Synthesis of 3-amino-4-hydroxyphenylarsonic acid

Preparation of 3-amino-4-hydroxyphenylarsonic acid

A mixture of a solution of 31.6 g of 3-nitro-4-hydroxyphenylarsonic acid in 600 ml. of methanol and 840 g. of 4% sodium amalgam is heated to reflux on a water bath until there is no more evolution of gas. The alcohol is removed by distillation, and the residue is treated with 120 ml. of water. The mercury is separated, and 150 ml. of concentrated hydrochloric acid is added to the aqueous phase. After standing for a day, the mixture is filtered and the filtrate treated with activated carbon. 0.1 N sodium hydroxide solution is added until the solution is just on the alkaline side of Congo red but is acid to litmus. 25 ml acetic acid are added to complete the precipitation of the 3-amino-4-hydroxyphenylarsonic acid, which is removed by filtration after cooling. The precipitate is washed with water until free of chloride ion and dried. The yield is around 87%.

Ber., 45, 757 (1912).

IUPAC Name

(3-amino-4-hydroxyphenyl)arsonic acid

InChI

InChI=1S/C6H8AsNO4/c8-5-3-4(7(10,11)12)1-2-6(5)9/h1-3,9H,8H2,(H2,10,11,12)

InChI Key

UAKCHCFOPKOOLI-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=C(C=C1[As](=O)(O)O)N)O

Depositor-Supplied Synonyms

3-Amino-4-hydroxyphenylarsonic acid, 2163-77-1, 4-Hydroxy-3-arsanilic acid, 3-Amino-4-hydroxybenzenearsonic acid, 2-AMINO-1-HYDROXYBENZENE-4-ARSONIC ACID, m-ARSANILIC ACID, 4-HYDROXY-, Benzenearsonic acid, 3-amino-4-hydroxy-, (3-AMINO-4-HYDROXYPHENYL)ARSONIC ACID, EINECS 218-494-3, NSC 18814, BRN 2834149, Arsonic acid, (3-amino-4-hydroxyphenyl)-, Kyselina 3-amino-4-hydroxybenzenarsonova [Czech], NSC18814, 4-Hydroxy-m-arsanilic acid, WLN: ZR BQ E-AS-QQO, CHEMBL1970917, SCHEMBL15413119, CTK7J9556, 3-amino-4-hydroxyphenylarsonicacid, AC1L2876, 7679AF, NSC-18814, (3-amino-4-hydroxy-phenyl)arsonic acid, Kyselina 3-amino-4-hydroxybenzenarsonova, LS-21706, NCI60_001568, OR011653, OR174694, Arsonic acid, (3-amino-4-hydroxyphenyl)- (9CI), 3B3-022800

Removed Synonyms

CID16555, 3-16-00-01129 (Beilstein Handbook Reference)

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