276286

(1R)-(−)-Camphorquinone

99%

• Synonym(s): (1R)-(−)-2,3-Bornanedione, 2,3-Bornanedione
• Empirical Formula (Hill Notation): C₁₀H₁₄O₂
• CAS Number: 10334-26-6
• Molecular Weight: 166.22
• Beilstein/REAXYS Number: 2327696
• MDL number: MFCD00082863
• UNSPSC Code: 12352115
• PubChem Substance ID: 24856697
• NACRES: NA.22

Properties

• assay: 99%
• optical activity: [α]20/D −101°, c = 2 in toluene
• mp: 200-203 °C (lit.)
• functional group: ketone
• SMILES string: CC1(C)[C@@H]2CC[C@@]1(C)C(=O)C2=O
• InChI: 1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3/t6-,10+/m1/s1
• InChI key: VNQXSTWCDUXYEZ-LDWIPMOCSA-N

Description

Application

(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.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H334
• pcodes: P261 - P264 - P270 - P284 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral - Resp. Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves