4-tert-butylthiophthalonitrile | 149548-78-7

• 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: 4-tert-butylthiophthalonitrile
• 英文别名: 4-Tert-butylsulfanylbenzene-1,2-dicarbonitrile
• CAS: 149548-78-7
• 化学式: C₁₂H₁₂N₂S
• 分子量: 216.307
• InChiKey: MJEKVEOTULGSAG-UHFFFAOYSA-N

物化性质

• 沸点：
  372.0±37.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-tert-butylthiophthalonitrile 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 C₃₈H₄₂N₆S₃
  参考文献：
  名称：

  不对称供体-π-受体型苯并氮杂-BODIPYs：简便的合成和比色性能

  摘要：

  新颖氮杂diisoindolylmethene及其BF 2 -chelating复合物（苯并稠合的氮杂- BODIPYs）大规模和从邻苯二甲腈以容易的方式合成吨丁醇钾-DMF溶液。在二氯甲烷中存在三氟乙酸（TFA）的情况下，独特的不对称供体-π-受体结构有助于BN键分离，从而导致颜色从红色急剧变为无色，最大吸收峰的色移超过250 nm。可以通过添加少量的质子接受溶剂或化合物来逆转这种比色过程。阿1 H和11乙NMR光谱研究，并且还密度泛函理论（DFT）计算表明，TFA诱导的B N键断裂可能会破坏BODIPY分子的整个π共轭，从而导致显着的比色行为。

  DOI：

  10.1002/anie.201501984
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 叔丁基硫醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以86%的产率得到4-tert-butylthiophthalonitrile
  参考文献：
  名称：

  烷基芳基硫醚与烷基化剂的烷基转移

  摘要：

  甲基碘与叔丁基苯硫在DMF中的反应导致烷基转移，生成甲基苯硫。通过1 H NMR光谱进一步研究了该烷基转移反应。溶剂的极性，硫原子上的电子密度以及烷基化剂（MeI，EtI，BuI，硫酸二甲酯或碳酸二甲酯）的强度在反应中起着重要作用。所建议的反应机理涉及形成二烷基芳基formation盐，该盐随后消除了该基团。观察到硫原子上具有更多支链烷基的化合物具有更高的转化率，从而支持了该机理，这可能导致形成更稳定的自由基。

  DOI：

  10.1016/j.tet.2017.12.039

文献信息

• Dolotova, O. V.; Bundina, N. I.; Derkacheva, V. M., Journal of general chemistry of the USSR, 1992, vol. 62, # 9, p. 1699 - 1708
  作者：Dolotova, O. V.、Bundina, N. I.、Derkacheva, V. M.、Negrimovskii, V. M.、Minin, V. V.、et al.

  DOI：——

  日期：——
• Dolotova, O. V.; Bundina, N. I.; Derkacheva, V. M., Journal of general chemistry of the USSR, 1992, vol. 62, p. 1699 - 1708
  作者：Dolotova, O. V.、Bundina, N. I.、Derkacheva, V. M.、Negrimovskii, V. M.、Minin, V. V.、et al.

  DOI：——

  日期：——
• Alkylthio-tetrasubstituted μ-Nitrido Diiron Phthalocyanines: Spectroelectrochemistry, Electrical Properties, and Heterojunctions for Ammonia Sensing
  作者：Zeynel Şahin、Rita Meunier-Prest、Fabienne Dumoulin、Ümit Işci、Marcel Bouvet

  DOI：10.1021/acs.inorgchem.9b02520

  日期：2020.1.21

  Alkylthio-tetrasubstituted mu-nitrido diiron phthalocyanine complexes are synthesized with n-butyl, iso-butyl, tert-butyl, and n-hexadecyl alkyl moieties. For the first time, a spectroelectrochemical investigation of mu-nitrido diiron phthalo-cyanines is achieved at all the redox steps. The complexes are stable in all their redox states, unlike their unsubstituted analogues. The interest of the present complexes is to prepare sensing devices by a solution processing method. Films are characterized by electronic absorption and Raman spectroscopies. Electrical measurements on resistors show the highly resistive behavior of these complexes, whatever the chain length. However, when combined with the lutetium bisphthalocyanine, an intrinsic semiconductor, these complexes form heterojunctions that exhibit a high sensitivity to ammonia, with a very good signal over noise ratio, at room temperature and under atmospheric conditions.
• Facile synthesis of phthalocyanine at low temperature with diisopropylamide anion as nucleophile
  作者：Wei Zheng、Cheng-Zhang Wan、Jing-Xuan Zhang、Cheng-Hui Li、Xiao-Zeng You

  DOI：10.1016/j.tetlet.2015.05.086

  日期：2015.7

  Phthalocyanine has been synthesized from phthalonitrile and lithium diisopropylamide (LDA) at ambient or even lower temperatures. In this novel, facile, and low reactant-consuming method, diisopropylamide anions work as nucleophile to initiate the low temperature reaction. The mechanism has been rationalized by density functional theory (DFT) calculation. Our method is also useful for the transformation of some phthalonitrile derivatives to phthalocyanine compounds. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis, characterization, conduction, and dielectric properties of tetra <i>tert</i>-butylsulfanyl substituted phthalocyanines
  作者：Saida Kaipova、Hatice Dinçer、Ahmet Altindal

  DOI：10.1080/00958972.2014.992340

  日期：2015.2.16

  The tert-butylsulfanylphthalonitrile has been prepared with optimized synthetic procedure. Metal free (H2Pc) and metallo phthalocyanines (Pcs) (ZnPc, CoPc, CuPc, PbPc) have been synthesized by cyclotetramerization of tert-butylsulfanylphthalonitrile in the presence of DBU and metal salts. Thus, tert-butylsulfanyl groups enhance the solubility, shift the Q band absorption to the red visible region, and inhibit efficient cofacial interaction of the Pcs (2-6) as evaluated by UV-vis spectra. The electrical conduction and dielectric properties of the synthesized Pc thin films sandwiched between indium tin oxide and aluminum electrodes (ITO-Pc-Al) were investigated from 300 to 500K. At low bias voltage the conduction is ohmic while at high bias voltage the conduction becomes space charge limited with an exponential distribution of traps. The measured ac conductivity data are discussed in terms of classical models based on pair approximation. It was found that the ac conductivity obeys the power law given by sigma(ac) = sigma(s)(0), in which the frequency exponent s decreases with temperature. The real and imaginary parts of the impedance are found to be dependent on both frequency and temperature.