2'-Methoxy-1'-acetonaphthone - ≥98% , CAS No.5672-94-6

CAS: 5672-94-6 Cat. No.: M404662 Fórmula: C₁₃H₁₂O₂ Peso molecular: 200.24 Número CE: 828-936-2

GRADE & PURITY ≥98%

Synonyms

MFCD11553477 | 1-(2-Methoxy-naphthalen-1-yl)ethanone | 1-(2-methoxynaphthalen-1-yl)ethanone | T72632 | EN300-1830002 | 2'-Methoxy-1'-acetonaphthone | 2-Methoxy-1-acetonaphthone | M2875 | 1-(2-methoxy-1-naphthyl)ethanone | Ethanone, 1-(2-methoxy-1-naphthal

Storage

Room temperature

Specifications

Sinónimos

MFCD11553477 | 1-(2-Methoxy-naphthalen-1-yl)ethanone | 1-(2-methoxynaphthalen-1-yl)ethanone | T72632 | EN300-1830002 | 2'-Methoxy-1'-acetonaphthone | 2-Methoxy-1-acetonaphthone | M2875 | 1-(2-methoxy-1-naphthyl)ethanone | Ethanone, 1-(2-methoxy-1-naphthal

Especificações e pureza

≥98%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥98%

Nomes e identificadores

Pubchem Sid

488189881

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488189881

Sorrisos canónicos

CC(=O)C1=C(C=CC2=CC=CC=C21)OC

IUPAC Name

1-(2-methoxynaphthalen-1-yl)ethanone

InChIKey

WFBBDKXOGOJOKY-UHFFFAOYSA-N

INCHI

1S/C13H12O2/c1-9(14)13-11-6-4-3-5-10(11)7-8-12(13)15-2/h3-8H,1-2H3

SMILES isoméricas

CC(=O)C1=C(C=CC2=CC=CC=C21)OC

Peso molecular

200.24

Reaxy-Rn

1874220

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1874220&ln=

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: Acetophenones Aryl alkyl ketones Anisoles Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthalene - Acetophenone - Aryl alkyl ketone - Aryl ketone - Anisole - Alkyl aryl ether - Ketone - Ether - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homopolycyclic compound
• Descrição: 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

Propriedades químicas e físicas

• Solubilidade: Soluble in Toluene
• Ponto de ebulição (°C): 158 °C/2 mmHg
• Ponto de fusão (°C): 58 °C
• Peso molecular: 200.230 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 200.084 Da
• Monoisotopic Mass: 200.084 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 237.000
• 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. No validated bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic procedures involving this compound, refer to the Reaction Conditions and Application notes in other sections.

Biological Roles

This material is a synthetic aromatic ketone used as a chemical building block. It does not have a recognized endogenous biological role.

General/literature context (non-clinical):

• Naphthalene derivatives can exhibit notable photophysical behavior (π–π* transitions), and methoxy substitution typically red-shifts absorption; such fragments may serve as scaffolds in fluorescent probe development, though this item is supplied strictly for research and synthesis.
• Aryl methyl ketones can act as enzyme substrates or inhibitors in mechanistic model studies after further derivatization (e.g., as propargylated or halogenated analogs), but no target specificity is implied for this compound.
• Metabolism (conceptual): if introduced into biological systems, aryl ketones often undergo phase I oxidation (benzylic/aryl hydroxylation) and O‑dealkylation of methoxy groups to phenols, followed by phase II conjugation (glucuronidation/sulfation). These are general biotransformation themes from the literature and not specific to this product.

Summary: use in biochemistry would be as a synthetic intermediate or hydrophobic chromophore fragment rather than as a buffer component, nutrient, or cofactor.

Buffer Applications

Not typically applicable. 2'-Methoxy-1'-acetonaphthone is a hydrophobic aromatic ketone and is not used to formulate aqueous buffer systems. For experimental work requiring aqueous media, dissolve first in a compatible co-solvent (e.g., DMSO, ethanol) and then dilute into buffer if the chemistry tolerates it.

Green Alternatives

While the compound itself is a specialty building block, greener choices primarily concern solvents and reagents used with it.

Greener solvent swaps (literature guidance):

• Replace dichloromethane/chloroform with ethyl acetate, 2‑MeTHF, CPME, or toluene where feasible (workup and chromatography often benefit).
• For enolate chemistry, 2‑MeTHF or CPME can substitute for THF, offering higher boiling points and improved safety; ensure base compatibility.
• For nitration/sulfonation or other EAS, consider acetic acid or propylene carbonate instead of nitrobenzene where reaction scope allows.

