This compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to 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.
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
160.170 g/mol
XLogP3
0.600
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
160.064 Da
Monoisotopic Mass
160.064 Da
Topological Polar Surface Area
52.900 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
216.000
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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Recensioni
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Application Protocols
No specific application protocols are provided in the Product Data for this item. As a small-molecule building block, use is highly context-dependent on the synthetic route selected (see Reaction Conditions, Synthetic Utility). For analytical characterization, standard protocols (1H/13C NMR, IR for C≡N and amide C=O bands, LC/HPLC purity assessment) are typically appropriate.
If you share your intended transformation (e.g., selective nitrile hydrolysis, deacetylation, or reduction), we can outline a tailored step-by-step lab protocol with reagent quantities, temperatures, and workup steps.
Biological Roles
This product is intended for research use only. No biological roles are specified in the Product Data.
General considerations (literature/background):
Aromatic anilides and nitriles are common motifs in medicinal chemistry scaffolds, where the amide serves as a hydrogen-bond donor/acceptor and the nitrile as a polar, compact electrophile or bioisostere.
N-(2-cyanophenyl)acetamide specifically can act as a protected form of 2‑aminobenzonitrile, a versatile intermediate in the synthesis of heterocycles (e.g., benzimidazoles, quinazolinones) used in biochemical probe development.
No endogenous metabolic role is known; metabolic transformations (if studied) typically involve amide hydrolysis (amidases) and potential nitrile hydrolysis (nitrilases) under biological conditions, but rates are generally slow without enzymes.
Important: Do not infer therapeutic or diagnostic properties from these remarks; any biological testing should be performed under appropriate institutional approvals, and this material is not intended for human or veterinary use.
Buffer Applications
Not typically applicable. N-(2-cyanophenyl)acetamide is a neutral organic solid and is not used to prepare aqueous buffer systems. For laboratory handling, choose compatible organic solvents (see Solvent Selection) and, if needed, prepare aqueous-organic mixtures for extractions or recrystallizations rather than buffered solutions.
Green Alternatives
Greener choices pertain primarily to solvent and reagent selection when using N-(2-cyanophenyl)acetamide in synthesis; the substrate itself is a stable, non-volatile solid.
Prefer bio-based or lower-toxicity solvents where feasible: ethyl acetate, 2‑MeTHF, CPME, and propylene carbonate can replace DMF/DMSO/MeCN in some steps (solubility permitting).
For hydrolysis, consider aqueous media with ethanol/ethyl lactate as co-solvents instead of high-boiling polar aprotics; use phase-transfer catalysts to improve rates.
For reductions of nitriles, adopt catalytic hydrogenation with recyclable Pd/C or Raney Ni and green solvents (EtOH, water/EtOH) over stoichiometric metal hydrides.
For workups, avoid chlorinated solvents when possible; EtOAc/hexanes or EtOAc/heptane systems can often replace DCM.
Comparison snapshot (general):
DMF/DMSO: excellent solvency; environmental and workup burdens are higher.
2‑MeTHF/CPME: good for extractions and many reactions; water immiscible; improved safety profiles; may reduce peroxides vs ethers like THF but still monitor.
Ethyl acetate: green, easily removed, good for crystallization/extraction.
Trade-offs:
Greener solvents may lower solubility, requiring temperature or co-solvent adjustments.
Catalytic hydrogenation reduces waste but needs gas-handling infrastructure and careful selectivity control to avoid acetanilide cleavage.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation use is provided in the Product Data. The material is supplied strictly for research use only.
General context (non-clinical, process chemistry focus):
Synthetic intermediate: The acetanilide can serve as a protecting group for 2‑aminobenzonitrile during multi-step synthesis of heteroaromatic scaffolds common in drug discovery.
Process considerations: The solid state and moderate polarity facilitate crystallization-based purifications and salt-free workups. The nitrile enables late-stage diversification (hydrolysis, reduction), which can be useful in parallel synthesis.
