This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
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
165.160 g/mol
XLogP3
2.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
165.059 Da
Monoisotopic Mass
165.059 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
181.000
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
Recensioni dei clienti
Application Protocols
No item-specific tested applications are provided. As a small-molecule building block, protocols depend on the intended chemical transformation.
General lab-use examples (literature-inspired; adapt to your system)
Stock solution preparation: Dissolve at 100 mM in dry DMSO or acetonitrile; filter (PTFE, 0.22 µm) if necessary. Store aliquots to minimize freeze–thaw.
Michael addition screening: Combine electrophile (1.0 eq), nucleophile (1.2 eq), base (0.1 eq) in MeCN (0.2 M) at RT; monitor by LC–MS every 15–30 min; quench with 0.1% AcOH.
Metathesis setup: Charge dry vial with substrate and olefin partner (3 eq), add Grubbs II (2 mol%) in DCM (0.1 M), stir under N2 at 40 °C; monitor by TLC; quench with ethyl vinyl ether; purify by silica.
For assay use, follow institutional SOPs for handling electrophilic small molecules. Consult primary literature for reaction-specific protocols and adjust for scale, solvent, and catalyst system.
Biological Roles
Scope note: This product is intended for research use only. No medical or clinical claims are made here.
Literature/general perspective
Chemical biology handle: α,β-Unsaturated amides function as electrophilic probes toward nucleophilic residues (notably cysteine) in proteins via Michael addition. N-aryl acrylamides are widely used as covalent warheads in probe design; the 3-fluorophenyl group modulates hydrophobicity and electronics.
Physicochemical profile: Moderate lipophilicity and H-bond accepting ability can promote cell-permeant behavior for related analogs; however, actual permeability and bioactivity are highly context-dependent and not established for this specific item.
Metabolic considerations: Typical biotransformations for aryl acrylamides include epoxide formation on the ring (CYP-mediated), conjugate reduction/hydrogenation of the double bond, hydrolysis to the corresponding aniline and acrylic acid derivatives, and glutathione conjugation via Michael addition (literature patterns).
Assay usage: In enzyme profiling or chemoproteomics, acrylamides can be used to assess nucleophile reactivity scales (e.g., thiol reactivity) and to benchmark selectivity trends versus amines or alcohols.
Caveats
Electrophilic reactivity entails potential off-target modification in biological mixtures. Employ appropriate controls (e.g., using saturated amide analogs) and quenching protocols. Any in vitro biological experimentation should follow institutional safety and ethical guidelines and is strictly for research.
Buffer Applications
Not typically applicable. N-(3-Fluorophenyl)-2-propenamide is not a buffering agent and lacks a conjugate acid/base pair suitable for preparing laboratory buffers in the physiological pH range.
Practical note
If solutions are needed for biochemical assays, dissolve in an appropriate co-solvent (e.g., DMSO or acetonitrile) and dilute into the assay buffer while keeping final organic content compatible with the system (commonly ≤1–2% v/v). Select buffers (e.g., phosphate, HEPES) based on the biology of interest rather than this compound’s properties.
Green Alternatives
Context: Selection of solvent and activation mode often dominates the environmental footprint when working with N-aryl acrylamides like N-(3-fluorophenyl)-2-propenamide.
Greener solvent choices (literature guidance)
Replace DMF/DMAc/NMP with:
2-Methyltetrahydrofuran (2-MeTHF) or CPME for many nucleophile additions and hydrogenations.
Ethyl acetate or IPA/EtOH as reaction or recrystallization media when solubility allows.
Water or water–ethanol with surfactants (micellar catalysis) for certain Michael additions.
Oxidant/reductant choices
Favor electrochemistry or photoredox using air/O2 as terminal oxidant where feasible, rather than stoichiometric peroxides or metal oxides.
Catalysis
Use organocatalysts (thiol–Michael, enamine/iminium catalysis) to avoid heavy metals.
If metathesis is required, employ second-generation ruthenium catalysts at ppm levels and recover catalyst by immobilization where possible.
Comparison snapshot (literature trends)
DMF vs. MeCN: MeCN offers lower toxicity and easier removal; DMF may be necessary for some couplings.
DCM vs. EtOAc: EtOAc is less problematic environmentally and often extracts/purifies just as effectively.
NMP vs. 2-MeTHF: 2-MeTHF is bio-derived and lower in reproductive toxicity concerns compared to NMP.
Waste minimization
Telescoping Michael addition → workup → crystallization can avoid chromatography.
