Synthesis of 3-amino-2,4,6-triiodobenzoic acid

Preparation of 3-amino-2,4,6-triiodobenzoic acid

A mixture containing 290 g of iodine chloride and 290 ml of concentrated hydrochloric acid (d 1.19) is run slowly into a stirred solution containing 68.5 g or 0.5 mole of m-aminobenzoic acid in 2000 ml of water and concentrated hydrochloric acid (d 1.19; 50 ml). The mixture is warmed gradually to 80-85°C and stirred for a further 3 hours at this temperature. The crude 3-amino-2,4,6-triiodobenzoic acid (about 92 %) that is precipitated is purified by twice recrystallizing its sodium salt from about five times its weight of water with addition of a little hydrogen sulfite. 3-Amino-2,4,6-triiodobenzoic acid m.p. 196.5-197.5°C (dec.), is obtained in about 70% yield.

 J. Amer. Chem. Soc, 74,4367 (1952).

IUPAC Name

3-amino-2,4,6-triiodobenzoic acid

InChI

InChI=1S/C7H4I3NO2/c8-2-1-3(9)6(11)5(10)4(2)7(12)13/h1H,11H2,(H,12,13)

InChI Key

QMQFFHSJUJDRPG-UHFFFAOYSA-N

Canonical SMILES

C1=C(C(=C(C(=C1I)N)I)C(=O)O)I

MeSH Synonyms

3-amino-2,4,6-triiodobenzoic acid, 3-amino-2,4,6-triiodobenzoic acid monosodium salt

Depositor-Supplied Synonyms

3-Amino-2,4,6-triiodobenzoic acid, 3119-15-1, 3-Amino-2,4,6-triiodo-benzoic acid, EINECS 221-493-0, 3-Amino-2,4,6-triiodo-Benzoicacid, MFCD00007681, NSC 60105, SBB057028, BRN 2113495, Acido 3-amino-2,4,6-triiodobenzoico [Italian], BENZOIC ACID, 3-AMINO-2,4,6-TRIIODO-, NSC60105, PubChem4987, AC1L2BXQ, ACMC-1CO9W, UNII-99H77D8MTD, C7H4I3NO2, SCHEMBL124763, 99H77D8MTD, CTK3J6413, DTXSID60185120, QMQFFHSJUJDRPG-UHFFFAOYSA-N, ZINC4235679, 2,4,6-triiodo-3-aminobenzoic acid, ANW-44823, NSC-60105, Acido 3-amino-2,4,6-triiodobenzoico, AKOS003382317, AN-7688, MCULE-9775464336, VZ26248, 67031-56-5 (mono-hydrochloride salt), AK-25750, KB-70340, LS-36066, OR174170, U348, ST2404868, FT-0614923, R1183, ST45027563, TL80090824, A18618, 4-14-00-01118 (Beilstein Handbook Reference), I01-0019, W-109863, 3-Amino-2,4,6-triiodobenzoic acid, 99% (dry wt.), may cont. up to 1 mole of water, InChI=1/C7H4I3NO2/c8-2-1-3(9)6(11)5(10)4(2)7(12)13/h1H,11H2,(H,12,13

Removed Synonyms

MolPort-001-783-519, CID18387, RT-003002

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