DIPAMP

DIPAMP

Names
IUPAC name Ethane-1,2-diylbis[(2-methoxyphenyl)phenylphosphane]
Identifiers
CAS Number	55739-58-7 (R,R) N 97858-62-3 (S,S) N
3D model (JSmol)	Interactive image Interactive image
ChemSpider	9594634 Y
ECHA InfoCard	100.151.292
PubChem CID	11419748
InChI InChI=1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m0/s1 Y Key: QKZWXPLBVCKXNQ-ACHIHNKUSA-N Y InChI=1/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m1/s1 Key: QKZWXPLBVCKXNQ-ROJLCIKYBJ InChI=1/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m0/s1 Key: QKZWXPLBVCKXNQ-ACHIHNKUBV
SMILES O(c1ccccc1[P@@](c2ccccc2)CC[P@](c3ccccc3)c4ccccc4OC)C O(c1ccccc1[P@](c2ccccc2)CC[P@@](c3ccccc3)c4ccccc4OC)C
Properties
Chemical formula	C28H28O2P2
Molar mass	458.47 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

DIPAMP is an organophosphorus compound that is used as a ligand in homogeneous catalysis. It is a white solid that dissolves in organic solvents. Work on this compound by W. S. Knowles was recognized with the Nobel Prize in Chemistry. DIPAMP was the basis for of the first industrial scale asymmetric hydrogenation, the synthesis of the drug L-DOPA.

DIPAMP is a chelating diphosphine. Each phosphorus centre, which is pyramidal, bears three different substituents - anisyl, phenyl, and the ethylene group. It therefore exists as the enantiomeric (R,R) and (S,S) pair, as well as the achiral meso isomer.

DIPAMP was originally prepared by an oxidative coupling reaction, starting from anisyl(phenyl)(methyl)phosphine.