10334-26-6

Basic information

• Product Name: (1R)-(-)-CAMPHORQUINONE
• Synonyms: R-(-)-CAMPHORQUINONE;3-Ketocamphor;CAMPHORQUINONE, -R-(-)-;(-)-CAMPHORQUINONE;D-2,3-BORNANEDIONE;D-CAMPHOROQUINONE;D-(-)-CAMPHORQUINONE;D-CAMPHORQUINONE
• CAS NO: 10334-26-6
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• EINECS: 220-446-1
• Product Categories: Anthraquinones, Hydroquinones and Quinones;Bicyclic Monoterpenes;Biochemistry;Terpenes
• Mol File: 10334-26-6.mol
• Article Data: 51

Chemical Properties

• Melting Point: 200-203 °C(lit.)
• Boiling Point: 254.44°C (rough estimate)
• Flash Point: 82.965 °C
• Appearance: /
• Density: 1.0060 (rough estimate)
• Vapor Pressure: 0.0817mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: almost transparency in Methanol
• BRN: 2327696
• CAS DataBase Reference: (1R)-(-)-CAMPHORQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-CAMPHORQUINONE(10334-26-6)
• EPA Substance Registry System: (1R)-(-)-CAMPHORQUINONE(10334-26-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 10334-26-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 10334-26-6 differently. You can refer to the following data:
1. (1R)-(-)Camphorquinone are used as visible light photoinitiator for biomedical applications such as in dental surgery.
2. (1R)-(?)-Camphorquinone can be used as a chiral starting material for the preparation of: α-Hydroxycamphors by selective reduction of keto groups using various vegetables. Camphor-1,2-diamine platinum(II) complexes for DNA interaction studies. Camphoric anhydride by unsensitized photo-oxidation in the presence of oxygen and polar solvents. Camphorquinone-based chiral homoallylic amine, which is reacted with aldehydes to produce homoallylic primary amines via imine formation followed by 2-azonia-Cope rearrangement.
3. (1R)-(-)-Camphorquinone may be used as an analytical standard for the determination of the analyte in dental resin composite restorations in the oral environment in contact with food and beverages, and biological samples by analytical techniques.

General Description

Camphorquinone, a 1,2-diketone, is a photoinitiator that finds wide use in the curing of resin composites. It functions by initiating the chain polymerization by free radical generation; typically with the aid of co-initiator amines.

Purification Methods

It can be purified by steam distillation, recrystallisation (yellow prisms) from EtOH, *C6H6 or Et2O/pet ether and it can be sublimed in a vacuum. The (±)-quinone forms needles from EtOH, m 197-198o, 203o. [Buxtorf & Flatt Helv Chim Acta 13 1026 1930, Asahena et al. Chem Ber 67 1432 1934, Beiltein 7 I 325.]

InChI:InChI=1/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3/t6?,10-/m0/s1

Upstream product

• 76-22-2 Camphor 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 104319-35-9 DL camphor-10-thiazine dioxide 
• 67-66-3 chloroform 
• 64-19-7 acetic acid 
• 10293-06-8 (1R)-3-endo-bromocamphor 
• 24022-14-8 (1R,4S)-2,2:3,3-bis(ethylenedioxy)-1,7,7-trimethylbicyclo[2.2.1]heptane 
• 134779-83-2 (1S,4R)-3,3-ethylenedioxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 464-17-5 1,7,7-trimethylbicyclo[2.2.1]hept-2-ene 
• 10373-81-6 3-hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 5338-41-0 (1R,4S)-(+)-3-(hydroxyimino)-2-oxo-1,7,7-trimethylbicyclo[2.2.1]heptane 
• 7647-01-0 hydrogenchloride 
• 33162-63-9 3-endo-aminobornan-2-one 

