Methoxime

Methoxime is an organic compound with the formula CH₃ON=CH₂. It is a simple oxime, which is a functional group characterized by the presence of a carbon-nitrogen double bond with an adjacent hydroxyl group. Methoxime is a colorless liquid that is used in various chemical applications, including as an intermediate in organic synthesis and as a reagent in analytical chemistry.

Structure and Properties

Methoxime is a small molecule with a molecular weight of 59.07 g/mol. The structure consists of a methoxy group (CH₃O-) attached to an oxime group (C=N-OH). The presence of the oxime group gives methoxime its characteristic reactivity, allowing it to participate in various chemical reactions.

The compound is relatively volatile, with a boiling point of 114 °C and a melting point of -30 °C. It is soluble in water, which makes it useful in aqueous reactions and processes.

Synthesis

Methoxime can be synthesized through the reaction of methanol with hydroxylamine in the presence of an acid catalyst. The reaction proceeds via the formation of an intermediate methoxyamine, which then undergoes dehydration to form methoxime:

CH₃OH + NH₂OH → CH₃ONH₂ + H₂O

CH₃ONH₂ → CH₃ON=CH₂ + H₂O

Applications

Methoxime is used in various applications, including:

• As an intermediate in the synthesis of pharmaceuticals and agrochemicals.
• As a reagent in analytical chemistry for the detection and quantification of carbonyl compounds.
• In the preparation of oxime ethers, which are used as protecting groups in organic synthesis.

Safety and Handling

Methoxime should be handled with care, as it can be irritating to the skin and eyes. It is recommended to use appropriate personal protective equipment, such as gloves and goggles, when handling the compound. In case of contact with skin or eyes, rinse immediately with plenty of water and seek medical advice if necessary.

Also see

• Oxime
• Hydroxylamine
• Organic synthesis
• Analytical chemistry