Synthesis of iodobenzene

Preparation of iodobenzene

Preparation of iodobenzene from aniline and potassium iodide

Preparation of iodobenzene from aniline and potassium iodide

Preparation of iodobenzene from aniline and potassium iodide

40 g of aniline are dissolved in 700 ml of water and 85 ml of concentrated hydrochloric acid. Ice is added until the temperature falls below 0° C and the solution diazotized with solution containing 35 g of sodium nitrite. During diazotization the temperature being kept below 10° C. A cold, concentrated solution of 85 g of potassium iodide is then slowly run in with continual stirring. At first rapid evolution of nitrogen takes place, but towards the end the reaction becomes less vigorous and must be continued by gentle warming. When no more nitrogen is evolved, the solution, which has become colored owing to the separation of iodine, is decolorized by the addition solution of sodium hydroxide, the heavy oil collected, washed with water, and steam-distilled. The oil which passes over is collected, dried with calcium chloride, and distilled. Iodobenzene forms a colorless, heavy oil which boils at 188° C. Yield almost quantitative.

Preparation of organic compounds, E. de. Barry Barnett, 75-76, 1912

Preparation of iodobenzene from benzene and iodine

Preparation of iodobenzene

Preparation of iodobenzene

To the round bottom flask which is cooled with ice water bath 22 g  silver perchlorate, 10 g CaCOand 100 ml benzene are placed. To this suspension during 15 min 25 g iodine is added. Until no further change takes place the reaction mixture is filtered, washed with water and dried with calcium chloride. Further purification by distillation leads to 16 g or 80 % of iodobenzene with boiling point 184° C.

Ber., 83, 2544, 1930; Ber., 64, 961, 1076, 1931; Ber., 67, 917, 1420, 1729, 1934

Preparation of iodobenzene from benzene, iodine and iodic acid

Preparation of iodobenzene from benzene, iodine and iodic acid

Preparation of iodobenzene from benzene, iodine and iodic acid

A mixture of 25 g of benzene, 80 ml of glacial acetic acid, 15 ml 50% sulfuric acid, 24.4 g of iodine, and 9.5 g of iodic acid is stirred for 1 hour at 90°, and then about 2 hours at 95° until the iodine is consumed. The product that is precipitated by water is dissolved in 50 ml of chloroform, washed with the sodium bisulfite solution, dried, and freed from chloroform and benzene by evaporation. 47.5 g of crude iodobenzene are diluted with light petroleum and passed through a column of alumina that has been pretreated dry with ammonia (dried over potassium hydroxide) until the initial warming ceases. Vacuum-distillation of the eluate affords 83% of iodobenzene.

Ann. Chem., 634, 100, (1960)

IUPAC Name

iodobenzene

InChI

InChI=1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H

InChI Key

SNHMUERNLJLMHN-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)I

MeSH Synonyms

iodobenzene, iodobenzene, 123I-labeled, iodobenzene, 125I-labeled, iodobenzene, 14C-labeled

Depositor-Supplied Synonyms

IODOBENZENE, 591-50-4, Phenyl iodide, Benzene, iodo-, Benzene iodide, IODOPHENYL, Iodo-benzene, Iodinebenzol, Iodo benzene, PHENYLIODIDE, SNHMUERNLJLMHN-UHFFFAOYSA-N, NSC 9244, EINECS 209-719-6, AI3-16898, 172484-65-0, iodanylbenzene, iodiobenzene, phenyl-iodide, 3-iodobenzene, 4-iodobenzene, benzene, iodo, 1-Iodobenzene, 2-iodo-benzene, IDOBENZENE, PubChem3921, ACMC-1ATSF, AC1L1XNC, UNII-9HK5L7YBBR, 9HK5L7YBBR, SCHEMBL1587, I7632_ALDRICH, KSC270G7T, AC1Q4P90, CHEMBL116296, PARAGOS 510022, CTK1H0379, TIMTEC-BB SBB040910, NSC9244, MolPort-000-156-438, LABOTEST-BB LTBB002078, LTBB002078, EBD41928, NSC-9244, STR02365, AKOS BBS-00004395, ANW-33176, ZINC01699878, AKOS000118942, AS02214, DB02252, RP17497, RTR-037196, AJ-30412, AK-88660, AN-21539, CJ-06647, CJ-28633, KB-52696, LS-30382, SC-05582, DB-029918, ST2413138, TR-037196, FT-0627260, FT-0627272, FT-0670366, I0050, 9604-EP2287141A1, 9604-EP2308872A1, 9604-EP2316829A1, M-6085, 72788-EP2272813A2, 72788-EP2275395A2, 72788-EP2284157A1, 72788-EP2284920A1, 72788-EP2295503A1, 72788-EP2301921A1, 72788-EP2305769A2, 72788-EP2308880A1, 72788-EP2309584A1, A832185, I01-0569, 3B3-084520, InChI=1/C6H5I/c7-6-4-2-1-3-5-6/h1-5

Removed Synonyms

IODOCYCLOHEXANE, M-ANISALDEHYDE, CID11575, 626-62-0, pih

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