6-Amino-2-naphthalenesulfonic acid

Description

2-Aminonaphthalene-6-sulfonic acid [93- 00-5]. (6-aminonaphthalene-2-sulfonic acid), Bronner acid, C10H9NO3S, Mr 223.24, crystallizes from water as the monohydrate in plates although only 0.2 % soluble at 100℃. Sulfonation with 20 % oleum at 20℃ gives a mixture of 1,6- and 6,8-disulfonic acids.

The Uses of 6-Amino-2-naphthalenesulfonic acid

6-Amino-2-naphthalenesulfonic Acid is used in the synthesis of diaryl urea derivatives bearing sulfonamide moiety with an in vitro antitumor activity.

Definition

ChEBI: 6-aminonaphthalene-2-sulfonic acid is an aminonaphthalenesulfonic acid.

Production Methods

2-Hydroxynaphthalene-6-sulfonic acid is aminated by a Bucherer reaction under conditions similar to those used for Tobias acid.

Flammability and Explosibility

Not classified

Purification Methods

Crystallise the acid from a large volume of hot water. The diethylamine salt has m 190.5-192o (from EtOH/isoBuOH), and the S-benzylisothiuronium salt has m 330o (from nBuOH). [Beilstein 14 H 760, 14 II 463, 14 III 2249, 14 IV 2804.]