Tris(cyanoethyl)phosphine

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]

Tris(cyanoethyl)phosphine
Names
Preferred IUPAC name
3,3′,3′′-Phosphanetriyltripropanenitrile
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.535
EC Number
  • 223-687-0
UNII
  • InChI=1S/C9H12N3P/c10-4-1-7-13(8-2-5-11)9-3-6-12/h1-3,7-9H2
    Key: CHZAMJVESILJGH-UHFFFAOYSA-N
  • C(CP(CCC#N)CCC#N)C#N
Properties
C9H12N3P
Molar mass 193.190 g·mol−1
Appearance white solid
Melting point 97 °C (207 °F; 370 K)
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H302, H311, H315, H319, H330, H331, H335, H350
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

References
  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.
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