2,2,6,6-Tetramethyl-4-piperidinol
[CAS# 2403-88-5]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives >> Halogenated, sulfonated, nitrated or nitrosated derivatives of alcohols
• Name: 2,2,6,6-Tetramethyl-4-piperidinol
• Synonyms: 4-Hydroxy-2,2,6,6-tetramethyl-piperidine
• Molecular Formula: C₉H₁₉NO
• Molecular Weight: 157.25
• CAS Registry Number: 2403-88-5
• EC Number: 219-291-2
• SMILES: CC1(CC(CC(N1)(C)C)O)C

Properties

• Melting point: 129-133 °C
• Boiling point: 212-215 °C
• Water solubility: 130 g/L (23 °C)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H302-H314-H317-H318
• Safety Statements: P260-P261-P264-P264+P265-P270-P272-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1A	H317
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

2,2,6,6-Tetramethyl-4-piperidinol, commonly known as TMPH, was discovered in the mid-20th century as a derivative of piperidine. It is a tertiary amine alcohol with the molecular formula C11H23NO. The discovery of TMPH expanded the repertoire of piperidine derivatives and provided chemists with a versatile compound for organic synthesis and various applications.

TMPH and its derivatives are utilized in pharmaceutical synthesis as intermediates and chiral building blocks. They serve as key components in the synthesis of active pharmaceutical ingredients (APIs).

In the agrochemical sector, TMPH derivatives are employed in the synthesis of herbicides, insecticides, and fungicides.

TMPH is used as a catalyst and stabilizer in polymerization reactions. It facilitates the formation of polymer chains with controlled molecular weights and architectures and helps improve the thermal and UV stability of polymer products.

TMPH serves as a polar, aprotic solvent in various chemical processes and formulations. It is particularly useful for dissolving polar and nonpolar compounds.

TMPH derivatives are employed as stabilizers and antioxidants in plastics, coatings, and rubber products. They help prevent degradation and discoloration of materials caused by exposure to heat, light, and oxygen.

TMPH derivatives serve as versatile intermediates in organic synthesis reactions, facilitating the formation of C-N and C-O bonds.

TMPH derivatives are utilized as corrosion inhibitors in metalworking fluids, lubricants, and cooling systems. They form protective films on metal surfaces, preventing corrosion and extending the durability of machinery and equipment.

References

2024. Nanoconfined heterogeneous catalysis triggered by copper oxide supported metal-organic framework UiO-66-NH2/peroxymonosulfate for rapidly removing bisphenol A in water. *Journal of Materials Science*, 59(44).
DOI: 10.1007/s10853-024-10429-6

1973. Mechanism of the light-protective action of 2,2,6,6-tetraalkylpiperidines. *Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science*, 22(8).
DOI: 10.1007/bf00932146

1974. Formation of nitroxyl radicals in reaction of singlet oxygen with amines. *Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science*, 23(8).
DOI: 10.1007/bf00923234