4-(Cyclopropylmethoxy)-1-naphthaldehyde , CAS No.883528-10-7

CAS: 883528-10-7 Cat. No.: C995730 Summenformel: C₁₅H₁₄O₂ Molekulargewicht: 226.270

Storage

Room temperature

Specifications

Storage

Room temperature

Namen und Kennungen

Kanonisches Lächeln

C1CC1COC2=CC=C(C3=CC=CC=C32)C=O

IUPAC Name

4-(cyclopropylmethoxy)naphthalene-1-carbaldehyde

InChIKey

YBOBITDWGSKKFY-UHFFFAOYSA-N

INCHI

1S/C15H14O2/c16-9-12-7-8-15(17-10-11-5-6-11)14-4-2-1-3-13(12)14/h1-4,7-9,11H,5-6,10H2

Molekulargewicht

226.270

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Naphthalenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Naphthalenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthalenes
• Alternative Parents: Phenol ethers Aryl-aldehydes Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthalene - Phenol ether - Aryl-aldehyde - Alkyl aryl ether - Ether - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aldehyde - Aromatic homopolycyclic compound
• Beschreibung: 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 226.270 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 226.099 Da
• Monoisotopic Mass: 226.099 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 272.000
• 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

No validated bioassay or immunoassay protocols are provided for this SKU. Typical laboratory use is as a synthetic intermediate. For assay inclusion (e.g., as a small-molecule probe), prepare stock solutions in dry DMSO or acetonitrile, verify solubility and stability of the aldehyde, and include appropriate vehicle controls. Always establish your own method development and validation for intended applications.

Biological Roles

This material is a synthetic aromatic aldehyde/aryl ether intended for research and chemical synthesis. No endogenous biological role is known for 4-(Cyclopropylmethoxy)-1-naphthaldehyde.

• Biochemical context (general)

  • The naphthalene core is a common motif in chemical biology probes and ligands; the cyclopropyl group is sometimes used to tune metabolic stability and lipophilicity in discovery campaigns.
  • Aldehydes can form reversible Schiff bases with primary amines; in biological matrices this can lead to nonspecific imine formation with proteins/peptides. Accordingly, handle with care to avoid unintended bioconjugation during bioassays.

• Use limitation

  • For research use only (from Product Data). Not for human or animal diagnostic or therapeutic use.

If a biological interaction profile is required, generate it empirically for your target system; no target-specific biological activity data are provided for this item.

Buffer Applications

Not typically applicable. 4-(Cyclopropylmethoxy)-1-naphthaldehyde is a hydrophobic aromatic aldehyde and is not used as a buffering agent. For aqueous work, dissolve in a suitable water-miscible organic co-solvent (e.g., DMSO, acetonitrile, or EtOH) before dilution into buffer, assessing solubility and stability of the aldehyde under the selected pH.

Green Alternatives

Opportunities to reduce environmental impact largely center on solvent/reagent choice rather than the substrate itself.

• Greener solvent swaps (general guidance)

  • Replace DCM/chloroform with EtOAc, Me-THF, CPME, or toluene when compatible with reactivity and separation.
  • Substitute THF with 2-MeTHF for organometallic additions and olefinations; similar performance with bio-based sourcing and easier solvent recovery.
  • Favor alcohols (EtOH, iPrOH) over MeOH where feasible due to lower toxicity.

• Comparative notes (literature/general)

  Greener option | Typical use | Pros | Trade-offs --- | --- | --- | --- 2-MeTHF | Organometallics, olefination | Bio-based, higher bp, less peroxide formation than THF | Slightly different solubility; water content control still needed EtOAc | Workup/extraction, some oxidations | Low toxicity, biodegradable | Lower polarity than DCM; may affect selectivity CPME | Reductions/condensations | Low peroxide tendency, hydrophobic azeotrope | Odor, cost, sometimes slower rates

• Reagent choices

  • Olefination: HWE with stabilized phosphonates often generates less waste vs. Wittig with stoichiometric phosphine oxide byproducts.
  • Oxidation to acids: Pinnick (NaClO2 with scavenger) can be milder/cleaner than permanganate/chromate systems.
  • Reduction: Catalytic hydrogenation (H2/Pd) can avoid stoichiometric metal hydride waste when chemoselectivity permits.

