Cinchonidine TCI C0347

Chemical Identity

CAS No.: 485-71-2
PubChem: CID 101744·SID 87565480
Formula: C19H22N2O
Molecular weight: 294.40 g/mol
Purity: >85.0%(qNMR)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
SMILES: C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
InChIKey: KMPWYEUPVWOPIM-KODHJQJWSA-N
MDL: MDL00006783

Rp 2.439.150,00

~~Rp 1.720.950,00~~ Rp 2.439.150,00

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TCI C0347 Cinchonidine, CAS 485-71-2, is a cinchona alkaloid that has long served as a workhorse reagent in asymmetric synthesis. Its quinoline ring, basic quinuclidine nitrogen, and secondary hydroxyl group at a stereogenic centre allow it to act simultaneously as a chiral base and a hydrogen-bond donor. It is applied as an organocatalyst, as a chiral modifier for heterogeneous hydrogenation catalysts, as a resolving agent for racemic acids, and as a starting material for cinchona-derived phase transfer catalysts and ligands. AMI Scientific offers this TCI product in 25 g and 100 g packs, with lot-specific data available from the manufacturer.

TCI brochures (PDF)

Asymmetric Organocatalysts 2025-06-12 · p. 8
Chiral Auxiliaries and Optical Resolving Agents 2025-06-17 · p. 6
Alkaloids 2025-10-10 · p. 5
Asymmetric Synthesis 2026-03-18 · p. 5

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(2018). Synthesis of (+)-Cinchonidine. Synfacts doi:10.1055/s-0037-1611233
Beresford (2004). Enantioselective Addition of Diethylzinc to N‐Diphenylphosphinoylimines Employing Cinchonidine and Cinchonine as Chiral Ligands.. ChemInform doi:10.1002/chin.200446025
Lindholm et al. (2003). Hydrosilylation of Cinchonidine and 9‐O‐TMS‐Cinchonidine with Triethoxysilane: Application of 11‐(Triethoxysilyl)‐10,11‐dihydrocinchonidine as a Chiral Modifier in the Enantioselective Hydrogenation of 1‐Phenylpropane‐1,2‐dione.. ChemInform doi:10.1002/chin.200318077

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.