3-(4-氯苯基)-1H-吡唑-4-甲醛 | 350997-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-氯苯基)-1H-吡唑-4-甲醛
• 中文别名: 3-(4-氯-苯基)-1H-吡唑-4-甲醛；吡唑-4-甲醛,3-(4-氯苯基)-；3-(4-氯苯基)-2H-吡唑-4-甲醛
• 英文名称: 3-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-(4-chlorophenyl)pyrazole-4-aldehyde；5-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde
• CAS: 350997-67-0
• 化学式: C₁₀H₇ClN₂O
• mdl: MFCD01993678
• 分子量: 206.631
• InChiKey: XSFZGZIGMMWQKR-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C(Solv: water (7732-18-5))
• 沸点：
  445.0±35.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933199090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-(4-Chloro-phenyl)-1h-pyrazole-4-carbaldehyde
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 3-(4-Chloro-phenyl)-1h-pyrazole-4-carbaldehyde
CAS number: 350997-67-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H7ClN2O
Molecular weight: 206.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(4-氯苯基)-1H-吡唑-4-甲醛 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 34.0h， 生成 4-(((3-(4-chlorophenyl)-1H-pyrazol-4-yl)methylene)amino)-2-((diphenylamino)methyl)-5-((o-tolyloxy)methyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Hep G2细胞中一些新的Schiff和Mannich碱基的合成，表征和体外细胞毒性

  摘要：

  合成了一系列的5-取代的4-氨基-3-巯基-1,2,4-三唑，并用各种3-取代的吡唑醛进行处理，以获得一系列新的席夫碱（3a – l）。在乙醇介质中（4a – e，5a – e），在甲醛存在下，通过与二苯胺/吗啉反应，很少有选定的席夫碱转化为曼尼希碱。这些新合成的化合物通过元素分析，IR，NMR和质谱研究进行了表征。使用MTT分析法对HepG2细胞中几种选定的Schiff和Mannich碱基的细胞毒性活性进行了比较研究。很少有经过筛选的希夫碱3a，3d，3e，3g和3h表现出剂量依赖性的细胞毒性活性，与标准药物阿霉素相比，3a最有效，IC 50值为0.018 g / l。在曼尼希碱中，5b活性最高，IC 50值为0.034 g / l。与衍生自其的曼尼希碱相比，席夫碱的活性更高。吗啉衍生的曼尼希碱比从二苯胺获得的碱更有效。

  DOI：

  10.1007/s00044-010-9433-z
• 作为产物：
  描述：

  p-chloroacetophenone semicarbazone 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-(4-氯苯基)-1H-吡唑-4-甲醛
  参考文献：
  名称：

  （Z）-5-（（3-苯基-1H-吡唑-4-基）亚甲基）-2-硫代噻唑烷酮-4-一衍生物的合成及抗菌性能评价。

  摘要：

  背景技术对现有抗微生物剂的致病性耐药性的惊人增加是一个严重的问题，并且这些细菌感染的治疗正变得越来越具有挑战性。因此，迫切需要开发新型抗微生物剂。目的作为我们正在进行的新型抗菌剂研究的一部分，一系列（Z）-5-（（3-苯基-1H-吡唑-4-基）亚甲基）-2-的合成和抗菌活性在这项研究中将讨论噻吩并噻唑烷-4-酮衍生物。方法设计，合成（Z）-5-（（3-苯基-1H-吡唑-4-基）亚甲基）-2-硫代噻唑烷酮-4-一衍生物，并评价其抗菌活性。通过IR，1 H NMR，13 C NMR和质谱确认结构。使用96孔微量滴定板和系列稀释方法在体外评估所有合成的化合物，以获得对多种不同菌株（包括耐多药临床分离株）的最低抑菌浓度（MIC）值。结果体外抗菌测试表明，系列7和9中的大多数化合物对厌氧菌（变形链球菌）菌株均表现出显着的抑制活性，MIC值为1 µg / mL。化合物7c和9c对MRSA的活性最高（3