Reagent considerations:

• Oxidations: use greener oxidants (Oxone, H2O2 with catalysts) instead of stoichiometric peracids or Cr(VI) reagents.
• Reductions: NaBH4 in green solvents (EtOH, 2‑PrOH) or catalytic hydrogenation over Raney Ni/Pd with ethanol as solvent.

Trade-offs (typical):

• 2‑MeTHF: better safety/renewable source, but water content can be higher; dry thoroughly for enolate steps.
• EtOAc: greener but less dissolving power than DCM; may need larger volumes or modest heating.
• H2O2-based oxidations: safer byproducts (water), but may require catalysts and careful control to avoid overoxidation.

Always validate on small scale; these are literature-based suggestions, not product specifications.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item. It is supplied for research use only.

General formulation context (literature; not product-specific claims):

• Aromatic ketone fragments like acetylnaphthalenes can appear in discovery-stage intermediates. When handled in formulation labs for screening, they are typically dissolved in DMSO or ethanol stocks for in vitro assays.
• Solid-state screening (if applicable) may include co-crystallization with benign coformers for property tuning; however, no such data are specified here.

Do not use in human or veterinary applications. No clinical or therapeutic claims are made or implied.

Physical Properties

Item-specific (from Product Data):

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

Literature/computed (general guidance; not product specifications):

• Physical state: aryl methyl ketones of this class are typically low-melting solids or high-boiling liquids.
• Volatility: low; aromatic ketones exhibit modest vapor pressure at ambient conditions.
• Polarity: moderately polar (due to the carbonyl), with enhanced lipophilicity from the naphthalene core; methoxy increases polarity slightly and can raise solubility in medium-polar organic solvents.
• Solubility profile (qualitative):
  • Good solubility in aromatic (toluene), chlorinated (DCM, CHCl3), and etheric solvents (THF, MTBE); limited in aliphatic hexanes; negligible in water.
• UV/Vis: naphthalene chromophore and aryl ketone typically absorb in the near-UV; methoxy substitution bathochromically shifts λmax (literature trend). Exact cutoff/ε: Not specified for this item.
• Acid/base: neutral; the benzylic α-protons (to the carbonyl) are mildly acidic and can form enolates under basic conditions (literature).
• Any exact numerical values (mp, bp, density, refractive index, logP, pKa) for this specific CAS: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

Item-specific (from Product Data):

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

General guidance:

• Without a stated grade (e.g., AR, Puriss, HPLC), assume standard research-grade material. For trace-analytics or photophysical studies, request a CoA with detailed impurity profile (e.g., GC/HPLC area %, residual solvents, and water content) before use.
• If offered as “high-purity” or “HPLC grade” in other contexts: such designations typically imply low UV-absorbing impurities and stringent control of residual solvents and metals. However, no such claims are made here.
• Stabilizers/inhibitors: None are listed in the Product Data. If inhibitor use is critical for your application (e.g., to prevent photooxidation), verify on the CoA. Do not assume the presence or absence of stabilizers.
• Batch qualification: For sensitive applications (photochemistry, catalysis), consider quick incoming QC: 1H/13C NMR, HPLC purity, HRMS, and melting range (if solid). IR can confirm the aryl ketone C=O near ~1680–1710 cm−1 (literature, not a spec).
• If your method is moisture- or base-sensitive (e.g., enolate chemistry), assess acid/base impurities by simple titration or by running a small-scale test reaction before committing material.

Reaction and Applications

This substrate features an aryl methyl ketone adjacent to a methoxy-substituted naphthalene, enabling diverse transformations.

Representative application families (literature; examples, not exhaustive):

• α‑Functionalization of the aryl methyl ketone:
  • Halogenation (NBS/NCS) at the benzylic position under acid or radical conditions.
  • Enolate alkylation or aldol-type condensations using LDA/NaHMDS in dry THF at −78 to 0 °C.
• Oxidations and reductions:
  • Baeyer–Villiger oxidation of the aryl ketone to the corresponding naphthyl acetate ester (peracids or mCPBA).
  • Selective reduction to the secondary alcohol (NaBH4, DIBAL‑H), preserving the methoxy group.
• Electrophilic aromatic substitution (EAS): methoxy directs strongly; acyl group is deactivating/meta-directing. Net regiochemistry arises from the balance of these groups on the naphthalene ring.
• Cross-coupling after halogenation: install Br/Cl via directed lithiation–quench or EAS halogenation, then engage in Suzuki/Miyaura or Buchwald–Hartwig steps on suitably functionalized derivatives.
• Photochemistry: aryl ketones undergo Norrish pathways under UV; methoxy substitution and naphthalene ring can tune triplet energies (use care if avoiding photoreactions).

Use cases:

• Intermediate for dye and OLED fragment synthesis (naphthalene chromophore).
• Precursor to ortho‑acylated anisole-type ligands and building blocks for polyaryl construction.
• Probe substrate to study directing effects (ortho‑methoxy vs acyl) on naphthalene substitution.

Reaction Conditions

General literature guidance (not product specifications; optimize for your substrate and scale):

• Enolate formation/alkylation: LDA (1.1–1.5 equiv) in dry THF at −78 to −20 °C; quench with primary alkyl halides or electrophiles (MeI, allyl bromide, aldehydes for aldol). Typical times 0.5–2 h; monitor by TLC/GC.
• α‑Halogenation: NBS or NCS (1.0–1.2 equiv) in MeCN, DCM, or CCl4 with or without radical initiator (AIBN) at 0–25 °C; expect rapid reaction; control temperature to minimize polyhalogenation.
• Reduction to secondary alcohol: NaBH4 (1.5–3.0 equiv) in MeOH/EtOH at 0–25 °C, 0.5–2 h; or DIBAL‑H in toluene at −78 to −40 °C for more chemoselective reductions.
• Baeyer–Villiger oxidation: mCPBA (1.2–1.5 equiv) in DCM at 0–25 °C, 2–16 h; buffers (NaHCO3) help neutralize acids; catalytic systems with H2O2 and Sn/Se or organocatalysts are greener alternatives.
• Electrophilic substitution: nitration/sulfonation typically requires controlled acidic media; solvent choices include AcOH, DCM, or nitromethane; maintain low temperatures to preserve regioselectivity.
• Demethylation (if desired): BBr3 (1–3 equiv) in DCM at −78 to 0 °C, 1–4 h, affording the phenolic analog; quench cautiously with MeOH/water.

Workup/purification:

• Typical aqueous quench, extraction with EtOAc or DCM, wash, dry (Na2SO4/MgSO4), and silica gel chromatography (hexanes/EtOAc gradient).
• Protect from strong UV during reactions when photoreactivity could complicate purity.

Yields: vary widely (40–90%) depending on transformation and substitution pattern (literature ranges).

Safety and Handling

Item-specific (from Product Data):

• Storage conditions: Room temperature
• GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.

General safety considerations for aryl methyl ketones and anisole derivatives (literature; not product-specific classifications):

• Likely hazards: may cause skin/eye irritation and respiratory irritation upon dust or vapor exposure. Avoid inhalation of dust and contact with skin/eyes.
• PPE: lab coat, nitrile gloves, safety glasses or face shield. Use in a chemical fume hood to minimize inhalation.
• Incompatibilities: strong oxidizers (risk of exotherm/oxidation), strong bases in presence of air (possible side reactions), strong reducing agents; avoid prolonged exposure to strong acids that may catalyze demethylation.
• Reactivity notes: benzylic (α to carbonyl) positions are susceptible to base-catalyzed enolization/halogenation; methoxy-substituted aromatics may undergo electrophilic substitution under Lewis/Brønsted acid catalysis.
• Thermal/photochemical behavior: aryl ketones can participate in photochemical reactions (n→π*, π→π*) under UV; protect from intense UV if purity is critical.
• First aid (overview; follow institutional protocol): move to fresh air if inhaled; rinse eyes cautiously with water for several minutes; wash skin with soap and water; seek medical attention if symptoms persist.
• Waste: collect as halogen-free organic waste unless your procedure adds halogenated solvents; follow local regulations.
• Always consult the SDS for authoritative hazard classification and response measures.

Solvent Selection

Applicability: as an aromatic methyl ketone with a methoxy substituent, this compound dissolves best in medium-polar organic solvents.

General solvent guidance (literature; not product specifications):

• Good solvents: dichloromethane, chloroform, THF, 2-MeTHF, ethyl acetate, acetone, acetonitrile, toluene.
• Limited solubility: alkanes (hexanes/heptane), especially at room temperature.
• Aqueous solubility: expected to be very low.

