90-30-2

Basic information

• Product Name: N-Phenyl-1-naphthylamine
• Synonyms: N-Phenyl-1-naphthylaMine reagent grade, 98%;Akrochem antioxidant PANA;Algerite;alpha-Naphthylphenylamine;alpha-Phenylnaphthylamine;amoco32;antigenepan;Antioxidant PAN
• CAS NO: 90-30-2
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.28
• EINECS: 201-983-0
• Product Categories: Rubber Chemicals;Industrial/Fine Chemicals;Organics
• Mol File: 90-30-2.mol

Chemical Properties

• Melting Point: 60-62 °C(lit.)
• Boiling Point: 226 °C15 mm Hg(lit.)
• Flash Point: >200°C
• Appearance: Pinkish to light brown/Crystals or Flakes
• Density: 1,1 g/cm3
• Vapor Pressure: 0.504 hPa (150 °C)
• Refractive Index: 1.7020 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 0.003g/l
• PKA: 0.78±0.30(Predicted)
• Water Solubility: insoluble
• Stability: Stable. Incompatible with strong oxidizing agents, strong acids.
• BRN: 2211174
• CAS DataBase Reference: N-Phenyl-1-naphthylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Phenyl-1-naphthylamine(90-30-2)
• EPA Substance Registry System: N-Phenyl-1-naphthylamine(90-30-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36/37/38-50/53-43
• Safety Statements: 26-36-61-37/39-29-60-36/37
• RIDADR: 3077
• WGK Germany: 2
• RTECS: QM4500000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 90-30-2(Hazardous Substances Data)

Usage

Uses

Used in Surfactant Analysis:
N-Phenyl-1-naphthylamine is used as a fluorescent probe for determining the critical micelle concentration (CMC) of surfactants. Its fluorescence properties allow for the sensitive detection and quantification of surfactant concentrations, which is crucial in understanding the behavior and performance of surfactants in various applications.
Used in Analytical Chemistry:
N-Phenyl-1-naphthylamine is employed in a method for determining the concentration of organolithium and organomagnesium reagents. Its interaction with these reagents enables the accurate measurement of their concentrations, which is essential in various chemical synthesis processes and research applications.
Used in Biophysical Studies:
N-Phenyl-1-naphthylamine serves as a hydrophobic probe to study the phase transitions of membrane lipids in whole cells. Its incorporation into cellular membranes allows researchers to investigate the structural and dynamic properties of lipid bilayers, providing insights into the mechanisms underlying membrane-related processes and their implications in cellular function and disease.

Air & Water Reactions

May be sensitive to prolonged exposure to air. Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Reactivity Profile

N-Phenyl-1-naphthylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N-Phenyl-1-naphthylamine emits toxic fumes.

Fire Hazard

Flash point data for N-Phenyl-1-naphthylamine are not available. N-Phenyl-1-naphthylamine is probably combustible.

Biochem/physiol Actions

N-Phenyl-1-naphthylamine turns fluorescent after binding to hydrophobic regions of cell membranes.

Contact allergens

Phenyl-alpha-naphthylamine is contained in some rubbers and oils as an antioxidant of the amine group. It is closely related to phenyl-beta-naphthylamine and to di-beta-naphthyl-p-phenylenediamine, but without cross-reactivity.

Purification Methods

Crystallise it from EtOH, pet ether or *C6H6/EtOH. Dry it under vacuum in an Abderhalden pistol. [Beilstein 12 H 1224.]

InChI:InChI=1/C16H13N/c1-2-9-14(10-3-1)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17H

Upstream product

• 60-29-7 diethyl ether 
• 86-57-7 1-Nitronaphthalene 
• 90-15-3 α-naphthol 
• 142-04-1 aniline hydrochloride 
• 134-32-7 1-amino-naphthalene 
• 45497-73-2 aniline hydroiodide 
• 62-53-3 aniline 
• 84-86-6 4-amino-1-naphthalenesufonic acid 
• 82-76-8 8-Anilino-1-naphthalenesulfonic acid 
• 27067-30-7 naphth-1-yl phenyl nitroxide 
• 130-14-3 sodium 1-naphthalenesulfonate 
• 91-20-3 naphthalene 
• 622-37-7 Phenyl azide 
• 99747-74-7 1-naphthyl triflate 

Downstream Products

• 59130-78-8 N-(1-naphthyl)-N-phenyl-acetamide 
• 876483-24-8 [1]naphthyl-phenyl-carbamoyl chloride 
• 105541-12-6 7-benzyl-benz[c]acridine 
• 859068-69-2 [1]naphthyl-phenyl-aminooxalyl chloride 
• 60129-39-7 2-(4-anilino-[1]naphthylazo)-benzoic acid 
• 52255-88-6 4,4'-(buta-1,3-diene-2,3-diyl)bis(methoxybenzene) 
• 10352-43-9 benzophenarsazine-7-chloride 
• 803-83-8 5-anilino-benzo[a]phenoxazin-9-one 
• 115605-85-1 1-hydroxy-[2]naphthoic acid-([1]naphthyl-phenyl-amide) 
• 82941-24-0 (4-anilino-[1]naphthyl)-bis-(4-dimethylamino-phenyl)-methane 
• 24308-76-7 phenyl-(4-phenylazo-[1]naphthyl)-amine 
• 6341-40-8 Phenyl-<1>naphthyl-nitrosamin 
• 69557-78-4 [1]naphthyl-(4-nitroso-phenyl)-amine 
• 225-83-2 benzophenothiazine 

Relevant articles and documents

New NIR dyes based on quinolizino[1,9-hi]phenoxazin-6-iminium chlorides: synthesis, photophysics and antifungal activity

