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676403 Sigma-Aldrich

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

≥95%

Synonym: (R) QuinoxP®

  • CAS Number 866081-62-1

  • Empirical Formula (Hill Notation) C18H28N2P2

  • Molecular Weight 334.38

  •  MDL number MFCD10565649

  •  PubChem Substance ID 24884852

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Other Chiral Ligands, Privileged Ligands and Complexes,
Quality Level   100
assay   ≥95%
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

Description

General description

(R,R)-(-)-2,3-Bis(tert-butylmethylphosphino)quinoxaline is an air-stable C2-symmetric P-stereogenic phosphine ligand.

Application

Air-Stable and Highly Efficient Chiral Ligands

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

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.

Yahav-Levi A, et al. "Aryl-bromide reductive elimination from an isolated Pt (IV) complex." Chemical Communications 46(19) (2010): 3324-3326.

Legal Information

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

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

QuinoxP* Ligands | Aldrich ChemFiles 2006, 6.10, 3 and Volume 8 Article 2

Various optically active phosphine ligands incorporating a chiral center at the phosphorus display exceptional enantiosectivities in metal-catalyzed asymmetric synthesis.1 For instance, known classes...
Aldrich ChemFiles 2006, 6.10, 3 and Volume 8 Article 2
Keywords: Addition reactions, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, transformation

Related Content

QuinoxP*

Various optically active phosphine ligands incorporating a chiral center at phosphorus display exceptional enantiosectivities in metal-catalyzed asymmetric synthesis.1 For instance, known classes P-c...
Keywords: Addition reactions, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, transformation

Peer-Reviewed Papers
15

References

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