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DL-CAMPHORQUINONE

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DL-CAMPHORQUINONE Basic information
Product Name:DL-CAMPHORQUINONE
Synonyms:DL-CAMPHORQUINONE FOR SYNTHESIS;(±)-camphandione;3-dione,1,7,7-trimethyl-,(+-)-Bicyclo[2.2.1]heptane-2;4,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione;7,7-trimethyl-3-dion(+/-)-bicyclo[2.2.1]heptane-1;Bicyclo[2.2.1]heptane-2,3-dione, 1,7,7-trimethyl-, (.+/-.)-;bicyclo[2.2.1]heptane-2,3-dione,1,7,7-trimethyl-;camphoquinone
CAS:10373-78-1
MF:C10H14O2
MW:166.22
EINECS:233-814-1
Product Categories:Bicyclic Monoterpenes;Biochemistry;Functional Materials;Photopolymerization Initiators;Terpenes;Building Blocks/Intermediates
Mol File:10373-78-1.mol
DL-CAMPHORQUINONE Structure
DL-CAMPHORQUINONE Chemical Properties
Melting point 197-203 °C (lit.)
alpha -5~+5°(20℃/D)(c=2, CHCl3)
Boiling point 234.44°C (rough estimate)
density 0.9817 (rough estimate)
refractive index 1.4859 (estimate)
storage temp. Store below +30°C.
solubility Soluble in ethanol, ethyl ether and benzene.
form Fine Crystalline Powder
color Yellow
Water Solubility slightly soluble 1.7g/L
BRN 1909463
Cosmetics Ingredients FunctionsFILM FORMING
InChIInChI=1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3
InChIKeyVNQXSTWCDUXYEZ-UHFFFAOYSA-N
SMILESC12(C)C(C)(C)C(CC1)C(=O)C2=O
LogP1.470 (est)
CAS DataBase Reference10373-78-1(CAS DataBase Reference)
EPA Substance Registry SystemBicyclo[2.2.1]heptane-2,3-dione, 1,7,7-trimethyl- (10373-78-1)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 20/21/22-36/37/38
Safety Statements 22-24/25-36-26
WGK Germany 3
TSCA TSCA listed
HS Code 2914 29 00
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
DL-CAMPHORQUINONE Usage And Synthesis
Chemical PropertiesYELLOW FINE CRYSTALLINE POWDER
Usesinitiator for visible-light-cured dental acrylic-composite materials.
UsesCamphorquinone derivative (i.e. carboxylated camphorquinone) is used as visible-light photoinitiator in biomedical applications. It is also used in dentistry and is often used in conjunction with hydrogen donating amine.
UsesCQ-amines are used as a photo initiators for free radical polymerization. CQ was used as an initiator in the preparation of silver nanoparticle/silica/ polymer nanocomposites. Photopolymerization kinetics of dimethacrylates were studied using the CQ/amine initiator system.
DefinitionChEBI: Bornane-2,3-dione is a bornane monoterpenoid that is bicyclo[2.2.1]heptane substituted by methyl groups at positions 1, 7 and 7 and oxo groups at positions 2 and 3. It is a bornane monoterpenoid and a carbobicyclic compound.
General DescriptionCamphorquinone (CQ) absorbs UV radiation in the region of 200-300nm due to the ΠΠ* transition and visible light (400-500nm) due to the n, Π* transition of the α-dicarbonyl chromophore.
Synthesis

In 1934, Evans et al. found that the direct oxidation of camphor with selenium dioxide in acetic acid can obtain camphor quinone. Typical conditions of the reaction is at 140-150 , heating 3-4h, to be the end of the reaction with acetic acid extraction, the extract is neutralized with concentrated alkali, the camphor quinone is insoluble in water and precipitated. Then it can be purified by sublimation method or recrystallization method. This method has simple steps and high yield, up to about 90%, so it is still widely used. However, the selenium dioxide used in the method is a highly toxic compound, and there is selenium residue in the product, which will limit the application of camphor quinone in medicine.

Purification MethodsPurification is the same as for above enantiomers. [Huckel & Fichtig Justus Liebigs Ann Chem 628 81 1962, Evans et al. J Chem Soc 137 1939, Beilstein 7 I 325.]
DL-CAMPHORQUINONE Preparation Products And Raw materials
Tag:DL-CAMPHORQUINONE(10373-78-1) Related Product Information
(1R)-(-)-10-Camphorsulfonic acid L(-)-10-Camphorsulfonyl chloride Rucaparib Camsylate D-CAMPHOR DL-CAMPHORQUINONE DL-Camphor DL-CAMPHORQUINONE,CAMPHOREQUINONE (1S)-(+)-CAMPHORQUINONE (1S,E)-(-)-Camphorquinone 3-oxime (1R)-(-)-CAMPHORQUINONE CAMPHORQUINONE-10-SULFONYLNORLEUCINE CAMPHORQUINONE-10-SULFONIC ACID, HYDRATE CAMPHORQUINONE, -R-(-)-(RG) CAMPHORQUINONE, -S-(+)-(RG) DI-CAMPHOREQUINONE DL-CAMPHORQUINONE, (2,3-BORNANEDIONE) AKOS BBS-00002008 7-(IODOMETHYL)-1,7-DIMETHYLBICYCLO[2.2.1]HEPTANE-2,3-DIONE

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