  DOI：

  10.2174/1573406412666160822160156

文献信息

• Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities
  作者：Wang Wang、Liangliang Xiong、Yutong Li、Zhuorui Song、Dejuan Sun、Hua Li、Lixia Chen

  DOI：10.1016/j.bmc.2022.116627

  日期：2022.2

  derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated that compound 23d exhibited excellently inhibitory activity on LPS-induced NO production in RAW264.7 cells (IC50 = 0.38 ± 0.18 μM). The preliminary structure–activity relationships (SARs) suggested

  作为我们正在进行的二萜衍生化工作，基于组合原理设计和合成了三个系列的二萜衍生物，包括吡唑、噻唑和呋喃部分。生物学评估表明，化合物23d对 LPS 诱导的 RAW264.7 细胞中的 NO 产生具有极好的抑制活性（IC 50  = 0.38 ± 0.18 μM）。初步构效关系 (SARs) 表明，苯磺酰基取代的呋喃部分具有最强的提高 lathyrane 二萜类化合物抗炎活性的能力。此外，化合物23d显着降低 ROS 水平。其分子机制与抑制Nrf2/HO-1通路的转录激活有关。基于这些考虑，23d可能是一种很有前途的抗炎剂，值得进一步探索。
• Design, synthesis and biological activities of 2,3-dihydroquinazolin-4(1H)-one derivatives as TRPM2 inhibitors
  作者：Han Zhang、Huan Liu、Xiao Luo、Yuxi Wang、Yuan Liu、Hongwei Jin、Zhenming Liu、Wei Yang、Peilin Yu、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.ejmech.2018.04.045

  日期：2018.5

  temperature sensor. However, few TRPM2 inhibitors have been reported, especially TRP-subtype selective inhibitors, which hampers the investigation and validation of TRPM2 as a drug target. To discover novel TRPM2 inhibitors, 3D similarity-based virtual screening method was employed, by which 2,3-dihydroquinazolin-4(1H)-one derivative H1 was identified as a TRPM2 inhibitor. A series of novel 2,3-dihydroquinazolin-4(1H)-one

  瞬态受体电位褪黑素2（TRPM2），可透过Ca2 +的阳离子通道，在胰岛素释放，细胞因子生成，体温调节和细胞死亡中起着关键作用，成为活性氧（ROS）和温度传感器。但是，很少有TRPM2抑制剂的报道，特别是TRP亚型选择性抑制剂，这阻碍了TRPM2作为药物靶标的研究和验证。为了发现新型TRPM2抑制剂，采用了基于3D相似性的虚拟筛选方法，将2,3-二氢喹唑啉-4（1H）-一衍生物H1鉴定为TRPM2抑制剂。随后合成和表征了一系列新颖的2,3-二氢喹唑啉-4（1H）-one衍生物。通过钙成像和电生理方法评估了它们对TRPM2通道的抑制活性。一些化合物表现出显着的抑制活性，尤其是D9，它对TRPM2的IC50为3.7μM，并且不影响TRPM8通道。总结的结构活性关系（SAR）为进一步开发特定TRPM2靶向抑制剂提供了宝贵的见识。
• Synthesis and antitubercular and antibacterial activity of some active fluorine containing quinoline–pyrazole hybrid derivatives
  作者：Nagabhushana Nayak、Jurupula Ramprasad、Udayakumar Dalimba

  DOI：10.1016/j.jfluchem.2016.01.011

  日期：2016.3

  Mycobacterium tuberculosis and antibacterial activity against three common pathogenic bacterial strains. Four derivatives (8b, 8c, 8j and 8o) displayed significant antitubercular activity. The compounds derived from 8-trifluoromethylquinoline and 6-fluoroquinoline scaffolds with halogen substitution on the pyrazole ring exhibited superior inhibition activity than corresponding 6-methoxyquinoline analogs.

