Camphorquinone

Last updated
Camphorquinone
Camphorquinone structure.svg
Names
IUPAC name
2,6-Bornanedione
Other names
Camphorquinone
6-Oxocamphor
CQ
CPQ
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.030.728 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 233-814-1
482102
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3
    Key: VNQXSTWCDUXYEZ-UHFFFAOYSA-N
  • CC1(C2CCC1(C(=O)C2=O)C)C
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Melting point 197–203 °C (387–397 °F; 470–476 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Camphorquinone, also known as 2,3-bornanedione, is an organic compound derived from camphor. A yellow solid, it is used as a photoinitiator in curing dental composites. [1] Camphorquinone is produced by the oxidation of camphor with selenium dioxide. [2]

Contents

Photocuring details

Polymerization is induced very slowly by camphorquinone, so amines such as N,N-dimethyl-p-toluidine, 2-ethyl-dimethylbenzoate, N-phenylglycine are generally added to increase the rate of curing. [1]

It absorbs very weakly at 468 nm (extinction coefficient of 40 M−1·cm−1) giving it a pale yellow color. [1] Photoexcitation results in nearly quantitative formation of its triplet state through intersystem crossing and very faint fluorescence. [3]

Reactions

It can be hydrolyzed by the enzyme 6-oxocamphor hydrolase.

Camphorquinone has been examined as a reagent in organic synthesis. [4]

References

  1. 1 2 3 Jakubiak, J.; Allonas, X.; Fouassier, J.P.; Sionkowska, A.; Andrzejewska, E.; Linden, L.Å.; Rabek, J.F. (August 2003). "Camphorquinone–amines photoinitating systems for the initiation of free radical polymerization". Polymer. 44 (18): 5219–5226. doi:10.1016/S0032-3861(03)00568-8.
  2. ↑ White, James D.; Wardrop, Duncan J.; Sundermann, Kurt F. (2002). "Camphorquinone and Camphorquinone Monoxime". Organic Syntheses. 79: 125. doi:10.15227/orgsyn.079.0125.
  3. ↑ Allonas, Xavier; Fouassier, Jean-Pierre; Angiolini, Luigi; Caretti, Daniele (19 September 2001). "Excited-State Properties of Camphorquinone Based Monomeric and Polymeric Photoinitiators". Helvetica Chimica Acta. 84 (9): 2577. doi:10.1002/1522-2675(20010919)84:9<2577::AID-HLCA2577>3.0.CO;2-Q.
  4. ↑ Luo, Yong-Chun; Zhang, Huan-Huan; Wang, Yao; Xu, Peng-Fei (2010). "Synthesis of α-Amino Acids Based on Chiral Tricycloiminolactone Derived from Natural (+)-Camphor". Accounts of Chemical Research. 43 (10): 1317–1330. doi:10.1021/ar100050p. PMID   20672798.
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