Synthesis of p-phenylenediamine

Preparation of p-phenylenediamine

Preparation of p-phenylenediamine

Preparation of p-phenylenediamine

150 ml water are placed in the reduction pot and heated up to 95 °C, and 100 g. p-nitroaniline are then added. 5 ml of conc. hydrochloric acid and about 100 g. of fine iron powder are added gradually, care being taken that the contents do not froth over.  Cooling should be applied to regulate the action. This process is carried on until the solution loses its yellow color, as may be shown by spotting on filter paper. A solution of sodium carbonate is then added until an alkaline reaction is obtained. It is boiled and filtered from the iron residue.  After the iron  residue is filtered off the filtrate is concentrated until the p-phenylenediamine base crystallises. Yield.-80% theoretical (60 g.). M.P. 17 ° C ; B.P. 267 ° C.

Systematic organic chemistry, by W. M. Cumming, 359, 1937.

IUPAC Name

benzene-1,4-diamine

InChI

InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2

InChI Key

CBCKQZAAMUWICA-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1N)N

MeSH Synonyms

1,4-benzenediamine, 1,4-phenyldiamine, 1,4-phenylenediamine, 4-phenylenediamine, 4-phenylenediamine bromide, ion(1+), 4-phenylenediamine dihydrochloride, 4-phenylenediamine diperchlorate, 4-phenylenediamine ion (1+), 4-phenylenediamine monohydrobromide, 4-phenylenediamine monohydrochloride, 4-phenylenediamine monohydroiodide, 4-phenylenediamine monooxalate, 4-phenylenediamine monoperchlorate, 4-phenylenediamine monosulfate, 4-phenylenediamine sulfate, black henna, p-phenylenediamine, para-phenylenediamine, paraphenylenediamine, Ursol-D

Depositor-Supplied Synonyms

p-Phenylenediamine, benzene-1,4-diamine, 1,4-BENZENEDIAMINE, 106-50-3, 1,4-Diaminobenzene, 1,4-Phenylenediamine, 4-Aminoaniline, p-Aminoaniline, p-Diaminobenzene, para-phenylenediamine, Orsin, 4-Phenylenediamine, Paraphenylenediamine, p-Benzenediamine, Fouramine D, Futramine D, Benzofur D, Developer PF, Fourrine D, Fur Yellow, Santoflex IC, Santoflex LC, Pelagol D, Durafur Black R, Pelagol DR, Pelagol Grey D, Peltol D, Fourrine 1, Furro D, Ursol D, Renal PF, Zoba Black D, Developer 13, Nako H, BASF ursol D, Oxidation base 10, Fenylenodwuamina, p-Phenyldiamine, C.I. Developer 13, Usaf ek-394, Fur Black 41867, Rodol D, FUR Brown 41866, P-PHENYLENE DIAMINE, Paraphenylen-diamine, C.I. Oxidation Base 10, paraphenylene-diamine, p-phenylenediamine base, p-Fenylendiamin, 4-aminophenylamine, CI Developer 13, CHEBI:51403, Phenylenediamine, para-, C.I. 76060, CI Oxidation Base 10, Fur Black 41866, NSC 4777, p-Fenylendiamin [Czech], Fenylenodwuamina [Polish], MFCD00007901, UNII-U770QIT64J, CI 76060, CCRIS 509, U770QIT64J, HSDB 2518, CBCKQZAAMUWICA-UHFFFAOYSA-N, EINECS 203-404-7, NCGC00159375-02, NCGC00159375-04, AI3-00710, DSSTox_CID_1138, DSSTox_RID_75969, DSSTox_GSID_21138, CAS-106-50-3, 4-amino-aniline, Aminogen II, p-phenylene-diamine, 1,4 diaminobenzene, paraphenylene diamine, 1,4-diamino benzene, Phenylenediamine, para, JAROCOL PPD, 1,4-phenylene diamine, PubChem22180, ACMC-1CUCB, WLN: ZR DZ, Epitope ID:114080, AC1L1PM0, AC1Q53DE, PHENYLENEDIAMINE, P-, SCHEMBL27981, 1,4-DIAMINO-BENZENE, PARA PHENYLENE DIAMINE, 1,4-Phenylenediamine-13N2, KSC174M0N, 78429_ALDRICH, P6001_SIGMA, HSDB 6256 (Salt/Mix), 561126_ALDRICH, AC1Q521T, AC1Q521U, AC1Q521V, AC1Q521W, CHEMBL403741, DTXSID9021138, 78429_FLUKA, CTK0H4606, NSC4777, 16245-77-5 (monosulfate), 624-18-0 (di-hydrochloride), 62654-17-5 (monooxalate), ATTERCOP-CHM AT126215, OTAVA-BB 1509975, BB_SC-7053, C.I. 76076 (Salt/Mix), LABOTEST-BB LTBB002107, 540-24-9 (mono-hydrochloride), ACT07286, NSC-4777, STR01091, ZINC8294962, Tox21_111615, Tox21_201993, Tox21_302943, ANW-15356, AR-1K9250, BBL011602, LS-402, STL163334, ZINC08294962, AKOS005716327, Tox21_111615_1, AS00466, CS18589, MCULE-9588027148, NE10526, RP09002, TRA0038404, UN 1673, NCGC00159375-03, NCGC00159375-05, NCGC00256482-01, NCGC00259542-01, AJ-57421, AK110185, AN-22438, CJ-13205, I809, KB-80078, OR000317, SC-77433, AB1002877, ST2419110, FT-0606928, P0170, EN300-19064, C19499, I01-4376, p-Phenylenediamine [UN1673] [Keep away from food], T6292277, p-Phenylenediamine [UN1673] [Keep away from food], 3B1-000655, 3B1-001622, F0001-0125, UNII-TJX894Z2PK component CBCKQZAAMUWICA-UHFFFAOYSA-N, 1,4-Benzenediamine; 1,4-Diaminobenzene; 1,4-Phenylenediamine, InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H, 56481-76-6, 82785-55-5

Removed Synonyms

Tertral D, PARA, black henna, PPDA, Vulkanox 4020, Ursol-D, 4-Aminobenzylamine, PHENYLENEDIAMINE, 1,4-phenyldiamine, 6PPD, Phenylenediamine, solid, 1,4-Diaminocyclohexane, 4-phenylenediamine sulfate, 1,4-Phenylenediamine Sulfate, 4-phenylenediamine monooxalate, 4-phenylenediamine monosulfate, 4-phenylenediamine ion (1+), 4-phenylenediamine diperchlorate, C6H8N2, 4-phenylenediamine dihydrochloride, 4-phenylenediamine monohydroiodide, 4-phenylenediamine monoperchlorate, CID7814, p-Phenylenediamine dihydrochloride, MolPort-001-766-737, UN1673, 4-phenylenediamine monohydrobromide, 4-phenylenediamine monohydrochloride, 4-phenylenediamine bromide, ion(1+), RTR-013269, PPD, C029728, 3114-70-3, Polyaniline (emeraldine salt) short chain, grafted to lignin, 119516-82-4, 688-78-8

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