ChemicalBook CAS DataBase List 4-IODO-2-NITROPHENOL

4-IODO-2-NITROPHENOL synthesis

11synthesis methods

Product Name:4-IODO-2-NITROPHENOL
CAS Number:21784-73-6
Molecular formula:C6H4INO3
Molecular Weight:265.01

88-75-5
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$15.00/5mg

21784-73-6
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$75.00/500mg

Yield:21784-73-6 94.6%

Reaction Conditions:

with N-iodo-succinimide in acetonitrile at 25 - 30; for 0.166667 h;regioselective reaction;

Steps:

General procedure for the monoiodination

General procedure: To a solution of 4-nitroaniline, 1a (1.0 g, 7.2 mmol) and sulfated polyborate (0.05 g, 5 wt%) in 7 mL anhyd. MeCN in a round bottom flask was added NIS solution (1.62 g, 7.2 mmol in 2 mL anhyd. MeCN) dropwise. The reaction mixture was stirred for 15 minutes at 25-30 °C, monitored by GC. After completion of the reaction, MeCN was distilled under vacuum at 40-45 °C. The residue was treated with 10 mL each of MDC and water, stirred the mixture for 10-15 minutes; MDC layer was separated and washed with 1% sodium thiosulphate, dried over sodium sulfate, and evaporated under vacuum to obtain 2-iodo-4-nitroaniline, 2a, 1.89 g (94% yield, 99.3% purity)

References:

Misal, Balu;Palav, Amey;Ganwir, Prerna;Chaturbhuj, Ganesh [Tetrahedron Letters,2021,vol. 74,art. no. 153154] Location in patent:supporting information

540-38-5 Synthesis