N-Phenyl-2-naphthylamine

Base Information

• Chemical Name: N-Phenyl-2-naphthylamine
• CAS No.: 135-88-6
• Deprecated CAS: 52907-17-2,84420-28-0,84420-28-0
• Molecular Formula: C16H13N
• Molecular Weight: 219.286
• Hs Code.: 29214500
• European Community (EC) Number: 205-223-9
• ICSC Number: 0542
• NSC Number: 37151
• UN Number: 3259
• UNII: 456KT854AJ
• DSSTox Substance ID: DTXSID4021131
• Nikkaji Number: J3.627G
• Wikidata: Q13872172
• Metabolomics Workbench ID: 45759
• ChEMBL ID: CHEMBL1543632
• Mol file: 135-88-6.mol

Synonyms:2-anilinonaphthalene;N-phenyl-2-naphthylamine;neosone D;neozon D;neozone;phenyl beta-naphthylamine

Chemical Property of N-Phenyl-2-naphthylamine

Chemical Property:

• Appearance/Colour: light grey powder or crystals
• Vapor Pressure: 0.005mmHg at 25°C
• Melting Point: 105-108 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 395.5 °C at 760 mmHg
• PKA: 0.78±0.30(Predicted)
• Flash Point: 209.2 °C
• PSA: 12.03000
• Density: 1.156 g/cm³
• LogP: 4.65640
• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Very Slightly)
• Water Solubility.: Insoluble.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 219.104799419
• Heavy Atom Count: 17
• Complexity: 232
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

N-Phenyl-2-naphthylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 36/38-40-43-51/53-53-51
• Safety Statements: 22-24/25-61-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Naphthylamines
• Canonical SMILES: C1=CC=C(C=C1)NC2=CC3=CC=CC=C3C=C2
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Description: Phenyl-naphtylamine is an amine coumpound. Sensitization was reported in patients with hypersensitivity to rubber.
• Uses: N-Phenyl-2-naphthylamine is used as an antioxidant in rubber processing; provides oxidation and flex-cracking resistance in natural rubber, synthetic rubbers, and latexes; stabilizer in electrical-insulating silicone enamels; antioxidant in otiJer polymers, greases, lubricating oils, and transformer oils; heat and light stabilizer; vulcanization accelerator; catalyst; polymerization inhibitor; component of rocket fuels, surgical plasters, and tin-electroplating batiJs; chemical intermediate; an inhibitor for butadiene; in the production of seven dyes; in rubber products made of natural rubber, styrene-butadiene, nitrile, butadiene, and chloroprene. Formerly as an antioxidant in rubber processing to impart heat, oxidation, and flexcracking resistance in natural rubber, synthetic rubbers, and latexes; as a stabilizer in electricalinsulating silicone enamels Formerly as an antioxidant in rubber processing to impart heat, oxidation, and flexcracking resistance in natural rubber, synthetic rubbers, and latexes; as a stabilizer in electricalinsulating silicone enamels

Technology Process of N-Phenyl-2-naphthylamine

There total 81 articles about N-Phenyl-2-naphthylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

sodium tetraphenyl borate (143-66-8) + naphthalen-2-ylamine (91-59-8) → N-Phenyl-2-naphthylamine (135-88-6,84420-28-0)

Guidance literature:

With copper(II) acetate monohydrate; triethylamine; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1055/s-0037-1610251

Reference yield: 98.0%

tri(naphthalen-2-yl) phosphate (7657-86-5) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6,84420-28-0)

Guidance literature:

With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; potassium carbonate; at 130 ℃; for 4h; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.9b00703

Reference yield: 97.0%

2-methylthionaphthalene (7433-79-6) + aniline (62-53-3) → N-Phenyl-2-naphthylamine (135-88-6,84420-28-0)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium hexamethyldisilazane; 1,2-bis-(dicyclohexylphosphino)ethane; In toluene; at 100 ℃; for 12h;

DOI:10.1021/acscatal.0c00393

upstream raw materials:

anthranilic acid

3-Hydroxy-2-naphthoic acid

[2]naphthyl-nitroso-phenyl-amine

acetic acid

Downstream raw materials:

furfuryl acrylate

2-(2-anilino-[1]naphthylazo)-benzoic acid

benz[a]acridine

2,2,5,5-tetramethyltetrahydrofuran

Refernces

• 1、 Canete,Melendrez,Saitz,Zanocco. "Synthesis of aminonaphthalene derivatives using the bucherer reaction under microwave irradiation". . p. 2143 - 2148. Retrieved 2001.
• 2、 Kym. "-". . p. 425. Retrieved 1890.
• 3、 -. "Triarylamine derivative and organic electroluminescent device thereof". Paragraph 0179-0182. . Retrieved 2021/09/15.
• 4、 -. "Organic compound, electronic component, comprising same and electronic device". Paragraph 0116; 0165-0168; 0173. . Retrieved 2021/07/17.