Synthesis of 4-aminoazobenzene

Preparation of 4-aminoazobenzene

Alternative Names: p-Aminoazobenzene; ANILINE YELLOW; 4-(phenyldiazenyl)aniline; Cellitazol R;

Preparation of 4-aminoazobenzene

Preparation of 4-aminoazobenzene

10 g powdered diazoaminobenzene are dissolved in 20 g aniline, and 5 g solid aniline hydrochloride are added. The mixture is warmed to 40-50° C, until a sample on warming with alcohol and hydrochloric acid no longer evolves gas (~ 1 hour). The reaction mixture is poured into excess of very dilute acetic acid, and the 4-aminoazobenzene base which separates is allowed to solidify, filtered off and washed with water. The substance is then boiled up with about 2 liter of water, and hydrochloric acid is carefully added until a sample of the bluish-red solution deposits pure blue crystals on cooling. The liquid is then filtered, and on cooling the hydrochloride of 4-aminoazobenzene separates out in steel-blue needles. The remainder of the substance can be precipitated from the solution by adding common salt. For the preparation of the free base the 4-aminoazobenzene hydrochloride is boiled with twice its weight of alcohol, and concentrated ammonia is added in drops until everything has dissolved and the colour has changed to light brown. On cautiously adding water the base separates in small yellow crystals. It may be recrystallized from dilute alcohol. The yield of 4-aminoazobenzene is about 15 g.

Introduction to the preparation of organic compounds, E. Fisher, 28-29, 1909

IUPAC Name

4-phenyldiazenylaniline

InChI

InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2

InChI Key

QPQKUYVSJWQSDY-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)N=NC2=CC=C(C=C2)N

MeSH Synonyms

4-(phenyldiazenyl)aniline, aniline yellow, C.I. Solvent Yellow 1, p Aminoazobenzene, p-Aminoazobenzene, para Aminoazobenzene, para-Aminoazobenzene

Depositor-Supplied Synonyms

4-Aminoazobenzene, p-Aminoazobenzene, ANILINE YELLOW, 4-(phenyldiazenyl)aniline, 60-09-3, Cellitazol R, 4-(Phenylazo)aniline, Aminoazobenzene, Organol Yellow, Induline R, Benzenamine, 4-(phenylazo)-, Sudan Yellow R, Sudan Yellow RA, Oil Yellow B, Oil Yellow R, Oil Yellow AN, Oil Yellow AAB, Stearix Brown 4R, Fast Spirit Yellow, Organol Yellow 2A, Somalia Yellow 2G, 4-(Phenylazo)benzenamine, C.I. Solvent Yellow 1, p-Aminoazobenzol, 4-Aminoazobenzol, 4-Amino-1,1′-azobenzene, Ceres Yellow R, 4-Phenylazoaniline, Fat Yellow AAB, Solvent Yellow 1, 4-Benzeneazoaniline, Brasilazina Oil Yellow G, p-Aminodiphenylimide, p-(Phenolazo)aniline, p-(Phenylazo)aniline, Azobenzene, 4-amino-, Fast Spirit Yellow AAB, Usaf ek-1375, C.I. Solvent Blue 7, Oil-Sol. Aniline Yellow, Aniline, p-(phenylazo)-, para-Aminoazobenzene, Oil Soluble Aniline Yellow, Paraphenolazo aniline, 4-Phenylazo-phenylamine, Zlut anilinova, p-Amimoazobenzene, Aminoazobenzene (indicator), C.I. 11000, p-Phenylazonaniline, p-Phenylazophenylamine, 4-[(E)-Phenyldiazenyl]aniline, 4-Phenylazophenylamine, p-AAZB, Zlut rozpoustedlova 1, CI Solvent Yellow 1, CHEBI:233869, 4-[(E)-2-phenyldiazenyl]aniline, Aniline Yellow (VAN), Zlut anilinova [Czech], p-(Phenylazo)phenylamine, Benzenamine, 4-(2-phenyldiazenyl)-, CCRIS 24, 4-AAB, Zlut rozpoustedlova 1 [Czech], HSDB 2137, NSC 2032, EINECS 200-453-6, AAB, NCGC00164077-02, CI 11000, AI3-00793, 4-[phenyldiazenyl]aniline, 4-(phenyldiazenyl)phenylamine, 25548-34-9, Solvent Yellow, Ceres Yellow, p-Aminoazaobenzene, p-Phenylazoaniline, p-Aminodiphenyldiimide, 4-phenyldiazenylaniline, ACMC-1CJPI, C.I.Solvent Yellow 1, WLN: ZR DNUNR, AC1Q4TED, DSSTox_CID_4460, Epitope ID:116049, 4-[(E)-phenylazo]aniline, AC1L1LP3, AC1Q51SH, AC1Q51SI, AC1Q51SJ, DSSTox_RID_77407, DSSTox_GSID_24460, 4-(Phenyldiazenyl)aniline #, MLS000419131, CHEMBL83761, SCHEMBL208182, UNII-57X2AH42T1, (E)-4-(phenyldiazenyl)aniline, 186368_ALDRICH, 46130_RIEDEL, ARONIS023721, CHEMBL1429559, 46130_FLUKA, CTK2F3201, CTK7D7049, 4-(2-phenyldiazen-1-yl)aniline, NSC2032, Benzenamine,4-(phenylazo)-(E)-, MolPort-000-564-806, MolPort-005-273-802, QPQKUYVSJWQSDY-CCEZHUSRSA-N, QPQKUYVSJWQSDY-UHFFFAOYSA-N, 57X2AH42T1, BB_SC-0020, C.I. Solvent Yellow 1 (8CI), HMS2702P12, NSC-2032, Tox21_400019, ANW-13577, AR-1I1884, BBL010329, LS-258, SBB051743, STK801547, ZINC18060741, AKOS000319539, Benzenamine, 4-(phenylazo)-, (E)-, 4-[(E)-2-phenyldiazen-1-yl]aniline, MCULE-7759276279, NE10521, RTR-020794, CAS-60-09-3, NCGC00164077-01, NCGC00164077-03, AJ-70258, AN-23628, KB-36486, NCI60_001708, OR033997, OR049237, OR175035, OR344673, SMR000319771, T831, TR-020794, TR-048216, FT-0617546, P0141, ST45255288, EN300-18330, C19187, BENZENAMINE,4-[(1E)-2-PHENYLDIAZENYL]-, AC-907/25014309, 3B4-0134, I14-10091, F0020-1827

Removed Synonyms

Oil Yellow 2G, Oil Yellow AB, p Aminoazobenzene, para Aminoazobenzene, Oil Yellow AB (VAN), 4-Aminoazobenzene hydrochloride, CID6051, D010128, 81691-68-1, 86408-71-1

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