2,2,6,6-Tetramethylpiperidine, abbreviated TMP, HTMP, or TMPH, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

of the

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

class. In appearance, it is a colorless liquid and has a "fishy", amine-like odor. This

is used in

chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...

as a

hindered Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is generally a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivi ...

base ( hindered amine). Although TMP finds limited use per se, its derivatives are a mainstay of hindered amine light stabilizers. TMP is the starting material for an even stronger base, lithium tetramethylpiperidide and the radical species

TEMPO In musical terminology, tempo (Italian for 'time'; plural 'tempos', or from the Italian plural), measured in beats per minute, is the speed or pace of a given musical composition, composition, and is often also an indication of the composition ...

. Another non-nucleophilic base is

N,N-diisopropylethylamine ''N'',''N''-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist . It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA, DIEA, o ...

. Its aqueous p''K''_aH (conjugate acid dissociation constant, a measure of basicity) is 11.07 at 25 °C, while its p''K''_a (acid dissociation constant, a measure of acidity) is approximately 37.

Preparation

Many routes for the synthesis of TMP have been reported. One method starts with a conjugate addition reaction of

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction. TMP synthesis

References

External links

DataSheet I

TMP applied in synthesis
in

Organic Syntheses ''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and expe ...

{{DEFAULTSORT:Tetramethylpiperidine, 2,2,6,6- Piperidines Reagents for organic chemistry Non-nucleophilic bases

Preparation

See also

References

External links