≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
🌡
Storage & shipping
Room temperature Ships Check lot-specific COA for exact specifications.
📋
Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
📚
Literature proof
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Panoramica
Description
2-Naphthaleneethanol undergoes esterification reaction with poly(ethylene glycol) monomethyl ether carboxylic acid. Emission spectra of 2-naphthaleneethanol reacted with UV-irradiated octadecylsiloxane self-assembled monolayers has been investigated.
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
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
Punto di ebollizione (°C)
180-184° C (lit.) at 15 mmHg
Punto di fusione (°C)
66-68° C (lit.)
Peso molecolare
172.220 g/mol
XLogP3
3.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
172.089 Da
Monoisotopic Mass
172.089 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
155.000
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
Calcolatori di soluzioni
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
No assay‑specific protocols are provided for this small‑molecule reagent. Typical laboratory uses involve standard organic synthesis procedures (oxidation, activation to leaving groups, ester/ether formation) as described under Reaction Conditions. For analytical purposes, prepare stock solutions in acetonitrile, methanol, DMSO, or toluene at appropriate concentrations, filter if needed (0.2 µm PTFE), and follow your method’s validated parameters.
Biological Roles
This product is offered strictly for research and laboratory use. No clinical or diagnostic claims are made.
Literature/general context:
2‑Naphthaleneethanol is a hydrophobic aromatic alcohol (a derivative of the polycyclic aromatic hydrocarbon naphthalene) with a benzylic primary alcohol functionality. It is not a native metabolite in common biochemical pathways.
In biochemical and materials research, aryl‑ethyl alcohol motifs are incorporated to modulate hydrophobicity, membrane interaction, or fluorescence of small molecules and probes; the naphthalene ring can contribute to π–π interactions and intrinsic fluorescence (emission typically in the near‑UV/blue region for naphthalene derivatives).
Enzymatic transformations: oxidative enzymes (e.g., alcohol dehydrogenases or peroxidases) can, in principle, oxidize benzylic alcohols to aldehydes/acids, though substrate compatibility is enzyme‑specific and not guaranteed.
Binding motifs: the naphthyl group is often used in medicinal chemistry as a hydrophobic/aromatic pharmacophore; the 2‑naphthylethyl fragment can serve as a lipophilic anchor in ligand design. These are conceptual design roles rather than established biological functions of the neat compound.
Safety note: Polycyclic aromatic derivatives may have enhanced bioaccumulation potential due to hydrophobicity; handle with appropriate lab safety measures and dispose of waste according to institutional guidelines.
Buffer Applications
2‑Naphthaleneethanol is not typically used as a buffering agent or pH control component. It lacks acid/base functionality in the physiological pH range and does not form conventional buffer systems.
Practical guidance:
For work involving this compound in aqueous systems, choose an external buffer compatible with your biology or assay (e.g., phosphate, HEPES, or acetate buffers). Dissolve 2‑naphthaleneethanol first in a miscible cosolvent such as DMSO or ethanol to prepare concentrated stocks, then dilute into the buffered medium while monitoring final cosolvent percentage to maintain solubility and avoid precipitation.
Green Alternatives
Green chemistry considerations for transformations of 2‑naphthaleneethanol (literature/general):
Oxidations:
Greener choice: catalytic TEMPO with bleach (NaOCl)/buffered pH in aqueous biphasic media; or Oxone®/NaCl systems to form aldehyde/acid with minimal heavy metals.
Trade‑off: careful pH and temperature control needed to avoid over‑oxidation or chlorination.
Activations to leaving groups:
Alternative to PBr3/SOCl2: use sulfonate esters (TsCl, MsCl) in greener solvents (2‑MeTHF, CPME) and milder bases (NEt3). Appel reactions can be adapted with catalytic PPh3 and green oxidants but still generate halogenated waste.
Esterifications:
Switch from DCM/DMF to 2‑MeTHF, EtOAc, or propylene carbonate where solubility allows. Enzymatic esterification (lipases) in green solvents or solvent‑free conditions can be effective for selective transformations.
Solvent selection for general steps:
Prefer 2‑MeTHF or CPME over THF/Et2O (lower peroxide tendency, bio‑derived options available). Replace DCM with EtOAc or cyclopentyl methyl ether when feasible.
Small comparison (illustrative):
THF vs 2‑MeTHF: similar polarity; 2‑MeTHF offers higher boiling point, reduced peroxide hazard, partly bio‑sourced; may alter reaction rates/selectivity.
