Synthesis of 4-nitroaniline

Preparation of 4-nitroaniline (para-nitroaniline; p-nitroaniline)

Preparation of 4-nitroaniline

Preparation of 4-nitroaniline

100 g of 4-nitroacetanilide is boiled with 250 ml of 25 % sulfuric acid in a round flask attached to a reflux condenser until 4-nitroaniline completely dissolves. The clear solution is poured into a beaker, and the free 4-nitroaniline base is precipitated by adding dilute sodium hydroxide solution till alkaline. After cooling, the 4-nitroaniline is filtered, recrystallized from hot water and dried yielding 70-75 g yellow needles or prisms with melting point 147° C.

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 202-203, 1905

Preparation of 4-nitroaniline from 4-nitrochlorobenzene and ammonia

Preparation of 4-nitroaniline from 4-nitrochlorobenzene and ammonia

Preparation of 4-nitroaniline from 4-nitrochlorobenzene and ammonia

157 g (1 mole) of 4-nitrochlorobenzene is heated for 10 hours in an autoclave at 170° C with 10 moles of 25% ammonia. The pressure rises to about 35 atmospheres. After the mixture in the autoclave have cooled, the pressure, which is still high, is released. The 4-nitroaniline has separated out in crystalline form, usually containing traces of unchanged 4-nitrochlorobenzene which is removed by recrystallizing the product from boiling water. Since the nitroaniline is somewhat volatile with steam and strongly poisonous, boiling is done under reflux. The yield is about 95% of the theoretical amount.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 92-93, 1949

Preparation of 4-nitroaniline

Preparation of 4-nitroaniline

18 g benzylideneaniline are added to 70 g of conc. sulphuric acid, the temperature being kept below 50° C. The product is cooled to about 5-10° C and maintained at this temperature while a mixture of 11 g of nitric acid (d=1.38 g/ml) and 11 g of conc. sulphuric acid is run in. After standing for 20 minutes the nitration mixture is added to an equal volume of water, and the benzaldehyde removed in a current of steam. The residual liquor is cooled, diluted with water, and neutralised with sodium hydroxide; this causes complete separation, in a very pure form, of the p-nitroaniline, which is filtered off, washed with water and dried. Yield 90%.

Systematic organic chemistry, by W. M. Cumming, 275, 1937.

IUPAC Name

4-nitroaniline

InChI

InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2

InChI Key

TYMLOMAKGOJONV-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1N)[N+](=O)[O-]

MeSH Synonyms

4-nitroaniline, 4-nitroaniline monohydrochloride, 4-nitroaniline sulfate (2:1), 4-nitroaniline, mercury (2+) salt (2:1), p-nitroaniline, para-nitroaniline, paranitronaniline

Depositor-Supplied Synonyms

4-NITROANILINE, p-Nitroaniline, 100-01-6, Benzenamine, 4-nitro-, p-Aminonitrobenzene, p-Nitraniline, 1-Amino-4-nitrobenzene, p-Nitrophenylamine, 4-Nitrobenzenamine, 4-Nitraniline, Developer P, para-Nitroaniline, Azoamine Red ZH, Nitrazol CF extra, Devol Red GG, Fast Red P Base, Fast Red P Salt, Aniline, p-nitro-, Fast Red Base GG, Fast Red GG Base, Fast Red GG Salt, Fast Red MP Base, Fast Red Salt GG, Diazo Fast Red GG, Red 2G Base, Fast Red 2G Base, Fast Red 2G Salt, Fast Red Base 2J, Fast Red Salt 2J, Aniline, 4-nitro-, Azofix Red GG Salt, Paranitroaniline, C.I. Developer 17, Naphtoelan Red GG Base, Azoic Diazo Component 37, Shinnippon Fast Red GG Base, p-Nitroanilina, C.I. Azoic Diazo Component 37, Rcra waste number P077, 4-nitrophenylamine, Azoamine Red 2H, 4-Aminonitrobenzene, CI Developer 17, para-Aminonitrobenzene, NCI-C60786, 4-NITRO-ANILINE, C.I. 37035, NSC 9797, p-Nitroanilina [Polish], PNA, PNA (VAN), RCRA waste no. P077, 4-NITRO-PHENYLAMINE, CI Azoic Diazo Component 37, CCRIS 1184, CHEBI:17064, HSDB 1156, TYMLOMAKGOJONV-UHFFFAOYSA-N, EINECS 202-810-1, SBB059787, NCGC00091426-02, CI 37035, AI3-08926, 4-Nitrobenzeneamine, 100-01-6 (Parent), Benzen-2,3,5,6-d4-amine-d2, 4-nitro-, p-nitro aniline, para-nitroanilin, 4-Nitroanilene, 4-nitro aniline, fast red p salt, 4-nitro-aminobenzene, azofix red gg sa lt, p-Nitroaniline, solid, PubChem2098, p-Nitroaniline sulfate, 4-Nitroaniline sulfate, (4-nitrophenyl)-amine, p-Nitroaniline bisulfate, AC1L1OUG, AC1Q5ATC, 66827-74-5, DSSTox_CID_961, UNII-1MRQ0QZG7G, PARA NITRO ANILINE, WLN: ZR DNW, 1MRQ0QZG7G, AC1Q51SB, ACMC-1B5R8, DSSTox_RID_75889, NCIOpen2_002864, DSSTox_GSID_20961, SCHEMBL16451, AURORA KA-7786, KSC174O4D, MLS002454441, CHEMBL14282, N2128_SIGMA, 185310_ALDRICH, 442419_SUPELCO, 45990_RIEDEL, SCHEMBL10163408, 72680_FLUKA, 72681_FLUKA, CTK0H4741, NSC9797, MolPort-000-884-056, AKOS 92446, HMS3039B17, LABOTEST-BB LTBB000466, LS-39, NSC-9797, Tox21_400031, ANW-14126, AR-1L1377, STK301653, ZINC03860644, p-Nitroaniline [UN1661] [Poison], 15873-51-5 (mono-hydrochloride), AKOS000119131, AS00442, LS10622, MCULE-4310869465, p-Nitroaniline [UN1661] [Poison], RP20413, NCGC00091426-01, NCGC00091426-03, 38013-32-0 (sulfate[2:1]), AJ-46033, AK108351, AN-24537, BC203717, CAS-100-01-6, CJ-10872, I577, KB-40072, SMR001372024, AB1002252, RT-005079, ST2418509, FT-0650287, N0119, ST45061409, AZ0001-0085, C02126, 66827-74-5 (mercury(2+) salt[2:1]), 78632-EP2270004A1, 78632-EP2305808A1, 78632-EP2308847A1, 78633-EP2272822A1, 78633-EP2272825A2, 78633-EP2308847A1, 78633-EP2380872A1, AE-641/01643038, I01-5241, T7100844, 3B3-033631, 4-nitroaniline1-amino-4-nitrobenzenep-nitrophenylamine, InChI=1/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H, p-Nitroaniline; p-Nitrophenylamine; 1-Amino-4-nitrobenzene; 4-Nitrobenzenamine, NIT

Removed Synonyms

paranitronaniline, UN 1661 (Related), 4-nitroaniline monohydrochloride, 4-nitroaniline sulfate (2:1), CID7475, UN1661, Benzenamine, 4-nitro-, sulfate (2:1), 4-nitroaniline, mercury (2+) salt (2:1), C019498, 10040-98-9, 38013-32-0, 68239-24-7

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