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]
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| Names | |
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| Preferred IUPAC name
3,3′,3′′-Phosphanetriyltripropanenitrile | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.021.535 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H12N3P | |
| Molar mass | 193.190 g·mol−1 |
| Appearance | white solid |
| Melting point | 97 °C (207 °F; 370 K) |
| Hazards | |
| GHS labelling: | |
  
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| 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).
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References
edit- ^ 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.