DCM vs EtOAc: EtOAc is biodegradable with lower toxicity; higher boiling point may lengthen evaporation but often acceptable.
Waste and work‑up:
Favor aqueous biphasic oxidations and carbonate bases to minimize halogenated waste.
Utilize solvent recovery (distillation) and minimize silica usage by adopting crystallization‑first purification strategies.
Pharmaceutical Uses
No therapeutic claims are made. The product is for research use only.
Literature/general formulation and process context:
Role as synthetic intermediate: 2‑naphthaleneethanol can be transformed into 2‑naphthylacetic acid, 2‑(2‑naphthyl)ethyl halides, sulfonates, or esters that serve as building blocks in active pharmaceutical ingredient (API) synthesis or probe development.
Excipient status: There is no common pharmacopeial excipient role for 2‑naphthaleneethanol. It is not listed among standard USP/NF excipients.
Analytical standards: Naphthyl alcohol derivatives may be used as internal standards or reference materials in method development; suitability depends on method selectivity and detection wavelength (naphthalene chromophore absorbs in UV).
Process considerations: Due to hydrophobicity, API intermediates derived from this scaffold may crystallize readily, aiding isolation. However, residual aromatic odors and low‑level fluorescence should be considered in analytical method development (HPLC with UV/fluorescence detectors).
Documentation for GMP or regulated uses: If considering this material for process development, ensure full traceability, impurity profiling, and alignment with internal specifications. Confirm that the grade, residual solvents, and metal limits meet project needs (consult CoA/Spec Sheet for this item).
Physical Properties
Item-specific specifications (for this SKU):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general physical data (for context; not product specifications):
Phase at ambient: typically crystalline solid or low‑melting solid, depending on purity and polymorph
Melting point (literature): reported around the mid‑40s to low‑50s °C range for the 2‑isomer
Boiling point (literature): on the order of ~290–310 °C at 1 atm (decomposes/slowly oxidizes if overheated in air)
Density (literature): approximately ~1.05–1.15 g/mL (at temperatures above the melt)
Solubility: sparingly soluble in water; freely soluble in common organic solvents (EtOH, MeOH, acetone, ethyl acetate, DMSO, THF, toluene)
LogP (literature): expected in the 2.0–3.0 range, reflecting aromatic hydrophobicity tempered by one hydroxyl group
Refractive index: not commonly reported for the solid; melts display nD around 1.60–1.63 (literature, indicative)
pKa: the –OH is nonacidic (pKa > 14 for alcohol proton); phenyl/benzylic C–H acidity not relevant under neutral conditions
Practical notes:
Hygroscopicity: generally low; however, surface moisture uptake may occur in finely powdered material.
Polymorphism: aromatic alcohols can show variable crystallinity; melting behavior may depend on history and purity.
Always consult the item’s CoA for exact physical specifications.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on grades (for context):
Research grade: suitable for most synthetic, analytical, and method‑development tasks. Purity often ≥95%, but exact assay and impurity profile are item‑specific.
High‑purity or GC/HPLC grades (when applicable) emphasize low nonvolatile residue and low UV background; these are advantageous if the compound is used as an analytical standard or for photo‑physical studies of aryl alcohols.
Metals/spec inorganic limits: Not specified for this item; refer to CoA/Spec Sheet when trace‑metal‑sensitive catalysis (e.g., cross‑coupling after derivatization) is envisioned.
Implications for use:
For sensitive downstream steps (e.g., PBr3 conversion to 2‑(2‑naphthyl)ethyl bromide followed by Pd‑catalyzed chemistry), tighter control of water and protic impurities is beneficial.
If employing the alcohol in stereospecific substitutions (e.g., Mitsunobu formation of 2‑naphthylethyl ethers), residual acids/bases can affect rate and selectivity; confirm acidity/neutrality on CoA.
Documentation:
For assay, residual solvents, water content (Karl Fischer), and any stabilizer use, consult the specific Certificate of Analysis and Specification Sheet for SKU N472264.
Reaction and Applications
Typical uses of 2‑naphthaleneethanol in synthesis (literature/general):
Oxidation to carbonyls/acids: selective oxidation of the benzylic primary alcohol affords 2‑naphthylacetaldehyde (e.g., Swern, Dess–Martin, TEMPO/bleach) and subsequently 2‑naphthylacetic acid (e.g., Pinnick, Jones). These are versatile intermediates for amide/ester libraries.
