Synthesis of 3,5-dibromosulfanilic acid

Preparation of 3,5-dibromosulfanilic acid

17 g of sulfanilic acid are dissolved in 500 ml of hot water, and to the solution thus obtained a solution of 10 g of bromine in 125 ml of 13 %, sodium hydroxide is added. By means of a tube reaching to the bottom of the vessel 21 g of concentrated hydrochloric acid are then slowly run in with continual stirring. When all the acid has been added, the solution is carefully neutralized with sodium hydroxide and a concentrated solution of 25 g of crystallized barium chloride added. The precipitated barium salt, which contains two molecules of water, is collected by filtration after the solution has cooled. To obtain the free acid the barium salt is suspended in water and decomposed with the calculated amount of sulfuric acid. The precipitated barium sulfate is removed by filtration and the clear filtrate concentrated until crystallization sets in. On cooling, 3,5-dibromosulfanilic acid separates out in long needles containing two molecules of water. It is easily soluble in cold water and hot alcohol. When heated it decomposes at about 180° C.

Preparation of organic compounds, E. de. Barry Barnett, 55-56, 1912

IUPAC Name

4-amino-3,5-dibromobenzenesulfonic acid

InChI

InChI=1S/C6H5Br2NO3S/c7-4-1-3(13(10,11)12)2-5(8)6(4)9/h1-2H,9H2,(H,10,11,12)

InChI Key

KQQQNGNCDHGIIR-UHFFFAOYSA-N

Canonical SMILES

C1=C(C=C(C(=C1Br)N)Br)S(=O)(=O)O

Depositor-Supplied Synonyms

3,5-Dibromosulfanilic acid sodium salt, 4-Amino-3,5-dibromobenzenesulfonic acid sodium salt, AC1NQCX0, AC1Q50HY, 268143_ALDRICH, SCHEMBL5028708, AKOS015889247, MCULE-7054459603, 4-amino-3,5-dibromobenzenesulfonic acid, 4-amino-3,5-dibromobenzenesulphonic acid, 4-amino-3,5-dibromobenzene-1-sulfonic acid, FT-0641695, I01-19006

Removed Synonyms

CID5173465, 4-amino-3,5-dibromo-benzenesulfonic Acid, 78824-10-9

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