苄膦

苄膦
識別
CAS號	14990-01-3
SMILES	c1ccccc1CP;
性質
化學式	C7H9P
莫耳質量	124.12 g·mol⁻¹
沸點	180 °C（453 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

苄膦是一種有機化合物，化學式為C₇H₉P。

合成

苄膦可由P-苄基膦酸二乙酯和氫化鋁鋰的還原反應製得。^[2]

白磷、鋰和叔丁醇在液氨中反應，得到膦基鋰，再向其中加入溴化苄，經萃取可得到苄膦。^[3]另一種方法是將膦-氫混合物通入氫氧化鉀的DMSO溶液中，在85~90 °C滴加氯化苄，反應結束後經萃取等提純操作後可得到苄膦。^[4]

反應

苄膦和五氯化磷在乙醚中反應，可以得到P-苄基二氯化膦。^[5]它和四氫呋喃甲硼烷反應，得到1：1加合物苄膦甲硼烷。^[6]它和甲醛反應，得到二羥甲基苄膦。^[7]

參考文獻

^ Horner, Leopold; Hoffmann, Hellmut; Beck, Peter. Phosphorus organic compounds. XVI. Routes for the preparation of primary, secondary, and tertiary phosphines. Chemische Berichte, 1958. 91: 1583-1588. ISSN: 0009-2940.
^ Geoffrey T. Woolley, Sean L. Kitson, R. Gordon Reid. Synthesis of the myoview™ ligand, [bisphosphinoethane-1,2-14C]tetrofosmin. Journal of Labelled Compounds and Radiopharmaceuticals. 2007-04, 50 (5-6): 468–470 [2021-04-21]. doi:10.1002/jlcr.1199 （英語）.
^ Lambert Brandsma, Johanes A. van Doom, Robert-Jan de Lang, Nina K. Gusarova, Boris A. Trofimov. Cleavage of PP Bonds in Phosphorus. An Efficient Method for the Preparation of Primary Alkylphosphines. Mendeleev Communications. 1995-01, 5 (1): 14–15 [2021-04-21]. doi:10.1070/MC1995v005n01ABEH000438. （原始內容存檔於2018-06-09）（英語）.
^ S. F. Malysheva, V. A. Kuimov, B. G. Sukhov, N. K. Gusarova. Reduction of Arylmethyl Chlorides with a Phosphine-Hydrogen Mixture in the KOH-DMSO System. Russian Journal of General Chemistry. 2005-04, 75 (4): 658–659 [2021-04-21]. ISSN 1070-3632. doi:10.1007/s11176-005-0291-1 （英語）.
^ Alexander N. Tavtorkin, Sofia A. Toloraya, Eduard E. Nifant』ev, Ilya E. Nifant』ev. A new method for the synthesis of dichlorophosphines. Tetrahedron Letters. 2011-02, 52 (7): 824–825 [2021-04-21]. doi:10.1016/j.tetlet.2010.12.048. （原始內容存檔於2018-06-11）（英語）.
^ Marcela Hurtado, Manuel Yánez, Rebeca Herrero, Andrés Guerrero, Juan Z. Dávalos, José-Luis M. Abboud, Brahim Khater, Jean-Claude Guillemin. The Ever-Surprising Chemistry of Boron: Enhanced Acidity of Phosphine⋅Boranes. Chemistry - A European Journal. 2009-04-27, 15 (18): 4622–4629 [2021-04-21]. doi:10.1002/chem.200802307 （英語）.
^ Andreas Orthaber, Michael Karnahl, Stefanie Tschierlei, Daniel Streich, Matthias Stein, Sascha Ott. Coordination and conformational isomers in mononuclear iron complexes with pertinence to the [FeFe] hydrogenase active site. Dalton Trans. 2014, 43 (11): 4537–4549 [2021-04-21]. ISSN 1477-9226. doi:10.1039/C3DT53268B （英語）.

[1] Horner, Leopold; Hoffmann, Hellmut; Beck, Peter. Phosphorus organic compounds. XVI. Routes for the preparation of primary, secondary, and tertiary phosphines. Chemische Berichte, 1958. 91: 1583-1588. ISSN: 0009-2940.

[2] Geoffrey T. Woolley, Sean L. Kitson, R. Gordon Reid. Synthesis of the myoview™ ligand, [bisphosphinoethane-1,2-14C]tetrofosmin. Journal of Labelled Compounds and Radiopharmaceuticals. 2007-04, 50 (5-6): 468–470 [2021-04-21]. doi:10.1002/jlcr.1199 （英語）.

[3] Lambert Brandsma, Johanes A. van Doom, Robert-Jan de Lang, Nina K. Gusarova, Boris A. Trofimov. Cleavage of PP Bonds in Phosphorus. An Efficient Method for the Preparation of Primary Alkylphosphines. Mendeleev Communications. 1995-01, 5 (1): 14–15 [2021-04-21]. doi:10.1070/MC1995v005n01ABEH000438. （原始內容存檔於2018-06-09）（英語）.

[4] S. F. Malysheva, V. A. Kuimov, B. G. Sukhov, N. K. Gusarova. Reduction of Arylmethyl Chlorides with a Phosphine-Hydrogen Mixture in the KOH-DMSO System. Russian Journal of General Chemistry. 2005-04, 75 (4): 658–659 [2021-04-21]. ISSN 1070-3632. doi:10.1007/s11176-005-0291-1 （英語）.

[5] Alexander N. Tavtorkin, Sofia A. Toloraya, Eduard E. Nifant』ev, Ilya E. Nifant』ev. A new method for the synthesis of dichlorophosphines. Tetrahedron Letters. 2011-02, 52 (7): 824–825 [2021-04-21]. doi:10.1016/j.tetlet.2010.12.048. （原始內容存檔於2018-06-11）（英語）.

[6] Marcela Hurtado, Manuel Yánez, Rebeca Herrero, Andrés Guerrero, Juan Z. Dávalos, José-Luis M. Abboud, Brahim Khater, Jean-Claude Guillemin. The Ever-Surprising Chemistry of Boron: Enhanced Acidity of Phosphine⋅Boranes. Chemistry - A European Journal. 2009-04-27, 15 (18): 4622–4629 [2021-04-21]. doi:10.1002/chem.200802307 （英語）.

[7] Andreas Orthaber, Michael Karnahl, Stefanie Tschierlei, Daniel Streich, Matthias Stein, Sascha Ott. Coordination and conformational isomers in mononuclear iron complexes with pertinence to the [FeFe] hydrogenase active site. Dalton Trans. 2014, 43 (11): 4537–4549 [2021-04-21]. ISSN 1477-9226. doi:10.1039/C3DT53268B （英語）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]