2-Naphthaleneacetamide - ≥95% , CAS No.36660-46-5

CAS: 36660-46-5 Cat. No.: N1064668 Formula: C₁₂H₁₁NO Peso molecolare: 185.220 Numero EC: 830-939-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1=CC=C2C=C(C=CC2=C1)CC(=O)N
• IUPAC Name: 2-naphthalen-2-ylacetamide
• InChIKey: LVYUDSCQJGQXBI-UHFFFAOYSA-N
• INCHI: 1S/C12H11NO/c13-12(14)8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7H,8H2,(H2,13,14)
• Peso molecolare: 185.220

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Naphthalenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Naphthalenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthalenes
• Alternative Parents: Primary carboxylic acid amides Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthalene - Primary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 185.220 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 185.084 Da
• Monoisotopic Mass: 185.084 Da
• Topological Polar Surface Area: 43.100 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 214.000
• 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

Application Protocols

Not applicable as standardized bioassay protocols (WB, IHC, IF, FC) do not pertain to this small-molecule building block. For synthetic use:

• Example stock solution preparation (general): dissolve in dry DMSO or DMF to 10–100 mM, filter (0.22 μm PTFE), and store small aliquots.
• Reaction setup: dry glassware, inert atmosphere if moisture-sensitive reagents are involved; choose solvent according to section “Solvent Selection.”

These are general laboratory practices and not item-specific validated protocols.

Biological Roles

This product is a synthetic aromatic amide used as a chemical building block. It is not a known endogenous metabolite or cofactor.

• Applicability

  • No specific biochemical role is established for 2-naphthaleneacetamide in natural systems (literature/general). Any biological interactions would arise from generic amide functionality and aromatic stacking rather than defined pathway roles.

• Practical lab context

  • If used in biochemical assays, it typically serves as a scaffold for SAR exploration rather than as a biological reagent per se.

• Safety

  • Do not use for diagnostic or therapeutic purposes. Research use only, as stated in Product Data.

For information on biological effects of particular derivatives or conjugates prepared from this scaffold, consult the primary literature; such properties are not intrinsic to the parent amide.

Buffer Applications

Not typically applicable. 2-Naphthaleneacetamide is a neutral organic solid used as a synthetic building block and does not function as a buffering agent. For solution-phase studies (e.g., analytical HPLC), prepare stock solutions in DMSO or DMF and dilute into the assay buffer as needed, verifying solubility and avoiding precipitation.

Green Alternatives

While 2-naphthaleneacetamide itself is a substrate rather than a solvent or reagent of concern, greener choices can be made for solvents and auxiliaries used with it.

• Greener solvent choices (literature/general)

  • Replace DMF/DMAc/NMP with safer polar aprotics when feasible: Cyrene, propylene carbonate, sulfolane (with caution), or acetonitrile/ethanol mixtures depending on reaction.
  • For extractions and chromatography, consider EtOAc/MeOH over chlorinated solvents; supercritical CO2 or greener reverse-phase methods can reduce solvent usage.

• Comparison (general guidance)

  • Traditional: DMF (reprotoxic), DCM (halogenated waste), NMP (SVHC in EU).
  • Greener: 2-MeTHF or CPME for medium-polarity needs; EtOAc or alcohols for many workups; water/ethanol blends for recrystallization when solubility permits.

• Reagent selection

  • Coupling: EDC/HOBt alternatives like COMU or OxymaPure reduce hazardous byproducts; avoid HOBt/HOAt dry solids due to explosivity concerns.
  • Bases: use carbonate bases instead of strong alkoxides where possible; employ catalytic DMAP rather than stoichiometric pyridine.

• Process considerations

  • Telescoping steps to avoid isolating intermediates; apply solubility-driven crystallizations to minimize chromatographic silica waste.

These are general green chemistry suggestions; validate compatibility with this substrate’s solubility and stability profile.

Pharmaceutical Uses

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

• General formulation context (no therapeutic claims)

  • As a small aromatic amide scaffold, 2-naphthaleneacetamide may be evaluated in discovery as a core structure for lead development or as an intermediate toward more complex candidates. The parent compound itself is not an established excipient.
  • If incorporated into screening libraries, typical considerations include solubility (use DMSO stock solutions), stability (amide generally robust), and analytical characterization (HPLC-UV due to strong naphthalene chromophore).