Choosing solvents by operation:

• Chromatography: start with hexanes/ethyl acetate (gradient); for very lipophilic behavior, add toluene or dichloromethane to improve elution and band shape.
• Crystallization: toluene, ethanol, or isopropanol mixed with a poorer solvent (hexanes) are typical systems; screen small-scale first.
• Reactions:
  • Electrophilic aromatic substitution: use nitrobenzene, DCM, or acetic acid depending on conditions; methoxy group is activating and ortho/para-directing relative to itself.
  • Enolate/α-functionalization: use dry THF, DME, or toluene with LDA or alkoxides; maintain rigorously anhydrous conditions.
• Spectroscopy: CDCl3 for NMR is conventional; DMSO‑d6 if solubility is limited.

Small comparison (literature trends):

• DCM vs EtOAc: DCM offers higher solubility and faster chromatography but is less green; EtOAc is greener and often sufficient.
• THF vs 2‑MeTHF: 2‑MeTHF gives similar polarity with improved safety/greenness and easier phase separations.

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:

• Keep container tightly closed in a dry, well-ventilated place. Reseal carefully under inert gas if long-term storage is planned, especially if frequent exposure to air/moisture is expected during use.
• Protect from strong light/UV to minimize potential photochemical changes typical of aryl ketones.
• If the material is a solid, minimize clumping by storing in a cool, dry environment and warming to ambient before opening to avoid condensation. If a liquid, check for crystallization on cold days and gently warm to redissolve if needed.
• Reconstitution/stock solutions: prepare concentrated stocks in dry DCM, THF, toluene, acetone, acetonitrile, ethanol, or DMSO as compatible with your application. Filter through a PTFE syringe filter (0.2 µm) if particulate is present.
• Stability: No specific shelf-life data are provided for this item; assess by periodic NMR/HPLC if stored for extended periods.
• For research use only. Not for human or veterinary use.

Structure and Identity

Item-specific (from Product Data):

• SKU: M404662
• Product name: 2'-Methoxy-1'-acetonaphthone
• CAS: 5672-94-6
• PubChem CID: 458194
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists: "396696", which is not a standard InChIKey format.)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/structure discussion (general):

• Expected scaffold: a naphthalene ring bearing an acylmethyl (acetyl) group (i.e., an aryl methyl ketone) and a methoxy substituent at the 2′-position relative to the carbonyl-bearing ring junction.
• Functional groups: aromatic polycyclic ring (naphthalene), aryl methyl ketone (–CO–CH3), and an anisole-type methoxy (–OCH3) substituent.
• 2D description: two fused benzene rings (naphthalene); an acetyl group attached to the 1′-position; a methoxy substituent at the adjacent 2′-position on the same ring, creating an ortho-methoxy–acyl motif capable of intramolecular interactions and directing effects in electrophilic substitution.
• Stereochemistry: none (achiral).

Synthetic Utility

Key reactive motifs and strategic value (literature):

• Aryl methyl ketone handle: enables enolate chemistry (alkylation, aldol, halogenation) and oxidative rearrangements (Baeyer–Villiger) to access esters/lactones bearing a naphthyl group.
• Methoxy-directing group: strongly ortho/para-directing in EAS; can steer regioselective functionalization on the naphthalene ring. Can serve as a removable protecting/directing group via O‑demethylation (e.g., BBr3) to give the corresponding phenol.
• Retrosynthesis: serves as a convergent fragment for assembling methoxy‑substituted naphthalene scaffolds; can be introduced via Friedel–Crafts acylation of a methoxy‑naphthalene or via acylation followed by selective O‑methylation.
• Cross-coupling compatibility: after installing a halogen (or via directed ortho‑metalation), the aryl system can engage in Suzuki, Negishi, or Kumada couplings to elaborate polycyclic architectures.
• Late-stage diversification: α‑position to carbonyl allows conversion to heteroatom-substituted derivatives (e.g., α‑azido/α‑amino via halogenation–substitution sequences) useful in probe or ligand synthesis.

Practical notes:

• Maintain dry, oxygen-free conditions for strong-base operations (LDA/NaHMDS).
• For electrophilic substitutions, balance the opposing directing effects of methoxy (activating) and acyl (deactivating) groups to predict regioselectivity on the naphthalene ring.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological reagent with defined binding specificity. No target, epitope, clone, or isotype information applies.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 5672-94-6, the molecular formula is C13H12O2, and the molecular weight is 200.24 g/mol. InChIKey WFBBDKXOGOJOKY-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.