CAS: 326-63-6
CID: 12269175
InChIKey: 65271 (as provided)
Storage: Room temperature; shipped at ambient conditions
Literature/computed identifiers and features (for reference; not specifications)
Structural description (2D): a benzene ring bearing F at the ortho position relative to a –CH2–C(=O)NH2 side chain. No stereocenters; planar aryl core with a conjugated amide carbonyl.
Notes
Where item-specific identifiers (e.g., exact SMILES/InChIKey) are required for regulated workflows, consult the product CoA/Spec Sheet and SDS for confirmation.
Synthetic Utility
Key reactive elements and how to leverage them (literature/generic guidance):
Benzylic CH2 alpha to amide carbonyl
Enolate or carbanion formation with strong, non-nucleophilic bases (LDA, LiHMDS, NaHMDS) enables C–C bond formation via alkylation/acylation and C–X installation (e.g., with NBS for bromination). Subsequent substitution opens access to diverse side-chain elaborations.
Oxidation at the benzylic position (e.g., via SeO2 or catalytic oxidants) can afford the corresponding ketoamide or acid after hydrolysis.
Amide functional group
Hydrolysis interconverts to 2-fluorophenylacetic acid, facilitating coupling to different amines (amide libraries) or esterification. Activation routes include CDI, EDCI, HATU (from the acid), or direct transamidation under catalytic conditions.
Dehydration to nitrile provides a handle for further transformations (e.g., reduction to amine, addition chemistry at the nitrile carbon).
Rearrangement chemistry (Hofmann from the amide, Curtius from the acid): routes to 2-fluorobenzylamine and urea/carbamate derivatives.
Aryl fluorine
Generally inert to many cross-coupling conditions; allows orthogonal chemistry on the side chain. Directed lithiation adjacent to the amide can enable halogenation/metalation followed by cross-coupling after installing a more labile halide.
Applications
Rapid parallel synthesis of fluorinated arylacetamide libraries.
Entry point to 2-fluorobenzylamine and 2-fluorophenethyl derivatives via contraction/expansion sequences.
Target Specificity
Not applicable. This product is a small-molecule aromatic amide, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies.
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