Synthesis of 2-amino-5-iodotoluene

Preparation of 2-amino-5-iodotoluene

Preparation of 2-amino-5-iodotoluene

Preparation of 2-amino-5-iodotoluene

40 g. of o-toluidine hydrochloride are mixed intimately with 71 g. of dry powdered iodine. To this is added 35 g. of finely divided calcium carbonate, and the mixture is thoroughly ground together. 200 ml of distilled water is added with vigorous shaking, and after standing 45 minutes the mixture is heated to 60-70° and held at this temperature for 5 minutes. The mixture is extracted several times with a total of 500 ml. of ether. The ethereal solution is dried over calcium chloride. Upon evaporation of the solution, the 2-amino-5-iodotoluene separates in 98% yield (64 g.). The material is recrystallized from 1:1 ethanol-water mixture to give 2-amino-5-iodotoluene melting at 87°.

J. Am. Chem. Soc., 47, 1710 (1925)





InChI Key


Canonical SMILES


Depositor-Supplied Synonyms

4-Iodo-2-methylaniline, 13194-68-8, 2-Amino-5-iodotoluene, 4-iodo-2-methylbenzenamine, 4-Iodo-o-toluidine, 4-Iodo-2-methyl-phenylamine, 4-iod-2-methylanilin, 2-methyl-4-iodoaniline, 4-iodo-2-methyl-aniline, 4-iodo-2-methylphenylamine, Benzenamine, 4-iodo-2-methyl-, BGKLFAQCHHCZRZ-UHFFFAOYSA-N, SBB043651, NSC60731, PubChem3318, ACMC-209boa, AC1Q2FKL, AC1Q4PJH, 4-iodo-2-methyl aniline, AC1L34YZ, Aniline, 4-iodo-2-methyl-, KSC490G5T, ARONIS27168, AURORA 1126, SCHEMBL218997, 454788_ALDRICH, CTK3J0359, TIMTEC-BB SBB043651, ZINC80446, 4 – Iodo – 2 – methylaniline, ATTERCOP-CHM AT132771, BUTTPARK 24\04-61, MolPort-000-145-454, HMS1760A15, ACT06479, EBD28821, AKOS BBS-00007953, EINECS 236-154-2, AKOS A1230-8434, ANW-19400, AR-1G2900, BBL018946, CK1165, NSC-60731, STL089346, ZINC00080446, AKOS000111238, AN-1955, AS02257, DS-0817, MCULE-8233941663, PS-3168, RL01495, RTC-010823, TRA0058798, AJ-10492, AK-33113, BC220172, BR-33113, CJ-00632, KB-39289, OR024175, SY018977, ZB002838, AB0004984, DB-020474, ST2418415, TC-010823, TL8000759, AM20060294, BB 0245922, FT-0618798, FT-0631480, I0690, ST50136060, X2915, M-5590, AE-641/01196008, I01-6187, T5215328, 3B3-018706, InChI=1/C7H8IN/c1-5-4-6(8)2-3-7(5)9/h2-4H,9H2,1H, 4-Iodo-2-methyl-phenylamine; 4-iodo-2-methylphenylamine; benzenamine, 4-iodo-2-methyl-

Removed Synonyms

CID83221, A2780, 13289-20-8

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