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359343

Sigma-Aldrich

Hydroquinidine

95%

Synonym(s):

(9S)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinidine

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About This Item

Empirical Formula (Hill Notation):
C20H26N2O2
CAS Number:
Molecular Weight:
326.43
Beilstein:
91441
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

optical activity

[α]25/D +226°, c = 2 in ethanol

mp

169-170 °C (lit.)

SMILES string

CC[C@H]1CN2CCC1CC2[C@@H](O)c3ccnc4ccc(OC)cc34

InChI

1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19+,20-/m0/s1

InChI key

LJOQGZACKSYWCH-LHHVKLHASA-N

Gene Information

human ... CYP2D6(1565)

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General description

Hydroquinidine, a cinchona alkaloid, is a structural analog of quinidine. It shows antiarrhythmic effect.

Application

Hydroquinidine can be used as a chiral catalyst to prepare:
  • Enantioselective axially chiral phosphamides by N-allylic alkylation reaction between Morita-Baylis-Hillamn (MBH) carbonate and phosphamides.
  • Enantioselective α-amino phosphonates by hydrophosphonylation of N-aryl ketimines.
  • Enantioselective α-hydrazino esters by α-hydrazination of 3-oxoindolines using azodicarboxylate via aza-Michael reaction.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids.
Nakamura S, et al.
Journal of the American Chemical Society, 131(51), 18240-18241 (2009)
Comparison of serum hydroquinidine determination by fluorescence polarization immunoassay and liquid chromatography.
Tod M, et al.
Journal of Pharmaceutical and Biomedical Analysis, 8(3), 279-282 (1990)
Asymmetric Synthesis of Axially Chiral Phosphamides via Atroposelective N-Allylic Alkylation
Yang GH et al.
ACS Catalysis, 10, 2324-2333 (2020)
Organocatalytic enantioselective amination of 2-substituted indolin-3-ones: A strategy for the synthesis of chiral $\alpha$-hydrazino esters
Yarlagadda S, et al.
Organic Letters, 19, 170-173 (2017)
Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids
Nakamura, S, et al.
Journal of the American Chemical Society, 131, 18240-18241 (2009)

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