Synthesis of N,N-dimethyl-p-phenylenediamine

Preparation of N,N-dimethyl-p-phenylenediamine

Preparation of N,N-dimethyl-p-phenylenediamine

Preparation of N,N-dimethyl-p-phenylenediamine

50 g of para-nitrosodimethylaniline or a corresponding amount of para-nitrosodimethylaniline hydrochloride, are added in small amounts to a warm solution of 225 g of stannous chloride in 450 ml of concentrated hydrochloric acid. The reaction flask should be occasionally cooled to prevent the mixture from getting hot during the addition of the para-nitrosodimethylaniline. The reduction reaction is completed by refluxing the mixture for 90 minutes, after which the flask is cooled. Part of the double tin salt of the aminodimethylaniline is deposited at this point, and the precipitation is completed by saturating the mixture at 0° C with hydrogen chloride. The salt is filtered and dissolved in water. As the base is readily oxidized by the air the acid solution is covered by a layer of ether, then ice is added, and the N,N-dimethyl-p-phenylenediamine is extracted by adding 50 % solution of sodium hydroxide, being sure that enough ice is present to keep the mixture cold. After shaking cautiously the ether is removed and the alkaline solution again shaken out several times with ether. The combined ethereal extracts are dried over sodium sulfate, ether is evaporated, and the residue is distilled in vacuum. The yield of N,N-dimethyl-p-phenylenediamine is 36 g., boiling at 146-80° C under a pressure of 24 mm. The final product is a crystalline mass which melts at 38-41°C. N,N-dimethyl-p-phenylenediamine is sensitive to the oxygen of the air and should be stored under inert atmosphere, or in glass-stoppered bottles.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 33-34, 1923

IUPAC Name

4-N,4-N-dimethylbenzene-1,4-diamine

InChI

InChI=1S/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3

InChI Key

BZORFPDSXLZWJF-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

dimethyl 1,4-phenylenediamine, dimethyl-4-phenylenediamine, dimethyl-4-phenylenediamine acetate, dimethyl-4-phenylenediamine dihydrochloride, dimethyl-4-phenylenediamine hydrochloride, dimethyl-4-phenylenediamine monohydrochloride, dimethyl-4-phenylenediamine oxalate (1:1), dimethyl-4-phenylenediamine oxalate (2:1), dimethyl-4-phenylenediamine sulfate (1:1), dimethyl-4-phenylenediamine sulfate (2:1), dimethyl-4-phenylenediamine, ion (1+), dimethyl-p-phenylenediamine, N,N-dimethyl phenylene diamine, N,N-dimethyl-para-phenylenediamine, p-aminodimethylaniline

Depositor-Supplied Synonyms

N,N-Dimethyl-p-phenylenediamine, 99-98-9, p-Aminodimethylaniline, N,N-Dimethyl-1,4-phenylenediamine, 4-(Dimethylamino)aniline, DMPD, N1,N1-Dimethylbenzene-1,4-diamine, p-Amino-N,N-dimethylaniline, 4-Amino-N,N-dimethylaniline, p-(Dimethylamino)aniline, Dimethyl-p-phenylenediamine, 4-Aminodimethylaniline, 1,4-Benzenediamine, N,N-dimethyl-, N,N-DIMETHYL-P-BENZENEDIAMINE, N,N-dimethylbenzene-1,4-diamine, p-Dimethylaminophenylamine, N,N-Dimethyl-1,4-benzenediamine, p-Phenylenediamine, N,N-dimethyl-, Dimethyl-4-phenylenediamine, 4-(Dimethylamino)benzenamine, 4-dimethylaminoaniline, C.I. 76075, NSC 1493, UNII-7GZH2FMK7X, 7GZH2FMK7X, 1,4-Benzenediamine, N1,N1-dimethyl-, p-(Dimethylamino)phenylamine, 4-(Dimethylamino)phenylamine, Dimethyl-para-phenylenediamine, N,N-Dimethyl-p-fenylendiamin, CCRIS 6024, CHEBI:15783, HSDB 5330, BZORFPDSXLZWJF-UHFFFAOYSA-N, Dimethyl-p-phenylenediamine (VAN), EINECS 202-807-5, SBB058715, N,N-Dimethyl-p-fenylendiamin [Czech], CI 76075, AI3-52360, (4-aminophenyl)dimethylamine, Wurster’s Red, 4-dimethylamino aniline, 4-dimethylamino-aniline, ACMC-209seo, DSSTox_CID_5149, 4-(dimethylamino)-aniline, AC1L1OU7, AC1Q53CX, Dimethyl-paraphenylenediamine, DSSTox_RID_77688, DSSTox_GSID_25149, SCHEMBL15246, KSC496G1T, CHEMBL36296, 4-(N,N-dimethylamino)aniline, (4-aminophenyl)-dimethyl-amine, 193992_ALDRICH, WLN: ZR DN1 & 1, BZORFPDSXLZWJF-UHFFFAOYSA-, CTK3J6319, NSC1493, 536-46-9 (di-hydrochloride), MolPort-001-768-943, N,N-dimethyl-1,4-diamino-benzene, N,N-dimethyl-benzene-1,4-diamine, NSC-1493, 2052-46-2 (mono-hydrochloride), N’,N’-dimethyl-p-phenylene diamine, N4,N4-dimethylbenzene-1,4-diamine, Tox21_200191, 6219-73-4 (unspecified sulfate), ANW-41086, AR-1K9666, FC1029, LS-287, N, N-dimethyl-para-phenylene diamine, STL255600, ZINC00056911, N’,N’-dimethyl-benzene-1,4-diamine, AKOS000101558, N1,N1-Dimethylphenylene-1,4-diamine, 1-N,1-N-dimethylbenzene-1,4-diamine, 4-N,4-N-dimethylbenzene-1,4-diamine, 536-47-0 (sulfate[1:1]), MCULE-4782652197, NE10522, RTR-033076, CAS-99-98-9, NCGC00091245-01, NCGC00091245-02, NCGC00257745-01, 24631-29-6 (oxalate[1:1]), 60160-75-0 (sulfate[2:1]), 62778-12-5 (oxalate[2:1]), AJ-09496, AK-87903, AN-24534, CJ-00416, KB-88471, SC-65295, ZB001880, 13806-04-7 (unspecified hydrochloride), AB1003350, TR-033076, 4CH-011916, D0779, ST24025677, ST51037495, C04203, I01-0448, 3B3-033801, InChI=1/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3, 4-(Dimethylamino)aniline; 4-Amino-N,N-dimethylaniline; N,N-Dimethyl-1,4-phenylenediamine; DMPPDA

Removed Synonyms

DMPPDA, N,4-benzenediamine, N,4-phenylenediamine, 1, N,N-dimethyl-, N,N’-Dimethyl-P-phenylenediamine, p-Phenylenediamine,N-dimethyl-, CID7472, (Z)-But-2-ene-1,2,3-tricarboxylate, 1,4-Benzenediamine, N,N-dimethyl-, sulfate (1:1), 536-47-0, 71552-25-5

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