Apply in-line FTIR/UPLC to minimize over-reaction and side-product formation, reducing solvent and energy use.
Note: Always validate greener options against reactivity/selectivity for this specific substrate.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; it is supplied for research use only.
Literature/general formulation context
Discovery chemistry: N-aryl acrylamides serve as electrophilic fragments/warheads in covalent ligand design and as intermediates for SAR exploration by selective modification at the vinyl position (e.g., Michael adduct libraries) or on the aryl ring.
Preformulation considerations: For in vitro screening, stock solutions are commonly prepared in DMSO (10–100 mM) and diluted into aqueous assay media. Solubility limits and adsorption to plastics should be assessed empirically.
Stability: Acrylamide motifs may undergo polymerization or hydrolysis under harsh conditions; formulate and store under conditions that minimize light, heat, and radical exposure. Incorporation of stabilizers is application-specific and not specified for this item.
Regulatory note
No therapeutic claims or clinical uses are made. Any use in drug product manufacture would require dedicated GMP grade material and full impurity/elemental profiling beyond the scope of this research-grade listing (if applicable).
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
Literature/general physical data for N-(3-fluorophenyl)-2-propenamide
Expected state: Low-molecular-weight N-aryl acrylamides are typically crystalline solids or low-melting solids (literature; specific MP for this exact isomer not located here).
Boiling point: Not readily reported; acrylamides generally decompose before boiling under ambient pressure (literature).
Melting point: Specific MP not located; structurally related N-aryl acrylamides often melt in the 80–160 °C range (literature trend; not a specification).
Density: Not found (literature); likely around 1.1–1.3 g/mL for melt/liquid phase typical of aryl amides (trend; not a specification).
LogP (cLogP, estimated): ~1.5–2.0 for N-aryl acrylamides of this size (literature/computational estimates; consult cheminformatics tools for an exact number).
pKa: Amide N–H is absent (N-aryl), so no acidic N–H; amide basicity is very weak (conjugate acid pKa typically −1 to −2 in water; literature trend).
Limited: Alcohols (MeOH/EtOH) at RT, depending on crystal packing.
Poor: Water (typical for N-aryl acrylamides).
UV characteristics: π→π* absorption expected in the near-UV due to aryl and amide conjugation; exact cutoff not located.
Note: For assay-critical work, verify exact values on the item’s CoA/SDS.
Quality and Grades
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on grades relevant to this compound class
Research grade: Suitable for most synthetic, screening, and method-development tasks. Verify impurity profile (unreacted aniline, polymeric content, residual acryloyl chloride, and hydrolysis products) when needed.
HPLC/LC–MS grade materials (if available): Feature low UV background and low metal/ionic residues; particularly beneficial when the compound is used as an analytical standard or in trace-level assays.
Pharmaceutical/compendial grades: Not applicable here unless specifically stated by the supplier.
Quality considerations for N-aryl acrylamides
Purity verification: 1H/13C NMR to confirm E-geometry and absence of polymer; IR bands around ~1650–1685 cm−1 (amide C=O) and ~1600 cm−1 (C=C). Look for disappearance of anilide NH if fully N-aryl substituted (consistent with this structure).
Stabilizer implications: If an inhibitor (e.g., MEHQ, BHT) is ever present, it can affect radical reactions or polymerization studies; remove by basic alumina or preparative chromatography as appropriate (only if listed on the item’s CoA).
Water/peroxide/metal specifications: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
This compound is an N-aryl α,β-unsaturated amide (acrylamide), functioning as a conjugated Michael acceptor and versatile synthetic handle.
Representative application families (literature)
Conjugate (Michael) addition: Soft nucleophiles (thiols, malonates, nitroalkanes, selenols) add to the β-carbon under base or organocatalyst mediation. Secondary amines can add to give β-aminocarbonyls; thiol–Michael reactions are often fast and chemoselective.
Radical additions: Under photoredox or thermal conditions with radical precursors (e.g., thiyl, carbon-centered radicals), the double bond undergoes anti-Markovnikov addition; subsequent oxidation can furnish diverse motifs.
Cycloadditions/annulations: Formal [2+2] or [4+2] processes with activated partners under photochemical or Lewis-acid conditions have been reported for acrylamides to build lactams/indolinones.
Cross-metathesis: The terminal alkene participates in olefin metathesis (Grubbs/Hoveyda catalysts) to diversify the side chain while retaining the amide.
Heck-type reactions: The alkene can couple with aryl halides under Pd catalysis to form substituted enamides.
