2,2,6,6-Tetramethylpiperidine

2,2,6,6-Tetramethylpiperidine (also known as TMP or Hunig's base) is an organic compound with the formula (CH3)2C5H10N. This amine is used as a stereospecific reagent in the production of certain polymers and pharmaceuticals. TMP is a strong, hindered base, useful in organic synthesis.

Structure and properties

2,2,6,6-Tetramethylpiperidine is a tertiary amine, meaning it has three organic substituents attached to the nitrogen atom. The molecule is symmetrical, with the nitrogen atom at the center of a six-membered ring. The four methyl groups are arranged in a tetrahedral fashion around the nitrogen atom, giving the molecule its name.

The molecular structure of TMP is characterized by its high degree of steric hindrance, which makes it a strong base. This property is useful in many chemical reactions, particularly in the production of polymers and pharmaceuticals.

Synthesis

2,2,6,6-Tetramethylpiperidine can be synthesized from diisopropylamine via a Michael addition reaction with acrylonitrile, followed by reduction of the resulting nitrile to an amine.

Applications

In the pharmaceutical industry, TMP is used as a base in the synthesis of various drugs. It is also used in the production of certain polymers, where its strong basicity and steric hindrance are advantageous.

In addition, TMP is used as a spin trap in electron paramagnetic resonance (EPR) spectroscopy. This application takes advantage of the molecule's ability to form stable radicals.

Safety

Like many amines, 2,2,6,6-Tetramethylpiperidine is a strong base and can cause burns on contact with skin or eyes. It should be handled with care, using appropriate personal protective equipment.

See also

• Piperidine
• Diisopropylamine
• Michael addition
• Acrylonitrile