Implement solvent recycling and microscale screenings to minimize waste.

Pharmaceutical Uses

No pharmacopeial excipient status or formulation role is provided in the Product Data. As a research-only building block, this compound may serve as an intermediate or scaffold in medicinal chemistry campaigns (general context), where the aldehyde facilitates rapid diversification (e.g., imine/oxime formation, olefination). Any use in drug product manufacture would require independent qualification, impurity profiling, and compliance with relevant GMP and regulatory standards.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are general/literature expectations for this structure; they are NOT specifications for this catalog item.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula / weight: C15H14O2; ~226.27 g/mol (literature/computed from structure).
• Boiling point: Not located in primary literature for this exact compound; many 1-naphthaldehyde ethers of similar mass have BPs in the 330–360 °C range at ambient pressure, or 140–180 °C under reduced pressure (literature, analogs). Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Aromatic aldehydes of similar substitution may be low-melting solids or oils; specific MP not located. Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• LogP: Expected moderately lipophilic due to naphthalene and cyclopropyl ether; estimated cLogP ~3–4 (literature/estimation for similar scaffolds). Not specified for this item.
• Solubility (general):
  • Organic: Readily soluble in aromatic solvents (toluene), chlorinated solvents (DCM, chloroform), ethers (THF, MTBE), esters (EtOAc), and moderately in alcohols (EtOH, iPrOH) (general guidance for aryl aldehydes).
  • Aqueous: Very low (general for non-ionizable aryl aldehydes).
• UV-Vis: Expected strong π–π* absorption in near-UV (around 220–280 nm) due to naphthalene; aldehyde substituent may red-shift slightly (literature, qualitative). Not specified for this item.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoffs, residual solvents, metal content, water, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Context for professional users:

• Research grade aromatic building blocks are typically provided with NMR and LC/MS identity/purity confirmation; consult the lot-specific CoA for actual assay and analytical methods.
• If LC suitability (e.g., HPLC grade) or photochemical purity is required (due to the conjugated naphthyl chromophore), verify UV background and impurity profile on the CoA before chromatographic use.
• Stabilizers: None indicated in Product Data. If your application is sensitive to trace acids, consider storing under inert atmosphere or adding a trace base scavenger in solution to suppress aldehyde-to-acid oxidation (laboratory practice note; not a product specification).
• Batch-to-batch consistency: For route-sensitive building blocks, inspect spectral fingerprints (1H/13C NMR, IR νCHO ~ 1680–1720 cm−1 region, literature guidance) and chromatographic purity to ensure consistent reactivity in multistep syntheses.

Reaction and Applications

As a conjugated aryl aldehyde bearing an ether substituent, 4-(Cyclopropylmethoxy)-1-naphthaldehyde is a versatile building block for alkene construction, alcohols, and downstream functionalizations.

• Carbon–carbon bond formations

  • Wittig/Schlosser/Still–Gennari olefinations: Convergent access to styrenyl naphthalene derivatives; the electron-rich aryl ring can stabilize the transition state, often affording E/Z-selectivity controllable by phosphorane type.
  • Horner–Wadsworth–Emmons (HWE) condensations: Efficient assembly of conjugated cinnamate-like motifs on a naphthalene core.
  • Knoevenagel/Doebner condensations with active methylenes (malonates, cyanoacetates) to generate push–pull alkenes.
  • Nucleophilic additions: Grignard/organolithium reagents yield the corresponding secondary alcohols; control temperature to suppress overaddition or side reactions.

• Functional group interconversions

  • Reductions: NaBH4 or catalytic hydrogenation to the benzyl alcohol; further transformations to ethers/esters.
  • Oxidations: Chemoselective oxidation to the carboxylic acid (e.g., Pinnick) or to the acid chloride for coupling.
  • Acetalization: Temporary protection of the aldehyde under acid catalysis (ethylene glycol, trimethyl orthoformate) for orthogonal chemistry on the aryl ether.

• Aryl ether handle

  • The cyclopropylmethyl ether is robust to many bases and nucleophiles; under strong Lewis/Brønsted acids, cleavage to reveal phenol is possible, enabling late-stage diversification.