Impurities control: Residual acetic acid or aniline derivatives from hydrolysis steps may require purge strategies (washing, carbon treatment). Trace metals (from hydrogenations) should be monitored if used upstream (metal limits: Not specified for this item; refer to CoA/Spec Sheet).
Note: No therapeutic claims are made or implied. Suitability for cGMP or regulatory filings must be determined independently, with supporting analytical packages as required.
Physical Properties
Item-specific numerical specifications are not provided in the Product Data.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point / Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Literature note (general): Aromatic acetanilides with additional nitrile substitution are typically crystalline solids with moderate to high melting points; thermal decomposition may precede boiling under ambient pressure.
Density, refractive index, UV cut-off, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative, literature/general):
Poorly soluble in water (neutral aromatic amide plus nitrile).
Soluble in polar aprotic organic solvents (e.g., DMSO, DMF, NMP, acetone) and moderately soluble in ethyl acetate; limited solubility in nonpolar hydrocarbons.
Trace solubility improvement with heating and/or addition of a small percentage of alcohols.
Acid–base properties (general): The amide is weakly acidic at nitrogen (non-basic); the nitrile is neutral. No appreciable ionization in neutral water.
Lipophilicity (qualitative): Moderate, owing to the aromatic ring balanced by one amide and one nitrile.
Notes: Provide/consult the item’s CoA/SDS for measured values applicable to a specific lot. Any numerical values required for process design should be verified experimentally.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
In the absence of an explicit grade, users should consult the CoA for assay method (e.g., HPLC/GC/NMR), impurity profile, and identity confirmation (NMR/IR/MS) used for the specific lot.
Context on common grades (general guidance):
Research grade: Suitable for most synthetic and discovery applications; baseline identity/purity confirmed, but not necessarily low-UV or low-metal.
Analytical reagent (AR) / ReagentPlus: Tighter impurity limits; useful where trace contaminants could impact spectroscopy or sensitive catalysis.
HPLC grade (solvents): Not applicable here (solid), but for recrystallization/analysis choose chromatography-grade solvents to minimize background.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Aromatic amides typically do not require stabilizers.
Practical recommendations:
Verify the purity assay basis (area%, weight%, qNMR) and ensure compatibility with your application (e.g., pharmaceutical intermediate vs. discovery chemistry).
If employing this material in metal-catalyzed transformations, consider pre-washing or recrystallization to reduce adventitious metal content when needed (metal limits: Not specified for this item; refer to CoA/Spec Sheet).
Reaction and Applications
This compound serves as an orthogonally functionalized building block: an anilide (acetanilide) protecting group masks the aniline, while the ortho-aryl nitrile provides a versatile handle.
Representative applications (literature/general):
Protected 2-aminobenzonitrile: Hydrolysis of the acetanilide (acidic or basic, reflux) regenerates 2‑aminobenzonitrile, a key intermediate for benzimidazoles, quinazolinones, and related heterocycles.
Nitrile transformations:
Hydrolysis to give the corresponding amides or acids (via amide → acid sequence) on the aryl ring.
Reduction (e.g., catalytic hydrogenation, borane, LiAlH4) to the aminomethyl derivative; careful control avoids concurrent deacetylation if protection must be retained.
Pinner-type or Ritter-like pathways to imidates/amidines under strongly acidic alcoholysis.
Directed metalation/electrophile introduction: Anilide groups can direct ortho-lithiation on the aryl ring under strong base (s‑BuLi/TMEDA), enabling installation of electrophiles at accessible positions not blocked by the nitrile.
Cyclization strategies: After deprotection to o‑aminobenzonitrile, intramolecular cyclizations to benzazoles (e.g., benzimidazoles) proceed under dehydrating/oxidative conditions.
Practical tips:
The amide is robust to many conditions (mild bases, oxidants), allowing selective manipulation of the nitrile.
For hydrolysis of the acetanilide, aqueous HCl or NaOH at reflux are common; monitor to prevent over-hydrolysis of the aryl nitrile if it must be preserved.
For reductions, select chemoselective reagents (e.g., BH3·THF for nitriles) and avoid conditions that cleave acetanilides unless deprotection is intended.
Reaction Conditions
The following conditions are general literature guidance for functional groups present in N-(2-cyanophenyl)acetamide; optimize for your substrate and scale.
Acetanilide hydrolysis (deprotection):
Acidic: 6 M HCl, reflux (80–100°C) for several hours; work up by basification and extraction to obtain 2‑aminobenzonitrile.
Basic: 2–4 M NaOH or KOH in EtOH/H2O, reflux; neutralize and isolate.
Notes: The aryl nitrile generally survives short hydrolyses but prolonged exposure can promote partial conversion to amide/acid.
Nitrile hydrolysis (on aryl ring):
To amide: Aqueous H2SO4 (conc.) or Na2CO3/K2CO3 with catalytic base in DMSO/H2O, 80–120°C;
To acid: Aqueous strong acid or base, reflux for extended times.
Selectivity between amide/acid controlled by time, temperature, and pH.
Nitrile reduction:
Catalytic hydrogenation (H2, Pd/C or Raney Ni) in EtOH or EtOAc, ambient–50°C, 1–5 bar; may reduce acetanilide under forcing conditions.
Hydride routes: BH3·THF (0–25°C) or LiAlH4 (0°C→reflux) afford the primary amine after aqueous workup; protect the anilide if needed.
Ortho-lithiation (anilide-directed):
s‑BuLi (1.1–1.5 equiv) with TMEDA in THF or Et2O, −78 to −40°C, then electrophile quench. Steric/electronic effects of the ortho-nitrile may limit accessible positions.
Monitoring and analytics:
Use HPLC/UPLC or qNMR for conversion and to distinguish deacetylation vs nitrile transformation.
Confirm identity by IR (amide C=O ~1650 cm−1; nitrile C≡N ~2220–2240 cm−1, literature) and 1H/13C NMR.
Safety and Handling
Hazard classifications and pictograms are not provided in the Product Data for this item. Always consult the SDS for authoritative guidance.
General safety considerations for aromatic amides and nitriles:
Likely hazards (general): May cause skin/eye irritation and respiratory irritation as dust. Combustible as an organic solid; fine dust can form explosive mixtures in air. Avoid inhalation of particulates and contact with skin/eyes.
GHS/Signal word: Not specified for this item; refer to SDS.
First aid (overview, 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 contact lenses if present and easy to do.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
PPE: Lab coat, safety glasses, and suitable chemical-resistant gloves (e.g., nitrile). Use a dust mask/respirator if generating particulates (per SDS/OSHA guidance).
Engineering controls: Handle powders in a fume hood to minimize dust exposure; employ local exhaust during charging/weighing.
Incompatibilities (general): Strong oxidizers; strong acids/bases under reflux can hydrolyze the acetanilide moiety. Avoid strong reducing agents if nitrile integrity is required.
Thermal stability: Heat may promote amide hydrolysis and/or decomposition; avoid excessive heating and open flames.
Waste disposal: Treat as organic laboratory waste; dispose per institutional and local regulations. For spill control, avoid dust generation; sweep up and collect in appropriate container.
Solvent Selection
As a neutral, moderately polar aromatic amide bearing a nitrile, N-(2-cyanophenyl)acetamide shows limited water solubility but dissolves well in polar aprotic media.
Polarity class (general): Moderately polar, hydrogen-bond donor (amide NH) and acceptor (amide carbonyl, nitrile nitrogen).
Preferred solvents (literature/general): DMSO, DMF, NMP, acetone, MeCN; moderate solubility in EtOAc and hot alcohols (MeOH/EtOH). Poor in alkanes/ethers unless heated or with co-solvent.
Aqueous workup: Typically isolates well by aqueous quench and extraction into EtOAc or dichloromethane, followed by concentration and recrystallization.
Crystallization: EtOAc/hexanes or EtOAc/toluene mixtures often effective. Slow cooling or anti-solvent addition can improve crystal quality.
