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676403

Sigma-Aldrich

(R,R)-(–)-2,3-Bis(tert-butylmethylphosphino)quinoxaline

≥95%

Synonym(s):
(R) QuinoxP
Empirical Formula (Hill Notation):
C18H28N2P2
CAS Number:
Molecular Weight:
334.38
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95%

form

solid

mp

100-104 °C

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

Related Categories

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.

Packaging

100 mg in clear glass bottle
500 mg in amber glass bottle

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

Citation

Yahav-Levi A, et al. "Aryl-bromide reductive elimination from an isolated Pt (IV) complex." Chemical Communications 46(19) (2010): 3324-3326.
Fang P and Hou XL. "Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines." Organic letters 11.20 (2009): 4612-4615.
Imamoto T, et al. "Highly enantioselective hydrosilylation of simple ketones catalyzed by rhodium complexes of P-chiral diphosphine ligands bearing tert-butylmethylphosphino groups." Tetrahedron: Asymmetry 17(4) (2006): 560-565.

Legal Information

QuinoxP is a registered trademark of Nippon Chemical Industry Co., Ltd.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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