TRISPHAT

TRISPHAT (full name tris(tetrachlorocatecholato)phosphate(1−)) is an inorganic anion with the formula P(O
₂C
₆Cl
₄)⁻
₃ often prepared as the tributylammonium ((C
₄H
₉)
₃NH⁺
) or tetrabutylammonium ((C
₄H
₉)
₄N⁺
salt. The anion features phosphorus(V) bonded to three tetrachlorocatecholate (C
₆Cl
₄O²⁻
₂) ligands. This anion can be resolved into the axially chiral enantiomers, which are optically stable (the picture shows the Δ enantiomer).

TRISPHAT

Names
IUPAC name Tetrabutylammonium tris(3,4,5,6-tetrachlorobenzene-1,2-diolato-κ2O1,O2)phosphorus(V)
Other names Tetrabutylammonium tris(tetrachlorocatecholato)phosphorus(1−) Bu4N+ PHAT− 1-Butanaminium, N,N,N-tributyl-, (OC-6-11-Δ)-tris[3,4,5,6-tetrachloro-1,2-benzenediolato(2-)-κO1,κO2]phosphate(1−) (1:1)
Identifiers
CAS Number	tetrabutylammonium salt:: 301687-57-0 Y
3D model (JSmol)	Interactive image tributylammonium salt:: Interactive image tetrabutylammonium salt:: Interactive image
ChemSpider	tetrabutylammonium salt:: 35467078
ECHA InfoCard	100.164.647
EC Number	tetrabutylammonium salt:: 636-891-3
PubChem CID	tetrabutylammonium salt:: 71310446
CompTox Dashboard (EPA)	DTXSID80746191 tetrabutylammonium salt:: DTXSID80746191
InChI tetrabutylammonium salt:: InChI=1S/C18Cl12O6P.C16H36N/c19-1-2(20)8(26)14-13(7(1)25)31-37(32-14,33-15-9(27)3(21)4(22)10(28)16(15)34-37)35-17-11(29)5(23)6(24)12(30)18(17)36-37;1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4/h;5-16H2,1-4H3/q-1;+1 Key: GCGVBYHPNKLLAV-UHFFFAOYSA-N
SMILES O1c0c(Cl)c(Cl)c(Cl)c(Cl)c0O[P-]123(Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O2)Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O3 tributylammonium salt:: O1c0c(Cl)c(Cl)c(Cl)c(Cl)c0O[P-]123(Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O2)Oc0c(Cl)c(Cl)c(Cl)c(Cl)c0O3.CCCC[N+H](CCCC)CCCC tetrabutylammonium salt:: CCCC[N+](CCCC)(CCCC)CCCC.C12=C(C(=C(C(=C1Cl)Cl)Cl)Cl)O[P-]34(O2)(OC5=C(O3)C(=C(C(=C5Cl)Cl)Cl)Cl)OC6=C(O4)C(=C(C(=C6Cl)Cl)Cl)Cl
Properties
Chemical formula	[C16H36N][C18Cl12O6P]
Molar mass	1011.06
Appearance	colourless solid
Solubility in water	CH2Cl2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

The TRISPHAT anion has been used as a chiral shift reagent for cations.^[1] 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 HCl

H[P(O₂C₆Cl₄)₃] + Bu₃N → Bu₃NH⁺ [P(O₂C₆Cl₄)₃]⁻

Using a chiral amine, the anion can be readily resolved.^[2]