• Applications in discovery chemistry (general)

  • The cyclopropyl motif imparts metabolic resilience and modulates lipophilicity; the aldehyde allows rapid SAR via parallel olefination/addition chemistry.

Reaction Conditions

General literature guidance for aryl aldehydes; adjust to your substrate and scale.

• Wittig/HWE olefination

  • Solvent: THF, toluene, or DCM (anhydrous).
  • Base: NaH, t-BuOK, or KHMDS (for ylide/phosphonate generation).
  • Temperature: −78 to 25 °C depending on reagent; 0–25 °C for stabilized ylides; −78 to 0 °C for non-stabilized.
  • Typical times: 1–16 h; monitor by TLC/LC.
  • Notes: Control E/Z via reagent choice (Still–Gennari for E-selectivity; Horner conditions for E-olefins).

• Grignard/organolithium additions

  • Solvent: Dry THF/2-MeTHF or toluene.
  • Temperature: −78 to 0 °C for reactive nucleophiles; 0–25 °C for less reactive reagents.
  • Quench: Aqueous NH4Cl or weak acid; avoid overbasic workups that can induce side reactions.

• Reductions of the aldehyde

  • NaBH4: MeOH, EtOH, or THF; 0–25 °C; minutes to hours.
  • Catalytic hydrogenation: H2 (1–5 bar), Pd/C in EtOAc/EtOH; RT to 50 °C.

• Oxidation to acid

  • Pinnick: NaClO2, NaH2PO4 buffer, scavenger (2-methyl-2-butene); tBuOH/H2O; 0–25 °C.

• Protection (acetalization)

  • Ethylene glycol, catalytic p-TsOH, Dean–Stark in toluene or molecular sieves in DCM; 25–110 °C.

Expected yields for these transformations on aryl aldehydes commonly range 60–90% (literature, substrate-dependent). These are general guidelines, not specifications.

Safety and Handling

Authoritative safety classification is not provided in the Product Data; consult the SDS for this SKU for definitive guidance. The following are general precautions for aromatic aldehydes and aryl ethers.

• GHS information

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

• Likely hazards (general chemistry knowledge)

  • Irritation: Aldehydes can be skin/eye irritants and may cause respiratory irritation.
  • Sensitization: Some aromatic aldehydes can be skin sensitizers (general risk; check SDS).
  • Combustibility: Organic compound; treat as combustible. Avoid ignition sources.

• Handling recommendations

  • Use in a fume hood to avoid inhalation of vapors or aerosols.
  • Wear appropriate PPE: lab coat, safety glasses, nitrile gloves. Consider splash goggles for scaled operations.
  • Avoid contact with strong oxidizers; aldehydes can be oxidized to acids.
  • Avoid strong bases with prolonged exposure which can promote aldol/cannizzaro in certain systems (less likely for aryl aldehydes but possible under forcing conditions).

• First-aid overview (general)

  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention per SDS.
  • Inhalation: Move to fresh air; get medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Storage incompatibilities and stability

  • Store tightly closed, away from light/air to minimize slow oxidation to the corresponding acid.
  • Segregate from strong oxidizers and strong bases. Use inert gas blanket for long-term storage if possible.
  • Peroxide formation: Not a dialkyl ether; aryl ethers are less prone, but check aged materials as a general precaution.

Always defer to the official SDS for this product for classification and response details.

Solvent Selection

This compound is a moderately lipophilic aromatic aldehyde/aryl ether and is generally handled in common organic solvents.

• Polarity and miscibility (general guidance)

  • Expected good solubility in DCM, chloroform, toluene, THF, MTBE, and EtOAc; moderate in alcohols; poor in water.
  • For moisture-sensitive reactions involving the aldehyde (e.g., Wittig/Still–Gennari), use rigorously anhydrous solvents (THF, toluene, DCM) and dry glassware.

• When to choose which solvent

  • Nucleophilic additions (Grignard, organolithium): Dry THF, 2-MeTHF, or toluene depending on reagent polarity and temperature control.
  • Condensations (Knoevenagel, Wittig, HWE): THF, toluene, DCM, or acetonitrile; for base-promoted variants, consider toluene or THF to balance solubility and basicity.
  • Oxidations/Reductions: DCM or EtOAc for TEMPO/Swern type manipulations; MeOH/EtOH or THF for NaBH4 or catalytic hydrogenation (for the –CHO to –CH2OH step if desired).

