Bis(diethylamino)chlorophosphine

Bis(diethylamino)chlorophosphine
Names
	Other names N,N,N',N'-tetraethylphosphorodiamidous chloride
Identifiers
CAS Number	685-83-6;
3D model (JSmol)	Interactive image;
ChemSpider	2015150;
ECHA InfoCard	100.155.896
PubChem CID	3316562;
CompTox Dashboard (EPA)	DTXSID10391390;
	InChI InChI=1S/C6H4Cl4P2/c7-11(8)5-3-1-2-4-6(5)12(9)10/h1-4H Key: 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 pictograms
GHS Signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	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 + 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

gollark: You can get an idea of what things are likely or unlikely. The monetary incentive is somewhat important.

gollark: This is one of those annoying things where we're limited to wild speculation so probably don't do anything weird businesswise.

gollark: Democratic ones theoretically allow more input from everyone, which should lead to decisions which consider their interests more and take into account information people know, but also run into whatever issues existing democracies have plus probably exciting new ones due to presumably having a direct democracy voting on a lot of things.

gollark: Hierarchical ones (theoretically) allow clear direction and management from the top but also lack input from lower levels and are vulnerable to the top people being wrong/bad.

gollark: Before trying to think of ideas for organization structure it might be good to clarify what exactly the organizational structure should do/allow/optimize.

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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[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.