(S,S)-dipamp

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 one of the first industrial scale asymmetric hydrogenation, the synthesis of the drug L-DOPA. thumb|center|550px|Synthesis of L-DOPA via hydrogenation with the C2-Symmetric ligands|C2-symmetric diphosphine DIPAMP.

Chemical data

Formula: C28H28O2P2
Molecular weight: 458.5 g/mol
IUPAC name: (2-methoxyphenyl)-[2-[(2-methoxyphenyl)-phenylphosphanyl]ethyl]-phenylphosphane
SMILES: COC1=CC=CC=C1[P@@](CC[P@@](C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4
InChIKey: QKZWXPLBVCKXNQ-ACHIHNKUSA-N
XLogP: 5.8
Polar surface area: 18.5 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

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Wikidata facts

Subclass of: chemical compound
Mass: 458.156

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chemical formula: C₂₈H₂₈O₂P₂
canonical SMILES: COC1=CC=CC=C1P(CCP(C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4
isomeric SMILES: COC1=CC=CC=C1[P@@](CC[P@@](C2=CC=CC=C2)C3=CC=CC=C3OC)C4=CC=CC=C4
Commons category: DIPAMP

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Encyclopedic overview

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Contents

References

DIPAMP is a C2-symmetric diphosphine. Each phosphorus centre, which is pyramidal, bears three different substituents - anisyl, phenyl, and the ethylene group. The ligand therefore exists as the enantiomeric (R,R) and (S,S) pair, as well as the achiral meso isomer.

Excerpted from Wikipedia’s “(S,S)-dipamp” article, available under the CC BY-SA 4.0 licence.