• Comparison notes

  • 2-MeTHF can replace THF for greener handling with similar solvation of organometallics and improved boiling point.
  • EtOAc often replaces DCM for extractions and workups with lower environmental impact.

Always verify solubility empirically at your working temperature and concentration.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Container: Store in a tightly closed container, preferably amber glass to limit light exposure of the conjugated chromophore.
• Atmosphere: For extended storage, consider an inert gas blanket (N2/Ar) to minimize slow aerobic oxidation of the aldehyde to the acid (general best practice).
• Humidity: Keep dry; moisture can promote hydrate formation or acetalization under acid traces.
• In-solution handling: Prepare solutions in dry, oxygen-free solvent for moisture/air-sensitive reactions. For stock solutions, use dry DMSO, acetonitrile, THF, or toluene; store at 2–8 °C if longer than a few days and check stability before use.
• Freeze–thaw: Not typically applicable to neat solids/liquids; if storing solutions, aliquot to avoid repeated freeze–thaw.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Note: No item-specific stabilizers, purity, or appearance are provided; consult the lot-specific CoA/SDS for definitive handling and storage guidance.

Structure and Identity

Brief description: 4-(Cyclopropylmethoxy)-1-naphthaldehyde is a naphthalene-derived aromatic aldehyde bearing an ether substituent at the 4-position and a formyl group at the 1-position.

• Product identifiers (from Product Data)

  • CAS: 883528-10-7
  • CID (PubChem): 23722964
  • InChIKey (as provided): 432950
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Synonyms: Not specified for this item; refer to CoA/Spec Sheet.

• Core structural features (general chemical description)

  • Ring system: Fused bicyclic naphthalene (two benzene rings).
  • Functional groups: Aromatic aldehyde (–CHO) at the 1-position; aryl ether (–O–CH2–cyclopropyl) at the 4-position.
  • Substituent: Cyclopropylmethyl ether, introducing a small, strained, lipophilic appendage.
  • Conjugation: The aldehyde is conjugated to the naphthalene π-system, influencing reactivity and spectroscopic properties.
  • Stereochemistry: None (achiral as named; no defined stereocenters or E/Z elements).

• Formula and formula mass (literature/computed; not item-specific specifications)

  • Typical molecular formula (computed from name): C15H14O2 (literature/computed)
  • Typical molecular weight: ~226.27 g/mol (literature/computed)

• 2D structure (verbal)

  • A naphthalene core bearing an aldehyde (–CHO) on ring position 1. At ring position 4, an ether oxygen links to a –CH2– that is bonded to a three-membered cyclopropyl ring.

Synthetic Utility

Key reactivity arises from the aldehyde and the aryl ether on a naphthalene core.

• Aldehyde chemistry

  • Electrophilic center for additions (RMgX/RLi → secondary benzylic alcohols; cyanide → cyanohydrins), condensations (Wittig/HWE/Knoevenagel), and heterocycle construction (Paal–Knorr analogs via downstream transformations).
  • Protect as acetals for orthogonal chemistry; deprotect under mild acid.

• Aryl ether handle

  • The cyclopropylmethyl ether is stable in many basic/nucleophilic media, allowing transformations elsewhere on the ring (e.g., directed lithiation adjacent to ether under strong bases, then quench with electrophiles). Under strong acid or Lewis acids, selective cleavage to regenerate the phenol can unlock cross-couplings (post-activation).

• Naphthalene platform

  • Amenable to electrophilic aromatic substitution (EAS) at remaining activated positions; nitration, halogenation, or sulfonylation can be orchestrated with directing effects of the ether.
  • Subsequent cross-couplings (Suzuki, Buchwald–Hartwig) can be accessed after installing suitable leaving groups.

• Retrosynthetic value

  • The aldehyde provides a convergent disconnection for elaborated alkenes or benzylic alcohols; the aryl ether can be introduced via Williamson ether synthesis from the corresponding phenol and cyclopropylmethyl halide.

Target Specificity

Not applicable. This product is a small-molecule aromatic aldehyde, not a biological macromolecule or affinity reagent. No antigen/epitope or species reactivity applies. No target specificity data are provided in the Product Data.