Lithium diphenylphosphide
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| Other names
Lithium Diphenylphosphanide
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C12H10LiP | |
| Molar mass | 192.13 g·mol−1 |
| Appearance | pale yellow solid |
| Solubility | ethers |
| Hazards | |
| GHS labelling: | |
  
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| Danger | |
| 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).
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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.
Synthesis and reactions
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 undergo hydrolysis to give diphenylphosphine:[4]
- (C6H5)2PLi + H2O → (C6H5)2PH + LiOH
With alkyl halides, 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.
Structure
Although treated as salts, alkali diphenylphosphides are highly aggregated in solution. They adopt polymeric structures as solids.
Related compounds
- Sodium diphenylphosphide (CAS RN 4376-01-6)
- Potassium diphenylphosphide (CAS RN 15475-27-1)
References
- ^ "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. 1986. doi:10.1021/ic00228a034.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine". Inorganic Syntheses. 13: 26–32. 1972. doi:10.1002/9780470132449.ch7.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine". Inorganic Syntheses. 17: 186–188. 1977. doi:10.1002/9780470132487.ch51.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ a b "Diphenylphosphine". Inorganic Syntheses. 16: 161–188. 1976. doi:10.1002/9780470132470.ch43.
{{cite journal}}: Cite uses deprecated parameter|authors=(help) - ^ "Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine". Inorganic Syntheses. 16: 188–192. 1976. doi:10.1002/9780470132470.ch50.
{{cite journal}}: Cite uses deprecated parameter|authors=(help)