4-Pyrrolidinylpyridine

4-Pyrrolidinylpyridine
Names
	IUPAC name 4-pyrrolidin-1-ylpyridine
	Other names 4-(1-pyrrolidinyl)pyridine
Identifiers
CAS Number	2456-81-7;
3D model (JSmol)	Interactive image;
ChemSpider	68092;
ECHA InfoCard	100.017.759
EC Number	219-534-2;
PubChem CID	75567;
UNII	DH59VKG9S4 ;
CompTox Dashboard (EPA)	DTXSID90179299 ;
	InChI InChI=1S/C9H12N2/c1-2-8-11(7-1)9-3-5-10-6-4-9/h3-6H,1-2,7-8H2 Key: RGUKYNXWOWSRET-UHFFFAOYSA-N;
	SMILES C1CCN(C1)C2=CC=NC=C2;
Properties
Chemical formula	C9H12N2
Molar mass	148.209 g·mol−1
Appearance	white solid
Melting point	55–56 °C (131–133 °F; 328–329 K)
Boiling point	170–171 °C (338–340 °F; 443–444 K) 12 TTor
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H314
Precautionary statements	P260, P264, P270, P280, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Pyrrolidinylpyridine is an organic compound with the formula (CH₂)₄NC₅H₄N. The molecule consists of a pyrrodinyl group ((CH₂)₄N-) attached via N to the 4-position of pyridine. It is a white solid. The compound has attracted interest because it (pK_a = 9.58) is more basic than dimethylaminopyridine (pK_a = 9.41).[1] It is a popular base catalyst.[2]

References

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". J. Org. Chem. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.
Nederberg, Fredrik; Connor, Eric F.; Möller, Michael; Glauser, Thierry; Hedrick, James L. (2001). "New Paradigms for Organic Catalysts: The First Organocatalytic Living Polymerization". Angewandte Chemie International Edition. 40 (14): 2712–2715. doi:10.1002/1521-3773(20010716)40:14<2712::AID-ANIE2712>3.0.CO;2-Z.

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[Kaljurand_2005_JOC-1] 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". J. Org. Chem. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.

[2] Nederberg, Fredrik; Connor, Eric F.; Möller, Michael; Glauser, Thierry; Hedrick, James L. (2001). "New Paradigms for Organic Catalysts: The First Organocatalytic Living Polymerization". Angewandte Chemie International Edition. 40 (14): 2712–2715. doi:10.1002/1521-3773(20010716)40:14<2712::AID-ANIE2712>3.0.CO;2-Z.