7502-06-9

Usage

Uses

Used in Chemical Production:
4-N-Hexadecyloxyaniline is used as a key component in the synthesis of various commercial products, leveraging its reactivity and structural properties to achieve desired outcomes in the final products.
Used in Research and Development:
4-N-HEXADECYLOXYANILINE is employed as a subject of study in scientific research, particularly to explore its potential applications and to understand its interactions with human health and the environment, thereby informing the development of safety regulations and handling protocols.
Used in Industry Safety Protocols:
4-N-Hexadecyloxyaniline is used as a reference material in the establishment of industry handling standards and safety regulations, ensuring that its use is conducted in a manner that minimizes risks to human health and the environment.

InChI:InChI=1/C22H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20-24-22-18-16-21(23)17-19-22/h16-19H,2-15,20,23H2,1H3

Upstream product

• 102703-33-3 4-hexadecyloxy-1-nitrobenzene 
• 123-30-8 4-amino-phenol 
• 100-02-7 4-nitro-phenol 
• 103-90-2 4-acetaminophenol 
• 112-82-3 hexadecanyl bromide 
• 95808-43-8 acetic acid-(4-hexadecyloxy-anilide) 

Downstream Products

• 96969-62-9 N,N'-bis-(4-hexadecyloxy-phenyl)-thiourea 
• 98459-15-5 Benzoic acid 4-{[(E)-4-hexadecyloxy-phenylimino]-methyl}-phenyl ester 
• 98459-05-3 Furan-2-carboxylic acid 4-{[(E)-4-hexadecyloxy-phenylimino]-methyl}-phenyl ester 
• 124778-84-3 4-Hexadecyloxy-benzoic acid 4-{[(E)-4-hexadecyloxy-phenylimino]-methyl}-3-hydroxy-phenyl ester 
• 1157855-63-4 C₃₇H₅₉NO₂ 
• 1157855-56-5 C₃₀H₄₅NO 
• 1157855-59-8 C₃₁H₄₇NO₂ 
• 1157855-57-6 C₃₀H₄₅NO₂ 
• 1157855-58-7 C₃₁H₄₇NO 
• 1157855-60-1 C₃₃H₅₁NO₂ 

Relevant academic research and scientific papers

Polarization effect in luminescent mesogenic BF2 complexes derived from heterocyclic benzothiazoles

Two series of benzo(thia)xazoles 1–2 and one series of boron difluoride complexes 2-BF2 derived from benzothiazoles 2 were reported, and their mesomorphic and optical properties were investigated. The crystal and molecular structures of compound 2 and 2-BF2 (all n = 8) were determined by means of X?ray structural analysis, and both crystallize in the triclinic P-1 and monoclinic P21/c. The geometry at boron center is perfectly tetrahedral, and the overall molecular shapes are considered as rod?shape. Both benzo(thia)xazoles 1 and 2 exhibited N or/and SmC phase, and boron complexes 2-BF2 formed N or/and SmC phase. Benzothiazoles 2 showed a much wider temperature range of mesophase than those of benzoxazoles 1, which were attributed to the better polarization by sulfur atom incorporated. Boron complexes 2-BF2 (n = 10, 12) emitted a yellow?to?green emission at λmax = 569–571 nm in CH2Cl2. This is the first mesogenic BF2 complexes derived from benzothiazoles.

Thermotropic Liquid-Crystalline and Light-Emitting Properties of Bis(4-aalkoxyphenyl) Viologen Bis(triflimide) Salts

A series of bis(4-alkoxyphenyl) viologen bis(triflimide) salts with alkoxy chains of different lengths were synthesized by the metathesis reaction of respective bis(4-alkoxyphenyl) viologen dichloride salts, which were in turn prepared from the reaction of Zincke salt with the corresponding 4-n-alkoxyanilines, with lithium triflimide in methanol. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance spectra and elemental analysis. Their thermotropic liquid-crystalline (LC) properties were examined by differential scanning calorimetry, polarizing optical microscopy, and variable temperature X-ray diffraction. Salts with short length alkoxy chains had crystal-to-liquid transitions. Salts of intermediate length alkoxy chains showed both crystal-to-smectic A (SmA) transitions, Tms, and SmA-to-isotropic transitions, Tis. Those with longer length of alkoxy chains had relatively low Tms at which they formed the SmA phases that persisted up to the decomposition at high temperatures. As expected, all of them had excellent thermal stabilities in the temperature range of 330-370 ?C. Their light-emitting properties in methanol were also included.