• Manufacturing/analytical notes

  • Ensure identity by orthogonal methods (1H/13C NMR, HRMS, IR amide bands ~1650 cm−1, literature/general). Residual solvent and purity should meet internal research specifications for use in pre-formulation studies.

Physical Properties

• Item-specific specifications

  • Appearance: 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 reference values (for context; not item-specific)

  • Expected physical state: crystalline aromatic amide (solid) at ambient conditions.
  • Approximate molecular formula and mass: C12H11NO; MW ~185.22 g/mol (literature).
  • Polarity/functional group: primary amide with hydrogen-bond donor and acceptor capability; benzylic methylene adjacent to carbonyl; hydrophobic aromatic core.
  • Solubility profile (qualitative): sparingly soluble in water typical of naphthalene amides; soluble in polar aprotic organic solvents (e.g., DMF, DMSO) and moderately soluble in alcohols; limited solubility in nonpolar hydrocarbons due to amide polarity (literature trends for arylacetamides).
  • Acid/base: largely neutral; amide pKa (conjugate acid) typically around −1 to 0; amide N–H pKa (in DMSO) typically >15 (literature generalization for primary amides).
  • Lipophilicity: logP expected in low-to-moderate range for aryl amides due to balance of aromatic core and amide polarity (literature trend).

• Refractive index, melting/boiling point, density, UV cutoff: Not specified for this item; for exact values, consult CoA/Spec Sheet and SDS. Avoid relying on unverified numeric data in critical applications.

Quality and Grades

• Item-specific quality information

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

• General guidance on quality for aromatic amide building blocks

  • Research grade material is typically suitable for synthetic, screening, and materials science workflows. If sensitive downstream steps (e.g., catalytic couplings, photophysical measurements) are planned, verify metal content, residual solvents, and water content on the CoA.
  • For chromatographic or spectroscopic work, impurities such as unreacted acid/acid chloride or naphthalene-type aromatics can influence UV baselines and fluorescence; HPLC or NMR purity confirmation is recommended.
  • If “high purity” or “>98%” claims are needed for regulated or analytical applications, require batch-specific CoA detailing assay, residual solvents (GC), and identity (1H NMR/IR/MS). UV cutoff and trace metals: Not specified for this item; refer to CoA/Spec Sheet.

• Practical notes

  • Amide solids can retain solvent in the lattice; gentle drying (vacuum, ambient temperature) before use can improve reproducibility.
  • If the item is offered unstabilized, store dry and closed at room temperature as provided; no peroxide-forming risk is expected for amides.

Reaction and Applications

• Typical roles in synthesis (literature/general)

  • Building block for derivatization at the amide nitrogen: N-acylation, N-alkylation (under strong base), sulfonylation to install protective or functional groups.
  • Transformations at the benzylic position: oxidation to the corresponding acylamides, halogenation (NBS) at benzylic site, or homologation strategies.
  • Amide activation to acids/esters/amines: hydrolysis to 2-naphthaleneacetic acid (acidic or basic conditions), Curtius/Hofmann-type rearrangements from related acyl precursors enabling amine access in stepwise sequences.
  • Cross-coupling after functionalization: install halogens or boronates on the aromatic ring followed by Suzuki, Buchwald–Hartwig (after conversion to amine), or other Pd-catalyzed couplings.
  • Directed metalation: the amide can serve as a weak directing group for ortho-lithiation on suitably substituted systems; though here the benzylic linker reduces classical DG proximity—auxiliary installation may be preferred.

• Practical laboratory tips

  • Drying: although amides are less hygroscopic than acids or amines, dry under vacuum before moisture-sensitive reactions (e.g., acylation with acid chlorides, CDI-mediated couplings).
  • Protection strategies: convert to N-Boc or N-acyl derivatives to modulate solubility and reactivity; for late-stage diversification, use mild peptide-coupling reagents (HATU/EDC) if coupling the amide nitrogen to electrophiles.
  • Analytics: strong UV at ~220–280 nm due to naphthalene; monitor reactions by HPLC/UPLC-UV.

• Application domains

  • Useful as an intermediate in materials and small-molecule discovery programs where an aromatic amide handle enables library diversification of naphthalene-containing scaffolds.

Reaction Conditions

General guidance for common transformations of arylacetamide scaffolds (literature; adjust to your system):

• Hydrolysis to 2-naphthaleneacetic acid

  • Conditions: aq. NaOH (2–5 M), reflux in EtOH/H2O or dioxane/H2O, 2–12 h; acidic workup to precipitate acid. Alternatively, acid-catalyzed (6 M HCl, reflux) for similar timescales.

• Dehydration to 2-naphthylacetonitrile

  • Reagents: POCl3 or SOCl2 (3–5 equiv) with base (pyridine or Et3N); solvent DCM or toluene; 0–25 C addition, then 60–100 C for 2–6 h.

• Benzylic bromination

  • Reagents: NBS (1.1–1.5 equiv), AIBN or light; solvent CCl4, DCE, or PhMe; reflux or hv; 2–4 h; monitor by TLC/HPLC.

• N-acylation/N-sulfonylation

  • Base: pyridine, Et3N, or NaH (for less reactive electrophiles). Solvent: DCM, DMF, or THF. Temperature: 0–25 C; 1–12 h. Use catalytic DMAP for acylations.

• Reduction to amine

  • BH3·THF (1–3 M) or borane–dimethylsulfide, 3–6 equiv; reflux in THF, 4–16 h; quench cautiously. Alternatively, catalytic hydrogenation after conversion to imidate/oxazoline derivatives.

• Analytical monitoring

  • Strong UV absorption 220–280 nm; use HPLC or UPLC with ACN/H2O + 0.1% TFA/FA for rapid tracking.

These conditions are literature-style starting points and not item-specific specifications. Optimize for scale, solvent sustainability, and safety.

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 considerations for aromatic primary amides (literature/general guidance)

  • Expected hazards: low-to-moderate acute toxicity; may cause skin/eye irritation; dust may be irritating to respiratory tract. Avoid ingestion and inhalation of dust.
  • PPE: use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to minimize dust exposure.
  • Incompatibilities: strong oxidizers; strong acids/bases may hydrolyze the amide under forcing conditions. Avoid contact with acyl-activating reagents unless intentionally reacting.
  • Thermal stability: amides are generally thermally stable; avoid overheating to decomposition. Combustible organic solid—keep away from ignition sources.
  • First aid (overview; defer to SDS):
    • Inhalation: move to fresh air; seek medical attention if symptoms persist.
    • Skin contact: wash with soap and water; remove contaminated clothing.
    • Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
  • Waste: dispose according to local regulations for organic laboratory solids; avoid release to the environment.

• Always consult the product-specific SDS for authoritative hazard classification and response procedures.

Solvent Selection

This compound is a neutral aromatic primary amide with a hydrophobic naphthalene core and a polar –CONH2 group, leading to amphiphilic behavior.

• Miscibility/solubility trends (literature/general)

  • Water: typically low solubility for arylacetamides with fused aromatics.
  • Polar aprotic: good solubility in DMF, DMSO, NMP, and often in acetone/MeCN upon warming.
  • Alcohols: moderate solubility in MeOH/EtOH; improved with mild heating.
  • Nonpolar solvents (toluene, hexanes): limited due to amide polarity; toluene may be viable at elevated temperatures.

• Selection guidance by task

  • Reaction medium: choose polar aprotic solvents (DMF, DMSO, DMAc, NMP) for coupling or N-derivatization; for electrophilic aromatic substitution on the ring, use chlorinated aromatics (DCE) or nitrobenzene if high temperatures are needed.
  • Purification: normal-phase silica gel chromatography using EtOAc/hexane or DCM/MeOH gradients typically separates amides from nonpolar byproducts; reverse-phase (C18, ACN/H2O + 0.1% acid) can aid with closely related aromatics.
  • Analytical: DMSO-d6 or CD3OD recommended for NMR if solubility in CDCl3 is insufficient; UV detection works well due to naphthalene chromophore.

