4-Hexadecylaniline - ≥97% , CAS No.79098-13-8

CAS: 79098-13-8 Cat. No.: H195075 Summenformel: C₂₂H₃₉N Molekulargewicht: 317.55 EG-Nummer: 626-524-5

GRADE & PURITY ≥97%

Synonyms

AS-75566 | AKOS015916700 | 4-Hexadecylaniline | SCHEMBL593206 | DTXSID30341271 | MFCD00007920 | RBCCQATUVPNPGQ-UHFFFAOYSA-N | FT-0641707 | 4-Hexadecylaniline, 97%

Storage

Room temperature

Shipped In

Normal

Übersicht

Ususlly used in simple solution based method for the gold (Au) metallization of DNA resulting in a Au nanowire network,in fabrication of hybrid organized molecular films by Langmuir-Blodgett (LB) technique and their photoluminescent properties has been investigated,in seed mediated synthesis of anisotropic rod shaped gold nanoparticles in organic media.

Specifications

Synonyme

AS-75566 | AKOS015916700 | 4-Hexadecylaniline | SCHEMBL593206 | DTXSID30341271 | MFCD00007920 | RBCCQATUVPNPGQ-UHFFFAOYSA-N | FT-0641707 | 4-Hexadecylaniline, 97%

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥97%

Namen und Kennungen

• Pubchem Sid: 488190366
• Kanonisches Lächeln: CCCCCCCCCCCCCCCCC1=CC=C(C=C1)N
• IUPAC Name: 4-hexadecylaniline
• InChIKey: RBCCQATUVPNPGQ-UHFFFAOYSA-N
• INCHI: 1S/C22H39N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-21-17-19-22(23)20-18-21/h17-20H,2-16,23H2,1H3
• Isomere SMILES: CCCCCCCCCCCCCCCCC1=CC=C(C=C1)N
• WGK Deutschland: 3
• Molekulargewicht: 317.55
• Reaxy-Rn: 2849883
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2849883&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Aniline and substituted anilines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Aniline and substituted anilines
• Intermediate Tree Nodes: Not available
• Direct Parent: Aniline and substituted anilines
• Alternative Parents: Primary amines Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aniline or substituted anilines - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as aniline and substituted anilines. These are organic compounds containing an aminobenzene moiety.
• 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

• Flammpunkt (°F): 235.4 °F
• Flammpunkt (°C): 113 °C
• Siedepunkt (°C): 254-255 °C/15 mmHg
• Schmelzpunkt (°C): 53-56°C
• Molekulargewicht: 317.600 g/mol
• XLogP3: 9.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 15
• Exact Mass: 317.308 Da
• Monoisotopic Mass: 317.308 Da
• Topological Polar Surface Area: 26.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 230.000
• 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

Referenzen

1. Zhibin Chen, Wenbo Wang, Jie Xiao.  (2023)  Computer simulation reveals interfacial distribution behaviors of gallic acid in zein particle and tween 20 co-stabilized pickering emulsions: Impact on oxidative stability.  FOOD HYDROCOLLOIDS,      [PMID:] [10.1016/j.foodhyd.2023.109316]

2. Zijun Zhao, Muwen Lu, Zhu Mao, Jie Xiao, Qingrong Huang, Xuechun Lin, Yong Cao.  (2020)  Modulation of interfacial phenolic antioxidant distribution in Pickering emulsions via interactions between zein nanoparticles and gallic acid.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:32068060] [10.1016/j.ijbiomac.2020.02.136]

3. Zhibin Chen, Zijun Zhao, Wenbo Wang, Qianyi Ye, Jie Xiao.  (2024)  Simulating the behavior of antioxidant to explore the mechanisms of oxidative stability in Pickering emulsion.  FOOD CHEMISTRY,      [PMID:38513478] [10.1016/j.foodchem.2023.138291]

Application Protocols

No item-specific tested application protocols are provided for this small-molecule reagent. Typical laboratory uses derive from standard synthetic organic chemistry procedures:

• Dissolution: Warm gently in toluene, chlorobenzene, THF, or CH2Cl2 to prepare stock solutions (0.1–1.0 M) for reactions or thin-film deposition experiments.
• Film/coating preparation (literature/general): Spin- or drop-cast from chlorobenzene or toluene onto substrates; slow solvent evaporation can promote ordered domains due to the C16 tail.
• Salt formation: Dissolve in minimal ethanol or isopropanol; add equimolar HCl in ether or ethanolic HCl to precipitate the anilinium chloride if desired for handling.