Halide formation/activation: conversion to 2‑(2‑naphthyl)ethyl halides via PBr3, SOCl2, or Appel conditions enables SN1/SN2 and Friedel–Crafts alkylations on external arenes.
Sulfonate esters: tosylation/mesylation generates excellent leaving groups for displacement with heteroatom or carbon nucleophiles to build 2‑naphthylethyl ethers, thioethers, or nitriles.
Etherification and Mitsunobu reactions: formation of 2‑naphthylethyl ethers with phenols/alcohols under Mitsunobu or Williamson conditions; useful as benzyl‑type protecting/anchoring groups.
Ester synthesis: coupling with carboxylic acids using DCC/EDC (DMAP‑catalyzed) affords 2‑naphthylethyl esters; the 2‑naphthylethyl (NPE) group can serve as a photolabile protecting/leaving group in specialized cases (literature precedents exist primarily for related aryl‑ethyl systems).
Redox/chain editing: hydrogenolysis or radical processes on 2‑naphthylethyl derivatives provide access to deprotected substrates or rearranged frameworks.
Applications context:
Scaffold for generating PAH‑containing ligands, fluorescent tags, and materials monomers.
Precursor to fluorescent 2‑naphthylethyl derivatives used as hydrophobic anchors or probes in supramolecular chemistry.
Practical tips:
Benzylic centers are oxidation‑prone; limit air/heat exposure during lengthy steps.
Control competing elimination (to styrenyl species) under strongly acidic/dehydrating conditions.
Employ anhydrous conditions for halide/sulfonate formations; quench carefully to avoid hydrolysis.
Reaction Conditions
General literature guidance for common transformations of 2‑naphthaleneethanol (not item‑specific specifications):
Oxidation to aldehyde:
Swern: DMSO, (COCl)2, −78→0 °C; then Et3N; typical isolated yields 70–90% for benzylic alcohols.
DIAD/DEAD, PPh3, THF or toluene, 0→rt; 60–90% typical, substrate‑dependent.
Williamson ether synthesis (after ROH deprotonation or via ROTs):
NaH or K2CO3, DMF/acetone, 0→reflux, 2–16 h; 60–90% typical.
Notes:
Maintain anhydrous conditions for activations; quench cautiously.
Benzylic rearrangements/elimination can occur under strongly acidic, high‑temperature conditions—monitor by TLC/GC/MS.
Choose greener solvents (2‑MeTHF, EtOAc) where compatible, as discussed under Green Alternatives.
Safety and Handling
Regulatory/SDS guidance:
GHS signal word, hazard statements, and pictograms: Not specified for this item; refer to SDS.
General expectation (literature): primary aromatic alcohols are typically classified as irritants; avoid inhalation of dust/vapors and contact with skin/eyes.
Personal protective equipment (PPE):
Recommended: lab coat, safety glasses or goggles, appropriate chemically resistant gloves (e.g., nitrile), and use within a fume hood when heating or generating vapors/aerosols.
Handling and engineering controls:
Avoid breathing dust/particles; minimize dust formation during milling or weighing.
Use inert atmosphere (N2/Ar) for moisture‑ or oxygen‑sensitive transformations (e.g., when converting to halides/esters).
Prevent contact with strong oxidizers; benzylic alcohols can be oxidized.
Incompatibilities and reactivity:
Incompatible with strong oxidizing agents (e.g., chromic acid, peroxides), strong bases in the presence of halogenating agents (risk of exotherm), and strong acids during dehydration.
Not prone to peroxide formation (unlike ethers), but benzylic oxidation on storage at elevated temperature/air is possible; keep containers tightly closed.
First‑aid overview (consult SDS for definitive instructions):
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
Inhalation: move to fresh air; assist breathing if needed; seek medical attention for symptoms.
Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel; obtain medical attention.
Fire safety:
Combustible organic solid; use CO2, dry chemical, or foam. Cool containers with water spray. Thermal decomposition may produce CO/CO2 and irritant fumes.
Solvent Selection
Compound role: 2‑Naphthaleneethanol is a moderately polar, nonionic aromatic primary alcohol. It is usually used as a reactant/starting material rather than as a solvent.
Polar protic: good solubility in MeOH, EtOH, i‑PrOH
Polar aprotic: soluble in acetone, acetonitrile, DMF, DMSO
Nonpolar aromatics/ethers: soluble in toluene, xylene, THF, dioxane
Selection guidance for working solutions and reactions:
For nucleophilic substitutions/activations (tosylation, mesylation): use dry DCM, THF, or pyridine as solvent/base systems.
For oxidations (PCC, Swern, TEMPO/bleach): choose DCM, DMSO, MeCN, or ethyl acetate per method; maintain anhydrous/low‑temperature conditions where required.
For esterifications (DCC/DMAP or EDC): DCM or DMF provide good solubility of both reagents and product.
For Mitsunobu etherification: THF or toluene are common; strictly anhydrous conditions.
Comparison (when choosing solvents):
THF vs DCM: THF offers better solubility for polar reagents and bases; DCM provides easier removal and lower boiling point.
DMF/DMSO: excellent solvation for salts/bases but can complicate work‑up; reserve for difficult solubility cases.
Practical notes:
Dry glassware and pre‑dry solvents for moisture‑sensitive transformations of the alcohol.
For analytical sample prep (HPLC/GC), prepare solutions in acetonitrile, methanol, or isooctane/toluene as dictated by the method’s detection and polarity.
Storage and Reconstitution
Storage (item-specific from Product Data): Store at room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Container: Keep tightly closed in a clean, dry, inert container. Minimize headspace oxygen for long storage if frequent heating/opening is expected.
General guidance (literature/practice):
Protect from prolonged exposure to air and light to limit slow benzylic oxidation. For long‑term storage, consider amber glass.
If material is a low‑melting solid, avoid warm storage areas; store in a temperature‑stable cabinet to prevent repeated melt/solidify cycles that can introduce impurities.
Desiccation: not strictly required, but storing over a desiccant (e.g., silica gel) helps maintain dryness for moisture‑sensitive downstream chemistry.
Reconstitution/solution preparation:
Prepare concentrated stock solutions in dry solvents (e.g., DCM, THF, toluene, MeCN, DMF, DMSO, EtOH) as appropriate for your application.
For aqueous work, first dissolve in a miscible organic cosolvent (DMSO, EtOH), then dilute into buffer while keeping final organic content to a level that maintains solubility and is compatible with your system.
Shelf‑life and QC:
Inspect periodically by TLC/HPLC/GC for signs of oxidation or decomposition (appearance of aldehyde/acid peaks). Refer to CoA for recommended retest period if provided.
Structure and Identity
Brief description: 2‑Naphthaleneethanol (naphthalene‑2‑ethanol) is a primary benzylic alcohol where a –CH2–CH2–OH side chain is attached at the 2‑position of the naphthalene ring system.
Item-specific identifiers from Product Data:
CAS: 1485-07-0
SKU: N472264
Category: Chemical and Biochemical Reagents (research use only)
InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Note: Structural and identifier values not explicitly provided in the Product Data are cited as literature/general information and are not item-specific specifications.
Benzylic position: amenable to radical and cationic transformations; potential for rearrangements under strongly acidic conditions.
Named/representative transformations:
Swern or Dess–Martin oxidation → 2‑naphthylacetaldehyde; followed by Pinnick/NaClO2 oxidation → 2‑naphthylacetic acid.
Mitsunobu coupling with phenols/carboxylic acids → 2‑naphthylethyl ethers/esters.
Williamson ether synthesis after tosylation → diverse 2‑naphthylethyl ethers.
Appel or PBr3 conversion → 2‑(2‑naphthyl)ethyl bromide/chloride → SN2 with nucleophiles; or Friedel–Crafts alkylation on external aromatics.
Carbon–carbon bond formation: activation to sulfonates then displacement with cyanide → nitrile; subsequent hydrolysis → acid/amide.
Retrosynthetic value:
Serves as a benzylic two‑carbon handle on a naphthalene core, enabling straightforward editing of oxidation state (alcohol ↔ aldehyde ↔ acid) and substitution at the terminal carbon.
Practicalities:
Protecting group behavior: the 2‑naphthylethyl (NPE) group can act as a removable auxiliary in specific contexts (not universally photolabile like p‑nitrobenzyl, but aryl‑ethyl esters/ethers can be cleaved under hydrogenolysis or oxidative conditions).
Purification: products often crystallize; otherwise, normal‑phase silica with aromatic modifiers (e.g., small % Et3N) can mitigate tailing of basic co‑products.
Target Specificity
Not applicable. This product is a small‑molecule aromatic alcohol, not a biological targeting reagent (e.g., antibody, peptide, or inhibitor with defined biological targets). No antigen/epitope, species reactivity, clone, or isotype information applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
