Tris(2,4,6-trimethoxyphenyl)phosphine
Chemical compound
From Wikipedia, the free encyclopedia
Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) is a large triaryl organophosphine whose strong Lewis-basic properties make it useful as an organocatalyst for several types of chemical reactions.
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| Names | |
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| IUPAC name
Tris(2,4,6-trimethoxyphenyl)phosphane | |
Other names
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| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C27H33O9P | |
| Molar mass | 532.526 g·mol−1 |
| Melting point | 79–81 °C (174–178 °F; 352–354 K) |
| Boiling point | 360 or 377 °C (680 or 711 °F; 633 or 650 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions
TTMPP removes the trimethylsilyl group from ketene silyl acetals (the enol ether of esters) to give enolates that can then act as strong nucleophiles. It thus serves as a catalyst for Mukaiyama aldol reactions[2] and group-transfer chain-growth polymerization reactions.[3]
TTMPP acts as potent Lewis-base catalyst in Michael addition reactions enabeling the use of alcohols as Michael donors.[4]
TTMPP can act as a Michael nucleophile itself to catalyze Baylis–Hillman reactions.[5]
Uses
TTMPP is used as a ligand to form palladium-phosphine catalysts which are more reactive than triphenylphosphine-based catalysts.[6]