Synthesis of 4,4′-dinitrobiphenyl

Preparation of 4,4′-dinitrobiphenyl

Preparation of 4,4'-dinitrobiphenyl

Preparation of 4,4′-dinitrobiphenyl

A cold solution of 21.6 g of copper(I) chloride in 100 ml of conc, hydrochloric acid is added to the diazonium solution prepared from 30 g of p-nitroaniline, 45 g of conc, sulphuric acid, 60 ml of water and 15.3 g of sodium nitrite. During the addition of the copper salt the whole is vigorously stirred. There is a brisk evolution of nitrogen, the mass turns black and a brownish-yellow substance is precipitated. When the liquid becomes green, the reaction is finished. The product is distilled in steam until no more p-chloronitrobenzene passes over. There remains in the distilling flask almost pure 4,4′-dinitrobiphenyl. It is filtered off, dried, and recrystal­lised from benzene. The by-product p-chloronitrobenzene is worked up by filtering it from the liquid portion of the distillate, drying on a porous plate, and recrystallising from benzene. The yield of 4,4′-dinitrobiphenyl is 55%; p-chloronitrobenzene 40% theoretical. 4,4′-Dinitrobiphenyl is a crystalline solid; m.p. 237° C; p-chloronitrobenzene is a crystalline solid; m.p. 83° C; b.p., 238.5° C.

Systematic organic chemistry, by W. M. Cumming, 163, 1937.

IUPAC Name

1-nitro-4-(4-nitrophenyl)benzene

InChI

InChI=1S/C12H8N2O4/c15-13(16)11-5-1-9(2-6-11)10-3-7-12(8-4-10)14(17)18/h1-8H

InChI Key

BDLNCFCZHNKBGI-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1C2=CC=C(C=C2)[N+](=O)[O-])[N+](=O)[O-]

MeSH Synonyms

4,4′-dinitrobiphenyl

Depositor-Supplied Synonyms

4,4′-DINITROBIPHENYL, 1528-74-1, 4,4′-Dinitrodiphenyl, Biphenyl, 4,4′-dinitro-, 1,1′-Biphenyl, 4,4′-dinitro-, 4,4′-Dinitrobifenyl, 4,4′-Dinitro-biphenyl, 1-nitro-4-(4-nitrophenyl)benzene, 4,4′-Dinitrobifenyl [Czech], CCRIS 3375, HSDB 5526, BDLNCFCZHNKBGI-UHFFFAOYSA-N, NSC 8738, EINECS 216-210-2, BRN 1882826, AI3-01806, ST51047551, ACMC-1BNPC, 4,4′-Dinitro biphenyl, WLN: WNR DR DNW, 1, 4,4′-dinitro-, AC1L25EW, SCHEMBL28198, CBDivE_013871, CHEMBL73297, UNII-6X8N704C9U, NSC8738, MolPort-003-710-907, 6X8N704C9U, 4,4′-Dinitro-1,1′-biphenyl #, NSC-8738, ZINC1648209, ANW-21416, BBL034698, STL426766, ZINC01648209, AKOS000120057, AKOS015965774, MCULE-1998422603, NE27385, AC-20953, CJ-26620, LS-44338, OR016146, OR104358, TR-006302, D0826, FT-0633639, X7907, I14-92943, 3B1-001615, 3B3-051779

Removed Synonyms

4,4-Dinitrobiphenyl, Biphenyl,4′-dinitro-, CID15216, 4-05-00-01827 (Beilstein Handbook Reference)

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