三(氰乙基)膦

三(氰乙基)膦
识别
CAS号	4023-53-4
PubChem	77639
ChemSpider	70043
SMILES	C(CP(CCC#N)CCC#N)C#N;
性质
化学式	C9H12N3P
摩尔质量	193.19 g·mol−1
外观	白色固体
熔点	97 °C（370 K）
危险性
	GHS危险性符号;
GHS提示词	危险
H-术语	H301, H302, H311, H315, H319, H330, H331, H335, H350
P-术语	P201, P202, P260, P261, P264, P270, P271, P280, P281, P284, P301+310, P301+312, P302+352, P304+340
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

三(氰乙基)膦是一种有机磷化合物，化学式为P(CH₂CH₂CN)₃。它是白色固体，在空气中稳定，这一性质在三烷基膦中并不常见。它可由丙烯腈和磷化氢的反应制备。^[2]四羟甲基硫酸𬭸^[3]或四羟甲基氯化𬭸^[4]也可作为原料反应。它在乙酸中被过氧化氢氧化，生成三(氰乙基)氧化膦。^[3]它也可作为配体与金属盐形成配合物。^[5]^[6]

参考文献

^ Valetdinov, R. K.; Kuznetsov, E. V.; Komissarova, S. L. Reaction of hydroxymethyl derivatives of hydrogen phosphide with acrylic acid nitrile（俄文）. Zhurnal Obshchei Khimii, 1969. 39 (8): 1744-1746. ISSN: 0044-460X.
^ Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. Phosphine in the synthesis of organophosphorus compounds. Russian Chemical Reviews. 1999, 68. doi:10.1070/RC1999v068n03ABEH000464.
^ ^3.0 ^3.1 Zhi-Wei Tan, Jian Sun, Min Zhang, Jin-Jun Qiu, Si-Qian Hu, Cheng-Mei Liu. Phosphorus-containing polymers from THPS. II: synthesis and property of phosphorus-containing hyperbranched aromatic-aliphatic polyamides. Designed Monomers and Polymers. 2015-04-03, 18 (3): 222–231 [2020-01-18]. ISSN 1568-5551. doi:10.1080/15685551.2014.999461. （原始内容存档于2020-02-04）（英语）.
^ Kevin Bruyninckx, Koen J.A. Jansens, Bart Goderis, Jan A. Delcour, Mario Smet. Removal of disulfide cross-links from wheat gluten and the effect thereof on the mechanical properties of rigid gluten bioplastic. European Polymer Journal. 2015-07, 68: 573–584 [2020-01-18]. doi:10.1016/j.eurpolymj.2015.03.047. （原始内容存档于2020-02-04）（英语）.
^ Ross J. Davidson, Eric W. Ainscough, Andrew M. Brodie, Graham H. Freeman, Geoffrey B. Jameson. Structural studies on tris(2-cyanoethyl)phosphine complexes of Cu(I): The sensitivity of the secondary nitrile coordination to the nature of the anion. Polyhedron. 2014-09, 79: 330–337 [2020-01-18]. doi:10.1016/j.poly.2014.05.034. （原始内容存档于2020-02-04）（英语）.
^ Valentina Gandin, Marina Porchia, Francesco Tisato, Alessandro Zanella, Emilia Severin, Alessandro Dolmella, Cristina Marzano. Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity. Journal of Medicinal Chemistry. 2013-09-26, 56 (18): 7416–7430 [2020-01-18]. ISSN 0022-2623. doi:10.1021/jm400965m. （原始内容存档于2020-02-04）（英语）.

[1] Valetdinov, R. K.; Kuznetsov, E. V.; Komissarova, S. L. Reaction of hydroxymethyl derivatives of hydrogen phosphide with acrylic acid nitrile（俄文）. Zhurnal Obshchei Khimii, 1969. 39 (8): 1744-1746. ISSN: 0044-460X.

[RussRev-2] Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. Phosphine in the synthesis of organophosphorus compounds. Russian Chemical Reviews. 1999, 68. doi:10.1070/RC1999v068n03ABEH000464.

[#1-3] 3.0 ^3.1 Zhi-Wei Tan, Jian Sun, Min Zhang, Jin-Jun Qiu, Si-Qian Hu, Cheng-Mei Liu. Phosphorus-containing polymers from THPS. II: synthesis and property of phosphorus-containing hyperbranched aromatic-aliphatic polyamides. Designed Monomers and Polymers. 2015-04-03, 18 (3): 222–231 [2020-01-18]. ISSN 1568-5551. doi:10.1080/15685551.2014.999461. （原始内容存档于2020-02-04）（英语）.

[4] Kevin Bruyninckx, Koen J.A. Jansens, Bart Goderis, Jan A. Delcour, Mario Smet. Removal of disulfide cross-links from wheat gluten and the effect thereof on the mechanical properties of rigid gluten bioplastic. European Polymer Journal. 2015-07, 68: 573–584 [2020-01-18]. doi:10.1016/j.eurpolymj.2015.03.047. （原始内容存档于2020-02-04）（英语）.

[5] Ross J. Davidson, Eric W. Ainscough, Andrew M. Brodie, Graham H. Freeman, Geoffrey B. Jameson. Structural studies on tris(2-cyanoethyl)phosphine complexes of Cu(I): The sensitivity of the secondary nitrile coordination to the nature of the anion. Polyhedron. 2014-09, 79: 330–337 [2020-01-18]. doi:10.1016/j.poly.2014.05.034. （原始内容存档于2020-02-04）（英语）.

[6] Valentina Gandin, Marina Porchia, Francesco Tisato, Alessandro Zanella, Emilia Severin, Alessandro Dolmella, Cristina Marzano. Novel Mixed-Ligand Copper(I) Complexes: Role of Diimine Ligands on Cytotoxicity and Genotoxicity. Journal of Medicinal Chemistry. 2013-09-26, 56 (18): 7416–7430 [2020-01-18]. ISSN 0022-2623. doi:10.1021/jm400965m. （原始内容存档于2020-02-04）（英语）.

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