676403

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

≥95%

• Synonym(s): (R) QuinoxP^®
• Empirical Formula (Hill Notation): C₁₈H₂₈N₂P₂
• CAS Number: 866081-62-1
• Molecular Weight: 334.38
• MDL number: MFCD10565649
• UNSPSC Code: 12352005
• PubChem Substance ID: 24884852
• NACRES: NA.22

Properties

• Quality Level: 100
• 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

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.

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 Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301 - H315 - H319 - H335 - H413
• Precautionary Statements: P273 - P301 + P310 + P330 - P302 + P352 - P305 + P351 + P338
• 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: 6.1C - 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves