Synthesis of 2-nitroaniline

Preparation of 2-nitroaniline (o-nitroaniline; o-nitraniline; benzenamine, 2-nitro-; 2-nitrobenzenamine)

Preparation of 2-nitroaniline from 2-nitrochlorobenzene and ammonia

Preparation of 2-nitroaniline (o-nitroaniline; o-nitraniline; benzenamine, 2-nitro-; 2-nitrobenzenamine)

Preparation of 2-nitroaniline (o-nitroaniline; o-nitraniline; benzenamine, 2-nitro-; 2-nitrobenzenamine)

157 g (1 mole) of 2-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

IUPAC Name

2-nitroaniline

InChI

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

InChI Key

DPJCXCZTLWNFOH-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

2-nitroaniline, o-nitroaniline, ortho-nitroaniline

Depositor-Supplied Synonyms

2-NITROANILINE, o-Nitroaniline, 88-74-4, o-Nitraniline, Benzenamine, 2-nitro-, 2-Nitrobenzenamine, 1-Amino-2-nitrobenzene, Devol Orange B, ortho-nitroaniline, Orange GRS Salt, o-Aminonitrobenzene, Azoic Diazo Component 6, 2-Aminonitrobenzene, Aniline, o-nitro-, Fast Orange O Base, Fast Orange O Salt, Devol Orange Salt B, Fast Orange Base GR, Fast Orange Base JR, Fast Orange GR Base, Fast Orange GR Salt, Fast Orange Salt GR, Fast Orange Salt JR, Orange Base Ciba II, Orange Base Irga II, Orange Salt Ciba II, Orange Salt Irga II, Azoene Fast Orange GR Salt, Diazo Fast Orange GR, Orthonitroaniline, Azofix Orange GR Salt, Azogene Fast Orange GR, Hindasol Orange GR Salt, 2-Nitro-phenylamine, Azoene Fast Orange GR Base, Natasol Fast Orange GR Salt, Hiltonil Fast Orange GR Base, Hiltosal Fast Orange GR Salt, Brentamine Fast Orange GR Base, Brentamine Fast Orange GR Salt, C.I. Azoic Diazo Component 6, o-nitro aniline, 2-NITRO-ANILINE, C.I. 37025, NSC 9796, CI Azoic Diazo Component 6, CCRIS 2317, HSDB 1132, 2-nitrophenylamine, DPJCXCZTLWNFOH-UHFFFAOYSA-N, EINECS 201-855-4, SBB040877, ONA, CI 37025, AI3-02916, DSSTox_CID_5726, DSSTox_RID_77895, DSSTox_GSID_25726, CAS-88-74-4, 2nitroaniline, o-Nitranilin, o-nitro-aniline, 2-nitro-anilin, 2-amino-nitrobenzene, 2-Nitro-benzeneamine, (2-nitrophenyl)-amine, 1-Nitro-2-aminobenzene, (2-nitro-phenyl)-amine, AC1L1NNJ, WLN: ZR BNW, AC1Q50TX, AC1Q5AV7, SCHEMBL6000, N9780_ALDRICH, KSC448I8H, 442363_SUPELCO, CHEMBL274009, SCHEMBL11911292, 72660_FLUKA, CTK3E8483, TIMTEC-BB SBB040877, NSC9796, MolPort-000-157-719, LABOTEST-BB LTBB000464, UNII-2519U0541L, EBD27017, NSC-9796, AKOS BBS-00004353, Tox21_202371, Tox21_303292, ANW-58055, AR-1K7437, BBL016375, LABOTEST-BB LT03333712, STL140693, ZINC03860642, o-Nitroaniline [UN1661] [Poison], AKOS000119116, AM87359, AS01504, LS-1884, MCULE-6119865345, NE10505, o-Nitroaniline [UN1661] [Poison], RP20415, RTR-027928, TRA0068876, NCGC00091373-01, NCGC00091373-02, NCGC00257171-01, NCGC00259920-01, AJ-46032, AK-96014, AN-24153, BP-21264, H442, AB1002378, DB-057102, KB-173959, KB-204396, ST2417126, TR-027928, 2519U0541L, FT-0613173, N0118, ST45255269, 71045-EP2275412A1, 71045-EP2308833A2, S01-0327, 3B3-020217, T0517-8612, InChI=1/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H

Removed Synonyms

null, NITROANILINE, Benzenamine, ar-nitro-, CU CPT 4a, UN 1661 (Related), CID6946, UN1661, 29757-24-2, 1279713-77-7, 5488-81-3

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