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675792

Sigma-Aldrich

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

97%

Synonym(s):

(S)-P-Phos

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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBF7298V
04216HE

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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)
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)
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)
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
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P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

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P-Phos, PhanePhos and BoPhoz™ Ligands

P-Phos ligand family enhances catalysis, featuring atropisomeric biaryl bisphosphine with unique structural elements.

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