Quinuclidine

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Quinuclidine[1]
Skeletal formula of quinuclidine Ball-and-stick model of quinuclidine
Identifiers
CAS number 100-76-5 YesY
PubChem 7527
ChemSpider 7246 YesY
ChEBI CHEBI:38420 YesY
ChEMBL CHEMBL1209648 YesY
Jmol-3D images Image 1
Properties
Molecular formula C7H13N
Molar mass 111.18 g/mol
Density 0.97g/cm3
Melting point 157–160 °C
Boiling point 149.5°C @760mmHg
Acidity (pKa) 12.1 (conjugate acid)
Hazards
Flash point 36.5 °C (97.7 °F; 309.6 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[citation needed]. 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[edit]

  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.