4-Acetamidobenzaldehyde - ≥98%(GC) , CAS No.122-85-0

CAS: 122-85-0 Cat. No.: A151024 Fórmula: C₉H₉NO₂ Peso molecular: 163.18 Beilstein Registry Number: 14(2)25 Número CE: 204-579-2

GRADE & PURITY ≥98%(GC)

Synonyms

4-Acetamidobenzaldehyde | 4-acetamido-benzaldehyde | 4-Acetomidobenzaldehyde | A804975 | Benzaldehyde, 4-acetamido- | InChI=1/C9H9NO2/c1-7(12)10-9-4-2-8(6-11)3-5-9/h2-6H,1H3,(H,10,12 | p-(Acetylamino)benzaldehyde | 2-Amino benzimidazole | AI3-18873 | Z104

Storage

Argon charged,Room temperature

Shipped In

Normal

Specifications

Sinónimos

4-Acetamidobenzaldehyde | 4-acetamido-benzaldehyde | 4-Acetomidobenzaldehyde | A804975 | Benzaldehyde, 4-acetamido- | InChI=1/C9H9NO2/c1-7(12)10-9-4-2-8(6-11)3-5-9/h2-6H,1H3,(H,10,12 | p-(Acetylamino)benzaldehyde | 2-Amino benzimidazole | AI3-18873 | Z104

Especificações e pureza

≥98%(GC)

Condições de armazenamento de armazenamento

Argon charged,Room temperature

Enviado em

Normal

Pureza

≥98%(GC)

Nomes e identificadores

• Pubchem Sid: 488184838
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488184838
• Sorrisos canónicos: CC(=O)NC1=CC=C(C=C1)C=O
• IUPAC Name: N-(4-formylphenyl)acetamide
• InChIKey: SKLUWKYNZNXSLX-UHFFFAOYSA-N
• INCHI: 1S/C9H9NO2/c1-7(12)10-9-4-2-8(6-11)3-5-9/h2-6H,1H3,(H,10,12)
• SMILES isoméricas: CC(=O)NC1=CC=C(C=C1)C=O
• WGK Alemanha: 3
• Peso molecular: 163.18
• Beilstein: 14(2)25
• Reaxy-Rn: 387304
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=387304&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Acetanilides
• Alternative Parents: N-acetylarylamines Benzoyl derivatives Benzaldehydes Acetamides Secondary carboxylic acid amides Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Acetanilide - N-acetylarylamine - Benzaldehyde - Benzoyl - N-arylamide - Aryl-aldehyde - Acetamide - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Aldehyde - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Descrição: 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

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

• Solubilidade: Solubility in Methanol very faint turbidity
• Sensibilidade: air sensitive
• Ponto de fusão (°C): 154-158°C
• Peso molecular: 163.170 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 163.063 Da
• Monoisotopic Mass: 163.063 Da
• Topological Polar Surface Area: 46.200 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 171.000
• 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

Referências

1. Guanyu Chi, Yinghua Lv, Shuang Chao, Chenxi Hou, Yuxin Pei, Zhichao Pei.  (2022)  Glyconanoparticles with Activatable Near-Infrared Probes for Tumor-Cell Imaging and Targeted Drug Delivery.  International Journal of Nanomedicine,      [PMID:35401000] [10.2147/IJN.S337082]

2. Xinyue Zhao, Lulu Ning, Xiaoman Zhou, Zhihui Song, Jianjian Zhang, Feng Guan, Xiao-Feng Yang.  (2021)  An Activatable Near-Infrared Fluorescence Hydrogen Sulfide (H2S) Donor for Imaging H2S Release and Inhibiting Inflammation in Cells.  ANALYTICAL CHEMISTRY,      [PMID:33689305] [10.1021/acs.analchem.0c05081]

3. Zhaolei Zhang, Fengyan Fang, Pingping Zhang, Xiaokang Zhang, Hongchao Ma, Yanhui Wei.  (2024)  Synergistic effect of inner filtering effect and host-guest interaction based on β-cyclodextrin fluorophore for promoted 4-nitrophenol detection.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2024.134087]

Application Protocols

No assay/diagnostic protocols are specified for this item; refer to CoA/Spec Sheet. As a synthetic intermediate, typical laboratory protocols involve:

• Dissolution in an appropriate organic solvent (e.g., MeCN, EtOH, DCM, DMF, DMSO)
• Execution of condensation/reduction/oxidation steps as outlined under Reaction Conditions
• Workup by aqueous quench, extraction, and purification by column chromatography or recrystallization

For any analytical methods (HPLC, GC, NMR), establish system suitability with authentic standards and internal controls. Always adapt conditions to the specific substrate set.

Biological Roles

This compound is a synthetic aromatic aldehyde and is not known to play a direct physiological role.

• General context (literature; not medical/clinical):
  • The para‑acetamidobenzaldehyde scaffold combines an anilide (acetamide) with an aldehyde, offering handles for derivatization into Schiff bases and heterocycles used as ligands or chromophores in biochemical assay development and coordination chemistry.
  • Deacetylation yields p‑aminobenzaldehyde, a well-known synthetic intermediate toward azo dyes and conjugated systems used in bioanalytical probes; however, the parent acetanilide aldehyde itself is primarily a laboratory building block.
  • Aromatic imines derived from this aldehyde can chelate transition metals to form complexes used as model systems in metalloenzyme mimics and catalytic studies (research context only).

No approved nutritional, metabolic, or therapeutic function is associated with this material. For work involving biological systems, ensure appropriate purity, endotoxin control, and solvent removal as required by your application (user-defined), and confirm compatibility via small-scale tests.

Buffer Applications

Not typically applicable. 4‑Acetamidobenzaldehyde is a neutral organic building block and does not function as a classical buffering agent. If used in biochemical experiments, it is usually dissolved in an organic co‑solvent (e.g., DMSO, ethanol) and introduced into pre-made aqueous buffers selected for the biological system (e.g., phosphate, HEPES). Ensure solvent content remains low to avoid denaturation effects in proteins or cells.

Green Alternatives

Greener strategy focuses on solvent and reagent choices rather than replacing the substrate itself.

• Preferred solvents (relative to traditional options; literature):
  • Ethanol/i‑PrOH: renewable, low toxicity; effective for imine/Knoevenagel condensations, often with catalytic acid/base and molecular sieves
  • Water/ethanol mixtures: possible for some condensations using surfactants or phase-transfer catalysts
  • 2‑MeTHF or CPME: greener ethers vs. THF/Et2O; improved safety and ease of recovery in extractions/reactions
• Avoid/limit:
  • Chlorinated solvents (DCM, DCE) where feasible; replace with EtOAc or MeCN for comparable performance in many condensations
  • DMF/NMP due to reproductive toxicity concerns; use MeCN, propylene carbonate, or green alcohols when possible
• Reagent selection and catalysis:
  • Organocatalysts (piperidine, proline, ammonium salts) or heterogeneous acids/bases (Amberlyst, Mg–Al hydrotalcites) can replace strong mineral acids/bases
  • Reductive amination with NaBH(OAc)3 in greener alcohols or catalytic hydrogenation with recyclable Pd/C under H2 minimizes cyanide use
• Workup/waste minimization:
  • Employ solvent recycling (EtOH/MeCN), and use molecular sieves rather than azeotropic removal when energy savings are desired

Trade-offs: While green solvents may lengthen reaction times or alter selectivity, optimization (temperature, catalyst loading, water scavengers) typically restores performance with a reduced environmental footprint.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet.

General information (non-clinical, research/manufacturing context only):

• Role: synthetic intermediate for discovery chemistry; the acetanilide protects the aniline functionality during transformations, enabling route scouting for API candidates and advanced intermediates.
• Applications in process R&D (literature):
  • Reductive amination and imine chemistry to elaborate into benzylic amines common in drug-like scaffolds
  • Deprotection to p‑aminobenzaldehyde, then conversion to ureas, sulfonamides, or azo motifs
• Formulation note: If used to prepare research compounds for screening, dissolve in suitable volatile solvents and ensure complete removal by vacuum drying. Any use in regulated manufacturing would require specification alignment (identity, assay, impurities, residual solvents) and compliance with appropriate guidelines; this listing is for research use only, as stated by the manufacturer.

Physical Properties

Item-specific specifications (this product):

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

Literature/typical properties for 4-acetamidobenzaldehyde (informational only):

• Physical state: crystalline aromatic solid
• Acid–base behavior: weakly acidic amide N–H; aldehyde carbonyl undergoes typical Schiff base and acyl anion chemistry (no intrinsic pKa commonly reported; amide pKa of conjugate acid typically <1, N–H pKa often >15 in DMSO; literature)
• Solubility profile: sparingly soluble in water; soluble in polar organic solvents (e.g., ethanol, methanol, acetone, acetonitrile, DMF, DMSO, THF) and in chlorinated solvents; decreased solubility in nonpolar alkanes (literature, qualitative)
• Polarity/logP: aromatic amide plus aldehyde give moderate polarity; expected medium logP consistent with aryl amide aldehydes (literature, qualitative)
• UV–Vis: shows aromatic/amide π→π* near 200–230 nm and n→π* of carbonyls ~280–320 nm (literature, qualitative)

Practical handling notes (general):

• Aldehydes can slowly oxidize to acids in air; limiting headspace oxygen and moisture helps preserve analyte.
• For analytical purposes, record melting point/HRMS/1H-13C NMR for lot confirmation; obtain item-specific values from the CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Context for professional users:

• Grades and what they imply
  • Research/technical grade: suitable for general synthetic and analytical work; impurities may be higher than HPLC/ACS grades.
  • HPLC/GC grade (if offered): extra filtration and low UV background for chromatographic applications.
  • ACS/AR grade (if offered): conforms to reagent specifications for analytical use.
• For aldehyde building blocks, key quality attributes are:
  • Aldehyde content vs. carboxylic acid over-oxidation byproducts
  • Amide integrity (no hydrolysis to p‑aminobenzaldehyde or anilide cleavage)
  • Low residual solvents and low colored impurities (important for catalysis/ligand synthesis)
• Stabilization/packaging: This item is supplied argon charged, which helps suppress oxidative degradation of the aldehyde functionality.
• Recommended QC upon receipt/use (general guidance):
  • 1H NMR: diagnostic aldehyde proton ~9.7–10.0 ppm; amide NH ~9–10 ppm (solvent-dependent); aromatic protons 7–8 ppm
  • 13C NMR: aldehyde carbonyl ~190–195 ppm; amide carbonyl ~165–175 ppm
  • IR: strong C=O stretches (~1680–1720 cm⁻¹ for amide/aldehyde, solvent-dependent)

For lot-specific assay, residual solvent levels, metals, and UV cutoffs, consult the CoA/Spec Sheet; do not rely on generic values.

Reaction and Applications

As a para-acetanilide-substituted aromatic aldehyde, 4‑acetamidobenzaldehyde enables diverse C=N/C=C bond-forming and downstream transformations.

• Imine (Schiff base) formation (literature):
  • With primary amines, forms imines/azomethines; use acid catalysis (e.g., p‑TsOH) or molecular sieves. These ligands are common precursors to salen/salophen‑type metal complexes, organic dyes, and sensors.
• Reductive amination:
  • One-pot imine formation followed by NaBH3CN/NaBH(OAc)3 or catalytic hydrogenation affords benzylic amines; the amide protects the aniline para to the aldehyde, improving chemoselectivity.
• Knoevenagel/aldol-type condensations:
  • Reaction with active methylenes (malononitrile, cyanoacetic esters) under piperidine/Et3N in EtOH/MeCN gives arylidenes, useful in push–pull chromophores and heterocycle synthesis.
• Hydroxylamine/semicarbazide condensations:
  • Oxime/semicarbazone derivatives for characterization or as intermediates in Beckmann-like rearrangements.
• Reduction/oxidation manifolds:
  • Selective reduction of –CHO to benzyl alcohol (NaBH4) or to methyl (Wolff–Kishner/Clemmensen). Controlled oxidation to the corresponding acid (e.g., Ag2O, KMnO4) when desired.
• Amide deprotection:
  • Hydrolysis of the acetamide (acidic or basic, aqueous-organic) unveils p‑aminobenzaldehyde, a valuable intermediate for azo dyes, heterocycles, and ligands; sequence allows orthogonal manipulation of the aniline functionality.
• Cross-coupling on the ring:
  • Though deactivated, halogenated derivatives of this scaffold participate in Suzuki/Heck/Sonogashira; the parent compound can be elaborated after directed metallation strategies adjacent to deactivating groups (advanced, literature).

Practical tips: maintain low moisture for iminations; use inert atmosphere (argon) to limit aldehyde oxidation; monitor by TLC/HPLC due to potential formation of imine dimers under basic conditions.

