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Piperidine

Piperidine
Piperidin.svg
Piperidine-equatorial-3D-balls-B.png
Piperidine-3D-vdW.png
Names
Preferred IUPAC name
Piperidine
Other names
Hexahydropyridine
Azacyclohexane
Pentamethyleneamine
Azinane
Identifiers
110-89-4 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:18049 YesY
ChEMBL ChEMBL15487 YesY
ChemSpider 7791 YesY
ECHA InfoCard 100.003.467
5477
PubChem 8082
RTECS number TM3500000
UNII 67I85E138Y YesY
Properties
C5H11N
Molar mass 85.15 g·mol−1
Appearance colourless liquid
Density 0.862 g/mL, liquid
Melting point −7 °C (19 °F; 266 K)
Boiling point 106 °C (223 °F; 379 K)
miscible
Acidity (pKa) 11.22
-64.2·10−6 cm3/mol
Viscosity 1.573 cP at 25 °C
Hazards
Safety data sheet MSDS1,MSDS2
Flammable (F)
Toxic (T)
R-phrases R11, R23/24, R34
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g., fluorine Special hazards (white): no codeNFPA 704 four-colored diamond
Related compounds
Related compounds
pyridine
pyrrolidine
piperazine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. the name comes from the genus name Piper, which is the Latin word for pepper. Although, piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids.

Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson and again, independently, in 1852 by the French chemist Auguste Cahours, who named it. Both men obtained piperidine by reacting piperine with nitric acid.

Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst:

Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol.

Piperidine itself has been obtained from black pepper, from Psilocaulon absimile (Aizoaceae), and in Petrosimonia monandra.

The piperidine structural motif is present in numerous natural alkaloids. These include piperine, which gives black pepper its spicy taste. This gave the compound its name. Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.


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