Hydrogenation/isomerization: Selective hydrogenation to the saturated amide; isomerization can shift the C=C geometry.
Fluoro-aryl handle
The meta-fluoro group modifies electronics and lipophilicity and can direct regioselectivity in electrophilic aromatic substitution. While aryl–F is typically inert in cross-coupling, specialized conditions (e.g., Ni catalysis with strong ligands or SNAr only with powerful ring deactivation, which is absent here) are generally required and often not favored.
Practical tips
Avoid strong base in protic media to limit amide hydrolysis or aza-Michael side reactions unless desired.
Exclude radicals/heat if polymerization is a concern; consider inhibitor-free vs. stabilized material per CoA.
Reaction Conditions
General, literature-based conditions for transformations of N-aryl acrylamides (illustrative; optimize for your lab setup):
Michael addition of thiols
Typical: Thiol (1.0–1.2 eq), base (Et3N 0.1–0.5 eq or DBU 0.05–0.1 eq), MeCN or EtOH, 0–25 °C, 0.5–4 h. Often high conversions; monitor by TLC/UPLC.
Catalyst options: Organobases or nucleophilic catalysts (DMAP). For enantioselective variants, chiral thioureas or squaramides in toluene/Et2O at 0 °C to RT.
Cross-metathesis
Catalyst: Grubbs II or Hoveyda–Grubbs II (1–5 mol%).
Conditions: 0.1–0.5 M in DCM, toluene, or 2-MeTHF, RT to 60 °C, 2–12 h; ethylene purge if necessary to drive equilibria.
Heck coupling at the alkene
Aryl halide (1.2 eq), Pd(OAc)2 (1–5 mol%) with phosphine ligand, base (Et3N, K2CO3), DMF/DMAc, 80–120 °C, 6–18 h.
Hydrogenation of C=C
Catalyst: Pd/C (5–10 wt% relative to substrate).
Solvent: EtOAc, MeOH, or EtOH; 1–3 bar H2; RT to 40 °C; 2–8 h.
Hydroboration–oxidation
9-BBN (1.2 eq) or BH3·THF (carefully), THF, 0 °C to RT; oxidative workup with H2O2/NaOH gives β-hydroxylated amide.
Notes
Avoid strong aqueous base for prolonged times to limit amide hydrolysis.
Aryl–F SNAr is generally ineffective without additional ring activation; pursue metalation or C–H functionalization strategies instead.
Always run small-scale scouts to establish selectivity (1,4- vs 1,2-addition) and stability.
Safety and Handling
Item-specific hazard data
GHS classification, pictograms, signal word, and H-statements: Not specified for this item; refer to the SDS.
Literature/general safety considerations for N-aryl acrylamides and acrylamide-like Michael acceptors
Hazards (general): α,β-Unsaturated amides are electrophilic Michael acceptors that may cause skin/eye irritation and can be harmful if swallowed or inhaled. Some acrylamides are skin sensitizers. Avoid contact and inhalation. Handle in a fume hood.
Polymerization risk: Acrylamide motifs can undergo polymerization, especially upon heating, exposure to radical initiators, or prolonged storage in light. Store away from radical sources; use inhibitors only if specified by the supplier (none specified for this item).
Incompatibilities: Strong bases/acids (can promote hydrolysis or conjugate addition), strong oxidizers, strong nucleophiles and thiols (may add across the double bond), and radical initiators.
Personal protective equipment (PPE): Lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Employ splash protection when preparing solutions.
First aid (overview; defer to SDS):
Skin/eye contact: Immediately flush with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; assist breathing if needed; seek medical attention.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Handling tips: Minimize exposure time; keep containers closed; weigh quickly to reduce moisture uptake and air exposure. Use dry, oxygen-reduced conditions if polymerization or oxidation is a concern.
Waste: Collect as halogenated/amide-containing organic waste per institutional and regulatory guidance.
Solvent Selection
Applicability: This is a moderately polar, conjugated N-aryl acrylamide. Solvent choice strongly influences solubility and reaction pathways (e.g., conjugate addition vs. hydrolysis).
Dielectric considerations: Higher dielectric constants (DMSO, DMF, MeCN) can accelerate polar conjugate additions and cross-couplings; nonpolar media may be preferred for radical reactions or to suppress side reactions.
When to choose which solvent
For nucleophile additions (Michael): MeCN, DMF, or alcoholic solvents (for soft nucleophiles like thiols) often provide high conversions.
For cross-couplings at the vinyl unit (Heck with aryl halides): Polar aprotic solvents (DMF, DMAc, NMP) at elevated temperature.
For purification: Ethyl acetate/hexanes or DCM/MeOH gradients commonly resolve N-aryl acrylamides on silica.
Small comparison (literature trends)
DMSO/DMF: Maximize solubility/reactivity; harder to remove.
MeCN: Good balance of polarity/volatility; suitable for photoredox/Michael chemistry.
THF/EtOAc: Easier workup; may require heating or higher concentration to dissolve fully.
Note: Verify solvent compatibility with bases, catalysts, and any inhibitor profile stated on the CoA.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for this compound class
Protection: Store in a tightly closed container, in a dry place, protected from light and sources of free radicals/initiators. Consider using an inert atmosphere (argon/nitrogen) if long-term storage is planned.
Stability notes: α,β-Unsaturated amides can slowly polymerize or undergo oxidative coloration upon prolonged exposure to heat/light. Keep away from strong acids/bases and nucleophiles.
Reconstitution and solution handling (research use)
Solubility: Readily dissolved in dry DMSO, DMF, or MeCN to make 10–100 mM stocks. For less polar media (EtOAc, THF, DCM), sonication or mild warming may help.
Filtration: Use PTFE syringe filters (0.22–0.45 µm) for solution clarification.
Aliquoting: Prepare single-use aliquots to minimize headspace oxygen and repeated opening. Label with concentration, solvent, and date.
Shelf life of solutions: At room temperature, non-aqueous stock solutions are best used within days to a few weeks; for longer storage, keep at 2–8 °C or frozen (avoid repeated freeze–thaw). Actual stability should be verified experimentally for your application.
Always defer to the product’s SDS/CoA for definitive storage and handling instructions.
Structure and Identity
Item-specific (from Product Data)
CAS: 519004-35-4
PubChem CID: 3440774
InChIKey: 388658 (as provided; truncated/atypical format in Product Data)
Storage conditions: Room temperature
Research use: For research use only
Literature/computed identity (general information about N-(3-fluorophenyl)-2-propenamide)
InChIKey (literature): Not specified here; refer to authoritative databases (e.g., PubChem CID 3440774)
Structural features (general description)
Core scaffold: An N-aryl acrylamide comprising an amide (–C(=O)–N–) linking an acryloyl fragment (–CH=CH–C(=O)–) to a 3-fluorophenyl substituent.
Functional groups: Conjugated α,β-unsaturated amide (Michael acceptor), secondary carboxamide (N-aryl), aryl C–F bond at the meta position.
Conjugation: The C=C–C=O unit is conjugated; the amide lone pair is partially delocalized into the carbonyl, diminishing nucleophilicity of N and stabilizing the E geometry around the C=C (literature, typical for acrylamides).
2D description: A benzene ring bearing F at the meta position is attached via nitrogen to an amide carbonyl, which in turn is α,β-unsaturated (CH2–CH–) toward the terminal alkene.
Synthetic Utility
Functional handles and reactivity (literature)
Michael acceptor: The β-carbon is activated toward conjugate addition by soft nucleophiles (thiols, malonates, stabilized carbanions), enabling rapid diversification to β-substituted amides.
Vinyl platform: The terminal alkene participates in:
Cross-metathesis (Grubbs/Hoveyda) to introduce diverse side chains.
Hydroboration–oxidation (anti-Markovnikov alcohols) or hydroamination.
Radical additions under photoredox catalysis.
Amide vector: The amide carbonyl engages in hydrogen bonding and can be carried through multistep routes with high chemoselectivity; N-aryl substitution prevents N–H participation but preserves resonance stabilization, improving robustness.
Aryl–F features
Electronic tuning: The m-fluoro substituent can decrease ring electron density, subtly affecting electrophilic aromatic substitution and π–π stacking. Although aryl–F is a poor leaving group, it can survive harsh cross-coupling conditions, serving as a latent handle for late-stage C–H functionalization elsewhere.
Retrosynthetic value
Accessible from 3-fluoroaniline and acryloyl chloride (or acrylic acid via coupling reagents) under standard amidation conditions. This orthogonal disconnection simplifies library synthesis where the aryl part varies independently of the acrylamide side chain.
Downstream transformations
After conjugate addition, β-functionalized amides can be oxidized/reduced or cyclized to lactams/oxindoles, enabling scaffold hopping to heterocycles commonly used in medicinal chemistry.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological macromolecule or affinity reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
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