Piperidine

Piperidine^[1]
Names
	IUPAC name Piperidine
	Preferred IUPAC name Piperidine
	Other names Hexahydropyridine; Azacyclohexane; Pentamethyleneamine; Azinane
Identifiers
CAS Number	110-89-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18049 ;
ChEMBL	ChEMBL15487 ;
ChemSpider	7791 ;
ECHA InfoCard	100.003.467
EC Number	203-813-0;
IUPHAR/BPS	5477;
KEGG	C01746;
PubChem CID	8082;
RTECS number	TM3500000;
UNII	67I85E138Y ;
UN number	2401
CompTox Dashboard (EPA)	DTXSID6021165 ;
	InChI InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 Key: NQRYJNQNLNOLGT-UHFFFAOYSA-N ; InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2; InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 Key: NQRYJNQNLNOLGT-UHFFFAOYAY;
	SMILES C1CCNCC1;
Properties
Chemical formula	C5H11N
Molar mass	85.150 g·mol−1
Appearance	Colorless liquid
Odor	Semen-like, fishy-ammoniacal, pungent
Density	0.862 g/mL
Melting point	−7 °C (19 °F; 266 K)
Boiling point	106 °C (223 °F; 379 K)
Solubility in water	Miscible
Acidity (pKa)	11.22 (protonated)
Magnetic susceptibility (χ)	−64.2·10−6 cm3/mol
Viscosity	1.573 cP at 25 °C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H311, H314, H331
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	3 3 0
Safety data sheet (SDS)	MSDS1
Legal status	BR: Class D1 (Drug precursors);
Related compounds
Related compounds	Pyridine; Pyrrolidine; Piperazine; Phosphorinane; Arsinane
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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, typical of amines.^[6] The name comes from the genus name Piper, which is the Latin word for pepper.^[7] Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.^[8]

^ "International Chemical Safety Card 0317". 28 January 2024.
^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 142. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Amoore, J. E. (1975). "Specific anosmia to 1-pyrroline: The spermous primary odor". J. Chem. Ecol. 1 (3): 299–310. Bibcode:1975JCEco...1..299A. doi:10.1007/BF00988831. S2CID 19318345.
^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ Frank Johnson Welcher (1947). Organic Analytical Reagents. D. Van Nostrand. p. 149.
^ Senning, Alexander (2006). Elsevier's Dictionary of Chemoetymology. Amsterdam: Elsevier. ISBN 978-0-444-52239-9.
^ Pianaro, Adriana; Fox, Eduardo G.P.; Bueno, Odair C.; Marsaioli, Anita J. (May 2012). "Rapid configuration analysis of the solenopsins". Tetrahedron: Asymmetry. 23 (9): 635–642. doi:10.1016/j.tetasy.2012.05.005.

[1] "International Chemical Safety Card 0317". 28 January 2024.

[iupac2013-2] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 142. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[3] Amoore, J. E. (1975). "Specific anosmia to 1-pyrroline: The spermous primary odor". J. Chem. Ecol. 1 (3): 299–310. Bibcode:1975JCEco...1..299A. doi:10.1007/BF00988831. S2CID 19318345.

[4] Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.

[5] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[6] Frank Johnson Welcher (1947). Organic Analytical Reagents. D. Van Nostrand. p. 149.

[7] Senning, Alexander (2006). Elsevier's Dictionary of Chemoetymology. Amsterdam: Elsevier. ISBN 978-0-444-52239-9.

[8] Pianaro, Adriana; Fox, Eduardo G.P.; Bueno, Odair C.; Marsaioli, Anita J. (May 2012). "Rapid configuration analysis of the solenopsins". Tetrahedron: Asymmetry. 23 (9): 635–642. doi:10.1016/j.tetasy.2012.05.005.

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