Comparison (general guidance):
DMSO/DMF: highest solvating power for polar substrates; harder to remove, higher bp.
MeCN/Acetone: good balance of polarity and volatility; may afford faster crystallizations.
EtOAc: greener extraction/crystallization solvent; moderate solubility can help induce crystallinity.
Selection tips:
For NMR, DMSO-d6 or CD3CN typically give clean spectra; CDCl3 may be marginal if solubility is low.
For reactions targeting the nitrile (e.g., hydrolysis/reduction), choose solvents compatible with aqueous acid/base or hydrogenation media, respectively.
Container: Keep tightly closed in a dry, well-ventilated place; use moisture-tight packaging to avoid caking and hydrolysis during long storage.
Light/air sensitivity: Aromatic amides and nitriles are generally stable; store away from strong acids/bases and oxidizers. No special inert-atmosphere requirements are typical for closed storage.
Reconstitution: Not applicable (solid). For solution preparation, dissolve in a suitable organic solvent (e.g., DMSO, DMF, MeCN, EtOAc) to the desired concentration; filter if particulates remain.
Stock solutions: For biological screening contexts (if any), prepare DMSO concentrates and store at 2–8°C or −20°C, protected from moisture; bring to room temperature before opening to prevent condensation. Stability of solutions is substrate- and solvent-dependent—verify by LC over time.
Shipping: Not specified for this item; refer to CoA/Spec Sheet. Room-temperature shipment is typically suitable for stable aromatic amides.
Always refer to the product’s SDS and lot-specific CoA for definitive handling and stability information.
Structure and Identity
N-(2-cyanophenyl)acetamide is an ortho-cyano-substituted acetanilide, i.e., the aniline nitrogen is acetylated and the aromatic ring bears a cyano group at the position ortho to the anilide nitrogen.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature (for identification only): CC(=O)NC1=CC=CC=C1C#N
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed: C9H8N2O
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed: ~160.17 g/mol
Structural features (general description):
Functional groups: neutral amide (acetanilide), aromatic ring, and a nitrile (–C≡N) at the ring ortho-position.
Connectivity (2D): an acetamide fragment (CH3–CO–NH–) bonded to an ortho-cyanophenyl ring. The ring carries –C≡N adjacent to the –NH– linkage.
Stereochemistry: none (achiral, no stereocenters).
Resonance considerations (general): conjugation across the anilide nitrogen into the aryl π-system; the nitrile is strongly electron-withdrawing and deactivating toward electrophilic aromatic substitution.
Synthetic Utility
Key reactivity stems from two orthogonal functional groups on an anilide framework:
Anilide (AcNH–):
Serves as a protecting group for anilines; readily cleaved under acidic or basic hydrolysis.
Can act as a directing group for ortho-metalation, enabling electrophile installation at positions not blocked by substituents.
Aryl nitrile (–C≡N):
Versatile handle for hydrolysis (amide/acid), reduction (to primary amine or aldehyde under controlled conditions), and cross-coupling after activation (e.g., via imidates or as pseudohalides in Ni catalysis; literature-advanced topic).
Can participate in annulations after deprotection to o‑aminobenzonitrile, forming benzimidazoles/quinazolinones.
Retrosynthetic value (general):
From 2‑aminobenzonitrile via acetylation (Ac2O, pyridine or Et3N) to install the protecting group.
Diversification at the aryl ring (electrophilic substitution, lithiation–quench, or metal-catalyzed C–H activation) can be orchestrated with the nitrile’s deactivating influence and the anilide’s directing effect.
Selectivity notes:
The nitrile is stable to many electrophiles and mild bases; it can be selectively transformed while retaining the acetanilide if desired.
Strong nucleophiles/bases or prolonged reflux in strong acid/base can lead to competing deacetylation and/or nitrile hydrolysis—monitor closely by TLC/HPLC.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting reagent or antibody. No antigen/epitope/clonal information is relevant.
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