276286

Sigma-Aldrich

(1R)-(−)-Camphorquinone

99%

Synonym(s):
(1R)-(−)-2,3-Bornanedione, 2,3-Bornanedione
Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
Molecular Weight:
166.22
Beilstein/REAXYS Number:
2327696
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

99%

optical activity

α20/D −101°, c = 2 in toluene

mp

200-203 °C (lit.)

SMILES string

CC1(C)C@@H2CCC@@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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

Packaging

5 g in glass bottle

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xn

Risk Statement

22-43

Safety Statement

36/37

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Synthesis of camphoric anhydride via unsensitized photo-oxidation of camphorquinone
Shun-Jun J, et al.
Synthetic Communications, 32(11), 1659-1663 (2002)
Angel M Montaña et al.
Bioorganic & medicinal chemistry, 16(4), 1721-1737 (2007-11-27)
The platinum(II) complex cis-[(1S,2R,3S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diamine]dichloroplatinum(II) (1) and its enantiomer (2) have been synthesized and physically and spectroscopically characterized. To obtain the enantiopure complexes the chiral pool approach was applied. The synthetic pathway has four steps, starting from (+/-)-diphenylethylenediamine (DPEDA) (3) and...
Masaharu Sugiura et al.
Journal of the American Chemical Society, 128(34), 11038-11039 (2006-08-24)
A camphorquinone-derived chiral homoallylic amine was found to react with various aldehydes via imine formation and asymmetric 2-azonia-Cope rearrangement to give optically active homoallylic primary amines. A practical level of enantioselectivity with high functional group tolerance has been attained in...
Stereoselective reduction of ketones by various vegetables
Utsukihara T, et al.
Journal of Molecular Catalysis. B, Enzymatic, 41(3-4), 103-109 (2006)
Tetrahedron Asymmetry, 17, 1179-1179 (2006)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.