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Bis(diethylamino)chlorophosphine

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Bis(diethylamino)chlorophosphine
Names
Other names N,N,N',N'-tetraethylphosphorodiamidous chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.896 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4Cl4P2/c7-11(8)5-3-1-2-4-6(5)12(9)10/h1-4HKey: IGYHSFVSIYJSML-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C(=C1)P(Cl)Cl)P(Cl)Cl
Properties
Chemical formula C8H20Cl4N2P
Molar mass 210,687
Appearance colorless liquid
Boiling point 87–90 °C (189–194 °F; 360–363 K) 2 torr
Hazards
GHS labelling:
Pictograms GHS05: Corrosive
Signal word Danger
Hazard statements H314
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

Bis(diethylamino)chlorophosphine is an organophosphorus compound with the formula (Et2N)2PCl (Et = ethyl). This colorless liquid 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:

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 → C6H42 + LiCl

Finally, the amino substituents are removed using hydrogen chloride:

C6H42 + 8 HCl → C6H4(PCl2)2 + 4 Et2NH2Cl

References

  1. 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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