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54060 Sigma-Aldrich

Hydrocinchonine

≥95.0% (sum of enantiomers, HPLC)

Synonym: Dihydrocinchonine

  • CAS Number 485-65-4

  • Empirical Formula (Hill Notation) C19H24N2O

  • Molecular Weight 296.41

  •  Beilstein/REAXYS Number 4296749

  •  EC Number 207-621-8

  •  MDL number MFCD00216716

  •  PubChem Substance ID 57651461

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Privileged Ligands and Complexes More...
Quality Level   100
assay   ≥95.0% (sum of enantiomers, HPLC)
  ≥97.0% (NT)
optical activity   [α]20/D +197±4°, c = 0.25% in ethanol
mp   269-272 °C (lit.)
SMILES string   CC[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c3ccnc4ccccc34
InChI   1S/C19H24N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3/t13-,14-,18+,19-/m0/s1
InChI key   WFJNHVWTKZUUTR-QAMTZSDWSA-N

Description

Application

Hydrocinchonine is an alkaloid that can be used as a chiral base in:
• The 1,3-dipolar cycloaddition reactions of alkenes and azomethine ylides using silver fluoride.
• The aza-Henry reaction for the synthesis of molecules with optically active quaternary centers.

Packaging

500 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
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

Articles

Cinchona Alkaloids - Aldrich ChemFiles 2008, 8.2, 74.

Cinchona alkaloids and their derivatives have proven to catalyze an astonishing array of enantioselective transformations, providing access to chiral products of high enantiopurity.1 The presence of ...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 74.
Keywords: Addition reactions, Aminations, Antimicrobials, Asymmetric synthesis, Catalysis, Desymmetrizations, Dihydroxylations, Ligands, Reductive aminations

Peer-Reviewed Papers
15

References

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