2-Iodoxybenzoic acid

2-Iodoxybenzoic acid

Structure of 2-Iodoxybenzoic acid

2-Iodoxybenzoic acid (IBX) is an organoiodine compound that is widely used as an oxidizing agent in organic chemistry. It is a hypervalent iodine compound, specifically a _⁵-iodane, and is known for its ability to selectively oxidize alcohols to aldehydes or ketones.

Structure and Properties

2-Iodoxybenzoic acid is characterized by the presence of an iodine atom in a +5 oxidation state, bonded to an aromatic ring. The iodine atom is also bonded to two oxygen atoms, forming an iodine-oxygen double bond and an iodine-oxygen single bond, which gives the compound its oxidizing properties.

Synthesis

Preparation of 2-Iodoxybenzoic acid

2-Iodoxybenzoic acid is typically synthesized from 2-iodobenzoic acid through oxidation. The oxidation is often carried out using strong oxidizing agents such as sodium periodate or potassium bromate in an acidic medium.

Applications in Organic Synthesis

2-Iodoxybenzoic acid is primarily used as an oxidizing agent in organic synthesis. It is particularly effective in the oxidation of primary and secondary alcohols to aldehydes and ketones, respectively.

Oxidation of Alcohols

Oxidation of alcohols using IBX

IBX is known for its mild and selective oxidation of alcohols. It can oxidize primary alcohols to aldehydes without over-oxidizing them to carboxylic acids. Secondary alcohols are oxidized to ketones.

Oxidative Cleavage

Oxidative cleavage using IBX

IBX can also be used for the oxidative cleavage of vicinal diols, leading to the formation of two carbonyl compounds. This reaction is useful in the degradation of complex molecules into simpler fragments.

Use in Dimethyl Sulfoxide (DMSO)

Oxidative cleavage in DMSO

In the presence of dimethyl sulfoxide (DMSO), IBX can facilitate the oxidative cleavage of certain substrates, providing a versatile method for the transformation of organic compounds.

Safety and Handling

2-Iodoxybenzoic acid is a powerful oxidizing agent and should be handled with care. It is important to use appropriate personal protective equipment and to work in a well-ventilated area to avoid exposure to its potentially harmful effects.

Related pages

• Hypervalent iodine chemistry
• Oxidation (chemistry)
• Organoiodine compound

Gallery

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  Example of IBX oxidation

2-Iodoxybenzoic_acid

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  2-Iodoxybenzoic acid structure

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  Preparation of 2-Iodoxybenzoic acid

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  IBX oxidation mechanism

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  Example of IBX acid reaction

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  IBX oxidative cleavage

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  IBX DMSO oxidative cleavage