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276286 Sigma-Aldrich

(1R)-(−)-Camphorquinone

99%

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

  • CAS Number 10334-26-6

  • Empirical Formula (Hill Notation) C10H14O2

  • Molecular Weight 166.22

  •  Beilstein/REAXYS Number 2327696

  •  MDL number MFCD00082863

  •  PubChem Substance ID 24856697

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Ketones, Organic Building Blocks More...
assay   99%
optical activity   [α]20/D −101°, c = 2 in toluene
mp   200-203 °C (lit.)
storage temp.   room temp
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.

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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