2-iodo-N,N,N',N'-tetramethyl-1,4-benzenediamine | 153969-81-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-iodo-N,N,N',N'-tetramethyl-1,4-benzenediamine
• 英文别名: 2-iodo-N,N,N',N'-tetramethyl-1,4-phenylenediamine；2-iodo-N,N,N',N'-tetramethylbenzene-1,4-diamine；2-iodo-1-N,1-N,4-N,4-N-tetramethylbenzene-1,4-diamine
• CAS: 153969-81-4
• 化学式: C₁₀H₁₅IN₂
• 分子量: 290.147
• InChiKey: YRCJIACTNLUCNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  336.0±32.0 °C(Predicted)
• 密度：
  1.547±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-iodo-N,N,N',N'-tetramethyl-1,4-benzenediamine 在 palladium on activated charcoal palladium diacetate 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 0.33h， 生成 2-(3-aminopropyl)-N,N,N',N'-tetramethyl-1,4-benzenediamine
  参考文献：
  名称：

  Donor−σ−Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor

  摘要：

  Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make the system tractable and provides a lipophilic region suitable for promoting Langmuir-Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene, tetramethylphenylenediamine, phenyl) through a short alkyl sigma bridge. Features of the H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.

  DOI：

  10.1021/jo035409w
• 作为产物：
  描述：

  聚合甲醛 、 2-碘-1,4-苯二胺 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 以57%的产率得到2-iodo-N,N,N',N'-tetramethyl-1,4-benzenediamine
  参考文献：
  名称：

  Donor−σ−Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor

  摘要：

  Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make the system tractable and provides a lipophilic region suitable for promoting Langmuir-Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene, tetramethylphenylenediamine, phenyl) through a short alkyl sigma bridge. Features of the H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.

  DOI：

  10.1021/jo035409w

文献信息

• Magnetic Properties of CT Complexes between 2,2″,5,5″-Tetrakis(dimethylamino)terphenyls and TCNQF₄
  作者：Yosuke Nakamura、Hiizu Iwamura

  DOI：10.1246/bcsj.66.3724

  日期：1993.12

  2,2″,5,5″-Tetrakis(dimethylamino)-p- and m-terphenyls (1 and 2), in which two N,N,N′,N′-tetramethyl-p-phenylenediamine (TMPD) moieties are linked through p- and m-phenylene units, respectively, were synthesized, and their CT complexes with TCNQF4 were prepared. In the complexes, 1 and 2 possess two S = 1/2 spins per molecule. The intramolecular interaction between the spins of the two TMPD moieties was found to be antiferromagnetic (2J/k = −42 K) in 1, and ferromagnetic (2J/k = 240 K) in 2.

  合成了 2,2″,5,5″-四（二甲基氨基）-对和间三联苯（1 和 2），其中两个 N,N,N′,N′-四甲基对苯二胺（TMPD）分子分别通过对和间三联苯单元连接，并制备了它们与 TCNQF4 的 CT 复合物。在复合物中，1 和 2 每个分子具有两个 S = 1/2 自旋。在 1 中，两个 TMPD 分子的自旋之间的分子内相互作用是反铁磁性的（2J/k = -42 K），而在 2 中则是铁磁性的（2J/k = 240 K）。
• Photochromism of a diarylethene charge-transfer complex: photochemical control of intermolecular charge-transfer interaction
  作者：Masakazu Morimoto、Seiya Kobatake、Masahiro Irie

  DOI：10.1039/b604388g

  日期：——

  A diarylethene derivative bearing a phenylenediamine group formed radical ions with an electron acceptor molecule in solution, and the concentration of the radical ions was modulated by the photochromic reaction of the diarylethene, reflecting the difference in the electron-donating character between the open- and closed-ring isomers.

  含有苯二胺基团的二芳基噻吩衍生物在溶液中与电子受体分子形成自由基离子，自由基离子的浓度受二芳基噻吩光致变色反应的调节，这反映了开环异构体和闭环异构体在电子供体性质上的差异。
• Donor−σ−Acceptor Molecules Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor
  作者：Lyle D. Wescott、Daniell Lewis Mattern

  DOI：10.1021/jo035409w

  日期：2003.12.1

  Donor-sigma-acceptor-lipid molecules were prepared by using perylenetetracarboxylic diimide as the acceptor, starting from perylenetetracarboxylic dianhydride. One imide nitrogen was attached to a "swallowtail" lipid (a long alkyl tail connected at midchain), which imparts enough solubility to make the system tractable and provides a lipophilic region suitable for promoting Langmuir-Blodgett monolayer formation. The other imide link was to a donor group (pyrene, ferrocene, tetramethylphenylenediamine, phenyl) through a short alkyl sigma bridge. Features of the H-1 and C-13 NMR spectra of swallowtailed perylenediimides are interpreted as resulting from restricted rotation about the imide C-N bond; the C-13 NMR spectra and stereochemistry of these molecules are contrasted with the case of the related bis-(2,5-di-tert-butylphenyl)perylenetetracarboxylic diimide.