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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/h1-3,7-9H2Key: CHZAMJVESILJGH-UHFFFAOYSA-N
SMILES C(CP(CCC#N)CCC#N)C#N
Properties
Chemical formula	C9H12N3P
Molar mass	193.190 g·mol
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 , 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. The compound has been the subject of much research. For example, it is an effective reagent for the desulfurization of organic disulfides.

References

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.

• Tertiary phosphines
• Nitriles