Tris(cyanoethyl)phosphine

Tris(cyanoethyl)phosphine
Identifiers
CAS Number	4023-53-4;
3D model (JSmol)	Interactive image;
ChemSpider	70043;
ECHA InfoCard	100.021.535
EC Number	223-687-0;
PubChem CID	77639;
CompTox Dashboard (EPA)	DTXSID2063268;
	InChI InChI=1S/C9H12N3P/c10-4-1-7-13(8-2-5-11)9-3-6-12/h1-3,7-9H2 Key: CHZAMJVESILJGH-UHFFFAOYSA-N;
	SMILES C(CP(CCC#N)CCC#N)C#N;
Properties
Chemical formula	C9H12N3P
Molar mass	193.190 g·mol−1
Appearance	white solid
Melting point	97 °C (207 °F; 370 K)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H302, H311, H315, H319, H330, H331, H335, H350
GHS precautionary statements	P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+310, P301+312, P302+352, P304+340, P305+351+338, P308+313, P310, P311, P312, P320, P321, P322, P330, P332+313, P337+313
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Tris(cyanoethyl)phosphine is the organophosphorus compound with the formula P(CH₂CH₂CN)₃. It is white solid that is air stable, which is unusual for a trialkylphosphine. It is prepared by the hydrophosphination of acrylonitrile with phosphine.[1] The compound has been the subject of much research. For example, it is an effective reagent for the desulfurization of organic disulfides.[2]

References

Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. (1999). "Phosphine in the synthesis of organophosphorus compounds". Russian Chemical Reviews. 68. doi:10.1070/RC1999v068n03ABEH000464.
Burns, John A.; Butler, James C.; Moran, John; Whitesides, George M. (1991). "Selective Reduction of Disulfides by Tris(2-carboxyethyl)phosphine". The Journal of Organic Chemistry. 56 (8): 2648–2650. doi:10.1021/jo00008a014.

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[RussRev-1] Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. (1999). "Phosphine in the synthesis of organophosphorus compounds". Russian Chemical Reviews. 68. doi:10.1070/RC1999v068n03ABEH000464.

[2] Burns, John A.; Butler, James C.; Moran, John; Whitesides, George M. (1991). "Selective Reduction of Disulfides by Tris(2-carboxyethyl)phosphine". The Journal of Organic Chemistry. 56 (8): 2648–2650. doi:10.1021/jo00008a014.