Skip to Content
Merck
CN
All Photos(1)

Documents

743585

Sigma-Aldrich

(S)-(−)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline

≥95.0% (qNMR)

Sign Into View Organizational & Contract Pricing
All Photos(1)
Synonym(s):
(S)-QUINAP
Empirical Formula (Hill Notation):
C31H22NP
CAS Number:
149341-33-3
Molecular Weight:
439.49
Beilstein:
6664856
MDL number:
MFCD01073773
UNSPSC Code:
12352005
PubChem Substance ID:
329765641
NACRES:
NA.22

Assay

≥95.0% (qNMR)

form

crystals

optical purity

enantiomeric excess: ≥98.0%

storage temp.

2-8°C

InChI

1S/C31H22NP/c1-3-13-25(14-4-1)33(26-15-5-2-6-16-26)29-20-19-23-11-7-9-17-27(23)30(29)31-28-18-10-8-12-24(28)21-22-32-31/h1-22H

InChI key

YMJAIEYASUCCMJ-UHFFFAOYSA-N

General description

(S)-QUINAP is a bidentate ligand used in catalytic asymmetric hydroboration, hydrogenation, oxidation, and allylic alkylation reactions.

Application

(S)-QUINAP can be used as a ligand:
  • In the asymmetric hydrosilylation of alkyl and α, β-unsaturated ketones in the presence of Fe(OAc)2.      
  • For the synthesis of chiral organoboron compounds by copper-catalyzed β-borylation of α,β-unsaturated esters.

[Ir(cod)Cl]2 treated with ligand (S)-QUINAP forms an iridium complex. This complex is used as a catalyst for the enantioselective hydrogenation of olefins. (S)-QUINAP–Rh complex can be employed as a catalyst in enantioselective hydroboration/oxidation of perfluoroalkenes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Practical Preparation and Resolution of 1-(2 `-Diphenylphosphino-1 `-naphthyl) isoquinoline: A Useful Ligand for Catalytic Asymmetric Synthesis
Lim CW, et al.
Organic Process Research & Development, 7(3), 379-384 (2003)
Anna M Segarra et al.
Chemical communications (Cambridge, England), (4), 464-465 (2004-02-07)
Enantioselective access to Markovnikov regioisomeric perfluoroalcohols is achieved in the presence of chiral cationic rhodium complexes and specific hydroborating reagents.
Enantioselective hydrogenation of olefins with axial chiral iridium QUINAP complex
Li X, et al.
Tetrahedron Letters, 48(22), 3915-3917 (2007)
William J Fleming et al.
Organic & biomolecular chemistry, 7(12), 2520-2524 (2009-06-09)
The synthesis and resolution of a new axially chiral Quinazolinap ligand are reported. The application of this and other related P-N ligands to the copper catalyzed beta-borylation of alpha,beta-unsaturated esters resulted in conversions of up to 100% and ee values
Iron-catalyzed enantioselective hydrosilylation of ketones.
Nadim S Shaikh et al.
Angewandte Chemie (International ed. in English), 47(13), 2497-2501 (2008-02-26)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service