Synthesis of 3-aminobenzenesulfonic acid

Preparation of 3-aminobenzenesulfonic acid

Preparation of 3-aminobenzenesulfonic acid

Preparation of 3-aminobenzenesulfonic acid

 

123 g. nitrobenzene are sulfonated as described in Preparation of 3-nitrobenzenesulfonic acid. 3-Nitrobenzenesulfonic acid is reduced by adding 10g. of iron borings to the solution of nitro-sulfonic acid at about 50° C; this causes the evolution of nitrous fumes. 256 g. of iron borings in total are added in portions at such a rate that the reduction proceeds briskly.; the agitation should be vigorous enough to keep the iron swirling round. After the reduction mixture is neutralised, the filtrate is concentrated to about 600 ml. Hydrochloric acid is added until an acid reaction to Congo is obtained. The metanilic acid then crystallises out. The separation may be assisted by adding common salt. Yield–80% theoretical. Crystallises with ½H2O of crystallisation.

Systematic organic chemistry, by W. M. Cumming, 359, 1937.

IUPAC Name

3-aminobenzenesulfonic acid

InChI

InChI=1S/C6H7NO3S/c7-5-2-1-3-6(4-5)11(8,9)10/h1-4H,7H2,(H,8,9,10)

InChI Key

ZAJAQTYSTDTMCU-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=CC(=C1)S(=O)(=O)O)N

MeSH Synonyms

3-aminobenzenesulfonic acid, metanilic acid, metanilic acid, monosodium salt

Depositor-Supplied Synonyms

3-AMINOBENZENESULFONIC ACID, Metanilic acid, 121-47-1, m-Sulfanilic acid, m-Anilinesulfonic acid, m-Aminobenzenesulfonic acid, 1-Aminobenzene-3-sulfonic acid, Aminobenzenesulfonic acid, Benzenesulfonic acid, 3-amino-, Kyselina metanilova, 3-Amino-benzenesulfonic acid, Aniline-m-sulfonic acid, 3-Sulfoaniline, Kyselina anilin-3-sulfonova, 3-Aminobenzenesulphonic acid, NSC 4504, UNII-OT03NUM20P, Kyselina metanilova [Czech], m-Amino benzenesulfonic acid, CCRIS 2760, CHEBI:27764, ZAJAQTYSTDTMCU-UHFFFAOYSA-N, EINECS 204-473-6, Kyselina anilin-3-sulfonova [Czech], SBB060550, BRN 0473264, AI3-23215, m-sulfoaniline, m-sulphanilic acid, aminobenzenesulfonicacid, 3-anilinesulfonic acid, PubChem18118, ACMC-209aba, aniline-3-sulphonic acid, WLN: ZR CSWQ, m-Aminophenylsulfonic acid, 3-amino-benzenesulfonicaci, DSSTox_CID_4462, AC1L1R2M, 3-amino benzenesulfonic acid, DSSTox_RID_77408, OT03NUM20P, DSSTox_GSID_24462, SCHEMBL29044, 3-Aminobenzene sulphonic acid, KSC489Q2D, 1-aminobenzene-3-sulfonicacid, ARONIS23915, 165794_ALDRICH, 3-aminobenzene-1-sulfonic acid, AC1Q51H1, AC1Q51H2, CHEMBL1456811, DTXSID6024462, 06998_FLUKA, CTK3I9821, NSC4504, NSC-4504, ZINC1530396, Tox21_201027, ANW-17636, LS-648, MFCD00065345, STK661724, AKOS000299087, AM91127, MCULE-6066979500, NE11138, RP23552, TRA0086788, VZ36217, 1126-34-7 (mono-hydrochloride salt), NCGC00091239-01, NCGC00091239-02, NCGC00258580-01, AJ-26658, AK-53376, AN-43391, CAS-121-47-1, KB-29719, OR025184, AB1009810, DB-041620, ST4022370, TR-003505, A0265, FT-0622397, ST24028400, EN300-19726, C06334, 4-14-00-02647 (Beilstein Handbook Reference), AE-562/43459497, I01-9728, W-108457, A1026/0048064

Removed Synonyms

null, 3-Aminobenzenesulfonate, C6H7NO3S, CID8474, MolPort-001-783-841, 3-AMINOBENZENE SULFONIC ACID, RTR-003505, R225, 1126-34-7

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