Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

675792

Sigma-Aldrich

(S)-(−)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine

97%

Synonym(s):

(S)-P-Phos

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C38H34N2O4P2
CAS Number:
362524-23-0
Molecular Weight:
644.64
MDL number:
MFCD04038734
UNSPSC Code:
12352005
PubChem Substance ID:
24885300
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D -98°, c = 1 in chloroform

mp

261-265 °C

functional group

phosphine

SMILES string

COc1cc(P(c2ccccc2)c3ccccc3)c(c(OC)n1)-c4c(OC)nc(OC)cc4P(c5ccccc5)c6ccccc6

InChI

1S/C38H34N2O4P2/c1-41-33-25-31(45(27-17-9-5-10-18-27)28-19-11-6-12-20-28)35(37(39-33)43-3)36-32(26-34(42-2)40-38(36)44-4)46(29-21-13-7-14-22-29)30-23-15-8-16-24-30/h5-26H,1-4H3

InChI key

JZOSBBLJKXSBBN-UHFFFAOYSA-N

Application

(S)-P-Phos can be used as a ligand:
  • In the asymmetic hydrogenation reactions.
  • For the preparation of chiral ketone functionalized polymers by copolymerization reaction.
  • To synthesize chiral alkynes by asymmetric hydroalkynylation of nonpolar alkenes or norbornadienes using iridium catalyst.
  • In the selective allylic alkylation of indoles using palladium catalyst.

Ligand employed in the asymmetic hydrogenation of ß-keto esters, 2-arylacrylates, aryl ketones , and other substrates.

Legal Information

Sold in collaboration with Johnson Matthey Catalyst for research purposes only. US5886182 and any patents arising therefrom apply.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBF7298V
04216HE

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Asymmetric hydroalkynylation of norbornadienes promoted by chiral iridium catalysts
Fan B-M, et al.
Angewandte Chemie (International Edition in English), 51(31), 7821-7824 (2012)
Asymmetric hydrogenation of isobutyrophenone using a [(diphosphine) rucl2 (1, 4-diamine)] catalyst
Grasa, Gabriela A and Zanotti-Gerosa, Antonio and Medlock, Jonathan A and Hems, William P
Organic Letters, 7(8), 1449-1451 (2005)
Jing Wu et al.
Accounts of chemical research, 39(10), 711-720 (2006-10-18)
This Account outlines our efforts in the design and synthesis of a family of highly effective atropisomeric dipyridylphosphine ligands (P-Phos and its variants) and in the development of their widespread applications in transition-metal-catalyzed asymmetric reactions including hydrogenation, hydrosilylation, and C-C
Kim-Hung Lam et al.
European journal of medicinal chemistry, 45(11), 5527-5530 (2010-09-14)
Following our previously reported pyridinyl phosphine oxides as antitumor agents, we targeted the commercially available C(2)-axial chiral organophosphine ligand catalysts, such as 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) 1 and 2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine (P-Phos) 2 as a convenient source for producing organophosphine oxides as antitumor leads.

Articles

P-Phos, PhanePhos and BoPhoz™ Ligands

The P-Phos ligand family was developed by Professor Chan of Hong Kong Polytechnic University and licensed to JM CCT in 2002. P-Phos is an atropisomeric biaryl bisphosphine with the unique feature of incorporating two methoxy-substituted pyridine rings in the backbone.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service