Hydroxy[(p-tolylsulfonyl)oxy]iodo benzene, CAS No. 27126-76-7

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27126-76-7

Catalog No. EBD7850

CAS 27126-76-7

Name Hydroxy[(p-tolylsulfonyl)oxy]iodo benzene

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Basic Information

Synonyms: hydroxy{[(4-methylphenyl)sulfonyl]oxy}phenyl-lambda~3~-iodane BSP 2-Benzene-sulfonyl-pyridine Koser'sReagent koser'sregent hydroxy(4-methylbenzenesulfonato-o)phenyliodine Hydroxy[(p-tolylsulfonyl)oxy]iodobenzene (hydroxy(tosyloxy)iodo)benzene Hydroxy(tosyloxy)iodobenzene Hydroxytosyloxyiodo]benzene HTIB~Iodosobenzene-I-mono-p-toluenesulphonate~Kosers [Hydroxy(tosyloxy)iodo]benzene

Molecular Formula: C13H13IO4S

Molecular Weight: 392.21

MDL Number: MFCD00134648

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Oxidizing Agents Synthetic Chemistry > Organic Building Blocks > Phosphorus Compounds

Product Description:

Hydroxy(tosyloxy)iodobenzene (HTIB), also known as Koser's reagent, is an organoiodine(III) compound with the formula PhI(OH)OTs. It is a white to off-white crystalline solid, commercially available, and serves as a powerful and versatile hypervalent iodine(III) reagent in organic synthesis. Its primary application is as an efficient oxidant and electrophilic reagent. It is extensively used for the α-tosyloxylation of ketones to generate α-tosyloxy ketones, which are valuable intermediates for further transformations into α-hydroxy ketones, α-haloketones, and other derivatives. Beyond this, HTIB facilitates a range of oxidative transformations, including the oxidation of alcohols to carbonyl compounds, the oxidative coupling of phenols, and the synthesis of heterocycles. It is particularly valued for its mild reaction conditions, high selectivity, and the generation of non-toxic iodobenzene as a byproduct. Due to its stability, ease of handling compared to some other iodine(III) reagents, and broad utility in constructing C-O and C-N bonds, HTIB is a staple reagent in research laboratories and process chemistry for the synthesis of pharmaceuticals, agrochemicals, and fine chemicals.

Physical Properties

Melting Point: 131-137 °C(lit.)

Storage: Refrigerator (+4°C)

Analytical Data

Appearance: Pale yellow crystalline powder