Synthesis of n-phenyl-2-naphthylamine

Preparation of n-phenyl-2-naphthylamine

In a round-bottomed flask fitted with a thermometer and a vertical tube, a mixture of 143 grams (1.0 mole) of 1-naphthylamine, 175 grams of aniline, and 3 grams of sulfanilic acid is boiled vigorously for 42 hours. Ammonia is liberated and the boiling point of the mixture increases to 215°C. from an initial value of about 195°. When the reaction is completed, the mixture is fractionated carefully in the vacuum. Three fractions are taken: about 80 grams of aniline, about 10 grams of an intermediate fraction containing some aniline, a little 1-naphthylamine, and mainly n-phenyl-2-naphthylamine, and finally, 190 to 200 grams of n-phenyl-2-naphthylamine which solidifies at about 53°. The residue is discarded. At 12 mm. pressure, the boiling point of aniline is about 73°, of 1-naphthylamine about 160°, and of n-phenyl-2-naphthylamine about 224°.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 179, 1949





InChI Key


Canonical SMILES


MeSH Synonyms

2-anilinonaphthalene, N-phenyl-2-naphthylamine, neosone D, neozon D, neozone, phenyl beta-naphthylamine

Depositor-Supplied Synonyms

N-Phenyl-2-naphthylamine, N-Phenylnaphthalen-2-amine, 135-88-6, N-(2-Naphthyl)aniline, Neozone, Stabilizator AR, AgeRite Powder, Aceto PBN, Antioxidant 116, PBNA, Anilinonaphthalene, 2-Phenylaminonaphthalene, 2-Anilinonaphthalene, 2-Naphthylphenylamine, Antioxidant PBN, Neosone D, Neozone D, Vulkanox PBN, Neozon D, Nonox D, Nonox DN, Nilox PBNA, 2-Naphthalenamine, N-phenyl-, Phenyl-2-naphthylamine, Stabilizer AR, Noclizer D, Nocrac D, Phenyl-beta-naphthylamine, Naftam 2, N-Phenyl-beta-naphthylamine, 2-NAPHTHYLAMINE, N-PHENYL-, AK 1 (stabilizer), NCI-C02915, N-Phenyl-2-naphthalenamine, N-2-Naphthylaniline, beta-Naphthylphenylamine, Phenyl-beta-naphtilamine, N-Fenyl-2-aminonaftalen, NSC 37151, .beta.-Naphthylphenylamine, Phenyl-.beta.-naphthylamine, CCRIS 853, Fenyl-beta-naftylamin [Czech], N-Phenyl-.beta.-naphthylamine, MLS002608023, N-(2-Naphthyl)-N-phenylamine, CHEBI:34877, HSDB 2888, N-Fenyl-2-aminonaftalen [Czech], KEQFTVQCIQJIQW-UHFFFAOYSA-N, EINECS 205-223-9, BRN 2211188, AI3-00068, DSSTox_CID_1131, DSSTox_RID_75962, DSSTox_GSID_21131, CAS-135-88-6, Stabilator AR, ac eto pbn, neosone d, Fenyl-beta-naftylamin, Fenyl-.beta.-naftylamin, AC1L1RHP, AC1Q1IST, AC1Q4TNM, ACMC-209c4p, WLN: L66J CMR, N–Phenyl-beta-naphthylamine, Oprea1_737712, SCHEMBL38433, 2-(N-Phenylamino)naphthalene, KSC491Q7L, BIDD:ER0357, N-beta-Naphthyl-N-phenylamine, UNII-456KT854AJ, 178055_ALDRICH, SCHEMBL6435930, Jsp002174, CHEMBL1543632, CTK3J1875, N-.beta.-Naphthyl-N-phenylamine, MolPort-000-514-795, 456KT854AJ, LS-19, N-Phenyl-.beta.-amino-naphthalene, NSC37151, ZINC1669780, Tox21_201891, Tox21_302900, ANW-19991, AR-1K8072, BBL000386, NSC-37151, STK367409, ZINC01669780, AKOS001426472, MCULE-5821072787, RL01609, RTR-004823, TRA0097315, NCGC00091111-01, NCGC00091111-02, NCGC00091111-03, NCGC00091111-04, NCGC00091111-05, NCGC00256440-01, NCGC00259440-01, AC-13068, AJ-29138, AK-58488, AN-23110, CJ-06100, CJ-27101, KB-55551, OR020107, OR215477, SMR000112180, DB-063104, TR-004823, P0198, ST24031437, ST50165453, T6903, V0380, C14694, 4-12-00-03128 (Beilstein Handbook Reference), A807001, T5883835, W-108255, I14-13875, 3B3-029170, 52907-17-2, InChI=1/C16H13N/c1-2-8-15(9-3-1)17-16-11-10-13-6-4-5-7-14(13)12-16/h1-12,17

Removed Synonyms

Antioxidant D, Agerite, AK 1, C16H13N, CID8679, T1678, 6165-39-5, 84420-28-0, PBN

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