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Piperidine
From Wikipedia, the free encyclopedia
| Piperidine | |
|---|---|
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| General | |
| Systematic name | Piperidine |
| Other names | Hexahydropyridine Azacyclohexane, pentamethylenamine |
| Molecular formula | C5H11N |
| SMILES | C1CCCCN1 |
| Molar mass | 85.15 g/mol |
| Appearance | colourless liquid |
| CAS number | [110-89-4] |
| Properties | |
| Density and phase | 0.862 g/ml, liquid |
| Solubility in water | miscible |
| Melting point | -7 °C |
| Boiling point | 106 °C |
| Acidity (pKa) | 11.24 |
| Basicity (pKb) | 2.87 |
| Viscosity | ? cP at ? °C |
| Hazards | |
| MSDS | External MSDS |
| EU classification | Flammable (F) Toxic (T) |
| NFPA 704 |
3
3
3
|
| R-phrases | R11, R23/24, R34 |
| S-phrases | S1/2, S16, S26, S27, S45 |
| Flash point | 16 °C |
| RTECS number | TM3500000 |
| Related compounds | |
| Related compounds | pyridine pyrrolidine piperazine |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Piperidine is an organic compound with the molecular formula C5H11N. It is a heterocyclic amine with a six-membered ring containing five carbon atoms and one nitrogen atom. It is a clear liquid with a pepper-like odor.
The piperidine structural motif is present in numerous natural alkaloids such as piperine and quinine, and is the main active chemical agent in black pepper and relatives (Piper sp.), hence the name. Piperidine is also a structural element of many pharmaceutical drugs such as raloxifene and minoxidil.
Piperidine is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1] due to its use (peaking in the 1970s) in the clandestine manufacture of PCP. It is also a byproduct of burning phencyclidine (PCP, phenylcyclohexylpiperidine).
Piperidine is often used as a solvent for its mild basic properties, most notably in Fmoc-strategy solid phase peptide synthesis.
The major industrial application of piperidine is for the production of dipiperidinyl dithium tetrasulfide, which is used as a rubber vulcanization accelerator.
Piperidine is naturally found in fire ant venom, and is the cause of the burning sensation associated with the bite of these insects.