Synthesis of 4,4′-methylenedianiline (4,4′-diaminodiphenylmethane)

Preparation of 4,4′-methylenedianiline

Preparation of 4,4'-methylenedianiline (4,4'-diaminodiphenylmethane)

Preparation of 4,4′-methylenedianiline (4,4′-diaminodiphenylmethane)

93 g (1 mole) of aniline are dissolved in 96 % alcohol and to the cooled solution with proper stirring 120 g (1 mole) of 40 % formaldehyde solution are gradually added. After the addition is completed a second molecular portion of aniline, 93 g (1 mole) of aniline are added and the reaction is continued until the odor of formaldehyde has disappeared. The complete the reaction the mixture is refluxed for 2 hours. 130 g (1 mole) of aniline hydrochloride are then added, and boiling continued for a further 12 hours. The alcohol is distilled off, the residue made alkaline with the solution of sodium hydroxide and the excess of aniline removed by distillation with superheated steam. The residual oil, which consists of 4,4′-diaminodiphenylmethane, is then purified by solution in dilute hydrochloric acid and reprecipitation with dilute alkali. The 4,4′-diaminodiphenylmethane base is filtered off, washed and dried.

Organic medical chemicals, by M. Barrowliff, 188-189, 1921

IUPAC Name

4-[(4-aminophenyl)methyl]aniline

InChI

InChI=1S/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H2

InChI Key

YBRVSVVVWCFQMG-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC=C1CC2=CC=C(C=C2)N)N

MeSH Synonyms

4,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane dihydrochloride, 4,4′-diaminodiphenylmethane, sodium chloride (3:1), 4,4′-MDA, 4,4′-methylene dianiline, 4,4′-methylenebisaniline, 4,4′-methylenedianiline, di(4-aminophenyl)methane, p,p’-diaminodiphenylmethane, Tonox

Depositor-Supplied Synonyms

4,4′-Methylenedianiline, 4,4′-DIAMINODIPHENYLMETHANE, 101-77-9, Dadpm, Methylenedianiline, Tonox, Dianilinomethane, p,p’-Methylenedianiline, Bis(4-aminophenyl)methane, p,p’-Diaminodiphenylmethane, Benzenamine, 4,4′-methylenebis-, Dianilinemethane, Bis(p-aminophenyl)methane, Epicure DDM, Epikure DDM, 4,4′-Diphenylmethanediamine, Jeffamine AP-20, Diaminodiphenylmethane, 4,4′-Methylene dianiline, 4-(4-Aminobenzyl)aniline, Curithane, Di-(4-aminophenyl)methane, 4,4′-Methylenebis(benzeneamine), 4,4′-Methylenebisbenzenamine, Sumicure M, 4,4-Methylenedianiline, Ancamine TL, 4,4′-Methylenebisaniline, 4-[(4-aminophenyl)methyl]aniline, Methylenebis(aniline), Aniline, 4,4′-methylenedi-, Bis-p-aminofenylmethan, Araldite hardener 972, Di(4-aminophenyl)methane, p,p’-Diaminodifenylmethan, NCI-C54604, 4,4′-Diaminodiphenylmethan, HT 972, 4,4′-Methylenebis(aniline), Avaldite HT 972, CHEBI:32506, bis-p-aminophenylmethane, NSC 4709, 4,4′-Dimethylenediamine, Methylenedianiline (VAN), di-(p-aminophenyl)methane, 4,4′-methanediyldianiline, CCRIS 1010, Bis-p-aminofenylmethan [Czech], HSDB 2541, alpha-(p-aminophenyl)-p-toluidine, YBRVSVVVWCFQMG-UHFFFAOYSA-N, p,p’-Diaminodifenylmethan [Czech], EINECS 202-974-4, 4,4′-Diaminodiphenylmethan [German], p-Toluidine, alpha-(p-aminophenyl)-, UN2651, Methylenebis[aniline], BRN 0474706, p-Toluidine, .alpha.-(p-aminophenyl)-, AI3-02615, DSSTox_CID_2422, DSSTox_RID_76586, DSSTox_GSID_22422, 4,4′-Methylenebis[aniline], 4-[(4-aminophenyl)methyl]phenylamine, CAS-101-77-9, Benzenamine, 4,4′-methylenebis-, hydrochloride (1:2), Bis(aminophenyl)methane, GG5LL7OBZC, UNII-GG5LL7OBZC, Aniline,4′-methylenedi-, Epitope ID:116050, WLN: ZR D1R DZ, AC1L1P2V, AC1Q2AM9, AC1Q51ZB, AC1Q51ZC, 4,4′-Methylenedibenzenamine, methylenebis(4-aminobenzene), Oprea1_406523, SCHEMBL28001, 4,4′-Methylene(bisaniline), Benzenamine,4′-methylenebis-, KSC174Q1B, MLS002303003, 32950_ALDRICH, 4,4′-Diaminodiphenyl methane, 4-(4-Aminobenzyl)phenylamine, BIDD:ER0255, CHEMBL85728, Dianiline, 4,4′-methylene-, 4,4′-DiaminodiPhenyl-Methane, 4,4′-methylenedi(phenylamine), 46092_RIEDEL, Jsp000240, Benzenamine,4-4′-methylenebis-, 32950_FLUKA, 4-(4-Aminobenzyl)phenylamine #, CTK0H4810, NSC4709, MolPort-001-765-126, BB_SC-0056, HMS3091M08, ACT07434, NSC-4709, Tox21_201723, Tox21_300141, 13552-44-8 (di-hydrochloride), ANW-14529, AR-1F8109, BBL022928, LS-338, SBB058722, STK988515, ZINC19014778, AKOS000118778, CCG-103567, MCULE-6272250876, RP25620, RTR-000437, SDCCGMLS-0066191.P001, UN 2651, NCGC00091159-01, NCGC00091159-02, NCGC00091159-03, NCGC00091159-04, NCGC00254163-01, NCGC00259272-01, AC-10921, AJ-70716, AK153946, AN-24584, KB-71820, SMR000019102, 21646-20-8 (hydrochlorideCl[3:1]), DB-058699, TR-000437, M0220, ST24042515, ST50406593, T7262, C14288, 4,4 inverted exclamation marka-Methylenedianiline, 3B4-1163, 4,4′-Diaminodiphenyl methane [UN2651] [Poison], 4,4′-Diaminodiphenyl methane [UN2651] [Poison], I14-7089, T7105954, 4,4 inverted exclamation marka-Diaminodiphenylmethane, 120859-32-7, 136601-30-4, 28602-61-1, InChI=1/C13H14N2/c14-12-5-1-10(2-6-12)9-11-3-7-13(15)8-4-11/h1-8H,9,14-15H

Removed Synonyms

DAPM, CID7577, 4,4′-MDA, 4,4′-Methylenedianiline dihydrochloride, 4,4′-diaminodiphenylmethane dihydrochloride, MDA, 4-13-00-00390 (Beilstein Handbook Reference), C009505, 4,4′-diaminodiphenylmethane, sodium chloride (3:1), DDM, 13552-44-8, 83712-44-1, 89315-28-6

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