Saltar al contenido
Merck
Todas las fotos(1)

Key Documents

View All Documentation

676403

Sigma-Aldrich

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

≥95%

Sinónimos:

(R) QuinoxP®

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(1)

About This Item

Fórmula empírica (notación de Hill):
C18H28N2P2
Número de CAS:
866081-62-1
Peso molecular:
334.38
MDL number:
MFCD10565649
UNSPSC Code:
12352005
PubChem Substance ID:
24884852
NACRES:
NA.22

Quality Level

100

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

Categorías relacionadas

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.

pictograms

Skull and crossbones
GHS06

signalword

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

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
MKCS3268
MKCV1905
MKCP9265
MKCP0168
MKCJ8509

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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)
Aryl-bromide reductive elimination from an isolated Pt (IV) complex.
Yahav-Levi A, et al.
Chemical Communications (Cambridge, England), 46(19), 3324-3326 (2010)
Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines.
Fang P and Hou XL.
Organic Letters, 11.20, 4612-4615 (2009)
Three-Hindered Quadrant Phosphine Ligands with an Aromatic Ring Backbone for the Rhodium-Catalyzed Asymmetric Hydrogenation of Functionalized Alkenes.
Zhang Z, et al.
The Journal of Organic Chemistry, 77(8), 4184-4188 (2012)
Ver todos los artículos relacionados

Artículos

QuinoxP*

QuinoxP*: Air-Stable and Highly Efficient and Productive Chiral Ligands

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico