Tris(2,4,6-trimethoxyphenyl)phosphine

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.

Tris(2,4,6-trimethoxyphenyl)phosphine

Names
IUPAC name Tris(2,4,6-trimethoxyphenyl)phosphane
Other names Tris(2,4,6-trimethoxyphenyl)phosphine TTMPP
Identifiers
CAS Number	91608-15-0
3D model (JSmol)	Interactive image
ChemSpider	11283
EC Number	811-745-3
PubChem CID	522987
CompTox Dashboard (EPA)	DTXSID60335128
InChI InChI=1S/C27H33O9P/c1-28-16-10-19(31-4)25(20(11-16)32-5)37(26-21(33-6)12-17(29-2)13-22(26)34-7)27-23(35-8)14-18(30-3)15-24(27)36-9/h10-15H,1-9H3 Key: JQKHNBQZGUKYPX-UHFFFAOYSA-N
SMILES COC1=CC(=C(C(=C1)OC)P(C2=C(C=C(C=C2OC)OC)OC)C3=C(C=C(C=C3OC)OC)OC)OC
Properties
Chemical formula	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). Infobox references

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]

As a Brønsted base, TTMPP can deprotonate various alcohols, giving nucleophilic alkoxides that can undergo Michael addition reactions.^[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]