Chemistry:Bis(diethylamino)chlorophosphine
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2PCl.svg)
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| Other names
N,N,N',N'-tetraethylphosphorodiamidous chloride
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3D model (JSmol)
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| ChemSpider | |
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 pictograms | 
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| GHS Signal word | Danger |
| H314 | |
| P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, 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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Tracking categories (test):
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.
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