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1,1-双(二苯基膦)甲烷

1,1-双(二苯基膦)甲烷
IUPAC名
亚甲基双(二苯基膦)
识别
CAS号 2071-20-7  checkY
ChemSpider 67509
SMILES
 
  • P(c1ccccc1)(c2ccccc2)CP(c3ccccc3)c4ccccc4
InChI
 
  • 1/C25H22P2/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25/h1-20H,21H2
InChIKey XGCDBGRZEKYHNV-UHFFFAOYAH
性质
化学式 C25H22P2
摩尔质量 384.39 g·mol⁻¹
外观 白色粉末或晶体粉末
熔点 118-122 °C
溶解性 水中不溶
危险性
警示术语 R:36/37/38
安全术语 S:22-24/25
MSDS External MSDS
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

1,1-双(二苯基膦)甲烷(dppm)是一种具有分子式CH2(PPh2)2有机磷化合物。Dppm外观为白色粉末或晶体状粉末,常在无机化学或有机金属化学中充当配体。[1] 它是一种特异性的鳌合配体,因其可与中心金属原子(膦基)通过两个或更多的供体原子成键。

合成与活性

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1,1-双(二苯基膦)甲烷第一次合成是通过二苯基膦钠(Ph2PNa)与二氯甲烷合成的: [2]

Ph3P + 2 Na → Ph2PNa + NaPh
2NaPPh2 + CH2Cl2 → Ph2PCH2PPh2 + 2 NaCl

在dppm(尤其是其络合物)中的亚甲基(CH2)具有温和的酸性。配体可以进行氧化得到相应的氧化物和硫化物CH2[P(E)Ph2]2 (E = O, S)。在这些衍生物当中亚甲基的酸性更强。

参考文献

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  1. ^ Humphrey, Mark G.; Lee, Jeanne; Hockless, David C.R.; Skelton, Brian W.; & White, Allan H. Mixed-Metal Cluster Chemistry. Organometallics. 1993, 12 (3468): 3468. doi:10.1021/om00033a017. 
  2. ^ W. Hewertson and H. R. Watson. The preparation of di- and tri-tertiary phosphines. J. Chem. Soc. 1962, 12: 1490–1494. doi:10.1039/JR9620001490. 
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1,1-双(二苯基膦)甲烷
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