Bis(diethylamino)chlorophosphine
Appearance
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Names | |
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Other names
N,N,N',N'-tetraethylphosphorodiamidous chloride
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.155.896 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C8H20Cl4N2P | |
Molar mass | 210,687 |
Appearance | colorless liquid |
Boiling point | 87–90 °C (189–194 °F; 360–363 K) 2 torr |
Hazards | |
GHS labelling: | |
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Danger | |
H314 | |
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, 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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Bis(diethylamino)chlorophosphine is an organophosphorus compound with the formula (Et2N)2PCl (Et = ethyl). A colorless liquid, it serves as a masked source of PCl2+.
Synthesis and reactions
The compound is prepared by treatment of phosphorus trichloride with diethylamine:
- 4 Et2NH + PCl3 → (Et2N)2PCl + 2 Et2NH2Cl
Illustrative of its utility is the synthesis of 1,2-bis(dichlorophosphino)benzene. The synthesis involves sequential lithiation of 1,2-dibromobenzene followed by treatment with (Et2N)2PCl:[1]
- C6H4Br2 + BuLi → C6H4(Br)Li + BuBr
- C6H4(Br)Li + (Et2N)2PCl → C6H4(Br)(P(NEt2)2) + LiCl
- C6H4(Br)(P(NEt2)2) + BuLi → C6H4(Li)(P(NEt2)2) + BuBr
- C6H4(Li)(P(NEt2)2) + (Et2N)2PCl → C6H4[P(NEt2)2]2 + LiCl
Finally, the amino substituents are removed using hydrogen chloride:
- C6H4[P(NEt2)2]2 + 8 HCl → C6H4(PCl2)2 + 4 Et2NH2Cl
References
- ^ Reetz, Manfred T.; Moulin, Dominique; Gosberg, Andreas (2001). "BINOL-Based Diphosphonites as Ligands in the Asymmetric Rh-Catalyzed Conjugate Addition of Arylboronic Acids". Organic Letters. 3 (25): 4083–4085. doi:10.1021/ol010219y. PMID 11735590.