2-(benzo[d]thiazol-2-yl)-4-nitrophenol | 6276-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(benzo[d]thiazol-2-yl)-4-nitrophenol
• 英文别名: 2-(2'-hydroxy-5'-nitrophenyl)benzothiazole；2-(2-Benzo[d]thiazolyl)-4-nitrophenol；2-(1,3-benzothiazol-2-yl)-4-nitrophenol
• CAS: 6276-77-3
• 化学式: C₁₃H₈N₂O₃S
• 分子量: 272.284
• InChiKey: NJTASTNGXOTNOF-UHFFFAOYSA-N

物化性质

• 熔点：
  219.1-219.6 °C
• 沸点：
  490.6±55.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(benzo[d]thiazol-2-yl)-4-nitrophenol 在 silica gel 、 三氟乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  A new series of D1‐A‐D2 type ESIPT‐TICT‐AIE active orange‐to‐red emissive unsymmetrical azines: Their all‐throughout mechanochemical synthesis and photophysical properties

  摘要：

  AbstractAzines are interesting compounds exhibiting aggregation‐induced‐emission (AIE) and twisted‐intramolecular‐charge‐transfer (TICT) properties that have exciting prospects in chemosensing and bioimaging applications. They commonly have symmetrical structures and there is no report on red‐emissive unsymmetrical azines. Herein, we report a novel class of orange‐to‐red emissive hydroxybenzothiazole(HBT)‐based unsymmetrical azines (BTDPA) with triple photophysical characteristics of ESIPT‐TICT‐AIE. The dyes were synthesized by an all‐throughout mechanochemical route in a sustainable way. They displayed D1‐A‐D2 character and fluoresce strongly both in organic solvents due to ESIPT and in the solid state by AIE via TICT. The incorporation of different electron‐withdrawing groups (EWGs) and electron‐donating groups (EDGs) at either HBT or diphenyl‐methylene moiety resulted in tunable fluorescence properties. The red‐emissive character was achieved by keeping EDG both at HBT (−OMe) and the diphenyl‐methylene moiety (−NMe2) (λem 680 nm). The dyes exhibited good quantum yields, large Stoke shifts (upto 293 nm) and were utilized in nitroaromatics and Cu2+ sensing.

  DOI：

  10.1002/asia.202300048
• 作为产物：
  描述：

  2-(3-nitrophenyl)benzothiazole 在 sodium persulfate 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以74%的产率得到2-(benzo[d]thiazol-2-yl)-4-nitrophenol
  参考文献：
  名称：

  Palladium catalyzed C_sp2–H activation for direct aryl hydroxylation: the unprecedented role of 1,4-dioxane as a source of hydroxyl radicals

  摘要：

  直接芳香族羟基化已通过使用多功能引导基团通过前所未有的1,4-二氧六环的羟基转移实现钯催化的Csp2-H活化。

  DOI：

  10.1039/c4cc06864e

文献信息

• Synthesis of bioactive 2-(2-(difluoromethoxy)aryl)benzo[d]thiazole derivatives via base-promoted one-pot process
  作者：Huiping Zeng、Puying Luo、Manling Luo、Hao Ding、Qiuping Ding

  DOI：10.1016/j.tet.2019.130472

  日期：2019.8

  A convenient synthesis of 2-(2-(difluoromethoxy)aryl)benzo[d]thiazoles from 2- (o-hydroxyaryl)benzothiazoles and commercially available ethyl difluoroiodoacetate (ICF2CO2Et) is described. The transformation was amenable to a one-pot, sequential three-component protocol from o-hydroxybenzaldehyde, o-aminothiophenol, and ICF2CO2Et promoted by KOH. Additionally, some of the prepared compounds exhibited

  描述了由2-（邻-羟基芳基）苯并噻唑和可商购的二氟碘乙酸乙酯（ICF 2 CO 2 Et）方便地合成2-（2-（二氟甲氧基）芳基）苯并[d]噻唑的方法。变换为适合于从一釜，顺序三组分协议ö羟基苯甲醛，ø -aminothiophenol，和ICF 2 CO 2的Et促进由KOH。另外，一些制备的化合物对人卵巢癌细胞显示出有希望的活性。
• A robust one-pot synthesis of benzothiazoles from carboxylic acids including examples with hydroxyl and amino substituents
  作者：Soraia Meghdadi、Mehdi Amirnasr、Peter C. Ford

  DOI：10.1016/j.tetlet.2012.10.035

  日期：2012.12

  The cyclocondensation of 2-aminothiophenol and carboxylic acids to give benzothiazoles has been carried out under mild conditions using tetrabutylammonium bromide (TBAB) as the reaction medium and triphenyl phosphite as the catalyst. Shorter reaction times, rapid isolation of the products, and excellent yields are advantages of this method. The reaction is found to be general and quite tolerant to

  已经在温和的条件下使用溴化四丁铵（TBAB）作为反应介质，并用亚磷酸三苯酯在2-氨基硫酚和羧酸的环缩合反应中生成苯并噻唑。该方法的优点是反应时间短，产物分离快，产率高。发现该反应是一般的，并且对取代的羧酸的性质相当宽容。
• 一种杂环类化合物及合成方法
  申请人：三峡大学

  公开号：CN106699777B

  公开（公告）日：2019-01-15

  本发明属于有机化工技术领域，特别是一种新型杂环化合物，所述杂环化合物的化学结构式为：其中，取代基R1和R2为氢或烷基或硝基或卤素或醛基，取代基位置、个数不固定。合成方法为以苯并噻唑类衍生物、溴化腈和碱一步法、无催化剂，得到的一类新型杂环化合物化合物，关键点在于一步法、无催化剂和温和反应条件的合成新方法，又因其杂环结构，有利于在生物体内活性的应用。
• Facile synthesis of novel [1,3]oxazino[2,3-c][1,2,4] thiadiazin-12-one derivatives
  作者：Jiaying Yan、Yang Zhou、Nuonuo Zhang、Hui Chen、Xiafeng He、Shuzhang Xiao、Kaibo Zheng

  DOI：10.1007/s11164-017-2934-3

  日期：2017.10

  Several novel fused heterocyclic systems which have rings containing N/O or N/S have been synthesized through a facile one-pot method by the treatment of substituted 2-(benzo[d]thiazol-2-yl)phenol and cyanogen bromide in THF and NEt3. This one-pot method contains tough ring-opening of thiazole, special intermolecular rearrangement and ring-closing reactions. The newly synthesized compounds were characterized

  通过简便的一锅法，通过在THF中处理取代的2-（苯并[d]噻唑-2-基）苯酚和溴化氰，合成了几种具有含N / O或N / S环的新颖稠合杂环系统和NEt 3。这种一锅法包含噻唑的强力开环，特殊的分子间重排和闭环反应。通过HR-MS，1 H-NMR，13 C-NMR光谱数据和DFT计算分析对新合成的化合物进行了表征。还通过X射线晶体学分析确定了2a。
• Regioselective ortho-hydroxylation of 2-arylbenzothiazole via substrate directed C–H activation
  作者：Arghya Banerjee、Anupam Bera、Srimanta Guin、Saroj Kumar Rout、Bhisma K. Patel

  DOI：10.1016/j.tet.2012.12.067

  日期：2013.3

  An efficient protocol has been developed for the direct ortho-hydroxylation of 2-arylbenzothiazole using Pd(OAc)2 as the catalyst and either of DIB/AcOH or Oxone®/TFA combinations under air atmosphere. Under both these conditions, the methodology tolerates a diverse array of substituents giving good to excellent yields of corresponding ortho-hydroxylated products. Regioselective hydroxylation is observed

  一种有效的协议已用于直接被开发邻的羟基化2- arylbenzothiazole使用Pd（OAc）2作为催化剂和任一的DIB / AcOH中或过硫酸氢钾® / TFA在空气气氛下的组合。在这两种条件下，该方法都能耐受各种各样的取代基，从而使相应的邻羟基化产物的收率极佳。在苯环的间位位置具有取代基的苯环的较少空间位阻的位点观察到区域选择性羟基化。