Bis(diethylamino)chlorophosphine

Last updated
Bis(diethylamino)chlorophosphine
(Et2N)2PCl.svg
Names
Other names
N,N,N',N'-tetraethylphosphorodiamidous chloride
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
Properties
C8H20Cl4N2P
Molar mass 317.04 g·mol−1
Appearancecolorless liquid
Boiling point 87–90 °C (189–194 °F; 360–363 K)2 torr
Hazards
GHS pictograms GHS-pictogram-acid.svg
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).
Infobox references

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 + 4 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

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The phosphonium cation describes polyatomic cations with the chemical formula PR+
4
. They are tetrahedral and generally colorless.

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Phosphorus trichloride chemical compound

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TRISPHAT chemical compound

Tributylammonium TRISPHAT is an organic salt with the formula [(C
4
H
9
)
3
NH+
][P(O
2
C
6
Cl
4
)
3
]
. The anion features phosphorus(V) bonded to three tetrachlorocatecholate ligands. This anion can be resolved into the enantiomers, which are optically stable.

1,3-Bis(diphenylphosphino)propane chemical compound

1,3-Bis(diphenylphosphino)propane (dppp) is an organophosphorus compound with the formula Ph2P(CH2)3PPh2. The compound is a white solid that is soluble in organic solvents. It is slightly air-sensitive, degrading in air to the phosphine oxide. It is classified as a diphosphine ligand in coordination chemistry and homogeneous catalysis.

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Phosphinous acids are usually organophosphorus compounds with the formula R2POH. They are pyramidal in structure. Phosphorus is in the oxidation state III. Most phosphinous acids rapidly convert to the corresponding phosphine oxide, which are tetrahedral and are assigned oxidation state V. Phosphorous acid OP(OH)2H is an example of an phosphinous acid lacking organic substituents.

1,2-Bis(dichlorophosphino)benzene

1,2-Bis(dichlorophosphino)benzene is an organophosphorus compound with the formula C6H4(PCl2)2. A viscous colorless liquid, it is a precursor to chelating diphosphines of the type C6H4(PR2)2. It is prepared from 1,2-dibromobenzene by sequential lithiation followed by treatment with (Et2N)2PCl (Et = ethyl), which affords C6H4[P(NEt2)2]2. This species is finally cleaved with hydrogen chloride:

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.