≥98% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Protected from light,Store at -20°C,Argon charged Spedizione Ice chest + Ice pads,FedEx DG Service. Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
Panoramica
Product Application:
2-Naphthylamine Hydrochloride is listed as a known human carcinogen used in the manufacturing of dyes and as antioxidant in rubber.
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Recensioni
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Application Protocols
No item-specific, validated protocols are provided in the product data. The following general outlines (literature-based) may aid method development; adjust to your lab’s SOPs and safety policies.
Liberation of free base from the chloride salt:
Suspend the salt in water; add saturated NaHCO3 or 1–2 M NaOH dropwise at 0–10 °C until basic (pH > 10).
Extract with DCM or EtOAc (3×), dry organic layer (Na2SO4), filter, and concentrate under reduced pressure.
Verify identity/purity by NMR/LCMS.
Diazotization (small-scale):
Dissolve the salt in 1–3 M HCl, cool to 0–5 °C.
Add aqueous NaNO2 slowly while maintaining temperature; monitor for nitrite excess (starch–iodide paper).
Use the diazonium solution immediately for coupling or Sandmeyer conversions.
These are general research procedures only; consult primary literature and your institutional safety office before execution.
Biological Roles
This compound is primarily used in synthetic chemistry and materials workflows; it does not serve as a biological buffer or nutrient. The following notes are general background on arylamines and are provided for context only.
Aromatic amines such as 2-naphthylamine are known substrates for xenobiotic metabolism (literature), undergoing N-oxidation (e.g., by cytochrome P450) to reactive intermediates. Such pathways underpin their toxicological profiles.
Protonation to the anilinium (ammonium) form increases aqueous solubility and can influence transport and ion-pairing in biological-like media, but this salt is not intended for cellular or in vivo use.
In biochemical studies, arylamines are sometimes used as model compounds to probe phase I/II metabolism (e.g., N-acetylation by NAT enzymes) in vitro. Any such use must be confined to controlled research settings.
Research Use Note: For research use only. No clinical or diagnostic applications are endorsed or supported for this product.
Buffer Applications
Not typically applicable. 2-Naphthylammonium chloride is not a standard buffering agent, and it lacks the conjugate acid/base pair characteristics and pKa spacing that define practical laboratory buffers.
For aqueous work with this material, choose an external buffer system suitable for your reaction (e.g., acetate pH ~4–5 for diazotization, phosphate pH ~6–8 for general aqueous handling) rather than relying on the compound itself.
If pH control is needed during diazotization, mineral acid (HCl) media at 0–5 °C are standard (literature).
Green Alternatives
Synthesis with aromatic amines has both safety and environmental dimensions. Consider greener solvents and alternatives to hazardous intermediates when feasible.
Greener solvent choices (literature guidance):
Replace chlorinated solvents (DCM) with ethyl acetate, 2-MeTHF, dimethyl carbonate, or green alcohols where compatible.
For polar aprotic needs, prefer propylene carbonate or sulfolane over high-toxicity solvents; use water/ethanol for diazotization and azo-coupling where solubility allows.
Process considerations:
Aqueous diazotization can reduce VOC usage; phase-transfer catalysis may enable water-rich media.
Use solid-supported nitrite or continuous-flow diazotization to minimize energetic intermediates and improve containment.
Alternative chemistries:
Where possible, replace diazotization/Sandmeyer steps with direct C–H functionalization or cross-coupling from halonaphthalenes, reducing reliance on energetic diazonium intermediates.
Consider pre-functionalized naphthalene building blocks to bypass handling of carcinogenic arylamines (risk substitution rather than reduction hierarchy).
Tradeoffs:
Salt forms like 2-naphthylammonium chloride improve handling and reduce volatility but still require stringent exposure controls.
Greener solvents may alter rates/selectivity; verify with small-scale DoE before scale-up.
Pharmaceutical Uses
No excipient or pharmacopeial role is indicated for this item.
Item-specific regulatory status: Not specified for this item; refer to CoA/Spec Sheet.
General note: Aromatic amines and their salts are typically handled as research chemicals and intermediates. They are not used as pharmaceutical excipients due to safety and toxicological considerations.
If used as a chemical intermediate in process R&D, ensure appropriate impurity controls and purge studies are in place; none of this implies suitability for clinical use.
Physical Properties
Item-specific numerical specifications are not provided in the product data. Consult the CoA/SDS for authoritative values.
Item-specific data:
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 properties (for reference only; not item specifications):
Physical state: Typically a crystalline aromatic ammonium chloride salt.
Acid–base: Conjugate acid of 2-naphthylamine; expected to be strongly protonated under acidic conditions. pKa (of the conjugate acid for related anilinium salts) generally ~4–5 (literature, method-dependent).
Solubility profile: Generally more water-soluble than the free base; soluble in polar protic solvents (water, methanol, ethanol). The free base is more soluble in less polar organics (e.g., DCM, toluene) after basification.
Thermal behavior: Many arylammonium chlorides exhibit high melting points and may decompose upon heating rather than boil under ambient pressure (literature observation for analogous salts). Specific MP/BP for this item: Not specified for this item; refer to CoA/Spec Sheet.
Partitioning: The salt form shows reduced apparent logP relative to the free amine due to ionization (qualitative, literature).
Refractive index, density, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific 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 for evaluating this material’s quality in research workflows:
Aromatic amine salts can hydrolyze or discolor upon prolonged exposure to moisture, light, or air; the provided storage conditions (−20 °C, protected from light, argon charged) are consistent with minimizing such degradation.
For analytical applications (e.g., as a reference material or starting point for quantitative synthesis), examine the CoA for assay method (e.g., HPLC/GC titration), residual moisture (Karl Fischer), and chloride content.
For chromatography-sensitive transformations, low UV-absorbing impurities and metal content may be critical. If not stated on the CoA, consider additional purification or pre-use testing (HPLC purity, NMR, IC for halide).
If a salt-to-base conversion is required, quantify conversion (acid–base titration or qNMR) to ensure accurate stoichiometry in subsequent reactions.
Batch-to-batch consistency: Verify melting behavior (if applicable), NMR (1H/13C), and HRMS of either the salt or the liberated free base as fit-for-purpose QA checks.
Reaction and Applications
2-Naphthylammonium chloride serves as a convenient, stable, and often safer-to-handle form of 2-naphthylamine for synthesis. It is widely used as a precursor to diazonium salts and as a feedstock for aryl–N and aryl–X bond-forming chemistry.
Representative application families (literature):
Diazotization/Azo coupling: Conversion to the 2-naphthyldiazonium salt (NaNO2/HCl, 0–5 °C) followed by electrophilic azo coupling to phenols/anilines for dye/pigment synthesis.
Sandmeyer-type transforms: From the diazonium, install Cl, Br, CN, or perform Schiemann-type fluorination or hypophosphorous reductions to hydrogen.
Acylation/Sulfonylation: Free base reacts with acyl/sulfonyl chlorides (e.g., to form amide/sulfonamide derivatives) often under base (Et3N, pyridine) in DCM/THF.
Buchwald–Hartwig and Ullmann-type C–N couplings: As a nucleophilic arylamine partner after basification; typical catalysts include Pd(0)/ligands (e.g., BINAP, XPhos) or CuI with diamine ligands.
Electrophilic aromatic substitution (EAS): The 2-aminonaphthalene core directs EAS to certain ring positions; protection (e.g., acylation) may be used to control reactivity.
Practical tips:
For organic-phase reactions, first liberate the free base and dry it (e.g., brine wash, anhydrous MgSO4) to improve yields.
During diazotization, maintain cold temperatures (0–5 °C) and use freshly prepared diazonium solutions to ensure stability.
Monitor conversions by TLC/HPLC; arylamine chromophores aid UV detection.
Reaction Conditions
General, literature-based guidance for transformations starting from 2-naphthylammonium chloride (convert to free base as needed):
Diazotization → Azo coupling:
Solvent: Aqueous HCl (ca. 1–3 M acid); add NaNO2 at 0–5 °C to form diazonium in situ.
Coupling partner: Activated phenols/anilines in mildly alkaline or buffered media (pH typically 8–10 for phenolic partners).
Notes: Maintain low temperature during diazotization; use freshly generated diazonium.
Buchwald–Hartwig C–N coupling (after basification to free amine):
Solvents: Toluene, dioxane, tert-amyl alcohol, or DMF/DMSO.
Catalysts/Ligands: Pd2(dba)3 or Pd(OAc)2 with ligands such as BINAP, XPhos, BrettPhos; base K3PO4, Cs2CO3, or tBuONa.
Temp: 80–120 °C; inert atmosphere.
Acylation/Sulfonylation:
Solvent: DCM, THF, or EtOAc.
Reagents: Acyl or sulfonyl chlorides; base Et3N, pyridine, or NaHCO3 (biphasic).
Reagents: CuX (X = Cl, Br) or CuCN in aqueous acid; control addition and temperature to manage exotherm.
All parameters are indicative literature ranges; optimize per substrate, scale, and safety constraints.
Safety and Handling
Always consult the SDS for authoritative safety and first-aid guidance. The following is general information for arylammonium chloride salts and aromatic amines.
GHS classification and hazard statements (item-specific): Not specified for this item; refer to SDS.
Known toxicological context (literature): 2-naphthylamine (the free base) is historically associated with significant toxicological concern. Handle the salt and any liberated free base with stringent controls to minimize exposure (dust, skin contact, inhalation).
Personal protective equipment (typical laboratory practice):
Wear lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles.
Use in a certified chemical fume hood to control vapors/dust, especially if basification or heating may liberate the free amine.
Handling notes:
Avoid generating dust; prevent contact with strong oxidizers and bases that could liberate free amine.
Follow the item’s storage guidance: protect from light, store at −20 °C, keep under inert gas (argon-charged), and tightly closed.
First-aid overview (general):
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect residues and contaminated materials as hazardous organic waste per institutional and local regulations.
Solvent Selection
As an arylammonium chloride, this material is polar and typically dissolves best in protic or highly polar media. For reactions, solvent choice often depends on whether you use the salt directly or first liberate the free base.
Good: Water, methanol, ethanol, aqueous mineral acids (as salt).
Moderate: DMSO, DMF, NMP (especially with slight acid present to keep it protonated).
Poor (as salt): Nonpolar organics (toluene, hexanes, ethers). Solubility improves after basification to the free amine.
When to choose each approach:
Use the salt directly in aqueous-phase transformations (e.g., diazotization) where the protonated form is required.
Liberate the free base (e.g., with NaHCO3/NaOH, then extract) for reactions in nonpolar or aprotic solvents (cross-coupling nucleophile, acylation, sulfonylation) to enhance solubility and nucleophilicity.
Comparison (literature trends):
Water/alcohols: Facilitate protonated form; useful for ionic processes (diazotization, salt metathesis).
DMSO/DMF: Dissolve both salt (to some extent) and free base; good for SNAr, coupling with appropriate base.
Chlorinated solvents (DCM): Favor free base; typically require prior neutralization of the salt.
Storage and Reconstitution
Item-specific storage and shipping (as provided):
Storage conditions: Protected from light; Store at −20 °C; Argon charged.
Allow the sealed container to equilibrate to ambient temperature inside secondary containment to minimize condensation, then open under an inert atmosphere if feasible.
Reseal promptly; purge headspace with argon or nitrogen after each use.
Reconstitution/Dissolution (general guidance):
For aqueous work (salt form): dissolve in deionized water or dilute HCl with stirring.
For organic-phase reactions: first liberate the free base (see Application Protocols) to dissolve in DCM, THF, toluene, or polar aprotics (DMF/DMSO) as required.
Filtration through a PTFE syringe filter (0.45 µm) can clarify solutions for analytical or reaction setup.
Stability notes:
Protect from prolonged light exposure and moisture to limit discoloration or decomposition.
Avoid repeated freeze–thaw cycles of solid stored in frost-prone environments; keep desiccated where possible.
Specifications such as water content, residual solvents, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
An arylammonium salt derived from 2-naphthylamine, supplied as the protonated ammonium chloride.
Item-specific identifiers (as provided):
SKU: N493715
Product name: 2-Naphthylammonium chloride
CAS: 612-52-2
CID (PubChem): 11925
InChIKey (as provided): 299208
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identity (for reference; not item-specific specs):
Molecular formula (literature): C10H10ClN (C10H9N·HCl)
Molecular weight (literature): ~179.65 g/mol
Structural features (general description):
Core ring system: Fused bicyclic naphthalene (two annulated benzene rings).
Functional group: Anilinium-type ammonium at the 2-position on the naphthalene ring, paired with chloride counterion.
Charge state: Positively charged aromatic ammonium cation with a non-coordinating halide anion.
2D description: The ammonium group is attached to the alpha position of naphthalene (position-2), orthogonal to the long axis of the fused ring; counterion chloride is not covalently bound.
Synthetic Utility
The 2-aminonaphthalene core embedded in this salt is a versatile synthon enabling multiple strategic disconnections.
Protect/deprotect via acylation (Ac2O), sulfonylation (TsCl, MsCl), or carbamate formation (Boc2O) after basification.
Convert to diazonium for further aryl functionalization (Sandmeyer, Meerwein arylation, azo coupling).
Retrosynthetic leverage:
Target 2-substituted naphthalenes via diazonium → X (Cl/Br/CN/OH) then cross-coupling (Suzuki/Negishi) or SNAr.
Build 2-arylamino naphthalenes (diarylamines) via Pd-catalyzed C–N coupling to electrophilic aryl halides.
Named reaction intersections (literature):
Buchwald–Hartwig amination (Pd/ligand, base) with aryl/vinyl halides.
Sandmeyer and Schiemann (diazonium conversions to halides/CF3/others with specialized reagents).
Azo coupling to phenols/anilines for dye/pigment scaffolds (pH-controlled electrophilic coupling).
Practical pointers:
The salt form offers easier weighing/handling; for nucleophilic coupling steps, generate the free base to maximize reactivity.
For regiocontrol in EAS on the naphthalene ring, consider temporary amide protection to modulate directing effects and reduce overreaction.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, enzyme inhibitor with defined biomolecular target), and no target specificity data are provided in the product data.
Domande frequenti
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 ?20 °C, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.
How is this product shipped?
This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 612-52-2, the molecular formula is C10H10ClN, and the molecular weight is 179.65 g/mol. InChIKey QKGIPGSKJBOHSL-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.
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