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(+)-DIOP

Basic information Safety Supplier Related

(+)-DIOP Basic information

Product Name:
(+)-DIOP
Synonyms:
  • (4S,5S)-(+)-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane (+)-DIOP (2S,3S)-(+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane
  • (+)-2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosp
  • (S)-DIOP
  • (S,S)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane
  • 1,1'-[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[1,1-diphenyl-Phosphine
  • (4S,5S)-(+)-4,5-Bis(diphenylphosphinoMethyl)-2,2-diMethyl-1,3-dioxolane,(S,S)-DIOP.
  • (+)-4,5-Bis(diphenylphosphinomethyl)-2,2-dimethyl-1,3-dioxolane
  • (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane
CAS:
37002-48-5
MF:
C31H32O2P2
MW:
498.54
EINECS:
253-307-9
Product Categories:
  • organophosphine ligand
  • Phosphine Ligands
  • Asymmetric Synthesis
  • Dioxanes & Dioxolanes
  • Dioxolanes
  • Synthetic Organic Chemistry
  • Chiral Phosphine
  • DIOP Series
Mol File:
37002-48-5.mol
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(+)-DIOP Chemical Properties

Melting point:
86-88 °C(lit.)
alpha 
+26° (c 2.0, CHCl3)
Boiling point:
590.3±25.0 °C(Predicted)
storage temp. 
Store below +30°C.
form 
Powder
color 
White
Water Solubility 
Sparingly soluble in water at 25°C 2.1E-5 g/L.
Sensitive 
Air Sensitive
BRN 
1630280
InChIKey
VCHDBLPQYJAQSQ-LOYHVIPDSA-N
CAS DataBase Reference
37002-48-5
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
10-23
HS Code 
29319090

MSDS

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(+)-DIOP Usage And Synthesis

Chemical Properties

white powder

Uses

It is employed as a ligand for the in situ preparation of chiral hydrogenation catalysts. It also finds it application for the in situ preparation of chiral hydrogenation catalysts, ligand for Rh(I)-catalyzed asymmetric hydrogenation of enamides, 1,4-disilylation of α,β-unsaturated ketones, Heck reaction of alkenyl iodides, and hydroformylation of olefins.

Purification Methods

It has been recrystallised from *C6H6/pet ether. After 2 recrystallisations from EtOH, it was pure by TLC on silica gel using Me2CO/hexane as solvent. [Kagan & Dang J Am Chem Soc 94 6429 1972.] Lanthanide shift reagents See in “Aliphatic Compounds”, Chapter 4, europium (III) acetate above and Eu(tmc)3 and Eu(tfc)3 below.

(+)-DIOPSupplier

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