675792

Sigma-Aldrich

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

97%

Synonym(s):
(S)-P-Phos
Empirical Formula (Hill Notation):
C38H34N2O4P2
CAS Number:
Molecular Weight:
644.64
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]20/D -98°, c = 1 in chloroform

mp

261-265 °C

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.

Packaging

100 mg in clear glass bottle
500 mg in amber glass bottle

Legal Information

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
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)
Enantioselective Pd-catalyzed allylic alkylation of indoles by a new class of chiral ferrocenyl P/S ligands
Cheung HY, et al.
Organic Letters, 9(21), 4295-4298 (2007)
Synthesis of Chiral Functionalized Polymers by Alternating Copolymerization of Propene and CO Using the Pd (OAc) 2/(S)-P-PHOS Catalyst
Lailai W, et al.
Chinese Journal of Catalysis, 32(1-2), 65-69 (2011)
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...
Articles
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.
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