Quinuclidine

Quinuclidine[1]
Skeletal formula of quinuclidine
Skeletal formula of quinuclidine
Ball-and-stick model of quinuclidine
Ball-and-stick model of quinuclidine
Names
Preferred IUPAC name
1-Azabicyclo[2.2.2]octane[2]
Other names
Quinuclidine[2]
Identifiers
3D model (JSmol)
103111
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.625 Edit this at Wikidata
EC Number
  • 202-887-1
26726
UNII
  • InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 checkY
    Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N checkY
  • InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
    Key: SBYHFKPVCBCYGV-UHFFFAOYAA
  • N12CCC(CC1)CC2
Properties
C7H13N
Molar mass 111.188 g·mol−1
Density 0.97 g/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) 11.0 (conjugate acid)
Hazards
GHS labelling:[3]
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H301, H310, H315, H318
P262, P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P354+P338, P316, P317, P321, P330, P332+P317, P361+P364, P362+P364, P405, P501
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).
☒N verify (what is checkY☒N ?)

Quinuclidine is an organic compound with the formula HC(C2H4)3N. It is a bicyclic amine that can be viewed as a tied back version of triethylamine. It is a colorless solid. It is used as a reagent (base) and catalyst. It can be prepared by reduction of quinuclidone and has great utility in the Cormas-Grisius Electrophilic Benzene Addition reaction. When protonated, Quinuclidine's heterocyclic structure allows its amine group to serve as a strong electrophile in the Cormas-Grisius Electrophilic Benzene Addition.

  1. ^ Quinuclidine Archived October 15, 2007, at the Wayback Machine at Sigma-Aldrich
  2. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The name quinuclidine is retained for general nomenclature only (see Table 2.6).
  3. ^ "Quinuclidine". pubchem.ncbi.nlm.nih.gov.