Quinuclidine

Quinuclidine[1] |

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Names
Preferred IUPAC name

1-Azabicyclo[2.2.2]octane[2]

Other names

Quinuclidine[2]

Identifiers

CAS Number

* 100-76-5 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 103111
ChEBI |

* CHEBI:38420 Y

ChEMBL |

* ChEMBL1209648 Y

ChemSpider |

* 7246 Y

EC Number |

* 202-887-1

Gmelin Reference

| 26726

PubChem CID

* 7527

UNII |

* XFX99FC5VI N

InChI

* InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 Y

Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N Y

* 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 | 111.188 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 pictograms |
GHS Signal word | Danger

GHS hazard statements

| H301, H310, H315, H318

GHS precautionary statements

| P262, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P280, P301+316Script error: No such module "Preview warning".Category:GHS errors, P302+352, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P317Script error: No such module "Preview warning".Category:GHS errors, P321, P330, P332+317Script error: No such module "Preview warning".Category:GHS errors, P361+364Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors, 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 YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

Quinuclidine is an organic compound with the formula HC(C

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.

## Structure and chemical properties

Regarding its structure, quinuclidine is unusual in that the methylene hydrogen atoms are eclipsed within each of the three ethylene linkages. Furthermore, the cyclohexane rings, of which there are three, adopt the chair conformations, not the usual boat conformations.[4]

Quinuclidine is a relatively strong organic base with pKa of the conjugate acid of 11.3.[5] The basicity of other quinuclidines have been evaluated: 3-hydroxy- quinuclidine (9.9), 3-acetoxyquinuclidine (9.3), 3-chloroquinuclidine (8.9), DABCO (8.7), and 3-quinuclidone (7.2).[6]

It forms adducts with a variety of Lewis acids. Because of its compact structure, quinuclidine binds to trimethylborane more tightly than does triethylamine.[7]

## Derivatives and analogues

left|190px|thumb|Quinine is a quinuclidine derivative.

Quinuclidine is structurally related to DABCO, in which the other bridgehead is also nitrogen, and to tropane, which has a slightly different carbon frame. Cinchona alkaloids, e.g. quinine, feature quinuclidine substituents.[7] Aceclidine, a simple quinuclidine derivative, is a drug used for treatment of glaucoma.

## References

1. ↑ Quinuclidine at Sigma-Aldrich
2. ↑ 2.0 2.1 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" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/7527#section=Safety-and-Hazards.
4. ↑ Blackstock, S. C.; Lorand, J. P.; Kochi, J. K. (1987). "Charge-Rransfer Interactions of Amines with Tetrahalomethanes. X-Ray Crystal Structures of the Donor-Acceptor Complexes of Quinuclidine and Diazabicyclo [2.2.2]Octane with Carbon Tetrabromide". The Journal of Organic Chemistry 52 (8): 1451–1460. doi:10.1021/jo00384a013.
5. ↑ 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.
6. ↑ Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y. (2003). "Correlation between pKa and Reactivity of Quinuclidine-Based Catalysts in the Baylis−Hillman Reaction: Discovery of Quinuclidine as Optimum Catalyst Leading to Substantial Enhancement of Scope". The Journal of Organic Chemistry 68 (3): 692–700. doi:10.1021/jo026671s. PMID 12558387.
7. ↑ 7.0 7.1 Hamama, Wafaa S.; El-Magid, Osama. M. Abd; Zoorob, Hanafi H. (2006). "Chemistry of quinuclidines as nitrogen bicyclic bridged-ring structures". Journal of Heterocyclic Chemistry 43 (6): 1397–1420. doi:10.1002/jhet.5570430601.

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*[CID]: Compound ID
*[H301]: Toxic if swallowed
*[H310]: Fatal in contact with skin
*[H315]: Causes skin irritation
*[H318]: Causes serious eye damage
*[P262]: Do not get in eyes, on skin, or on clothing
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …