diphenyl (4‐aminophenyl) phosphine | 33834-35-4

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenyl (4‐aminophenyl) phosphine
• 英文别名: 4-(diphenylphosphino)benzeneamine；(4-Aminophenyl)diphenylphosphine；(4-aminophenyl)diphenylphosphane；(p-aminophenyl)diphenylphosphine；4-(diphenylphosphino)benzenamine；diphenyl(4-aminophenyl)phosphine；4-(Diphenylphosphaneyl)aniline；4-diphenylphosphanylaniline
• CAS: 33834-35-4
• 化学式: C₁₈H₁₆NP
• 分子量: 277.305
• InChiKey: JRTOLVNURLQVBB-UHFFFAOYSA-N

物化性质

• 沸点：
  412.3±28.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  diphenyl (4‐aminophenyl) phosphine 在 双氧水 作用下， 以 乙醚 为溶剂， 生成 (4-aminophenyl)diphenylphosphine oxide
  参考文献：
  名称：

  Synthesis and Solid-State Structure of Substituted Arylphosphine Oxides

  摘要：

  We describe the preparation and characterization of several new arylphosphine oxides, which are of interest as second-order nonlinear optical materials, (4-Aminophenyl)diphenylphosphine oxide (la), bis(4-aminophenyl)phenylphosphine oxide (2a), and (4-aminophenyl)bis[4'-(trifluoromethyl)phenyl]phosphine oxide (5) were prepared by addition of aryl Grignard and organolithium reagents containing protected amines to phosphorus oxyhalides. Alternatively, 1a was prepared by treatment of (4-bromophenyl)diphenylphosphine oxide with azidomethyl phenyl sulfide, followed by hydrolysis. (4-Aminophenyl)(4'-nitrophenyl)phenylphosphine oxide (6) was prepared by nucleophilic aromatic substitution of bis(4-fluorophenyl)phenylphosphine oxide to give the corresponding dinitro compound, followed by selective mono-reduction. The X-ray crystal structure of (4-aminophenyl)diphenylphosphine oxide (1a), along with those of mono-, di-, and trihydroxy triphenylphosphine oxides 1b, 2b, and 3b, exhibit extensive intermolecular hydrogen bonding. The hydrogen bonding in 1a and 1b produces chains of arylphosphine oxide molecules with a head-to-tail alignment; the chains pack in an antiparallel manner to produce solid-state structures that display only slight deviations from centrosymmetry.

  DOI：

  10.1021/jo00116a042
• 作为产物：
  描述：

  二苯基膦 在 caesium carbonate 、 三乙胺 、 copper dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 17.0h， 生成 diphenyl (4‐aminophenyl) phosphine
  参考文献：
  名称：

  铜催化芳基卤化物与酰基膦偶联合成三芳基膦

  摘要：

  报道了使用酰基膦作为磷源的Cu 催化的 C(sp 2 )–P 键形成反应；以CuCl 2为催化剂，34个实例的芳基碘化物和芳基溴化物以良好至优异的产率转化为三芳基膦。对该机制进行了初步研究，发现不涉及自由基中间体。该反应是酰基膦在铜催化反应中应用的延伸，并显示了它们作为叔膦合成中的膦化试剂的潜力。

  DOI：

  10.1055/a-2067-4165

文献信息

• A practical synthesis of unsymmetrical triarylphosphines by heterogeneous palladium(0)-catalyzed cross-coupling of aryl iodides with diphenylphosphine
  作者：Zhaotao Xu、Pingping Wang、Qiurong Chen、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2018.04.018

  日期：2018.7

  The heterogeneous cross-coupling reaction of aryl iodides with diphenylphosphine was achieved in DMAc at 130 °C in the presence of 1.0 mol% of MCM-41-supported tridentate nitrogen palladium(0) complex [MCM-41-3N-Pd(0)] with KOAc as base, yielding a variety of unsymmetrical triarylphosphines in good to excellent yields. The turnover frequency (TOF) of the catalyst can reach 30.67 h−1. This new heterogeneous

  在1.0 mol％MCM-41负载的三齿氮钯（0）络合物[MCM-41-3N-Pd（0）用KOAc作为碱，可产生各种不对称的三芳基膦，收率良好至极佳。催化剂的周转频率（TOF）可以达到30.67h -1。这种新的多相钯（0）催化剂可以通过简单的方法轻松地从市售试剂中制备，并显示出与均相Pd（OAc）2或Pd（PPh 3）4相同的催化活性。可以通过过滤反应溶液进行回收，并循环至少七次而不会显着降低催化活性。
• An efficient heterogeneous cross-coupling of aryl iodides with diphenylphosphine catalyzed by copper (I) immobilized in MCM-41
  作者：Zhiqiang Fang、Mingzhong Cai、Yang Lin、Hong Zhao

  DOI：10.1002/aoc.4417

  日期：2018.8

  The heterogeneous cross‐coupling reaction of aryl iodides with diphenylphosphine was achieved in toluene at 115 °C in the presence of 10 mol% of phenanthroline‐functionalized MCM‐41‐supported copper (I) complex (Phen‐MCM‐41‐CuI) with Cs2CO3 as base, yielding various unsymmetric triarylphosphines in good to excellent yields. This protocol can tolerate a wide range of functional groups and does not need

  在10 mol％的邻菲咯啉官能化的MCM-41-负载的铜（I）络合物（Phen-MCM-41-CuI）和10 mol％的存在下，芳基碘化物与二苯膦的异质交叉偶联反应在115°C的甲苯中完成以Cs 2 CO 3为碱，以良好或优异的产率产生各种不对称的三芳基膦。该方案可以耐受各种官能团，不需要使用昂贵的添加剂或苛刻的反应条件。这种非均相的Cu（I）催化剂具有与均相CuI / Phen系统相同的催化活性，可以通过简单过滤反应溶液轻松回收，并循环使用七次而不会显着降低活性。
• Effect of triarylphosphane ligands on the rhodium-catalyzed hydrosilylation of alkene
  作者：Mei Xue、Jiayun Li、Jiajian Peng、Ying Bai、Guodong Zhang、Wenjun Xiao、Guoqiao Lai

  DOI：10.1002/aoc.3092

  日期：2014.2

  functionalized triarylphosphane ligands are characterized by a very high catalytic effectiveness for the hydrosilylation of alkene. Among these catalysts tested, RhCl3/diphenyl(2‐(trimethylsilyl)phenyl)phosphane (8a) exhibited excellent catalytic properties. Using this silicon‐containing phosphane ligand for the rhodium‐catalyzed hydrosilylation of styrene, both higher conversion of alkene and higher β‐adduct

  合成了一系列三芳基膦（1a，2a，3a，4a，5a，6a，7a，8a，9a，10a，11a）。（2-溴苯基）二苯基膦（1a）的X射线晶体结构分析明确证实了官能化膦的组成。RhCl 3催化苯乙烯与三乙氧基硅烷的硅氢化反应研究了三芳基膦。与经典的威尔金森氏催化剂相比，具有官能化三芳基膦配体的铑配合物的特征是对烯烃的氢化硅烷化具有很高的催化效率。在这些测试过的催化剂中，RhCl 3 /二苯基（2-（三甲基甲硅烷基）苯基）膦（8a）表现出优异的催化性能。使用这种含硅的膦配体进行铑的苯乙烯氢化硅烷化反应，与威尔金森催化剂相比，烯烃的转化率更高，β-加合物的选择性更高。版权所有©2014 John Wiley＆Sons，Ltd.
• Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation
  作者：Lu Zheng、Dan Zheng、Yanru Wang、Chengyuan Yu、Kun Zhang、Hua Jiang

  DOI：10.1039/c9ob01649j

  日期：——

  A series of chiral bisphosphine ligands were designed and synthesized based on single-handed quinoline oligoamide foldamers. The bisphosphine ligands can coordinate with Rh(cod)2BF4 in a 1 : 1 stoichiometry and the resulted chiral Rh(I) catalysts were applied in the asymmetric hydrogenation of α-dehydroamino acid esters, in which excellent conversions and promising levels of enantioselectivity were

  基于单手喹啉寡酰胺折叠剂设计和合成了一系列手性双膦配体。双膦配体可以以1：1的化学计量比与Rh（cod）2 BF 4配位，并将所得的手性Rh（I）催化剂用于α-脱氢氨基酸酯的不对称加氢中，其中出色的转化率和对映选择性水平很有希望实现了。
• SULFONE HYBRID PRECURSOR, METHOD OF SYNTHESIZING SAME, AND USES THEREOF
  申请人：Barboiu Mihail-Dumitru

  公开号：US20110190526A1

  公开（公告）日：2011-08-04

  The present invention relates to a novel sulfone hybrid precursor, to the synthesis method thereof, and to the uses thereof, particularly for preparing proton-exchanging electrolyte membranes as the functional hybrid charge in a host structure; for the manufacture of functional hybrid nanoparticles by sol-gel polymerization; for the use as a fluidifying agent; for the production of surface coverings through chemical grafting by means of sol-gel polymerization; for the use as a hygroscopic agent; and for the use as a bonding or structuring agent.

  本发明涉及一种新型砜杂化前体，其合成方法以及用途，特别是用于制备质子交换电解质膜作为宿主结构中的功能性杂化电荷；用于通过溶胶-凝胶聚合制备功能性杂化纳米颗粒；用作流变剂；通过溶胶-凝胶聚合化学嫁接制备表面覆盖层；用作吸湿剂；以及用作粘合剂或结构剂。