Synthesis of 4,4′-diamino-2,2′-stilbenedisulfonic acid

Preparation of 4,4′-diamino-2,2′-stilbenedisulfonic acid

Preparation of 4,4′-diamino-2,2′-stilbenedisulfonic acid

Preparation of 4,4′-diamino-2,2′-stilbenedisulfonic acid

The sodium salt of the dinitrostilbenedisulfonic acid is dissolved in 300 ml hot water, and hydrochloric acid is added to neutralize if necessary. The solution is run on to 200 g. of iron turnings, which have been previously etched by standing in 20 ml of 40% acetic acid. The reduction proceeds in the normal way. The solution is made strongly acid to Congo red with hydrochloric acid, and the diaminostilbinedisulfonic acid separates as yellow crystals. After 10 hours it is filtered off and washed. Yield-about 40%.

Systematic organic chemistry, by W. M. Cumming, 360, 1937.

IUPAC Name

5-amino-2-[(E)-2-(4-amino-2-sulfophenyl)ethenyl]benzenesulfonic acid

InChI

InChI=1S/C14H14N2O6S2/c15-11-5-3-9(13(7-11)23(17,18)19)1-2-10-4-6-12(16)8-14(10)24(20,21)22/h1-8H,15-16H2,(H,17,18,19)(H,20,21,22)/b2-1+

InChI Key

REJHVSOVQBJEBF-OWOJBTEDSA-N

Canonical SMILES

C1=CC(=C(C=C1N)S(=O)(=O)O)C=CC2=C(C=C(C=C2)N)S(=O)(=O)O

Isomeric SMILES

C1=CC(=C(C=C1N)S(=O)(=O)O)/C=C/C2=C(C=C(C=C2)N)S(=O)(=O)O

MeSH Synonyms

4,4′-diacetamido-2,2′-stilbene disulfonate, 4,4-diaminostilbene-2,2′-disulfonic acid, amsonic acid, amsonic acid, disodium salt, amsonic acid, sodium salt, DADS, DAS, DASD, DASSA, DSD acid

Depositor-Supplied Synonyms

81-11-8, Flavonic acid, Tinopal BHS, Amsonsaeure, DASD, 4,4′-Diaminostilbene-2,2′-disulfonic acid, Amsonic acid, 4,4′-Diaminostilbene-2,2′-disulphonic acid, NSC 163, 2,2′-Disulfo-4,4′-stilbenediamine, UNII-H68088WVJL, Diaminostilbenedisulfonic acid, p,p’-Diaminostilbene-o,o’-disulfonic acid, CCRIS 4778, NSC163, Diamino stilbene disulfonic acid, HSDB 4239, 4,4′-DIAMINO-2,2′-STILBENEDISULFONIC ACID, 2,2′-Stilbenedisulfonic acid, 4,4′-diamino-, REJHVSOVQBJEBF-OWOJBTEDSA-N, NCI-C60162, p,p’-Diaminodiphenylethylene-o,o’-disulfonic acid, EINECS 201-325-2, MFCD00024946, BRN 0629516, 4-4′-Diamino-2,2′-stilbenedisulphonic acid, (E)-4,4′-Diamino-2,2′-stilbendisulfonsaeure, 2,2′-ethene-1,2-diylbis(5-aminobenzenesulfonic acid), 2,2′-(1,2-Ethenediyl)bis(5-amino-benzenesulfonic acid), 2,2′-(1,2-Ethylenediyl)bis(5-aminobenzenesulfonic acid), Benzenesulfonic acid, 2,2′-(1,2-ethenediyl)bis(5-amino-, Benzenesulfonic acid, 2,2′-(1,2-ethenediyl)bis[5-amino-, 2,2′-(E)-ethene-1,2-diylbis(5-aminobenzenesulfonic acid), Benzene, 1,1′-(1,2-ethenediyl)bis-, diamino disulfo deriv., 5-amino-2-[(E)-2-(4-amino-2-sulfo-phenyl)vinyl]benzenesulfonic acid, 28096-93-7, NCGC00164487-01, NCGC00164487-02, p,o’-disulfonic acid, NSC659761, AC1NR4CG, AC1Q6WFM, AC1Q51RV, 6,6′-(Ethene-1,2-diyl)bis(3-aminobenzenesulfonic acid), SCHEMBL38871, Benzene, 1,1′-(1,2-ethenediyl)bis-, diamino disulfo deriv, Benzenesulfonic acid, 2,2′-(1,2-ethylenediyl)bis(5-amino-, ARONIS27064, Bio-0462, 5-amino-2-[2-(4-amino-2-sulfophenyl)ethenyl]benzenesulfonic acid, H68088WVJL, CHEMBL1698380, DTXSID60182371, C14H14N2O6S2, ZINC3844586, AR-1D1707, BBL000014, SBB041131, STK386223, AKOS000269621, 7336-20-1 (di-hydrochloride salt), AS01260, AC-10923, AJ-45829, AK-44108, AN-24036, K443, OR034607, OR344147, SC-18190, 4,4-Diaminostilbene-2,2-disulphonic acid, LS-170804, TC-102356, D0121, FT-0617028, ST24042500, T6981, 25394-13-2 (unspecified hydrochloride salt), (E)-4,4′-Diaminostilbene-2,2′-disulfonic acid, 3-14-00-02266 (Beilstein Handbook Reference), 4,4′-Diamino-2,2′-stilbenedisulfonic acid, (E)-, 4,4-Diaminostilbene-2,2-Disulfonic Acid Sodium Sal, I04-9450, Benzenesulfonic acid,2′-(1,2-ethenediyl)bis[5-amino-, Benzene,1′-(1,2-ethenediyl)bis-, diamino disulfo deriv., Benzenesulfonic acid, 2,2′-(1,2-ethenediyl)bis[5-amino, UNII-899GJ5MP05 component REJHVSOVQBJEBF-OWOJBTEDSA-N, 2,2′-[(E)-1,2-ethenediyl]bis [5-aminobenzenesulfonic acid], 2,2′-[(E)-1,2-Ethenediyl]bis[5-aminobenzenesulfonic acid], Benzenesulfonic acid, 2,2′-[(E)-1,2-ethenediyl]bis[5-amino-, Benzenesulfonic acid, 2,2′-(1,2-ethylenediyl)bis(5-amino- (9CI), 2-[(1E)-2-(4-amino-2-sulfophenyl)vinyl]-5-aminobenzenesulfonic acid, 5-amino-2-[(E)-2-(4-amino-2-sulfophenyl)ethenyl]benzene-1-sulfonic acid, 5-amino-2-[(E)-2-(4-amino-2-sulfophenyl)ethenyl]benzenesulfonic acid, BENZENESULFONIC ACID, 2,2′-(1,2-ETHENEDIYL)BIS[5-AMINO-, (E)-, 65941-98-2

Removed Synonyms

2,4′-stilbenediamine, 2, 4,4′-diamino-, 4,2′-stilbenedisulfonic acid, NSC-163, MolPort-000-519-060, CID5284378, 4,4-Diamino stiben-2,2-disulfonic acid, 4,4′-Diaminodiphenylethylene-2,2′-disulfonic acid, DAS

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