Synthesis of flavonic acid

Preparation of flavonic acid

Preparation of flavonic acid

Preparation of flavonic acid

100 g of difficultly soluble sodium salt of dinitrostilbenedisulfonic acid are dissolved in 300 ml. hot water, and the free sodium hydroxide present is neutralized with dilute hydrochloric acid. The resulting solution is added during the course of 30 minutes to 200 grams of iron turnings which have been etched with 20 ml. 40 % acetic acid. The reduction then proceeds in the normal way and when the reduction is complete, the reaction mixture is neutralized with sodium carbonate, filtered to remove the iron sludge, and made strongly acid to Congo red with hydrochloric acid, precipitating flavonic acid (diaminostilbenedisulfonic acid) as a yellowish, finely crystalline material. After 10 hours, the product is filtered off and washed thoroughly. The yield is about 70 grams.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 168, 1949

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

Flavonic acid, 81-11-8, Tinopal BHS, Amsonsaeure, DASD, Amsonic acid, 4,4′-Diaminostilbene-2,2′-disulfonic 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, 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, NCGC00164487-01, NCGC00164487-02, p,o’-disulfonic acid, NSC659761, AC1NR4CG, AC1Q6WFM, AC1Q51RV, 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, C14H14N2O6S2, MolPort-000-519-060, ZINC3844586, AR-1D1707, BBL000014, MFCD00024946, SBB041131, STK386223, AKOS000269621, 7336-20-1 (di-hydrochloride salt), AS01260, AC-10923, AJ-45829, AK-44108, AN-24036, K443, OR034607, OR344147, SC-18190, 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), 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)-, 28096-93-7, 65941-98-2

Removed Synonyms

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

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *