Phenyl-l-naphthylamine

AMINES - AMINES,AROMAHC - DIARYLAMINES] (Vol2) N-[4-(l-methyl-l-phenylethyl)phenyl]-l-naphthylamine [17418-49-4]... 

A -Phenyl-l-naphthylamine [90-30-2] M 219.3, m 63.7-64.0°, pK j, -0.1. Crystd from EtOH, pet ether or benzene/EtOH. Dried under vacuum in an Abderhalden pistol. 

Stabilisers are usually determined by a time-consuming extraction from the polymer, followed by an IR or UV spectrophotometric measurement on the extract. Most stabilisers are complex aromatic compounds which exhibit intense UV absorption and therefore should show luminescence in many cases. The fluorescence emission spectra of Irgafos 168 and its phosphate degradation product, recorded in hexane at an excitation wavelength of 270 nm, are not spectrally distinct. However, the fluorescence quantum yield of the phosphate greatly exceeds that of the phosphite and this difference may enable quantitation of the phosphate concentration [150]. The application of emission spectroscopy to additive analysis was illustrated for Nonox Cl (/V./V -di-/i-naphthyl-p-phcnylene-diamine) [149] with fluorescence ex/em peaks at 392/490 nm and phosphorescence ex/em at 382/516 nm. Parker and Barnes [151] have reported the use of fluorescence for the determination of V-phenyl-l-naphthylamine and N-phenyl-2-naphthylamine in extracted vulcanised rubber. While pine tar and other additives in the rubber seriously interfered with the absorption spectrophotometric method this was not the case with the fluoromet-ric method. 

Wang H, Wang D, Dzeng R Carcinogenicity of A/-phenyl-l-naphthylamine and N-phenyl-2-naphthylamine in mice. Cancer Res 44 3098-3100, 1984... 

Studies (2, 3) have also been reported of the reaction of phosphorus trichloride with diarylamines containing p-methyl or p-chloro substituents. In every case, the expected ring-substituted derivatives of 1 and 2 were obtained after the reaction mixture was treated with water. The interaction of (V-phenyl-o-toluidine and phosphorus trichloride at 200°C also gave a reaction mixture from which the expected phosphine oxide was isolated (3). None of the corresponding spirophosphonium chloride, however, could be obtained. The failure to isolate this substance can not be explained simply by the presence of an ortho substituent in the diarylamine, since it had been previously found that a 34% yield of a spirophosphonium chloride can be obtained via the interaction of fl/-phenyl-l-naphthylamine and phosphorus trichloride (2). No dihydropheno-phosphazine derivatives at all were obtained by the interaction of di-o-tolylamine and phosphorus trichloride at 200°C (3). 

Amines have been used for the following purposes related to expls,propellants, pyrotechnic compositions and fuels a)Stabilizers for NC propellants(eg, diphenylamine, nitro-diphenylamine and phenyl-/l-naphthylamine, the last examined in Ftance(Ref 3) b)Sensi-tizers for some expl and propellent compns (Ref 4 and addnl ref d) c)Smoke-producing compds (Addnl Ref d) d)Liquid fuels for rockets in conjunction with strong oxidizers, such as nitric acid(some of these are hyper-golic) (Refs 6 8 and addnl refs e,g,i,k8fl)... 

The fluorescence of iV-phenyl-l-naphthylamine (81) is quenched by proton acceptors such as dioxane, nitriles, esters and amines. Probably a charge transfer interaction between the proton donor and the proton acceptor through the hydrogen bond is the mechanism which accounts for the quenching147. 

The presence of 7V-phenyl-l-naphthylamine as inhibitor considerably reduces the development of peroxide in the ether. 

For instance, passing ammonia into a boiling solution of 2,4-dinitro-l-naphthyl -toluene-sulfonate gives 2,4-dinitro-l-naphthylamine quantitatively, and 2,4-dinitro-TV-phenyl-l-naphthylamine is obtained in 98% yield by use of aniline.854... 

A-Phenyl-l-naphthylamine 355e This amine, which cannot be prepared smoothly by the Bucherer reaction, is obtained as follows. 1-Napthylamine (143 g), aniline (175 g), and sulfanilic acid (3 g) are heated for 40-48 h under reflux in a flask fitted with a thermometer and a long air-condenser. Ammonia is evolved and the boiling point of the mixture rises from about 195° to 215°. Then, on fractionation in a vacuum, aniline (80-85 g) distils at 70°/12 mm, followed with bumping an dfoaming by an intermediate fraction (8-10 g) that contains a little A-phenyl-1 -naphthylamine. The bulk of the latter (190-195 g) boils at 212 to 216°/12 mm the residue distils up to 225°/12 mm. The total yield is 91 % (about 200 g) of colorless needles, m.p. 62° (from a little ethanol). 

Calmodulin is involved in calcium signaling and the activation of intracellular enzymes. In the presence of calcium, calmodulin exposes a hydrophobic surface, which can Interact with other proteins. This surface can also bind hydrophobic probes. Calmodulin was mixed with one of three different probes, 9-anthroxycholine (9-AC), ANS, or A -phenyl-l-naphthylamine (NPN). In aqueous solutiem, these probes are all weakly flucu cent in the absence o[ protein (Figure 6.36. —). Addition of calmodulin, without... 

Figure 5.12 Separation of amine antioxidants and antiozonants by one-dimensional thin-layer chromatography. Solvent benzene - acetone - concentrated ammonium hydroxide (100 5 0.1) development distance 15 cm indicator 4% benzoyl peroxide in benzene. 1 = N-phenyl-l-naphthylamine 2 = N-phenyl-2-naphthylamine 3 = p-(p-tolylsulfonylamido)-diphenylamine 4 = nonylated diphenylamines 5 = octylated diphenylamines 6 = octylated diphenylamines 7 = octylated diphenylamines 8 = 4,4-dimethoxydiphenylamine 9 = 4-isopropoxydiphenylamine 10 = 4"-isopropyl-aminodiphenylamine 11 = N, N-diisopropyl-p-phenylenediamine 12 = N,N -6i-sec-h xtyi-p-p)Lieny emdizTmne. Reproduced from [119]...

The cmc of a nanostructure is an important property and can readily be measnred in the laboratory using surface tension measnrements or fluorescent probes such as pyrene (Fignre 1). This is achieved by monitoring pyrene s characteristic strong finorescence in nonpolar domains and weak finorescence and polar shift of the excitation peak in polar solvents. This shift can be utilized to probe the local pyrene environment at different concentrations. Experimentally, an increase in intensity of the pyrene corresponds to its encapsulation in a hydrophobic environment and hence nanostructure formation. Although, it should be noted that more recently A-phenyl-l-naphthylamine (PNA) has been utilized as a probe as it has been proposed to have improved... 

Dibutyl diphenylamine 4,4 -Dihexyl diphenylamine 4,4 -Dioctyl diphenylamine Tetrabutyl diphenylamine Tetraoctyl diphenylamine 1-Naphthylamine Butylphenyl-l-naphthylamine Hexylpheny 1-1 -naphthylamine Octylphenyl-l-naphthylamine 4,4 -Dipentyl diphenylamine 4,4 -Diheptyl diphenylamine 4,4 -Dinonyl diphenylamine Tetrahexyl diphenylamine Tetranonyl diphenylamine N-Phenyl-l-naphthylamine Pentylphenyl-l-naphthylamine Heptylpheny 1-1 -naphthylamine Nonylphenyl-l-naphthylamine... 

Fig. 11-29 XPS N is spectra (A) neutral poly(diphenylamine), (B) oxidized poly(diphenylamine),and(C)oxidizedpoly(N-phenyl-l-naphthylamine). Dashed lines are the results of deconvolution. After Reference [24], reproduced with permission.

It is known that molecularly imprinted [3-CD polymer may be used as optical receptor for detection of organic compounds. The molecularly imprinted [3-CD polymer was prepared from [3-CD, using TDI as a crosslinking agent in this procedure A-phenyl-l-naphthylamine (35) served as a template. The molecularly inprinted polymer was fluorometrically characterized using a fibre optic cable attached to a flow-cell. The above sensor was investigated for analytical determination of 35 [82]. 

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