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C80407 Sigma-Aldrich

Cinchonidine

96%

Synonym: (−)-Cinchonidine

  • CAS Number 485-71-2

  • Empirical Formula (Hill Notation) C19H22N2O

  • Molecular Weight 294.39

  •  Beilstein/REAXYS Number 89690

  •  EC Number 207-622-3

  •  MDL number MFCD00006783

  •  PubChem Substance ID 24893015

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Resolution Reagents, Chiral Resolving Reagents,
Quality Level   200
assay   96%
optical activity   [α]23/D −109.2°, c = 1.5 in ethanol
mp   204-206 °C (lit.)
SMILES string   O[C@@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)c3ccnc4ccccc34
InChI   1S/C19H22N2O/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/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1
InChI key   KMPWYEUPVWOPIM-KODHJQJWSA-N
Gene Information   human ... CYP2D6(1565)

Description

General description

Cinchonidine is a cinchona alkaloid, which belongs to the orthorhombic crystal system and P212121 space group.

Application

The enantioselective hydrogenation of ethyl pyruvate in the presence of cinchonidine modified platinum/alumina catalyst leads to the enantiomeric excess of ethyl (R)-lactate.

Packaging

10, 100 g in poly 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
RTECS 
GD2975000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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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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