Synthesis of diazoaminobenzene

Preparation of diazoaminobenzene

Alternative Names:  1,3-Diphenyltriazene; (1E)-1,3-diphenyltriaz-1-ene; 1-Triazene, 1,3-diphenyl-; Cellofor;

Preparation of diazoaminobenzene

Preparation of diazoaminobenzene

10 g aniline are dissolved in a mixture of 100 ml water and the quantity of concentrated hydrochloric acid calculated for 2 molecules of aniline. The solution is then carefully cooled from outside by means of ice water, and finally by throwing in pieces of ice, and is then converted into diazobenzene chloride by the addition of the exact amount of sodium nitrite required for 1 molecule of aniline, dissolved in a little water. An excess of nitrite must be carefully avoided, while an insufficient amount of it does not affect the purity of the diazoamidobenzene, but only the yield. During the diazotisation a further 10-11 g aniline are dissolved in 50 ml water and just the requisite amount of hydrochloric acid (at most 1 mole hydrochloric acid to 1 mole aniline); the mixture is well cooled and added to the solution of the diazobenzene chloride, and then the whole solution is treated with about 40 g sodium acetate dissolved in a little water. This precipitates the diazoaminobenzene as a pure yellow, crystalline substance. If the product is dark-yellow or brown, either an excess of diazo-compound is present, or the temperature of the liquid has been too high. The separation of the  diazoaminobenzene continues for some time. When after about half an hour a sample of the mother-liquor gives no further precipitate on addition of more sodium acetate, the solid is filtered off through a porcelain funnel at the pump, carefully washed with cold water, and well pressed to free it as far as possible from the water. The mass is then at once dissolved in hot ligroin (b. p. 70-100° C) or thereabouts, and the solution is filtered hot to remove the water suspended in it. On cooling, the diazoaminobenzene separates in well-formed, dark yellow crystals. If the preparation has been badly carried out, the crystals have a brown colour. The yield of diazoaminobenzene is 15 g.

Introduction to the preparation of organic compounds, E. Fisher, 25-28, 1909

IUPAC Name

N-phenyldiazenylaniline

InChI

InChI=1S/C12H11N3/c1-3-7-11(8-4-1)13-15-14-12-9-5-2-6-10-12/h1-10H,(H,13,14)

InChI Key

ALIFPGGMJDWMJH-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

1,3-diphenyl-1-triazene, diazoaminobenzene, diphenyl-triazene

Depositor-Supplied Synonyms

Diazoaminobenzene, 1,3-Diphenyltriazene, 136-35-6, (1E)-1,3-diphenyltriaz-1-ene, 1-Triazene, 1,3-diphenyl-, Cellofor, DAAB, Diazoaminobenzen, Diazoaminobenzol, p-Diazoaminobenzene, Aniline, N-(phenylazo)-, 1,3-DIPHENYL-1-TRIAZENE, Anilinoazobenzene, Benzeneazoanilide, Benzeneazoaniline, Triazene, 1,3-diphenyl-, Diazobenzeneanilide, Cellofor [Czech], 1-3-Diphenyltriazine, N-phenyldiazenylaniline, Diazoaminobenzen [Czech], NSC 2077, Diazoaminobenzol [German], 1,3-diphenyltriaz-1-ene, CCRIS 4779, HSDB 5410, EINECS 205-240-1, 1-Triazene, 1,3-diphenyl-, (E)-, BRN 0957560, ST001652, AI3-04858, DSSTox_CID_4934, phenyl(phenyldiazenyl)amine, DSSTox_RID_77588, DSSTox_GSID_24934, 93589-89-0, CAS-136-35-6, N-phenylazoaniline, ACMC-20dnry, 1,3-Diphenyltriazine, Triazene,3-diphenyl-, WLN: RNUNMR, AC1L1RID, AC1Q4SWJ, 1-Triazene,3-diphenyl-, phenyl-phenyldiazenyl-amine, ACMC-209c5r, UNII-5T4EEW75HJ, N-[(E)-phenylazo]aniline, 1-Triazene,1,3-diphenyl-, 5T4EEW75HJ, 1,3-Diphenyl-1-triazene #, ARONIS24395, SCHEMBL310943, CHEMBL573540, CTK3F5859, CTK4C0265, NSC2077, ALIFPGGMJDWMJH-UHFFFAOYSA-N, MolPort-001-766-734, MolPort-005-273-811, (1E)-1,3-Diphenyl-1-triazene, 109665_SIAL, ALBB-004122, NSC-2077, Tox21_202253, Tox21_303249, 3966AD, ANW-20029, LS-792, SBB047161, STK502933, ZINC18044027, AKOS000321245, MCULE-5988992001, NCGC00091555-01, NCGC00091555-02, NCGC00091555-03, NCGC00091555-04, NCGC00257132-01, NCGC00259802-01, AN-23115, KB-10444, OR015487, OR079724, OR171716, OR171752, U380, TC-108774, TR-058013, BB 0240841, D0136, FT-0606719, R1053, EN300-20072, 4-16-00-00904 (Beilstein Handbook Reference), A807066, S01-0551, 3B3-033019

Removed Synonyms

diphenyl-triazene, CID8689, C402345

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