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Sigma-Aldrich

(1R)-(−)-Camphorquinone

99%

Synonym(s):

(1R)-(−)-2,3-Bornanedione, 2,3-Bornanedione

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About This Item

Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
Molecular Weight:
166.22
Beilstein:
2327696
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

99%

optical activity

[α]20/D −101°, c = 2 in toluene

mp

200-203 °C (lit.)

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

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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.

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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