N-Ethyl-2-naphthylamine Hydrobromide - ≥98% , CAS No.381670-27-5

CAS: 381670-27-5 Cat. No.: N404388 Formula: C₁₂H₁₃N•HBr Peso molecolare: 252.16

GRADE & PURITY ≥98%

Synonyms

DTXSID90659900 | N-Ethyl-2-naphthylamine Hydrobromide | N-Ethylnaphthalen-2-amine hydrobromide | E0156 | N-Ethylnaphthalen-2-aminehydrobromide | SCHEMBL3103373 | N-ethylnaphthalen-2-amine;hydrobromide | SB82065 | F87892 | MFCD00060158 | N-Ethylnaphthalen-

Storage

Room temperature

Specifications

Sinonimi

DTXSID90659900 | N-Ethyl-2-naphthylamine Hydrobromide | N-Ethylnaphthalen-2-amine hydrobromide | E0156 | N-Ethylnaphthalen-2-aminehydrobromide | SCHEMBL3103373 | N-ethylnaphthalen-2-amine;hydrobromide | SB82065 | F87892 | MFCD00060158 | N-Ethylnaphthalen-

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

Pubchem Sid

488201063

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488201063

Sorrisi canonici

CCNC1=CC2=CC=CC=C2C=C1.Br

IUPAC Name

N-ethylnaphthalen-2-amine;hydrobromide

InChIKey

VGVKYMICLQRIRC-UHFFFAOYSA-N

INCHI

1S/C12H13N.BrH/c1-2-13-12-8-7-10-5-3-4-6-11(10)9-12;/h3-9,13H,2H2,1H3;1H

Isomeri SMILES

CCNC1=CC2=CC=CC=C2C=C1.Br

Peso molecolare

252.16

Reaxy-Rn

49451140

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=49451140&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: Secondary alkylarylamines Hydrocarbon derivatives Hydrobromides
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthalene - Secondary aliphatic/aromatic amine - Secondary amine - Organic nitrogen compound - Hydrocarbon derivative - Hydrobromide - Organonitrogen compound - Amine - 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

• Punto di fusione (°C): 213 °C
• Peso molecolare: 252.150 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 251.031 Da
• Monoisotopic Mass: 251.031 Da
• Topological Polar Surface Area: 12.000 Ų
• Heavy Atom Count: 14
• 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: 2

XLogP3

Application Protocols

No application protocols are specified in the Product Data for this item.

• General lab workflows (informational)
  • Salt-to-free-base conversion prior to N‑acylation: basify aqueous solution and extract into DCM; dry and use immediately.
  • Preparation of sulfonamides: dissolve free base in DCM, cool to 0–5 °C, add base and sulfonyl chloride dropwise; warm to RT and monitor by TLC.
  • Recrystallization of the hydrobromide: dissolve in hot ethanol, filter hot, and induce crystallization by slow cooling and addition of ether as antisolvent.

These are general, non‑validated suggestions; adapt and optimize for your specific research objective. Always consult the CoA/SDS and perform appropriate risk assessments.

Biological Roles

This product is supplied strictly for research and laboratory use. No biological function or role is assigned in the Product Data.

• General context (literature)

  • Aromatic amines and naphthylamine derivatives serve as chromophoric units and electron‑donating motifs in molecular probes, sensors, and materials. N‑alkylation (e.g., N‑ethyl) modulates basicity and photophysics, which can influence binding behavior in supramolecular systems.
  • As small organic scaffolds, naphthylamines may be incorporated into ligands for protein labeling or as components of dye intermediates; any biological interactions are highly context‑dependent on the final conjugate.

• Metabolic/biochemical notes (general)

  • Free aromatic amines can undergo N‑oxidation, N‑dealkylation, and conjugation (e.g., glucuronidation/sulfation) in biological systems; however, this information is not specific to this item and is provided solely as general chemical knowledge.

No claims are made regarding biological activity, safety, or suitability for clinical use. For any work involving biological matrices, ensure appropriate controls and approvals are in place.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare biological or analytical buffer systems.

