DIPAMP

DIPAMP: DIPAMP

IUPAC name

Ethane-1,2-diylbis[(2-methoxyphenyl)phenylphosphane]

Identifiers

CAS number 55739-58-7, (R,R)
97858-62-3 (S,S)

PubChem 11419748

ChemSpider 9594634^Y

Jmol-3D images Image 1
Image 2

SMILES

O(c1ccccc1[P@@](c2ccccc2)CC[P@](c3ccccc3)c4ccccc4OC)C
O(c1ccccc1[P@](c2ccccc2)CC[P@@](c3ccccc3)c4ccccc4OC)C

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

Properties

Molecular formula C₂₈H₂₈O₂P₂

Molar mass 458.47 g/mol

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

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.^[1] DIPAMP was the basis for of the first practical 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.

Reference

^ William S. Knowles "Asymmetric Hydrogenations (Nobel Lecture)" Angewandte Chemie International Edition, 2002, Volume 41, Issue 12, pages 1998–2007. doi:10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8

Categories:
Bisphosphanes

DIPAMP

IUPAC name Ethane-1,2-diylbis[(2-methoxyphenyl)phenylphosphane]
Identifiers
CAS number	55739-58-7, (R,R) 97858-62-3 (S,S)
PubChem	11419748
ChemSpider	9594634^Y
Jmol-3D images	Image 1 Image 2
SMILES O(c1ccccc1[P@@](c2ccccc2)CC[P@](c3ccccc3)c4ccccc4OC)C O(c1ccccc1[P@](c2ccccc2)CC[P@@](c3ccccc3)c4ccccc4OC)C
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
Properties
Molecular formula	C₂₈H₂₈O₂P₂
Molar mass	458.47 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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