(R,R)-Chiraphos - CAS 74839-84-2

(R,R)-Chiraphos is a chiral phosphine ligand for enantioselective synthesis with high yield and high enantioselective results.

Product Information

Canonical SMILES
C[C@H]([C@@H](C)P(c1ccccc1)c2ccccc2)P(c3ccccc3)c4ccccc4
InChI
InChI=1S/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m1/s1
InChI Key
FWXAUDSWDBGCMN-DNQXCXABSA-N
Purity
98%
MDL
MFCD00075403
Physical State
Solid
Storage
Inert atmosphere. Room temperature.
Boiling Point
529.19 °C(Predicted) / 760 mmHg
Melting Point
104-109 °C
Solubility
Soluble in chloroform. Insoluble in water.
TSCA
No
WGK Germany
3
Packing Groups
III

Safety Information

Signal Word
Warning
Precautionary Statement
P261 - P305+P351+P338
Hazard Statements
H315 - H319 - H335

Application

(2R,3R)-(+)-Bis(diphenylphosphino)butane is used for enantio-selective hydrogenations

Reference Reading

1. Diastereoselectivity an chiral ruthenium complexes of chiraphos monoxide ligands: epimerization, Quasiracemates, And lewis acid catalysis.
J W Faller, J Parr, X Liu. Chirality. 2000 Jun; 12(5-6): 325-37. DOI: 10.1002/(SICI)1520-636X(2000)12: 5/63.0.CO; 2-6. PMID: 10824147.
Heterobidentate chelating ligands comprising P,O-donor sets produce chiral metal centers when bound to arene-ruthenium complexes. The cymene complex [CyRu(eta2-chelate-P,O)Cl]+ cations are precursors to 16-electron dicationic strong Lewis acids which have potential use in asymmetric catalysis. Sixteen-electron complexes of this type, however, also provide a pathway with a low energy barrier to epimerization of the metal center in intermediates. With the chiral ligand (R,R)-chiraphos monoxide, the metal center in [CyRu(eta2)-(R,R)-Ph2PCHMeCHMe Ph2PO-P,O)Cl]+ epimerizes to minimize steric interactions in the two diastereomers yielding a 8. 2:1 dr in solution. Nevertheless, upon crystallization a new equilibrium is obtained in the solid and the crystals obtained have a 1:1 dr. These crystals are quasiracemates, which contain equal amounts of the (RRu) and (SRu)-CyRu-P-O-Cl stereocenters within the same crystal. The doubly charged Lewis acid, [CyRu(eta2-(R, R)-Ph2PCHMeCHMe Ph2PO-P,O)(solvate)]2+ derived from the chloro complex by chloride abstraction with AgSbF6 gave modest ee's (30%) in the Diels-Alder reaction of methacrolein with cyclopentadiene.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Related Products

USA
  • International: 1-631-504-6093
  • US & Canada (Toll free): 1-844-BOC(262)-0123
  • 45-16 Ramsey Road, Shirley, NY 11967, USA
  • Email: info@bocsci.com
  • Fax: 1-631-614-7828
UK
  • 44-20-3286-1088
  • 85 Great Portland Street, London, W1W 7LT
  • Email: info@bocsci.com
Copyright © 2025 BOC Sciences. All rights reserved.
Top

We use cookies to understand how you use our site and to improve the overall user experience. This includes personalizing content and advertising. Read our Privacy Policy

Accept Cookies
x