Tris(cyanoethyl)phosphine

Tris(cyanoethyl)phosphine
Names
	Preferred IUPAC name 3,3′,3′′-Phosphanetriyltripropanenitrile
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;
UNII	846HYB5W2B ;
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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H311, H315, H319, H330, H331, H335, H350
Precautionary statements	P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
	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 (3): 215–227. Bibcode:1999RuCRv..68..215T. doi:10.1070/RC1999v068n03ABEH000464. S2CID 250775640.
^ 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.

[RussRev-1] Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. (1999). "Phosphine in the synthesis of organophosphorus compounds". Russian Chemical Reviews. 68 (3): 215–227. Bibcode:1999RuCRv..68..215T. doi:10.1070/RC1999v068n03ABEH000464. S2CID 250775640.

[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.

[1]

[2]