Luminescent mesogenic borondifluoride complexes with the Schiff bases containing salicylideneamines and β-enaminoketones core systems

Three new families of borondifluoride complexes 1a–c derived from salicylideneamines 2a and β-enaminoketonates 2b–c were reported, and their mesomorphic and optical properties were also investigated. One single crystal and molecular structure of nonmesogenic BF2 complex 1c (n = 10) was resolved and the geometry of the central boron atom was tetrahedron. A larger dihedral angle of 81.3° between the two phenyl rings observed in crystal lattice was attributed to the lack of liquid crystallinity. Boron complexes 1a formed monotropic SmA phases, while boron complexes 1b exhibited enantiotropic SmC mesophases. The optical property of the boron complexes was dependent on their molecular structures, and they emitted a blue–to–green emission at λmax = 476–541 nm in the solution and 488–550 nm in the solid state. This is the first group of mesogenic BF2 complexes with the Schiff bases derived from respective salicylideneamines and β-enaminoketones.

Columnar self-assembly of bowl shaped fluorescent liquid crystals based on calix[4]arene with Schiff base units

A new family of bowl-shaped molecules with a calix[4]arene rigid core and appended on four-sides, that display a wide range of hexagonal columnar phases, has been synthesised and well characterized. The thermal behaviours of the present compounds were established using a combination of polarising optical microscopy (POM), differential scanning calorimetry (DSC) and a high-temperature powder X-ray diffraction method (XRD). It is found that all of the synthesised materials show an enantiotropic hexagonal columnar liquid crystal phase. The structural and conformation characterization of these newly synthesised compounds was achieved by FT-IR, 1H NMR, and 13C NMR spectroscopy. All of the synthesised compounds exhibited good blue luminescence in solution under long wavelength UV light. To explore the structure property correlations, the alkoxy side chain group was varied from a lower alkyl spacer to a higher alkyl spacer on the lower rim of the calix[4]arene. The present research specified that the introduction of linking groups on the lower rim with an n-alkoxy side group is an influential approach to obtaining a supramolecular bowl shape liquid crystal which has good thermal and photophysical behaviour.

Benzene ring containing cationic gemini surfactants: Synthesis, surface properties and antibacterial activity

New quaternary ammonium gemini surfactants of the general formula CnH2n?+?1-Ph-NHCOCH2N+(CH3)2-(CH2)s-N+(CH3)2CH2CONH-Ph-CnH2n?+?1 (with n?=?8, 10, 12, 14, 16 and s?=?2, 4, 6) have been synthesized by an efficient synthetic pathway based on the quaternization of N,N,N′,N′-tetramethylalkylenediamine with 2-bromo-N-(4-(alkyloxy) phenyl) acetamides. Their surface properties were investigated by surface tension, electrical conductivity and dynamic light scattering (DLS) measurements. The study shows that the incorporation of a benzene ring in the hydrophobic tail prompts micelle formation which leads to a smaller cmc values in the range of 0.21–0.009?mM compared to analogous geminis bearing alkyl hydrophobic chains. The length of the spacer and the hydrophobic chain has a pronounced effect on the aggregation behavior of surfactants molecules. This was confirmed by the average surfaces occupied by these molecules at the water–air interface calculated from the Gibbs equation. The size of the aggregates was measured by employing dynamic light scattering technique. The antimicrobial activity of investigated surfactants was evaluated against three microorganisms: Staphylococcus aureus, Escherichia coli and Candida albicans.

Mesogenic heterocycles derived from quinoxaline Schiff Bases

Three new series of heterocyclic quinoxaline Schiff Bases 1–2 were prepared, characterized and their mesomorphic properties were investigated. These compounds 1 and 2 are in fact geometric isomers in which an imine moiety (e.g., [sbnd]C[dbnd]N) is inversely incorporated into quinoxaline, leading to an opposite local dipole. Two single crystallographic structures 1 (m=8, n=8) and 2a (m=12, n=8) were determined by X-ray crystallographic analysis in order to understand the effect of mesomorphic properties. Weak H-bonds, CH–π and π–π interactions were found in both crystals, which were attributed to the formation of mesomorphic behavior. Variable temperature FT-IR experiments were performed to confirm the induced H-bonds. All series?of compounds 1–2 exhibited N/SmC or SmC phases, which were identified by optical microscope and confirmed by powder X-ray diffraction experiments. Compounds 2a have a slightly wider range of mesophase temperatures than that of compounds 1 and 2b.

Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors

A series of new low molecular organogelators (LMOGs) with thermotropic mesophase were synthesized via the reaction of 3,6-dimethyl-pyrazine-2,5- dicarboxylic acid with p-alkoxyl anilines. These compounds readily formed stable gels in a variety of organic solvents and their self-assembly behavior, structure-property relationship were investigated by scanning electron microscopy (SEM), X-ray diffraction (XRD), 1H nuclear magnetic resonance (1H NMR), Fourier transform infrared spectroscopy (FTIR) and ultra-violet-visible spectroscopy (UV). The results showed a combination of intra-hydrogen bonding, π-π stacking and van der Waals interaction resulted in the aggregation of the organogelators to form three-dimension fibrous networks. The gels formed were multi-responsive to environmental stimuli, such as temperature, fluorinion, and shear stress. More importantly, all the organogelators exhibited thermotropic hexagonal column mesophase as revealed by differential scanning calorimetry (DSC), polarized optical microscopy (POM), and variable temperature XRD studies. A control compound was synthesized and its gelling ability was also checked.

Designer ionic liquid crystals based on congruently shaped guanidinium sulfonates

Ionic liquid crystals are mesogenic compounds that consist of cations and anions, usually rod-like cations and spherical anions. Herein we report a new method for the synthesis of ionic liquid crystals by using cations and anions of the same molecular shape with oppositely charged head groups. Thus, 4-alkoxyphenylpentamethylguanidinium 4-alkoxyphenylsulfonate ion pairs have been synthesised. 4-Alkoxyphenylpentamethylguanidinium iodides were also prepared to determine the influence of congruently shaped anions, in comparison with their spherical counterparts, on mesophase behaviour, which was investigated by differential scanning calorimetry (DSC), polarising optical microscopy (POM) and X-ray diffraction (XRD). All the liquid crystalline salts exhibit smectic A mesophases with strongly interdigitated bilayer structures. The guanidinium sulfonate ion pairs show mesomorphic properties from shorter alkyl chain lengths (≥C9) and lower melting points (≈10 K), whereas the corresponding guanidinium iodides are liquid crystalline for longer alkyl chain lengths (≥C14). For chains with ≥C18, however, the mesophase range decreases for the sulfonate ion pairs, but not for the iodide salts. Tuning mesophase stability: Guanidinium sulfonate ion pairs with congruently shaped anions and cations with short alkyl chains R (see scheme) have favourable mesogenic properties with respect to mesophase stability in comparison with their guanidinium counterparts with spherical iodide anions. Copyright

Studies of calamitic liquid crystalline compounds involving ester-azo central linkages with a biphenyl moiety

Two mesogenic homologous series involving ester-azo central linkages with a biphenyl moiety have been synthesized, such as 4'-[(4-n-alkoxyphenyl)diazenyl] biphenyl-4-ol (series I) and 4'-[(4-n-alkoxyphenyl) diazenyl]-4-butoxy phenyl biphenyl-4-carboxylate (series II). Azobiphenyl of series I having a free hydroxyl group with strong hydrogen bonding exhibits a high-temperature enantiotropic smectic phase. Whereas in series II, compounds containing C 1-C8 carbon atoms exhibit only a monotropic smectic phase and compounds with C10, C12, C14, and C 16 atoms show an enantiotropic smectic phase. These compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral studies. The phase transition and mesogenicity of these substances were studied by polarizing optical microscopic and differential scanning calorimetric techniques. Their thermal stabilities and other characteristics are discussed. Copyright Taylor &Francis Group, LLC.

Role of terminal heterocyclic ring on mesomorphic properties of homologous series

Two new homologous series of compounds with a heterocyclic ring having sulfur and oxygen as a hetero atom derived from p-hydroxy acetophenone and alkoxy aniline containing cinnamate-azomethine as central linkages have been synthesized. viz. 4(furalacryloxy) α-methyl benzylidine-4′-alkoxy aniline and 4(thianylacryloxy) α-methyl benzylidine-4′-alkoxy aniline. The compound of both the series have been characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectrometry method. Their liquid crystalline properties have been investigated by optical polarizing microscopy and differential scanning calorimetry (DSC) studies. All the derivatives are mesomorphic in nature showing the nemetic phase. The mesomorphic properties of the present two series are compared with other structurally related series to evaluate the effect of thiophene and furan on mesomorphism. Copyright Taylor & Francis Group, LLC.