Synthesis of N,N-dimethyl-4-nitrosoaniline (nitrosodimethylaniline)

Preparation of N,N-dimethyl-4-nitrosoaniline

Preparation of N,N-dimethyl-4-nitrosoaniline (nitrosodimethylaniline)

Preparation of N,N-dimethyl-4-nitrosoaniline (nitrosodimethylaniline)

100 g of dimethylaniline is dissolved in 345 ml of concentrated hydrochloric acid, and ice added till the temperature reaches below 0° C. 60 g of sodium nitrite, dissolved in a small quantity of water, is slowly added, the reaction mixture is stirred and the temperature is not allowed to rise above 8° C. The N,N-dimethyl-4-nitrosoaniline hydrochloride separates out, and, after standing, is filtered, washed with a little dilute hydrochloric acid, and dried yielding yellow needles with melting point 177° C. N,N-dimethyl-4-nitrosoaniline hydrochloride is converted to N,N-dimethyl-4-nitrosoaniline base by treating with stereochemical amount of NaOH.

The Synthetic Dyestuffs and the Intermediate Products from which They are Derived, by J. C. Cain, 205, 190

IUPAC Name

N,N-dimethyl-4-nitrosoaniline

InChI

InChI=1S/C8H10N2O/c1-10(2)8-5-3-7(9-11)4-6-8/h3-6H,1-2H3

InChI Key

CMEWLCATCRTSGF-UHFFFAOYSA-N

Canonical SMILES

CN(C)C1=CC=C(C=C1)N=O

MeSH Synonyms

4-nitrosodimethylaniline, 4-nitrosodimethylaniline monohydrochloride, N,N-dimethyl-4-nitrosoaniline, NDMA nitrosodimethylaniline, p-nitrosodimethylaniline, para-nitrosodimethylaniline

Depositor-Supplied Synonyms

N,N-Dimethyl-4-nitrosoaniline, 138-89-6, Accelerine, N,N-DIMETHYL-P-NITROSOANILINE, 4-Nitroso-N,N-dimethylaniline, 4-Nitrosodimethylaniline, p-Nitroso-N,N-dimethylaniline, p-Nitrosodimethylanilide, p-Nitrosodimethylaniline, Paranitrosodimethylanilide, Dimethyl(p-nitrosophenyl)amine, Ultra Brilliant Blue P, p-(Dimethylamino)nitrosobenzene, 4-(Dimethylamino)nitrosobenzene, Benzenamine, N,N-dimethyl-4-nitroso-, p-(N,N-Dimethylamino)nitrosobenzene, N,N-Dimethyl-4-nitrosobenzenamine, Aniline, N,N-dimethyl-p-nitroso-, NCI-C01821, N,N-dimethyl-4-nitroso-aniline, Dimethyl-p-nitrosoaniline, NSC 2775, p-Nitroso dimethylaniline, CCRIS 3057, CHEBI:59990, HSDB 1320, NSC2775, CMEWLCATCRTSGF-UHFFFAOYSA-N, EINECS 205-343-1, UN1369, BRN 0607293, AI3-15393, DSSTox_CID_5138, DSSTox_RID_77682, DSSTox_GSID_25138, AB-131/40181212, dimethyl(4-nitrosophenyl)amine, CAS-138-89-6, Accelerene, Vulcaniline, NDMA (Substrate 4), AC1L1RMD, ACMC-1BT6K, Aniline, 4-nitrosodimethyl, AC1Q6R2N, UNII-726V2ETM9E, SCHEMBL103850, Aniline,N-dimethyl-p-nitroso-, 726V2ETM9E, 4-nitroso-N,N-di-methylaniline, N,N’-dimethyl-4-nitrosoaniline, CHEMBL1569493, WLN: ONR DN1 & 1, CTK4C1449, D172405_SIAL, MolPort-001-779-726, Benzenamine,N-dimethyl-4-nitroso-, dimethyl-(4-nitroso-phenyl)-amine, 1-(Dimethylamino)-4-nitrosobenzene, NSC-2775, Tox21_202129, Tox21_303049, ANW-20478, AR-1K2432, Benzenamine,N,N-dimethyl-4-nitroso-, LS-808, SBB058598, STL264252, ZINC03860417, 42344-05-8 (mono-hydrochloride), AKOS005208791, AM86573, MCULE-1263861636, N,N-dimethyl-N-(4-nitrosophenyl)amine, PS-4800, UN 1369, VZ36433, NCGC00091697-01, NCGC00091697-02, NCGC00091697-03, NCGC00091697-04, NCGC00091697-05, NCGC00257004-01, NCGC00259678-01, AJ-46001, AK-58941, AN-23149, TX-017820, FT-0619300, N0262, ST51031610, C19680, 4-12-00-01558 (Beilstein Handbook Reference), A807455, S01-0549, p-Nitrosodimethylaniline [UN1369] [Spontaneously combustible], p-Nitrosodimethylaniline [UN1369] [Spontaneously combustible], InChI=1/C8H10N2O/c1-10(2)8-5-3-7(9-11)4-6-8/h3-6H,1-2H

Removed Synonyms

NDMA, para-nitrosodimethylaniline, NDMA nitrosodimethylaniline, CID8749, 4-nitrosodimethylaniline monohydrochloride, C008651, 1294-07-1

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