For detailed, validated protocols relevant to your application, consult primary literature or adapt standard methods for anilines while accounting for the long alkyl chain’s solubility and phase behavior.

Biological Roles

This product is supplied for research use only and is not intended for biological administration.

General observations (literature/general):

• 4-Hexadecylaniline is a synthetic aromatic amine with a long alkyl tail; it does not occur naturally. Its amphiphilic nature can promote adsorption to hydrophobic interfaces and ordering in thin films or self-assembled layers.
• As a primary aromatic amine, it can be protonated to anilinium salts, increasing ionic character and altering interfacial behavior. Such salts can be used to template or organize materials in research contexts (e.g., thin-film assembly, nanoparticles), but specific biological pathways or receptor interactions are not established.
• The aniline motif can engage in electron donation to aromatic systems and can serve as a chromophore/auxochrome in azo dyes. Any biological interaction of derivatives (e.g., dyes, polymers) depends on the broader molecular architecture rather than the parent amine itself.

No specific enzymatic, metabolic, or signaling roles are attributed to 4-hexadecylaniline. Handle as a general hydrophobic amine; avoid extrapolating biological activity from the presence of an aniline group due to safety and toxicity concerns associated with aromatic amines.

Buffer Applications

Not typically applicable. 4-Hexadecylaniline is a hydrophobic aromatic amine with very low water solubility at neutral pH, and it is not used as a buffering agent. If aqueous handling is necessary, formation of anilinium salts (e.g., with HCl) can increase apparent solubility, but well-defined buffering capacity is not a standard application. For aqueous systems requiring amine buffering, select established buffers (e.g., Tris, HEPES) instead.

Green Alternatives

Greenness considerations involve both solvent choice and processing energy, as the substrate itself is a high-carbon hydrophobic amine.

• Substrate alternatives: There is no direct “green substitute” for 4-hexadecylaniline if the C16 tail and aniline headgroup are functionally required (e.g., for interfacial assembly or electronics). If only hydrophobic primary amine functionality is needed, simpler fatty amines (e.g., hexadecylamine) may suffice and can be sourced from bio-based feedstocks (literature/general).

Greener solvent choices (literature/general):

| Use case | Conventional | Greener option | Notes | |---|---|---|---| | Acylation/imidization | CH2Cl2 | EtOAc or toluene | EtOAc reduces chlorinated waste; ensure solubility. | | Imine formation | Toluene (Dean–Stark) | 2-MeTHF or CPME | Both enable azeotropic water removal; better safety/green profiles than toluene/THF. | | Diazotization/coupling | AcOH/MeCN | Water/EtOH blends | Maintain low temperature; verify stability/solubility. | | Workup | Hexanes | Heptane/isoheptane | Lower VOC reactivity; similar nonpolarity. |

Operational improvements:

• Use solid-supported acids/bases to aid purification and reduce aqueous waste when forming salts or doing acylations.
• Apply microwave or flow to reduce reaction time/energy where compatible with the amine and solvents.
• Prefer catalytic methods (e.g., catalytic acyl transfer) over stoichiometric reagents when feasible.

Trade-offs:

• Greener solvents may reduce solubility of long-chain substrates; modest heating and higher dilution can compensate. Always validate crystallization and recovery profiles to minimize solvent volumes.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item.

Context (literature/general):

• 4-Hexadecylaniline is primarily a synthetic intermediate/building block. The hydrophobic C16 tail is useful for designing amphiphilic molecules, pro-moieties, or materials that interact with lipid phases. Any use would be at the R&D stage for structure–property exploration (e.g., in dye chemistry, polymer additives, or surface modifiers), not as an approved pharmaceutical ingredient.
• As an aromatic primary amine, it can be transformed into amides, ureas, carbamates, imines, and diazonium-derived products that may be evaluated during medicinal chemistry campaigns. However, aromatic amines raise safety flags (e.g., potential for reactive metabolites), so derivatives are typically modified or masked.

Compliance note: Aladdin Scientific supplies this compound for laboratory research use only. It is not intended for human or animal therapeutic, diagnostic, or clinical applications.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (High, typical for long-chain anilines; literature expectation >350 °C under ambient pressure.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Long-chain para-anilines often are low-melting waxy solids; literature values vary by chain length and polymorph.)
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/general):
  • Organic: Good in nonpolar/aprotic media (toluene, chlorinated solvents, THF, ethers, hot hexanes). Solubility increases with temperature.
  • Aqueous: Very low at neutral pH; forms water-soluble anilinium salts in acidic media (e.g., HCl), though long C16 chain limits overall aqueous miscibility.
• Lipophilicity: High (long alkyl chain; high logP expected, literature/general).
• pKa (literature/general): Anilinium conjugate acid typically pKa ~4.6–5.2; para-alkyl substitution can slightly increase basicity relative to aniline.
• Vapor pressure: Very low at ambient conditions (literature/general for C16-substituted aromatics).

Notes for practice (literature/general):

• The material may exhibit semi-crystalline behavior; gentle heating may be required for dissolution in less polar solvents.
• Salt formation (e.g., HCl) enhances protonation and can aid processing in polar environments.

Quality and Grades

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

Guidance on grades and implications (general):

• For synthetic applications (acylation, diazotization, Schiff-base formation, cross-coupling), residual water and peroxides are typically less critical than for air/moisture-sensitive organometallics, but trace acidic/oxidizing impurities can quench amines or promote side reactions.
• If HPLC/UV-grade solvent compatibility is needed (e.g., analytical workup), low UV-absorbing solvents are preferred; the amine itself absorbs in the UV due to the anilide chromophore.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Aromatic amines are commonly supplied without stabilizers; if present, review compatibility with planned transformations.

Verification and release testing (typical for research grade; general):

• Identity: 1H/13C NMR, MS, and FTIR (aniline N–H stretches; aromatic C–H; aliphatic C–H).
• Purity: GC or HPLC with UV/ELSD detection; melting range if solid. Water by KF for process control as needed.
• Metals/ionic residues: Not typically specified for this class unless for electronic-grade applications; check CoA if required.

Recommendation: Consult the CoA for exact assay, residual solvent content, and any stabilizer or inhibitor present for this specific SKU (H195075).

Reaction and Applications

As a para-alkylated aniline, 4-hexadecylaniline is a versatile hydrophobic amine for building amphiphiles, surface modifiers, and functional materials.

Key transformations (literature/general):

• Acylation to amides: Reaction with acid chlorides/anhydrides (e.g., acylation to long-chain anilides) under base (pyridine, triethylamine) in CH2Cl2 or toluene; useful for tailoring mesogenic or surfactant properties.
• Schiff bases/imine formation: Condensation with aldehydes/ketones (e.g., salicylaldehydes) to give hydrophobic imines or salen-type ligands (further metalation possible). Water removal (Dean–Stark or sieves) accelerates conversion.
• Diazotization/azo coupling: Formation of the corresponding p-hexadecylbenzenediazonium salt (NaNO2/HCl, 0–5 °C), enabling azo dye/pigment synthesis or aryl-radical grafting onto carbon surfaces (graphene, CNTs) and metals.
• N-alkylation/quaternization: Alkyl halides under basic conditions yield secondary/tertiary anilines; quaternary anilinium salts can modulate solubility and interfacial behavior.
• Cross-coupling as nucleophile: Participates in C–N bond formation reactions (e.g., Buchwald–Hartwig amination) when used as the amine partner with aryl halides/triflates to generate N-aryl derivatives embedding a C16 tail.
• Electrophilic aromatic substitution (EAS): Strongly activating –NH2 directs ortho/para; however, para is occupied—ortho functionalization (nitration, sulfonation, acylation) is feasible with protection (e.g., acylated or Boc-protected aniline) to control reactivity.

Practical tips:

• Consider temporary N-protection (Boc, acetyl) to modulate basicity/reactivity in multi-step sequences.
• Long alkyl chain may cause gelation/mesophases—use elevated temperature and vigorous stirring to maintain homogeneity.

