Quinuclidine

Quinuclidine^[1]

Names
IUPAC name 1-Azabicyclo[2.2.2]octane
Identifiers
CAS Number	100-76-5
ChEBI	CHEBI:38420
ChEMBL	ChEMBL1209648
ChemSpider	7246
Jmol interactive 3D	Image
PubChem	7527
InChI InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 Key: SBYHFKPVCBCYGV-UHFFFAOYAA
SMILES N12CCC(CC1)CC2
Properties
Chemical formula	C7H13N
Molar mass	111.18 g/mol
Density	0.97g/cm3
Melting point	157 to 160 °C (315 to 320 °F; 430 to 433 K)
Boiling point	149.5 °C (301.1 °F; 422.6 K) at 760 mmHg
Acidity (pKa)	12.1 (conjugate acid)
Hazards
Flash point	36.5 °C (97.7 °F; 309.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 11.0.^[2] This is due to greater availability of the nitrogen lone pair . It can be prepared by reduction of quinuclidone.

The compound is structurally related to DABCO in which the other bridgehead is also nitrogen and tropane with a slightly different carbon frame.

Quinuclidine is found as a structural component of some biomolecules including quinine.

References

1. Quinuclidine at Sigma-Aldrich
2. Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. (1998). "Azatriquinanes: Synthesis, Structure, and Reactivity". J. Org. Chem. 63 (17): 6016–6020. doi:10.1021/jo980788s. PMID 11672206.