TRISPHAT

Chembox new
ImageFileL1 = Trisphat.png ImageSizeL1 = 170
ImageFileR1 = Delta-TRISPHAT-3D-balls.png ImageSizeR1 = 170
IUPACName = Tetrabutylammonium Phosphorus(V) tris(tetrachlorocatecholate)PHAT
OtherNames = Bu₃NH⁺ PHAT^-
Section1 = Chembox Identifiers
CASNo = 301687-57-0
PubChem =
SMILES =
Section2 = Chembox Properties
Formula = [C₁₆H₃₆N] [C₁₈Cl₁₂O₆P]
MolarMass = 1011.06
Appearance = colourless solid
Density =
MeltingPt =
BoilingPt =
Solubility = CH₂Cl₂
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition = Tributylammonium TRISPHAT is the an organic salt with the formula [(C₄H₉)₃NH] + [P(O₂C₆Cl₄)^3-] . The anion features phosphorus(V) bonded to three tetrachlorocatecholate (C₆Cl₄O₂^2-) ligands. This anion can be resolved into the enantiomers, which are optically stable (the picture shows the Δ enantiomer).

The TRISPHAT anion has been used as a “chiral shift reagent” for cations. It improves the resolution of ¹H NMR spectra by forming diastereomeric ion pairs.

Preparation

The anion is prepared by treatment of phosphorus pentachloride with tetrachlorocatechol followed by a tertiary amine gives the anion::PCl₅ + 3 C₆Cl₄(OH)₂ → H [P(O₂C₆Cl₄)₃] + 5 HClH [P(O₂C₆Cl₄)₃] + Bu₃N Bu₃NH⁺ [P(O₂C₆Cl₄)₃] ^-Using a chiral amine, the anion can be readily resolved. [F. Favarger, C. Goujon-Ginglinger, D. Monchaud, J. Lacour “Large-Scale Synthesis and Resolution of TRISPHAT [Tris(tetrachlorobenzenediolato) Phosphate(V)] Anion” Journal of Organic Chemistry, 2004, volume 69, pp. 8521 -8524, 2004. DOI: 10.1021/jo048641q.]

References