A series of new quinolizino[1,9-hi]phenoxazinium dyes built on julolidine and naphthalen-1-amine derivatives or anthracen-1-amine were prepared. The N-terminal of these quinolizino[1,9-hi]phenoxazinium chlorides contains aromatic or aliphatic substituents, along with the functionalities such as chloro, hydroxyl and carboxyl. The photophysical behaviour of these compounds was studied in anhydrous ethanol and aqueous medium under acidic and basic conditions. These fluorophores display absorption and emission maxima up to 675 and 712 nm, respectively, can serve as alternative sensing tools in biological assays. All the quinolizino[1,9-hi]phenoxazinium chlorides were evaluated against the yeast Saccharomyces cerevisiae in a broth microdilution assay. It was found that their antifungal activity depended on the substituent at 14-amino position in benzo[a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chlorides, and also on the addition of a fused benzene ring, which occurs in naphtho[2,3-a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chloride. The highest activity, with a MIC of 0.78 μM, was obtained for benzo[a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chloride with a 3-chloropropyl substituent at the 14-amino position of the heterocycle core.

Fabrication of TiO2 Nanoparticles by electrostatic jet using the low dielectric constant solvent

Tert-butyl alcohol (TBA) was used as a low dielectric constant solvent for the fabrication of TiO2 nanoparticles by electrostatic jet. The phase, morphology and diameter distribution properties of the resulting TiO2 nanoparticles were characterized by XRD and SEM, respectively. As the PVAc content of the precursor solutions increased, the diameter of the electrostatic jet PVAc/butyl titanate composite nanoparticles increased. The resulting composite nanoparticles possessed a smooth surface and displayed perfect spherical structures when the PVAc content was 3 wt%, where as a PVAc content of 9 wt% or more led to a co-continuous structure of nanoparticles and fibers, other were erythrocyte-liked in shape and contained large pits on their surface. Anatase TiO2 nanoparticles were formed from the butyl titanate/PVAc nanoparticles following their calcination at 550 °C. The diameter distribution of the TiO2 nanoparticles was wide, with the values falling in the range of 623-8±122-8 to 1328-3±247-6 nm. When its diameter is 238 nm and adding content is 2 g/L, the 40 min degradation rate of methylene blue catalyzed by titanium oxide nanoparticles is 92.39%.

Hole Transfer Compound and Organic Light-Emitting Diodes Using The same

The present invention relates to a hole transport compound represented by a chemical formula 1, and an organic light emitting device including the same. The hole transport compound according to the present invention is based on high hole transport properties and reduces ionization potential to improve hole transport ability, has high compatibility with other layers of general OLED devices and has high hole mobility and long lifespan.

Nitrogen-containing compound, organic electroluminescent device, and electronic device

The invention provides a nitrogen-containing compound, an organic electroluminescent device and an electronic device, and belongs to the technical field of organic materials. The structure of the nitrogen-containing compound is represented by Chemical Formula 1: wherein X1, X2, Y1, Y2 are the same or different from each other and are each independently a single bond, O, S, N(R3), C(R4R5), Ge(R6R7), Si(R8R9), Se, wherein X1 and Y1 are not single bonds simultaneously and X2 and Y2 are not single bonds simultaneously.

Organic compound, and electronic element and electronic device using same

The invention relates to an organic compound. The structure of the organic compound is shown as a formula I. When the organic compound is used as a hole adjustment layer material of an electronic element, driving voltage can be reduced, the luminous efficiency of a device can be improved, and the service life of the device can be prolonged.

Organic compound and electronic device and device containing the same

The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent material 9 with 10 -9 dihydro 9 -10 -dimethyl and oxanthrene and arylamine groups, an electronic device containing the compound and a device. The organic electroluminescent device has lower driving voltage. Higher luminous efficiency and longer service life.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF

In the present invention, provided is a novel compound capable of improving luminance efficiency, stability, and service life of an element, an organic electronic element using the same, and an electronic device thereof. By using the compound of the present invention, high luminance efficiency, low driving voltages, and high heat resistance of the element can be achieved, and color purity and service life of the element can be greatly improved.

Nickel-Catalyzed Amination of Aryl Nitriles for Accessing Diarylamines through C?CN Bond Activation

A nickel-catalyzed amination to access diarylamines has been developed through C?CN bond activation of aryl nitriles with anilines. In this developed catalytic protocol, various aromatic and heteroaromatic nitriles could be utilized as the electrophiles to couple with substituted anilines. A diversity of diarylamines were obtained in 15–95% yields. (Figure presented.).

Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation

Reaction of 1,4-diazabutadiene (p-RC6H4N = C(H)(H)C = NC6H4R-p; R = OCH3, CH3, H and Cl; abbreviated as L-R) with CuCl2·2H2O in methanol at ambient temperature (25 °C) affords a group of doubly chloro-bridged dicopper complexes of type [{CuI(L-R)Cl}2], designated as 1-R. Similar reaction carried out in acetonitrile furnishes a family of doubly chloro-bridged dicopper complexes of type [{CuII(L-R)Cl2}2], designated as 2-R. Molecular structures of 1-OCH3 and 2-OCH3 have been determined by X-ray crystallography. While copper(I) is having a nearly tetrahedral N2Cl2 coordination sphere in 1-OCH3, the N2Cl3 coordination sphere around copper(II) is distorted square pyramidal in nature in 2-OCH3. Isolated 2-R complexes, on dissolution in methanol, are found to undergo facile reduction of the metal center to generate the corresponding 1-R complexes. The 1-R and 2-R complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the 1-R and 2-R complexes shows both metal-centered and ligand centered redox responses. The 1-R complexes are found to efficiently catalyze C-N cross-coupling reactions between arylboronic acids and aryl amines; while the 2-R complexes display notable catalytic efficiency for nitroaldol reactions.

Chan-Evans-Lam C?N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).