Downstream Products

• 595-29-9 camphoric anhydride 
• 15210-83-0 2,2,3-trimethyl-4-oxo-cyclohexanecarboxylic acid 
• 872820-67-2 3-(4-oxy-phenylimino)-camphor 
• 53684-40-5 3-hydroxy-1,7,7-trimethyl-3-phenylbicyclo[2.2.1]heptan-2-one 
• 10373-81-6 3-hydroxy-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 124-83-4 D-(+)-camphoric acid 
• 59599-25-6 (1R)-(-)-cis-3-hydroxyisoborneol 
• 54914-34-0 3-(2-chloro-phenylimino)-bornan-2-one 
• 303115-42-6 1,7,7-trimethyl-3-(PhHN-imino)bicyclo[2.2.1]heptan-2-one 
• 110463-08-6 (+/-)-3-(3-ethoxy-phenylimino)-bornan-2-one 
• 110463-08-6 (1R)-3-(3-ethoxy-phenylimino)-bornan-2-one 
• 3278-94-2 homocamphorquinoline 
• 21488-68-6 (1R)-3exo-hydroxy-bornan-2-one 
• 10373-79-2 DL-3-endo-(4-Methyl-benzyl)-3-exo-hydroxy-bornan-2-on 

Relevant articles and documents

Synthesis of 1,11,11-trimethyl-3,6-diazotricyclo [6.2.1.0 2,7]undeca-2,6-diene and 1,15,15-trimethyl-3,10-diazotetracyclo[10.2. 1.02,11.04,9]pentadeca-2,4(9),5,7,10-pentaene from camphoroquinone enantiomers

Optically active camphordihydro-2,3-pyrazine and camphorquinoxaline were prepared from camphoroquinone enantiomers. It was shown that (1S,4R)-(+)-camphoroquinone was formed by oxidation of (1S,3R, 4R)-(-)-3-bromocamphor and (1R,4S)-(-)-camphoroquinone from (1R,3S, 4S)-(+)-3-bromocamphor, respectively. Camphor anhydride was a side product (6-10%) of the reaction. Springer Science+Business Media, Inc. 2007.

An improved synthesis of camphorquinone-3-oxime

Camphorquinone 3-oxime is prepared in 77% yield in one step from camphor. The synthesis avoids the use of toxic selenium reagents, and provides the syn compound as the major stereoisomer.

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The Role of Side-Arms for Supramolecular Affinity Materials Based on 9,9′-Spirobifluorenes

An eightfold functionalized D2d-symmetric 9,9′-spirobifluorene was condensed with a collection of diketones with elaborated structural features to form three-dimensional supramolecular architectures with active surfaces. Gas-sorption measuremen

Synthesis and evaluation of camphor and cytisine-based cyanopyrrolidines as DPP-IV inhibitors for the treatment of type 2 diabetes mellitus

In this study, bornyl- and cytisine-based cyanopyrrolidines as potent dipeptidyl peptidase-IV (DPP-IV) inhibitors were synthesised. The in vitro inhibiting activities of bornyl- and cytisine derivatives towards DPP-IV were evaluated. Bornyl-based cyanopyrrolidines were shown to have moderate inhibitory activity with regard to DPP-IV (1.27–15.78 μM). A docking study was performed to elucidate the structure-activity relationship of the obtained compounds. The in vivo hypoglycemic activities of the same compounds were evaluated with the oral glucose tolerance test (OGTT) in mice. Bornyl-based cyanopyrrolidines were shown to have good hypoglycemic activity.

An environment friendly preparation of 3-bromocamphor and camphorquinone

The bromination of camphor has been carried out on a multi-gram scale by a mixture of KBr and KBrO3 in the presence of acid or with HBr/NaBr - H+ and H2O2/oxone as the oxidant. The 3-bromocamphor is then efficiently converted to camphorquinone by an improved oxidation protocol using DMSO and sodium carbonate of tetrabutyl ammonium iodide.

Stereoselective cyclopalladation of 2,3-camphorquinone 3-diphenylmethylimine

A reaction of (1R,4 S)-3-diphenylmethylimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one with lithium tetrachloropalladate gives a palladium(II) complex with a monodentately coordinated ligand, whereas chiral palladacyclic compounds are formed in the case o

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Selectively polymerizable compositions and methods of use in vivo

Otologic materials and methods are provided. For example, a cell-adhesive, biodegradable hydrogel scaffold loaded with time-released drugs for repairing chronic tympanic membrane perforations is disclosed, methods of making same and administering same are provided. This hydrogel may promote vascular in-growth and epithelial cell growth of the tympanic membrane with the purpose of closing the perforation and providing a barrier between the external and middle ear. The hydrogel is initially a liquid polymer that only gels upon exposure to specific conditions, such as exposure to light. This scaffold may simultaneously induce repair of the tympanic membrane while preventing or alleviating middle ear infection, thus filling a void in current tympanic membrane perforation therapies.