Synthesis of 4-methyl-3-nitroaniline

Preparation of 4-methyl-3-nitroaniline

Preparation of 4-methyl-3-nitroaniline

Preparation of 4-methyl-3-nitroaniline

10 g p-toluidine are dissolved in 200 g conc. sulphuric acid. The solution is cooled by a freezing mixture to just below 0° C. A mixture of 7.5 g nitric acid (d=1.48 g/ml) and 30 g conc. sulphuric acid is allowed to flow into the well-stirred solution, the temperature being maintained at 0° C. When all tie mixed acid has been added the mixture is allowed to stand for a short time and is then poured into 500 ml of ice-cold water, the temperature being kept below 25° C by the addition of more ice if necessary. The solution is now filtered from impurity and diluted to 3 times its bulk and neutralised with solid sodium carbonate, the temperature being kept as low as possible. The precipitate is then filtered off, pressed dry and finally recrystallised from alcohol. Yield 65-70%, yellow monoclinic noodles; m.p. 77.5° C.

Systematic organic chemistry, by W. M. Cumming, 128, 1937.

IUPAC Name

4-methyl-3-nitroaniline

InChI

InChI=1S/C7H8N2O2/c1-5-2-3-6(8)4-7(5)9(10)11/h2-4H,8H2,1H3

InChI Key

GDIIPKWHAQGCJF-UHFFFAOYSA-N

Canonical SMILES

CC1=C(C=C(C=C1)N)[N+](=O)[O-]

MeSH Synonyms

4-amino-2-nitrotoluene, 4-amino-2-nitrotoluene monohydrochloride, 4-amino-2-nitrotoluene, conjugate monoacid

Depositor-Supplied Synonyms

4-Methyl-3-nitroaniline, 119-32-4, 3-Nitro-4-methylaniline, 3-Nitro-p-toluidine, 4-Amino-2-nitrotoluene, m-Nitro-p-toluidine, 2-Nitro-4-aminotoluene, p-Toluidine, 3-nitro-, 5-Nitro-4-toluidine, Benzenamine, 4-methyl-3-nitro-, GL-Amin [Czech], Gl-amin, 4-methyl-3-nitro-aniline, NSC 7731, 3-Nitro-4-toluidin [Czech], CCRIS 3003, 3-Nitro-4-toluidin, EINECS 204-314-0, BRN 0638984, CHEBI:81670, GDIIPKWHAQGCJF-UHFFFAOYSA-N, LS-614, 4-Amino-2-nitro-toluene, 5-Nitro-4-Toluidine, 4-Amino-2-Nitrotoluene, 4-methyl-3-nitrophenylamine, AC-907/25014173, ZINC00157566, 4Am2NT, AC1L1QWB, AC1Q2EFL, AC1Q5ACY, DSSTox_CID_5633, 3-nitro-4-methyl-aniline, 4-methyl-3-nitro aniline, ACMC-209a2c, UNII-SM8UZ1Q81F, WLN: ZR D1 CNW, 4-methyl-3-nitrobenzenamine, DSSTox_RID_77860, SM8UZ1Q81F, DSSTox_GSID_25633, 5-Amino-2-methylnitrobenzene, M59807_ALDRICH, 4-methyl-3-nitro-phenylamine, KSC174O5J, SCHEMBL100616, (4-methyl-3-nitrophenyl)amine, 45929_RIEDEL, CHEMBL1350617, 45929_FLUKA, CTK0H4754, META NITRO PARA TOLUIDINE, NSC7731, 1-Amino-3-nitro-4-methylbenzene, 4-Amino-1-methyl-2-nitrobenzene, MolPort-000-146-047, (4-methyl-3-nitro-phenyl)-amine, ZINC157566, EBD19508, NSC-7731, Tox21_200103, ANW-17314, AR-1F4630, BBL002361, FC0977, SBB007596, STK387113, AKOS000119120, AC-1739, AS06938, MCULE-1521427788, PS-5957, RP21602, RTR-003252, TRA0127952, NCGC00091307-01, NCGC00091307-02, NCGC00257657-01, AJ-15059, AK-32960, AN-14666, BC685798, BP-20389, BR-32960, CAS-119-32-4, CJ-01688, KB-72720, OR001323, OR124828, ZB006724, DB-041463, TL8000515, TR-003252, AM20060491, FT-0619031, N0278, ST24032818, ST45255286, C18320, M-4200, M-6397, AB00514384-03, 125449-EP2281563A1, 125449-EP2289894A2, 125449-EP2295424A1, 4-12-00-01997 (Beilstein Handbook Reference), A804255, I01-0472, T7100843, 3B3-013330, InChI=1/C7H8N2O2/c1-5-2-3-6(8)4-7(5)9(10)11/h2-4H,8H2,1H

Removed Synonyms

3-Nitro-4-toluidine, Fast Red GL Base, 2-NITRO-P-TOLUIDINE, CID8390, c1339, 952-75-0

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