Pyrrolidine

Pyrrolidine
Names
	Preferred IUPAC name Pyrrolidine
	Other names Azolidine; Azacyclopentane; Tetrahydropyrrole; Prolamine; Azolane
Identifiers
CAS Number	123-75-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	102395
ChEBI	CHEBI:33135 ;
ChEMBL	ChEMBL22830 ;
ChemSpider	29008 ;
ECHA InfoCard	100.004.227
EC Number	204-648-7;
Gmelin Reference	1704
PubChem CID	31268;
RTECS number	UX9650000;
UNII	LJU5627FYV ;
UN number	1922
CompTox Dashboard (EPA)	DTXSID3059559 ;
	InChI InChI=1S/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 Key: RWRDLPDLKQPQOW-UHFFFAOYSA-N ; InChI=1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 Key: RWRDLPDLKQPQOW-UHFFFAOYAX;
	SMILES C1CCNC1;
Properties
Chemical formula	C4H9N
Molar mass	71.123 g·mol−1
Appearance	Clear colorless liquid
Density	0.866 g/cm3
Melting point	−63 °C (−81 °F; 210 K)
Boiling point	87 °C (189 °F; 360 K)
Solubility in water	Miscible
Acidity (pKa)	11.27 (pKa of conjugate acid in water),; 19.56 (pKa of conjugate acid in acetonitrile)
Magnetic susceptibility (χ)	-54.8·10−6 cm3/mol
Refractive index (nD)	1.4402 at 28°C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	highly flammable, harmful, corrosive, possible mutagen
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314, H332
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)	3 3 1
Flash point	3 °C (37 °F; 276 K)
Autoignition; temperature	345 °C (653 °F; 618 K)
Safety data sheet (SDS)	MSDS
Related compounds
Related nitrogen heterocyclic compounds	Pyrrole (aromatic with two double bonds); Pyrroline (one double bond); Pyrrolizidine (two pentagonal rings)
	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

Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH₂)₄NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic odor that has been described as "ammoniacal, fishy, shellfish-like".^[4] In addition to pyrrolidine itself, many substituted pyrrolidines are known.

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
^ Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". The Journal of Organic Chemistry. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.
^ Pyrrolidine Archived 2017-11-21 at the Wayback Machine, The Good Scents Company

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 142. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[2] Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". Journal of the American Chemical Society. 79 (20): 5441–5444. doi:10.1021/ja01577a030.

[3] Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". The Journal of Organic Chemistry. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.

[4] Pyrrolidine Archived 2017-11-21 at the Wayback Machine, The Good Scents Company

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