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]
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| Names | |
|---|---|
| IUPAC name
2,6-Bornanedione
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| Other names
Camphorquinone
6-Oxocamphor CQ CPQ | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.030.728 |
| EC Number |
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| 482102 | |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H14O2 | |
| Molar mass | 166.220 g·mol−1 |
| Melting point | 197-203 |
| Hazards | |
| GHS labelling:[1] | |
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| 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).
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Photocuring details
editPolymerization 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
editIt can be hydrolyzed by the enzyme 6-oxocamphor hydrolase.
Camphorquinone has been examined as a reagent in organic synthesis.[4]
References
edit- ^ a b c 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)00568-8.5219-5226&rft.date=2003-08&rft_id=info:doi/10.1016/S0032-3861(03)00568-8&rft.aulast=Jakubiak&rft.aufirst=J.&rft.au=Allonas, X.&rft.au=Fouassier, J.P.&rft.au=Sionkowska, A.&rft.au=Andrzejewska, E.&rft.au=Linden, L.Å.&rft.au=Rabek, J.F.&rfr_id=info:sid/en.wikipedia.org:Camphorquinone" class="Z3988">
- ^ White, James D.; Wardrop, Duncan J.; Sundermann, Kurt F. (2002). "Camphorquinone and Camphorquinone Monoxime". Organic Syntheses. 79: 125. doi:10.15227/orgsyn.079.0125.
- ^ 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.
- ^ 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 20672798.1317-1330&rft.date=2010&rft_id=info:doi/10.1021/ar100050p&rft_id=info:pmid/20672798&rft.aulast=Luo&rft.aufirst=Yong-Chun&rft.au=Zhang, Huan-Huan&rft.au=Wang, Yao&rft.au=Xu, Peng-Fei&rfr_id=info:sid/en.wikipedia.org:Camphorquinone" class="Z3988">