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676403

Sigma-Aldrich

(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:
866081-62-1
Molecular Weight:
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

Related Categories

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

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335,H413

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

676403-100MG:
676403-BULK:
676403-VAR:
676403-500MG:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9265
MKCP0168
MKCJ8509
MKCG6499
MKCF5477

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A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions.
Ji Y, et al.
Chemical Science (2017)
Optimization of the Preparation of (R)-3, 5-Bis (trifluoromethyl)-?-methyl-N-methylbenzylamine l-(?)-Malic Acid Salt through Classical Resolution.
Brandel CM, et al.
Organic Process Research & Development, 19(12), 1954-1965 (2015)
Rhodium?Catalyzed Dynamic Kinetic Asymmetric Allylation of Phenols and 2?Hydroxypyridines.
Li C and Breit B
European Journal of Chemistry, 22(41), 14655-14663 (2016)
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)
Enantioselective Nitroso Aldol Reaction Catalyzed by a Chiral Phosphine?Silver Complex.
Yanagisawa A, et al.
European Journal of Organic Chemistry, 2016(32), 5355-5359 (2016)
View All Related Papers

Articles

QuinoxP*

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

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