2-(2-苯基偶氮)-1H-咪唑 | 34938-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-苯基偶氮)-1H-咪唑
• 英文名称: 2-(phenylazo)imidazole
• 英文别名: 2-(phenyldiazenyl)imidazole；2-(imidazoleazo) benzene；Pai-H；HaaiH；2-(Phenylazo)-1H-imidazole；1H-imidazol-2-yl(phenyl)diazene
• CAS: 34938-47-1
• 化学式: C₉H₈N₄
• 分子量: 172.189
• InChiKey: IWKTVWFSQDLTHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-(2-苯基偶氮)-1H-咪唑 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,3-dimethyl-2-(phenylazo)imidazolium iodide
  参考文献：
  名称：

  Mallick; Sarker; Saha, Journal of the Indian Chemical Society, 2011, vol. 88, # 12, p. 1817 - 1825

  摘要：

  DOI：
• 作为产物：
  描述：

  咪唑 、 苯胺 在 盐酸 、 sodium nitrite 、 sodium carbonate 作用下， 以 水 为溶剂， 以83.7%的产率得到2-(2-苯基偶氮)-1H-咪唑
  参考文献：
  名称：

  Properties and applications of designable and photo/redox dual responsive surfactants with the new head group 2-arylazo-imidazolium

  摘要：

  具有结构可扩展性和可逆响应光电刺激的2-芳基偶氮咪唑基咪唑表面活性剂，可用于溶胶-凝胶过程的进一步应用。

  DOI：

  10.1039/c6ra04448d

文献信息

• Syntheses and characterization of η5-cyclopentadienyl and η5-indenyl ruthenium(II) complexes of arylazoimidazoles: The molecular structure of the complex [(η5-C5H5)Ru(PPh3)(C6H5–N N–C3H3N2)]+
  作者：Padavattan Govindaswamy、Chittaranjan Sinha、Mohan Rao Kollipara

  DOI：10.1016/j.jorganchem.2005.04.042

  日期：2005.7

  R′ = CH3 (3), R = H, R′ = C2H5 (4), R = CH3, R′ = H (5), R, R′ = CH3 (6), R = CH3, R′ = C2H5 (7)}. The complex [(η5-C9H7)Ru(PPh3)2(CH3CN)]+ (8) undergoes reactions with a series of N,N-donor azo ligands in methanol yielding complexes of the type [(η5-C9H7) Ru(PPh3)(RaaiR′)]+ where R, R′ = H (9), R = H, R′ = CH3 (10), R = CH3, R′ = H (11), R = CH3, R′ = C2H5 (12)}, respectively. These complexes were characterized

  络合物[（η 5 -C 5 H ^ 5）的Ru（PPH 3）2 CL]（1）具有若干arylazoimidazole（RaaiR'）配位体，即发生反应，2-（苯偶氮基）咪唑（班派-H），1-甲基-2-（苯基偶氮）咪唑（Phai-Me），1-乙基-2-（苯基偶氮）咪唑（Phai-Et），2-（甲苯基）咪唑（Tai-H），1-甲基-2-（甲苯基基）咪唑（大-ME）和1-乙基-2-（tolylazo）咪唑（泰-ET），得到的类型的配合物[（η 5 -C 5 H ^ 5）的Ru（PPH 3）（RaaiR'）] + 其中R，R'= H（2），R = H，R'= CH 3（3），R = H，R'= C 2 H在图5（4）中，R ＝ CH 3，R′＝ H（5），R，R′＝ CH 3（6），R ＝ CH 3，R′＝ C 2 H 5（7）}。络合物[（η 5 -C 9 ħ 7）的Ru（PPH 3）2（CH
• Properties and applications of designable and photo/redox dual responsive surfactants with the new head group 2-arylazo-imidazolium
  作者：Changxu Lin、Long Yang、Mengchun Xu、Qi An、Zheng Xiang、Xiangyang Liu

  DOI：10.1039/c6ra04448d

  日期：——

  2-Arylazo-imidazolium grafted imidazolium surfactants with structural extensibility and reversible responsiveness to photo and electrochemical stimuli for further usage in a sol–gel process.

  具有结构可扩展性和可逆响应光电刺激的2-芳基偶氮咪唑基咪唑表面活性剂，可用于溶胶-凝胶过程的进一步应用。
• Photochromic Reaction of a Novel Room Temperature Ionic Liquid: 2-Phenylazo-1-hexyl-3-methylimidazolium Bis(pentafluoroethylsulfonyl)amide
  作者：Akio Kawai、Daiki Kawamori、Tomoo Monji、Tooru Asaka、Nobuyuki Akai、Kazuhiko Shibuya

  DOI：10.1246/cl.2010.230

  日期：2010.3.5

  We synthesized a new room temperature ionic liquid, [2PA-Hmim][Pf2N], and characterized the photochromic behavior by absorption spectroscopy. [2PA-Hmim][Pf2N] was found to be a photochromic liquid where solvent itself undergoes photochromic reaction.

  我们合成了一种新的室温离子液体[2PA-Hmim][Pf2N]，并通过吸收光谱法对其光致变色行为进行了表征。[2PA-Hmim][Pf2N]是一种光致变色液体，溶剂本身会发生光致变色反应。
• Arylazoimidazoliumchloride and chlorometallates: Spectroscopic and structural characterization
  作者：S. Halder、G. Saha、B.G. Chand、A.D. Jana、G. Mostafa、J. Cheng、T.-H. Lu、C. Sinha

  DOI：10.1016/j.ica.2010.02.006

  日期：2010.6

  Protonation or dialkylation of 2-(arylazo)imidazoles (RaaiH) has generated azoimidazolium motif (RaaiH(2)(+), RaaiR'H+, RaaiR(2)'(+) where R = H, CH3 and R' = Me, Et, -CH2Ph). Electrostatic attraction between imdazolium cation and counter ions like Cl, ZnCl42-, PtCl62- has generated hydrogen bonded azoimidazolium-chloride/chlorometallated networks. The single crystal X-ray structure of 1-benzyl-2-(phenylazo) imidazolium chloride shows tape like 1-D network of [Cl(H2O)(4)]. Aquated Cl forms 10 membered supracycle through hydrogen bonding with imidazolium ion. The X-ray structures of [HaaiMe(2) (1,3)](+)[Me2NH2](+) [ZnCl4](2) and [MeaaiH(2)(+)center dot H2O](2)[PtCl6](2) show hydrogen bonded chlorometallate chain penetrated into the channel developed by organic motif. Azoimidazolium units are associated through pi center dot center dot center dot pi and C-H center dot center dot center dot pi interactions to strengthen the supramolecular geometry. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis, structure, photochromism, mesogenic property and DFT computations of silver(I) complexes of long chain alkyl group containing 1-alkyl-2-(arylazo)imidazoles
  作者：Avijit Nandi、Chandana Sen、Suman Roy、Debasish Mallick、Randhir Sinha、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.poly.2014.04.066

  日期：2014.9

  The complexes [Ag(Raai-C-n,H2n+1)]ClO4 (where Raai-CnH2n+1 refer to 1-alkyl-2-(arylazo)imidazoles; R = H, Me and n = 4-22 (even numbers)) have been characterized by spectroscopic studies (UV-Vis, FT-IR, H-1 NMR). The X-ray structure of [Ag(Haai-C22H45)(2)]ClO4 confirms a distorted tetrahedral geometry. UV light irradiation (365-370 nm) of an acetonitrile solution of [Ag(Raai-CnH2n+1)(2)]ClO4 shows E-to-Z (trans-to-cis) isomerization of the coordinated Raai-CnH2n+1 group. The reverse transformation, Z-to-E (cis-to-trans), is very slow upon visible light irradiation, but becomes significantly faster on increasing the temperature (298-313 K). The rates and quantum yields (phi(E -> Z)) of the E-to-Z isomerization of the free ligands are higher than those of the complexes, which have proved the effect of rotor volume, rotor mass and the 1-alkyl chain length (-CnH2n+1)center dot[Ag(Haai-C18H37)(2)]ClO4 shows a metallomesogenic property and undergoes phase transitions: the Cr (46.7 degrees C) - SmC (106.4 degrees C) - I phase sequence on heating and I (106.4 degrees C) - SmA (46.4 degrees C) - Cr on cooling. The SmC phase appears as the typical fan-shaped texture. DFT computations on the optimized structure were carried out to explain the spectral properties. (C) 2014 Elsevier Ltd. All rights reserved.