Reaction Conditions

General literature guidance for common transformations with 4‑acetamidobenzaldehyde (optimize per substrate; values illustrative):

• Imine (Schiff base) formation

  • Solvent: toluene (Dean–Stark), MeOH/EtOH, or MeCN
  • Catalyst: p‑TsOH (1–5 mol%) or none with 3Å molecular sieves
  • Temperature/time: RT to reflux, 1–16 h; drive to completion by water removal
  • Notes: Use inert atmosphere to limit oxidation; monitor by TLC (vanillin/UV)

• Reductive amination

  • Solvent: MeOH, EtOH, DCE, or MeCN
  • Reagents: NaBH(OAc)3 (3–4 equiv) with AcOH (0.5–1 equiv) or H2 (1–3 bar)/Pd‑C (5–10 wt%)
  • Temperature: 0–25 °C (borohydride) or RT–40 °C (hydrogenation); 2–6 h typical

• Knoevenagel condensation (e.g., with malononitrile)

  • Solvent: EtOH or MeCN
  • Base: piperidine (10 mol%) or ammonium acetate (1–2 equiv)
  • Temperature/time: RT–78 °C, 0.5–6 h; often high E‑selectivity in arylidenes

• Oxime formation

  • Solvent: EtOH/H2O (4:1)
  • Reagents: NH2OH·HCl (1.2–1.5 equiv), NaOAc (1.5–2 equiv)
  • Temperature: RT–60 °C, 1–3 h

• Amide deprotection

  • Acidic: 6 M HCl, reflux, hours; or H2SO4/EtOH aqueous
  • Basic: NaOH (aq)/EtOH, reflux; monitor for aldehyde stability; protect –CHO if necessary (acetalization with ethylene glycol/p‑TsOH)

These conditions are representative literature practices and not product specifications. Validate on small scale before scale-up.

Safety and Handling

Item-specific hazard data:

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification/Pictograms: Not specified for this item; refer to SDS.

General safety information for aromatic aldehydes/anilide amides (literature/good practice):

• Likely hazards: irritation to skin/eyes/respiratory tract; aldehydes may be sensitizers for some users. Avoid dust formation and inhalation.
• PPE: lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid exposure to vapors/dust.
• Handling: minimize exposure to air and moisture to limit aldehyde oxidation. Keep containers tightly closed under inert gas as indicated for this item.
• Incompatibilities: strong oxidizers (may over-oxidize the aldehyde), strong bases (can promote condensation/polymerization), strong acids (can catalyze self‑condensation/imine formation with amines). Avoid reactive reducing agents unless intended.
• First aid (overview; consult SDS): move to fresh air if inhaled; rinse skin/eyes with water for at least 15 minutes upon contact; seek medical attention if symptoms persist. If ingested, rinse mouth; do not induce vomiting—get medical attention.
• Spills/leaks: avoid dust; sweep up into suitable container; wash spill area with mild detergent; ventilate area.
• Fire: use CO2, dry chemical, or foam. Combustion may form CO/CO2 and nitrogen oxides.

Always consult the product SDS for authoritative safety and regulatory details.

Solvent Selection

Selection guidance for 4-acetamidobenzaldehyde (solid building block with moderate polarity):

• Polarity/miscibility (literature, qualitative):
  • Readily soluble: DMSO, DMF, NMP, acetonitrile, acetone, ethanol, methanol, THF, dichloromethane, ethyl acetate
  • Limited solubility: water, alkanes (hexanes, heptane)
  • Dielectric context: prefer polar aprotic or protic solvents that can solvate the amide and aldehyde functions while supporting target reaction (e.g., imine formation, condensations)
• When to choose which solvent:
  • Imine/Schiff bases with amines: toluene or benzene with Dean–Stark, or MeOH/EtOH with molecular sieves; acetonitrile for room‑temp iminations
  • Knoevenagel condensations: EtOH, MeOH, or acetonitrile with secondary amine base (e.g., piperidine)
  • Reductive amination: MeOH/EtOH/i-PrOH or DCE/MeCN with NaBH(OAc)3 or H2/Pd
  • Electrophilic aromatic substitution (on ring is deactivated by –CHO/–CONHAc): use polar solvents and stronger catalysts if attempted
• Small comparison (literature, general):
  • EtOH: green, supports condensations; may form acetals/imines—monitor
  • MeCN: polar aprotic, clean workups; low boiling
  • DMSO/DMF: excellent solubility; challenging removal; reserve for difficult dissolutions
  • DCM/EtOAc: fast reactions; easier removal; consider sustainability and safety

Drying note: Water suppresses imine/condensation equilibria; pre-dry solvents or employ sieves as needed.

