1-(4-羧基苯基)-1H-吡唑-3-羧酸 | 72899-92-4

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4-羧基苯基)-1H-吡唑-3-羧酸
• 英文名称: 1-(4-carboxyphenyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 1H-Pyrazole-3-carboxylic acid, 1-(4-carboxyphenyl)-；1-(4-carboxyphenyl)pyrazole-3-carboxylic acid
• CAS: 72899-92-4
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: PAUMWDAXVWCUOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  499.0±25.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

应用

1-(4-羧基苯基)-1H-吡唑-3-羧酸用作有机合成中间体和医药中间体，主要用于实验室研发过程和化工生产过程中。

反应信息

• 作为反应物：
  描述：

  cadmium(II) nitrate tetrhydrate 、 1-(4-羧基苯基)-1H-吡唑-3-羧酸 在 N-甲基吡咯烷酮 作用下， 以 水 为溶剂， 生成 [Cd₂L₂(H₂O)₄]·3H₂O
  参考文献：
  名称：

  A dual‐function Cd‐based coordination polymer for the detection of moxifloxacin and SiO32− ions

  摘要：

  A 1D coordination polymer (CP) [Cd2L2(H2O)4] ⋅ 3H2O (1) was prepared by solvothermal method using 1‐(4‐carboxyphenyl)‐1H‐pyrazole‐3‐carboxylic acid (H2L) as single ligand. Fluorescence sensing experiments show that 1 has dual‐function specific recognition ability for moxifloxacin (MXF) and silicate (SiO32−), which can be used as the turn‐off sensing material for their detection. When 1 specifically identifies MXF, the Ksv is as high as 6.46×105 M−1 (6–20 μM) and the limit of detection (LOD) is as low as 14 nM. 1 is the second example of a CP‐based fluorescent probe for the detection of MXF, which has confirmed that the Ksv is the largest to date for the detection of MXF, with a detection sensitivity increase of more than three times. For SiO32− ions detection, the fluorescence intensity ratio has a good linear correlation with the concentration of SiO32− ions in the concentration range of 0–100 μM, with a slope of 1.33×104 M−1, and the LOD is as low as 0.68 μM. According to the reported literature, 1 is the only example of SiO32− ions sensing by CP‐based fluorescence sensor so far. In order to better understand the sensing phenomenon, we also discussed the sensing mechanism for MXF and SiO32− ions.

  DOI：

  10.1002/ejic.202300711

文献信息

• A Coordination Polymer for the Fluorescence Turn-On Sensing of Saccharin, 2-Thiazolidinethione-4-carboxylic Acid, and Periodate
  作者：Shan Zhu、Qicheng Wang、Xiaomei Wang、Jiajun Pan、Tao Yang、Xinhui Zhou、Hongping Xiao、Yujian You

  DOI：10.1021/acs.inorgchem.3c02552

  日期：2023.10.9

  A luminescent 1D coordination polymer (CP) [Zn2L2(H2O)4]·H2O (1, H2L = 1-(4-carboxyphenyl)-1H-pyrazole-3-carboxylic acid) was prepared by a solvothermal method. 1 shows excellent fluorescence properties and has an obvious fluorescence “turn-on” phenomenon for saccharin (SAC), 2-thiazolidinethione-4-carboxylic acid (TTCA), and periodate (IO4–). Between 0 and 60 μM concentration range of SAC, the fluorescence

  发光一维配位聚合物(CP) [Zn 2 L 2 (H 2 O) 4 ]·H 2 O ( 1 , H 2 L = 1-(4-羧基苯基)-1 H-吡唑-3-羧酸)采用溶剂热法制备。图1显示了优异的荧光性能，对糖精（SAC）、2-噻唑烷硫酮-4-羧酸（TTCA）和高碘酸盐（IO 4 –）具有明显的荧光“开启”现象。在SAC的0至60 μM浓度范围内， 1的荧光增强效率( K EC )达到1.00 × 10 5 M –1，检测限(LOD)为90 nM。1是第一个用于SAC检测的CP基传感材料。对于TTCA检测，在25-80 μM浓度范围内，K EC为2.73 × 10 5 M –1 ，LOD为33 nM，是目前检测TTCA的传感器中最低的LOD。对于IO 4 -离子检测，当IO 4 -离子浓度范围为0至10 μM时，K EC为2.34 × 10 5 M –1，LOD低至39 nM。为了更好地理解传感现象，我们还详细讨论了
• Introduction of Organic Dyes into Cadmium(II) MOF for Tunable Light Emission and Highly Sensitive Probing Antibiotics
  作者：Haozhen Wu、Guo‐Ping Yang、Yao‐Yu Wang

  DOI：10.1002/ejic.202400101

  日期：2024.7

  This work focuses on the design of a new highly stable dye@MOF fluorescence materials for tunable light emission and highly sensitive detection of metronidazole (MDZ) and dimetronidazole (DMZ) by encapsulating dyes in Cd(II) MOFs through post-synthesis modification (PSM). The luminescent dyes rhodamine B (RhB) and fluorescein (FL) were selected based on the excellent optical and electronic properties

  本工作重点是通过后合成修饰（PSM）将染料封装在 Cd(II) MOF 中，设计一种新型高度稳定的染料@MOF 荧光材料，用于可调光发射和高灵敏度检测甲硝唑 (MDZ) 和二甲硝唑 (DMZ) ）。基于优异的光学和电子性能，选择了发光染料罗丹明 B (RhB) 和荧光素 (FL)。
• A highly selective Cd‐based metal‐organic framework fluorescent probe for rapid recognition of cephalothin in water
  作者：Qicheng Wang、Shan Zhu、Zhenqi Tan、Yue Quan、Yufen Li、Tao Yang、Xinhui Zhou、Yujian You、Ru Wang

  DOI：10.1002/aoc.7557

  日期：2024.7

  Nowadays, the problem of antibiotic pollution in the water environment is becoming more and more serious, which has caused great harm to human health and the circulatory system. Therefore, it is extremely crucial to design an effective and sensitive method for the recognition of antibiotics in water. In this research, 1‐(4‐carboxyphenyl)‐1H‐pyrazole‐3‐carboxylic acid (H2L) was used as a ligand to prepare a luminescent two‐dimensional (2D) metal–organic framework (MOF), CdL·H2O (1). 1 can specifically recognize antibiotic cephalothin (CET) in aqueous environments through a fluorescence‐enhanced response, which demonstrated a favorable linear correlation between the fluorescence intensities of 1 and the concentrations of CET (0–50 μM) with a linear fluorescence enhancement slope KEC value of 5.4750 × 104 M−1 and a limit of detection (LOD) of 165 nM. The fast response, good selectivity, anti‐interference ability, and reusability for CET recognition were also verified. 1 represents the inaugural MOF‐based fluorescent material designed for the recognition of CET. Additionally, the detection mechanism for CET was explored in detail with a view to better understanding the fluorescence sensing process.