676403
(R,R)-(–)-2,3-Bis(tert-butylmethylphosphino)quinoxaline
≥95%
Synonym(s):
(R) QuinoxP®
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About This Item
Empirical Formula (Hill Notation):
C18H28N2P2
CAS Number:
Molecular Weight:
334.38
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Quality Level
assay
≥95%
form
solid
mp
100-104 °C
functional group
phosphine
SMILES string
CP(c1nc2ccccc2nc1P(C)C(C)(C)C)C(C)(C)C
InChI
1S/C18H28N2P2/c1-17(2,3)21(7)15-16(22(8)18(4,5)6)20-14-12-10-9-11-13(14)19-15/h9-12H,1-8H3/t21-,22-/m0/s1
InChI key
DRZBLHZZDMCPGX-VXKWHMMOSA-N
General description
(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an air-stable C2-symmetric P-stereogenic phosphine ligand.
Application
Efficient ligand exhibiting high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed 1,4-addition of arylboronic acids to alkylative ring opening to asymmetric hydrogenation.
Features and Benefits
Advantages of the QuinoxP* Ligands:
- It is not oxidized nor epimerized at ambient conditions in air
- Enantioselectivities are outstanding for various reaction paradigms
- Hydrogenations proceed under mild reaction conditions
- Low catalyst loadings yield high TONs
Legal Information
QuinoxP is a registered trademark of Nippon Chemical Industry Co., Ltd.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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Articles
QuinoxP*: Air-Stable and Highly Efficient and Productive Chiral Ligands
Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups.
Imamoto T, et al.
Tetrahedron Asymmetry, 17(4), 560-565 (2006)
A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions.
Ji Y, et al.
Chemical Science (2017)
Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines.
Fang P and Hou XL.
Organic Letters, 11.20, 4612-4615 (2009)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 676403-100MG | 04061833549674 |
| 676403-500MG | 04061833549681 |