Storage and Reconstitution

Item-specific storage/shipping (from Product Data):

• Storage Conditions: Room temperature, Argon charged
• Shipped In: Normal

General best practices for this class of aldehydes:

• Store tightly closed under inert gas (argon or nitrogen) in a dry place, away from light and moisture to minimize oxidation of the aldehyde to the corresponding acid.
• If frequent access is expected, consider aliquoting to reduce headspace oxygen exposure. Include a desiccant in secondary containment when appropriate.
• Reconstitution/solubility (literature, qualitative): readily dissolves in DMSO, DMF, MeCN, acetone, EtOH/MeOH, THF, DCM, and EtOAc; sparingly soluble in water. Warm gently if needed; avoid prolonged heating.
• Stability notes: Avoid strong acids/bases during storage. For long-term storage, maintaining an inert atmosphere and low humidity is more critical than refrigeration for this substrate.

Always consult the SDS and CoA/Spec Sheet for lot-specific stability, impurity profiles, and any additional handling precautions.

Research Use Only: As stated by the manufacturer, this product is for research use only.

Structure and Identity

Brief overview: 4-Acetamidobenzaldehyde is a para-substituted aromatic aldehyde bearing an acetanilide (acetamido) group opposite an aldehyde on a benzene ring; a versatile building block for imine/Schiff base chemistry and downstream heterocycles.

• Item-specific (from Product Data)
  • CAS: 122-85-0
  • CID: 73942
  • InChIKey: 338317 (as provided)
  • Storage note: Room temperature, Argon charged
• Literature/computed identifiers and features (informational; not item-specific specs)
  • Common name: 4-(Acetamido)benzaldehyde; p-Acetamidobenzaldehyde
  • Molecular formula: C9H9NO2 (literature)
  • Molecular weight: ~163.17 g/mol (literature)
  • SMILES: CC(=O)NC1=CC=C(C=C1)C=O (literature)
  • Key functional groups: aromatic aldehyde (–CHO), acetanilide amide (–NH–C(=O)–CH3)
  • Substitution pattern: para (1,4-) relationship between –CHO and –NHCOCH3 on benzene
  • Structural description (2D): A benzene ring bearing an aldehyde at C1 and an acetamido at C4; the amide N is directly attached to the ring (anilide), conferring conjugation across the ring–amide–carbonyl system.
• Stereochemistry: None (achiral, planar aromatic core)

Note: For authoritative identifiers tied to your specific lot, refer to the CoA/Spec Sheet.

Synthetic Utility

Key functional elements and their implications:

• Aldehyde (–CHO)
  • Electrophile for imine (Schiff base) formation with primary amines; oxime/semicarbazone formation with hydroxylamine/semicarbazide
  • Engages in Knoevenagel condensations with active methylene compounds; provides access to styryl/arylidenes used in chromophores and Michael acceptors
  • Can be selectively reduced (NaBH4) or homologated (e.g., Wittig/Horner–Wadsworth–Emmons) to alkenes with defined geometry
• Acetanilide (–NH–C(=O)–CH3)
  • Serves as a protecting group for an aniline; deprotects under acidic or basic hydrolysis to reveal –NH2 para to the aldehyde, enabling orthogonal downstream diversification (diazotization, coupling, sulfonylation)
  • Electron-withdrawing through resonance/induction, deactivating the ring toward EAS and influencing regioselectivity in metalation or cross-coupling (after pre-halogenation)

Retrosynthetic value:

• The scaffold can be traced back to p‑aminobenzaldehyde via acetylation, or to p‑hydroxybenzaldehyde via nucleophilic aromatic substitution/Smiles rearrangements in some routes (literature, advanced).

Named/typical tactics (literature):

• Schiff base, Knoevenagel, Wittig/HWE, reductive amination, oxime/semicarbazone formation, and amide hydrolysis. Combine with orthogonal protecting groups for multi-step sequences with minimal functional group interference.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity applies.