• Practical guidance
  • If used in aqueous studies, maintain pH control with established buffers (e.g., phosphate, citrate, HEPES) and consider the amine’s protonation state (secondary amines are protonated under acidic conditions).
  • For spectroscopic work, verify that your chosen buffer does not react with amines (avoid nitrite in acidic buffers to prevent nitrosamine formation).

Refer to dedicated buffering agents for pH control; see applicable sections on Solvent Selection and Reaction Conditions for handling this amine salt in water-containing systems.

Green Alternatives

Greener choices relate primarily to solvent/media selection and handling of the amine as salt vs free base. The substrate itself is fixed; process design offers the leverage.

• Media selection (general guidance)

  • Favor water/ethanol for salt handling, recrystallization, and salt exchange where feasible.
  • For acylations/sulfonylations of the free base, consider 2‑MeTHF or CPME in place of DCM/THF; use carbonate bases (K2CO3/Na2CO3) as milder, lower‑hazard alternatives to pyridine.
  • For extractions, EtOAc often substitutes for DCM with lower environmental impact.

• Comparison (illustrative; literature/general)

  • DCM vs 2‑MeTHF: 2‑MeTHF is bio‑derived, higher boiling, and less volatile; DCM offers superior polarity and ease of removal but has higher toxicity and environmental burden.
  • THF vs CPME: CPME resists peroxide formation, has favorable azeotropes for water removal, and broader stability range; THF is widely available but peroxide‑prone.
  • MeCN vs EtOH/H2O: where solubility allows, ethanol/water blends reduce hazardous waste and worker exposure.

• Operational improvements

  • Salt-to-free-base conversions in biphasic water/green ether systems minimize chlorinated waste.
  • Use solid‑supported bases (polymer‑bound tertiary amines) to simplify workup and reduce aqueous neutralization steps.

• Waste and safety

  • Avoid nitrosating agents; this reduces potential formation of N‑nitrosamines—an environmental and safety concern.

Always validate greener swaps on small scale to confirm reaction rate, selectivity, and isolation efficiency.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided in the Product Data for this item. This product is for research use only.

• General formulation context (literature/general)

  • Hydrobromide salts are commonly used in pharmaceutical development to increase aqueous solubility, reduce volatility/odor of basic amines, and improve crystallinity for handling. Such considerations can apply in preclinical chemistry workflows, salt screening, and intermediate isolation.
  • For synthetic intermediates, isolating the hydrobromide can simplify purification, enable controlled release of the free base on demand, and support impurity purging through recrystallization.

• Development considerations

  • If the compound (or its derivatives) is explored as a building block in drug discovery, standard developability screens (salt form selection, hygroscopicity, polymorph evaluation) may be informative; these are general practices and not specific to this SKU.

No therapeutic or clinical claims are made. Any use in pharmaceutical research must follow institutional and regulatory guidelines.

Physical Properties

Item-specific numerical specifications (mp, bp, density, UV cutoff, residuals) are not provided in the Product Data for this SKU.

• Item-specific values

  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not applicable to salt in practice (decomposes); Not specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Refractive index: Not applicable; solid salt. Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations for similar hydrobromide salts (for planning only)

  • Physical form: typically crystalline solids; many arylammonium hydrobromides are hygroscopic.
  • Solubility profile: often freely soluble to very soluble in water and polar protic solvents (methanol, ethanol); low solubility in nonpolar solvents (toluene, hexanes). Free base shows improved solubility in aprotic organics (DCM, EtOAc, THF).
  • Thermal behavior: hydrobromide salts of secondary anilines tend to decompose before boiling; expect darkening on overheating.
  • pKa (conjugate acid, literature context): secondary anilinium ions typically pKa ~5–6 in water; N‑alkylation and extended conjugation can slightly adjust basicity.

• Computed formula/Mr (literature/computed)

  • Empirical formula (salt form): C12H14NBr (computed from structure).
  • Formula mass: ~252.15 g/mol (computed).

Always consult the item-specific CoA/SDS for authoritative physical property data prior to process design.

