Lithium diphenylphosphide

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Lithium diphenylphosphide
Preferred IUPAC name
Lithium diphenylphosphanide
3D model (JSmol)
  • InChI=1S/C12H10P.Li/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;/q-1;+1
  • [Li+].C1=CC=C(C=C1)[P-]C2=CC=CC=C2
Molar mass 192.13 g·mol−1
Appearance pale yellow solid
Reacts with water
Solubility Ethers, hydrocarbons
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
H302, H312, H314, H332, H410
P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lithium diphenylphosphide contains lithium and the organophosphorus anion with the formula (C6H5)2PLi. It is an air-sensitive solid that is used in the preparation of diphenylphosphino compounds. As an ether complex, the lithium salt is dark red.

Part of the polymeric structure of LiPPh2(Et2O).[1]

Synthesis and reactions[edit]

The lithium, sodium, and potassium salts are prepared by reduction of chlorodiphenylphosphine,[2] triphenylphosphine,[3][4] or tetraphenyldiphosphine with alkali metals (M):

(C6H5)2PCl + 2 M → (C6H5)2PM + MCl
(C6H5)3P + 2 M → (C6H5)2PM + MC6H5
(C6H5)4P2 + 2 M → 2 (C6H5)2PM

They can also be obtained by deprotonation of diphenylphosphine.

With water, the salts convert to diphenylphosphine:[4]

(C6H5)2PLi + H2O → (C6H5)2PH + LiOH

With halocarbons, the salts react to give tertiary phosphines:[5]

(C6H5)2PM + RX → (C6H5)2PR + MX

When treated with metal halides, lithium diphenylphosphide gives transition metal phosphido complexes.


Although treated as salts, alkali diphenylphosphides are highly aggregated in solution. They adopt polymeric structures as solids.

Related compounds[edit]

  • Sodium diphenylphosphide (CAS RN 4376-01-6)
  • Potassium diphenylphosphide (CAS RN 15475-27-1)


  1. ^ Ruth A. Bartlett, Marilyn M. Olmstead, Philip P. Power (1986). "Structural Characterization of the Solvate Complexes of the Lithium Diorganophosphides [{Li(Et2O)PPh2}], [{Li(THF)2PPh2}], and [{Li(THF)P(C6H11)2}]". Inorg. Chem. 25: 1243–1247. doi:10.1021/ic00228a034.{{cite journal}}: CS1 maint: uses authors parameter (link)
  2. ^ R. Goldsberry Kim Cohn (1972). "Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)-phosphine". Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine. Inorganic Syntheses. Vol. 13. pp. 26–32. doi:10.1002/9780470132449.ch7. ISBN 9780470132449.{{cite book}}: CS1 maint: uses authors parameter (link)
  3. ^ George W. Luther, III, Gordon Beyerle (1977). "Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine". Inorganic Syntheses. Inorganic Syntheses. Vol. 17. pp. 186–188. doi:10.1002/9780470132487.ch51. ISBN 9780470132487.{{cite book}}: CS1 maint: uses authors parameter (link)
  4. ^ a b V. D. Bianco, S. Doronzo (1976). "Diphenylphosphine". Inorganic Syntheses. Inorganic Syntheses. Vol. 16. pp. 161–188. doi:10.1002/9780470132470.ch43. ISBN 9780470132470.{{cite book}}: CS1 maint: uses authors parameter (link)
  5. ^ W. Levason, C. A. Mcauliffe (1976). "Cis -2-Diphenylarsinovinyldiphenylphosphine and 2-Diphenylarsinoethyldiphenylphosphine". Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine. Inorganic Syntheses. Vol. 16. pp. 188–192. doi:10.1002/9780470132470.ch50. ISBN 9780470132470.{{cite book}}: CS1 maint: uses authors parameter (link)