• Comparison notes

  • Compared with aliphatic amides, aryl-fused systems are less water-soluble but offer stronger UV absorbance; compared with carboxylic acids, amides elute later on normal-phase and are less reactive.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (per Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General handling

  • Keep container tightly closed in a dry, well-ventilated place; protect from prolonged light and heat. Use desiccant if ambient humidity is high.
  • For solution stocks: prepare in dry DMSO or DMF (typical 10–100 mM), dispense into inert-atmosphere vials or tightly sealed microtubes, and store at 2–8 C or −20 C to prolong stability. Allow to reach room temperature before opening to minimize moisture ingress.
  • Avoid repeated freeze–thaw of solution stocks; aliquot as needed.

• Reconstitution (if supplied as a solid)

  • Choose solvent based on application: DMSO/DMF for maximum solubility; warm ethanol or isopropanol for less polar matrices. Sonication and mild heating (≤40 C) may aid dissolution.

For any lot-specific stability, hygroscopicity, or solution shelf-life data, consult the CoA/Spec Sheet and SDS.

Structure and Identity

Brief description: 2-Naphthaleneacetamide is an aromatic amide consisting of a naphthalene ring substituted at the 2-position with a –CH2–CONH2 acetamide side chain.

• Item-specific identifiers (from Product Data)

  • SKU: N1064668
  • CAS: 36660-46-5
  • Category Path: 全部 / 可售 / 生命科学
  • InChIKey: 210620 (as provided; note: this string is not in standard InChIKey format)
  • Storage Conditions: Room temperature
  • Research Use Note: For research use only

• Literature/structural identifiers (general reference; not item-specific)

  • Preferred name: 2-Naphthaleneacetamide (aka 2-(naphthalen-2-yl)acetamide)
  • Molecular formula (literature): C12H11NO
  • Molecular weight (literature): ~185.22 g/mol
  • SMILES (literature): NC(=O)Cc1ccc2ccccc2c1
  • Core structural features: polycyclic aromatic hydrocarbon (naphthalene) fused bicyclic ring; benzylic methylene linking to a primary amide (–CONH2); planar aromatic system; no stereocenters.
  • 2D structure in words: a naphthalene ring (two fused benzene rings) bearing at the 2-position a –CH2–C(=O)–NH2 substituent; amide carbonyl is conjugated through the benzylic methylene to the aromatic system.

• Notes

  • Any definitive structural identifiers for this specific lot/item should be confirmed on the CoA/Spec Sheet.

Synthetic Utility

• Functional group reactivity

  • Primary amide enables transformations to acids (hydrolysis), nitriles (dehydration, e.g., SOCl2, POCl3), amines (via reduction, e.g., borane or catalytic hydrogenation of related derivatives), and imidates (Pinner-type from activated precursors). Benzylic position adjacent to the aromatic ring allows selective functionalization (e.g., radical bromination with NBS).

• Strategic roles

  • Protecting/anchoring group: amide can serve as a stable handle during multi-step sequences on the naphthalene ring; later conversion to acid or amine broadens exit vectors.
  • Diversification: N-acyl, N-sulfonyl, and N-alkyl derivatives modulate electronics and solubility; ring functionalization via electrophilic substitution or cross-coupling after preactivation extends chemical space.
  • Photophysical tag: naphthalene core provides UV activity aiding reaction monitoring and purification.

• Retrosynthetic value

  • Access from 2-naphthaleneacetic acid via coupling (amide formation) or from 2-naphthylacetonitrile via hydration; conversely, it is a precursor to those functionalities for downstream elaboration.

• Representative named methods (literature/general)

  • Amide coupling: EDCI/HOBt, HATU, or mixed anhydrides from 2-naphthaleneacetic acid.
  • Dehydration to nitrile: Burgess reagent, POCl3, SOCl2 with base.
  • Reduction: amide to amine with BH3·THF; to alcohol via hydrosilylation–hydrolysis sequences (after conversion).

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, enzyme, or ligand with defined selectivity). No antigen/epitope/clone information is associated with this item.