743585
(S)-(−)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline
≥95.0% (qNMR)
Synonym(s):
(S)-QUINAP
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About This Item
Empirical Formula (Hill Notation):
C31H22NP
CAS Number:
Molecular Weight:
439.49
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Beilstein/REAXYS Number:
6664856
Assay:
≥95.0% (qNMR)
Form:
crystals
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:
[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.
- 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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 743585-50MG | 04061833555637 |
| 743585-250MG | 04061833555620 |