Quality and Grades

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

• Interpreting common grades (general guidance)

  • Research-grade: suitable for synthetic and analytical laboratory workflows; impurity limits defined on CoA.
  • Purified salt forms: hydrobromide salts often provide enhanced stability and handling versus free bases by minimizing volatility and odor; residual inorganic bromide is typical and accounted for in assay.
  • HPLC/UV grades (if applicable): place emphasis on low UV background; significant for photometric quantitation—consult UV cutoff if chromatography is intended.

• Stabilizers/anti-oxidants

  • None stated in Product Data. If present, they would be listed on the CoA/label. Hydrobromide salts of anilines usually do not require added stabilizers but benefit from dry storage.

• What to check on receipt (practical)

  • Appearance and lot-specific assay (salt basis vs free-base equivalent), water content (Karl Fischer) if your process is moisture-sensitive, and residual inorganic content (e.g., bromide) if conducting elemental analysis.
  • If you need a specific residual solvent or metal profile, request the CoA/Spec Sheet—do not assume trace specifications.

• Batch consistency

  • For reproducibility in synthesis, document salt-to-free-base conversion factors (MW ratio) when calculating equivalents; confirm via potentiometric titration or NMR integration if critical.

Reaction and Applications

N‑Ethyl‑2‑naphthylamine hydrobromide is a convenient, bench‑stable salt of a secondary aromatic amine. It is primarily used as a synthetic building block after conversion to the free base.

• Typical applications (general/literature)

  • Amide, urea, and carbamate formation via acylation/isocyanate trapping of the free base; reagents: acyl chlorides, anhydrides, CDI, DSC, or triphosgene equivalents; base: Et3N, DIPEA, or NaHCO3.
  • Sulfonamide synthesis using sulfonyl chlorides (e.g., TsCl, MsCl) under mild base, affording naphthylsulfonamides with defined electronic properties.
  • Electrophilic aromatic substitution (EAS) on the naphthalene ring directed by the amino substituent (strong ortho/para director on the substituted ring); nitration, sulfonation, and Friedel–Crafts can be tuned to access regioisomers.
  • N‑functionalization: quaternization to ammonium salts (e.g., alkyl halides) or selective dealkylation strategies for protecting‑group manipulations.
  • Ligand/scaffold role in materials/fluorophores: naphthylamines provide emissive chromophores; N‑ethyl substitution modulates photophysical properties.

• Practical notes

  • Free base liberation: partition salt between aqueous base (Na2CO3/NaHCO3) and an immiscible organic solvent (DCM/EtOAc); maintain pH >10 to ensure deprotonation; dry and use promptly.
  • Secondary anilines do not form stable diazonium salts; avoid nitrosation conditions (NaNO2/H+) to prevent nitrosamine formation.
  • For chromatographic purification of cationic species, add 0.1–1% NEt3 to eluents to suppress tailing.

• Downstream chemistry examples (literature)

  • Coupling to activated esters for label installation.
  • Condensation with aldehydes/ketones to imines (less favored than primary anilines), followed by reduction to tertiary amines.

Reaction Conditions

The following are general literature guidelines for secondary anilines like N‑ethyl‑2‑naphthylamine; optimize for your specific substrate and lot. Item‑specific conditions are not provided in the Product Data.

• Liberation of free base

  • Typical: dissolve/suspend the hydrobromide in water; basify to pH 10–12 with Na2CO3 or NaOH; extract with DCM or EtOAc (3×); dry (Na2SO4), filter, concentrate. Keep under inert atmosphere if storing the free base.

• N‑Acylation

  • Solvent: DCM, THF, 2‑MeTHF, or MeCN.
  • Base: Et3N or DIPEA (1.5–2.5 equiv) or Na2CO3 (aq/bi‑phasic).
  • Temperature: 0–25 °C for acyl chlorides/anhydrides; 25–60 °C for activated esters (e.g., CDI intermediates).
  • Time: 0.5–16 h; monitor by TLC/LC‑MS.

• Sulfonylation

  • Reagents: TsCl/MsCl (1.1–1.5 equiv), base (2–3 equiv).
  • Solvent: DCM or pyridine alternatives; 0–25 °C.

• Reductive amination to tertiary amines

  • Solvent: MeOH or DCE.
  • Conditions: aldehyde/ketone (1.1–1.5 equiv), AcOH (catalytic), NaBH3CN or NaBH(OAc)3; 0–25 °C; 2–12 h.

• Electrophilic aromatic substitution

  • Conditions vary by electrophile; the amino group activates the ring. Control regioselectivity by temperature and solvent polarity. Protect N if over‑acylation is undesirable.

• Workup/purification

  • Add base modifiers (0.1–1% NEt3) to chromatographic eluents to reduce streaking. Recrystallize salts from EtOH/Et2O or iPrOH/MTBE as needed.

These conditions are general literature guidance and should be validated experimentally.

Safety and Handling

GHS classification and specific hazard statements are not provided in the Product Data for this item. Defer to the Aladdin SDS for definitive safety information.

• Item-specific hazard data

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements / pictograms: Not specified for this item; refer to SDS.

• General safety profile for aromatic amine hydrobromide salts (informational)

  • Likely hazards: irritant to skin, eyes, and respiratory tract; dust may cause discomfort. Aromatic secondary amines can form N‑nitrosamines upon nitrosating conditions—strictly avoid nitrite in acidic media.
  • Incompatibilities: strong oxidizers; strong bases (will liberate free base); nitrosating agents (NaNO2/H+); elevated heat causing decomposition and HBr release.
  • PPE: lab coat, safety glasses, nitrile gloves; use dust control (weighing in fume hood). For scale-up, consider splash goggles and respirator per risk assessment.
  • First aid (general): eye/skin contact—rinse with water for ≥15 min; inhalation—move to fresh air; ingestion—rinse mouth; seek medical attention as appropriate.
  • Fire response: use CO2, dry chemical, or foam; decomposition may release HBr and nitrogen oxides—firefighters should wear SCBA.
  • Spills: avoid dust generation; sweep with minimal agitation; neutralize residues with sodium bicarbonate solution if acidic.

• Storage notes

  • Store tightly closed at room temperature (per Product Data). Protect from moisture and light; use desiccant if hygroscopic behavior is observed.

For research use only. Not for human or veterinary use.

Solvent Selection

As supplied, the compound is a protonated ammonium hydrobromide; solvent behavior reflects ionic character.

• Polarity and miscibility (general/literature)

  • Salt form: typically highly soluble in water and polar protic solvents (MeOH, EtOH); variably soluble in DMF/DMSO; poorly soluble in nonpolar solvents (toluene, MTBE, hexanes).
  • Free base (after basification): substantially more soluble in moderately polar aprotic solvents (DCM, EtOAc, THF, CPME); limited water solubility at neutral pH.

• Practical selection by task

  • Purification: recrystallization from alcohols or alcohol/ether mixtures is common for hydrobromide salts. For free base, use hexanes/EtOAc trituration or column chromatography in DCM/MeOH with base modifier (e.g., 0.5–1% Et3N).
  • Reaction setup: if acylation/sulfonylation is planned, liberate free base and dissolve in DCM, THF, or acetonitrile with a non-nucleophilic base.
  • Salt exchange: water/EtOH mixtures facilitate conversion to other acid salts (e.g., HCl) if required.

• Comparison (general)

  • Water: best for handling the salt, workups, and extractions of the protonated form.
  • DCM/EtOAc: preferred once free base is generated for many transformations and extractions.
  • Alcohols (MeOH/EtOH/iPrOH): dual role solvents for recrystallization of the salt and as media for catalytic hydrogenation or reductions (if relevant to derivatives).

Select solvents in alignment with downstream operations (e.g., avoid strongly basic media if you wish to maintain hydrobromide form). Always verify solubility on the specific lot.

Storage and Reconstitution

• Storage (from Product Data)

  • Store at room temperature.

• Packaging/handling

  • Keep tightly closed in a dry place. Protect from moisture and prolonged exposure to air to limit deliquescence or caking common to ammonium salts.
  • If long‑term storage is planned, consider a desiccator or inert atmosphere packaging; record opening dates for hygroscopic tracking.

• Reconstitution and preparation (general)

  • Aqueous: dissolve the hydrobromide directly in deionized water; gentle warming and stirring may assist. Adjust pH as needed for downstream steps.
  • Organic: if organic solubility is required, first convert to the free base by basification (e.g., NaHCO3/Na2CO3) and extract into DCM, EtOAc, THF, or 2‑MeTHF. Dry organic phases over anhydrous Na2SO4 or MgSO4.
  • Filtration: for particulate removal, filter through 0.2–0.45 µm PTFE/nylon membranes compatible with your solvent.

• Stability

  • Avoid elevated temperatures and strong light. Do not expose to nitrosating conditions. If discoloration or unusual odor develops, assess by NMR/LC‑MS before use.

• Shipping

  • Shipped condition is not specified in Product Data. Hydrobromide salts are typically stable for ambient shipment; verify with the lot-specific documentation if temperature control is required.

Structure and Identity

A secondary aromatic amine presented as a hydrobromide salt; the amine nitrogen is N‑ethylated and bound to the 2‑position of a naphthalene ring system.

• Product identifiers (from Product Data)
  • SKU: N404388
  • Product name: N‑Ethyl‑2‑naphthylamine Hydrobromide
  • CAS: 381670-27-5
  • CID: 44630276
  • InChIKey: 378712 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Composition and formula
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Note: the neutral free base is commonly C12H13N; the hydrobromide salt would correspond to C12H14NBr, literature/computed.)
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed for C12H14NBr ~252.15 g/mol.)
• Structural features (general/literature)
  • Core: fused bicyclic aromatic naphthalene (two linearly fused benzene rings).
  • Substitution: secondary aniline-type nitrogen at the 2‑position of naphthalene, bearing an N‑ethyl substituent; supplied as the protonated ammonium (hydrobromide) salt.
  • Functional groups: protonated secondary amine (ammonium), polycyclic aromatic hydrocarbons (PAH) ring system.
  • Ionization: exists as an ammonium bromide in the solid state; free base obtainable by mild basification for synthetic use.
• 2D description (general)
  • The naphthalene plane bears –NH–Et at C‑2. Under hydrobromide form, the nitrogen is protonated (–NH2+–Et) and paired with Br−. No stereocenters are present; planar aromatic scaffold dominates.

Synthetic Utility

The substrate is a secondary aniline embedded on a naphthalene core (2‑substituted), supplied as a hydrobromide salt. Its utility stems from nucleophilicity at nitrogen and activation/directing effects on the aromatic system.

• Transformations (general/literature)

  • N‑Acylation/Carbamoylation/Sulfonylation to access amides, ureas, carbamates, and sulfonamides—common in medicinal chemistry and materials.
  • Quaternization to benzyl/alkyl ammonium salts, enabling phase‑transfer catalysis or ionic material precursors.
  • Reductive alkylation: formation of tertiary anilines via iminium pathways (with aldehydes/ketones + reducing agent such as NaBH3CN/BH(OAc)3) once free base is generated.
  • Directed EAS on the naphthalene ring to introduce additional substituents; the amino group is a strong activator and ortho/para director relative to its ring.
  • Cross‑coupling strategies apply to halogenated derivatives (not this compound directly), where the N‑ethyl‑2‑naphthylamine motif is retained.

• Strategic roles

  • Handle as hydrobromide for stable storage/transport; convert to free base immediately prior to use to maximize reactivity and solubility in organic media.
  • Use the salt as a transient protecting/activation form: protonation suppresses basicity/nucleophilicity during certain operations (e.g., selective electrophilic substitutions), then neutralize post‑step.

• Cautions

  • Secondary anilines are prone to N‑nitrosation; exclude nitrite under acidic conditions and minimize exposure to nitrosating atmospheres.
  • For chromatographic work, tailing is mitigated by base modifiers in the mobile phase.

Target Specificity

Not applicable. This product is a small‑molecule chemical reagent, not a biological targeting reagent or antibody.

• No antigen/epitope, clone, isotype, or species reactivity is associated with this item.

For intended uses, see the sections on Synthetic Utility and Reaction & Applications.