Reaction Conditions

General, literature-based guidance for common transformations of 4-hexadecylaniline (optimize per substrate):

• Acylation to amides: Acid chloride (1.05–1.2 equiv), base (2–3 equiv Et3N or pyridine), CH2Cl2 or toluene, 0 °C → rt (2–16 h). Work up with aqueous bicarbonate then brine. Typical isolated yields: 70–95% for unhindered acyls.
• Imine formation: Aromatic aldehyde (1.0–1.2 equiv), toluene or 2-MeTHF, Dean–Stark or 3 Å molecular sieves, 80–110 °C (2–8 h). Catalytic p-TsOH (0.5–5 mol%) may accelerate. Reversible—drive by water removal.
• Diazotization/azo coupling: Dissolve amine in 2–6 M HCl at 0–5 °C; add aqueous NaNO2 (1.05–1.2 equiv) keeping temperature ≤5 °C; couple immediately to activated aromatics/phenols or reduce on surfaces. Maintain cold chain; avoid isolation of dry diazonium salts for safety.
• N-alkylation: Alkyl halide (1.1–1.5 equiv), base (K2CO3/NaHCO3 for mild; NaH or tBuOK for more forcing), DMF/THF, 0 °C → rt (2–12 h). Monitor for over-alkylation to tertiary amines.
• Buchwald–Hartwig as amine partner: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%), bulky phosphine ligand (e.g., XPhos/BrettPhos), base (NaOtBu or Cs2CO3), toluene or dioxane, 80–110 °C (6–24 h). Sterics/electronics dictate rate; preforming the amide (less basic) may be helpful for challenging couplings.

Notes:

• Long-chain substrates can gel; use elevated temperature, efficient stirring, and dilution.
• Salt forms (anilinium) are less nucleophilic; free-base the amine before nucleophilic transformations.

Safety and Handling

Item-specific hazard data were not provided. Always consult the SDS for authoritative, up-to-date hazard classifications and response instructions.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• General hazards (aromatic amines; literature/general): May be harmful if swallowed, inhaled, or absorbed through skin; can cause skin/eye irritation; some anilines can induce methemoglobinemia upon significant exposure. Use engineering controls to minimize inhalation and dermal exposure.
• Personal protective equipment (PPE):
  • Lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Avoid skin contact with neat material and solutions.
  • Use in a fume hood to control vapors/aerosols during heating, diazotization, or acid/base treatments.
• Handling notes (practical):
  • Avoid strong oxidizers and nitrosating agents except under controlled synthetic procedures (e.g., diazotization with strict temperature control).
  • Prevent contamination with acids/bases unless intentional; protonated salts may have different solubility and handling properties.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; obtain medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire & reactivity (literature/general): Combustible organic solid/liquid; use CO2, dry chemical, or foam for extinguishing. Thermal decomposition may release nitrogen oxides.
• Storage incompatibilities: Segregate from strong oxidizers and strong acids when not in controlled use. Keep containers tightly closed to limit oxidation/discoloration.

Solvent Selection

Solvent choice should reflect the amphiphilic nature: a weakly basic aromatic headgroup with a long hydrophobic tail.

• Polarity/miscibility profile (literature/general):
  • Highly soluble: Toluene, xylene, chlorobenzene, chloroform, dichloromethane, THF, CPME, diethyl ether (warming may help), hot hexanes/heptane/isooctane.
  • Poorly soluble: Alcohols at room temperature (improves on heating), acetonitrile, DMF/DMSO moderate to good depending on temperature. Negligible in water at neutral pH; soluble as anilinium salts in dilute mineral acids.
• Selection tips:
  • For electrophilic acylation/alkylation or coupling: Toluene or chlorobenzene offer good solubility and thermal headroom.
  • For diazotization: A biphasic or mixed medium (e.g., AcOH/H2O or HCl/EtOH) is typical; ensure temperature control (0–5 °C) regardless of solvent.
  • For Schiff-base formation: Toluene or toluene with a Dean–Stark trap to remove water; or ethanol with molecular sieves if solubility permits.
  • For surface grafting via diazonium: Aqueous acidic media to generate diazonium, then transfer or in situ reduction on the substrate in acetonitrile/DMF, depending on substrate compatibility.

Mini comparison (literature/general):

• Toluene vs chlorobenzene: chlorobenzene provides higher boiling point for sluggish reactions; toluene is easier to remove, less hazardous.
• THF vs CPME: CPME offers better peroxide stability and green metrics; THF dissolves amines well and is widely used but forms peroxides.

Storage and Reconstitution

• Storage conditions (product data): Room temperature; ship under normal conditions.
• Container: Keep tightly closed in an inert container (glass with PTFE-lined cap recommended) to minimize air/acid exposure and potential discoloration.
• Atmosphere: Ambient storage is generally acceptable; for long-term purity, optional storage under inert gas and away from light can slow oxidative darkening (general guidance for aromatic amines).
• Incompatibilities: Store away from strong oxidizers, nitrosating agents, and strong acids/bases unless intended for controlled reactions.

Reconstitution and preparation (literature/general):

• To prepare stock solutions, warm gently (30–60 °C) and dissolve in toluene, chlorobenzene, chloroform, DCM, THF, CPME, or hot heptane. Typical concentrations: 0.1–1.0 M depending on solvent and temperature.
• For aqueous processing, form anilinium salts by adding equimolar mineral acid (e.g., HCl) in ethanol or isopropanol, then dilute with water; note that the long alkyl chain limits true water miscibility even in salt form.
• Avoid repeated freeze–thaw of solutions; prepare fresh as needed. Solutions in chlorinated solvents or ethers should be stored in amber glass at 2–8 °C if kept more than a few days.

Always refer to the product’s CoA/Spec Sheet and SDS for item-specific stability, assay, and handling details.

Structure and Identity

A para-substituted aniline bearing a linear C16 alkyl chain; the molecule combines an anilinyl headgroup with a long hydrophobic tail, giving amphiphilic character.

• Product name: 4-Hexadecylaniline (p-hexadecylaniline; p-n-hexadecylaniline)
• CAS: 79098-13-8 (product data)
• PubChem CID: 571906 (product data)
• Molecular formula: C22H39N (computed from structure; literature-consistent)
• Molecular weight: ~317.56 g/mol (computed; literature value)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product data lists “311726,” which is incomplete for an InChIKey.)

Structural features (descriptive, literature/general):

• Core ring: Benzene ring with a para-oriented amino group (–NH2) and a para n-hexadecyl (–(CH2)15CH3) substituent.
• Functional groups: Primary aromatic amine (weakly basic), long saturated alkyl chain (hydrophobic, lipophilic).
• Topology: Para substitution maximizes symmetry, minimizing steric interaction between substituents; chain confers mesogenic/ordering tendencies in condensed phases.
• 2D description: Aniline ring with –NH2 at position 1; a straight C16 chain at position 4 extending from the ring para to –NH2; no stereocenters; no heteroatoms beyond the aniline nitrogen.

Synthetic Utility

Functional group set and reactivity (literature/general):

• Primary aromatic amine (–NH2): Nucleophilic at nitrogen; forms amides (acylation), ureas/carbamates (phosgene equivalents or CDI), imines (with carbonyls), and can undergo N-alkylation. The amine can be temporarily protected (Boc, acetyl, Ts) to direct electrophilic aromatic substitutions.
• Para C16 alkyl substituent: Strongly lipophilic, electronically weakly donating via hyperconjugation; modulates solubility and aggregation, enabling hydrophobic interactions and film formation.

Named/standard reactions:

• Diazotization (NaNO2/HCl, 0–5 °C) → diazonium salts for azo coupling or aryl radical grafting to surfaces.
• Buchwald–Hartwig amination (Pd-catalyzed) as the amine partner to install N-aryl linkages onto the aniline nitrogen, generating tertiary anilines with tailored electronics/solubility.
• Schiff-base formation (Dean–Stark, aromatic aldehydes) → ligands, sensors, mesogens.
• Acylation (acid chlorides/anhydrides, base) → long-chain anilides with altered H-bonding and mesophase behavior.
• Electrophilic aromatic substitution (EAS) at ortho positions when N-protected: nitration, sulfonylation, Friedel–Crafts acylation of the ring (with appropriate protection/conditions) to build densely substituted architectures.

Retrosynthetic value:

• Serves as a convergent handle to append a C16 tail onto an aniline core early, then diversify at nitrogen (N-substitutions) or at the ring (post-protection EAS/cross-coupling), enabling access to surfactant-like targets, azo dyes, and functional coatings.

Target Specificity

Not applicable. This product is a small-molecule reagent, not an antibody, enzyme, or probe with defined biological target specificity. No antigen/epitope, species reactivity, clone, or isotype information applies.