  为了开发出新的抗结核和抗菌药物以抵抗不断增加的细菌耐药性，我们采用分子杂交方法设计了新的喹啉-吡唑类似物（8a – u）。通过单晶X射线衍射（SC-XRD）分析清楚地证实了最终化合物之一8a的结构。评价目标化合物对结核分枝杆菌的抗结核活性和对三种常见致病细菌菌株的抗菌活性。四个导数（8b，8c，8j和8o）具有明显的抗结核活性。衍生自在吡唑环上具有卤素取代基的8-三氟甲基喹啉和6-氟喹啉骨架的化合物表现出比相应的6-甲氧基喹啉类似物更好的抑制活性。细胞毒性研究表明，活性化合物对正常Vero细胞系无毒，选择性指数值≥10，表明这些化合物适用于进一步的药物开发。的在计算机芯片上的分子对接研究表明用的靶酶（INHA，CYP121和TMPK）化合物的强的结合亲和力的结核分枝杆菌。此外，化合物8b，8c，8d和8g的体外抗菌活性 与参考药物环丙沙星相当。
• Synthesis of 3-Substituted Arylpyrazole-4-carboxylic Acids
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、E. A. Kovaleva、O. L. Ustinova、I. B. Kozhevnikov

  DOI：10.1007/s11176-005-0318-7

  日期：2005.5

  3-aryl-substituted pyrazole-4-carboxylic acids, involving Vilsmeier formylation of semicarbazones of 26 available mono- and disubstituted acetophenones and 2-acetylthiophene followed by oxidation of the resulting 3-aryl-substituted pyrazole-4-carboxaldehydes under the action of potassium permanganate. The mechanism of the formylation reaction is discussed. The method successfully works even with acetophenones

  提出了一种制备以前未知的3-芳基取代的吡唑-4-羧酸的方法，该方法包括将26种可用的单和双取代的苯乙酮和2-乙酰基噻吩的半咔唑的Vilsmeier甲酰化，然后氧化所得的3-芳基取代的吡唑-。 4-羧醛在高锰酸钾的作用下。讨论了甲酰化反应的机理。该方法即使对含有烷基取代基的苯乙酮也能成功地起作用。在后一种情况下，使用另外的步骤，该步骤涉及分离吡唑-4-羧酸作为其甲硅烷基酯。
• Synthesis and Biological Evaluation of Some Pyrazole Derivatives, Containing (Thio) Semicarbazide, as Dual Anti-Inflammatory Antimicrobial Agents
  作者：Zhaochang Liang、Yuping Huang、Shiben Wang、Xianqing Deng

  DOI：10.2174/1570180816666190325163117

  日期：2019.9.11

  Background: Several series of pyrazole derivatives containing (thio) semicarbazide (4a-4h, 5a-5l, 6a-6f, 7a-7c) were designed and synthesized to screen dual inflammatory and antimicrobial activities. Methods: The products were characterized by1H NMR, 13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their antiinflammatory activity. Their

  背景：设计并合成了一系列含有（硫）氨基脲（4a-4h，5a-5l，6a-6f，7a-7c）的吡唑衍生物，以筛选双重炎症和抗菌活性。 方法：通过1 H NMR，13 C NMR和HRMS对产物进行表征。用体外LPS诱导的TNF-α模型和体内二甲苯诱导的耳水肿模型评估其抗炎活性。使用系列稀释法针对几种革兰氏阳性菌株，革兰氏阴性菌株和真菌菌株评估了它们的体外抗菌活性。 结果：生物测定表明，大多数化合物在浓度为20 µg / mL时均可显着抑制TNF-α的表达。化合物5i，6b和7b在50 mg / mL剂量下具有与参考药物地塞米松相当的体内抗炎活性。公斤。此外，几种化合物对不同菌株显示出抗菌活性，化合物5g和5h分别显示对肺炎链球菌CMCC 31968和金黄色葡萄球菌CMCC 25923的有效抑菌活性，MIC值为8 µg / mL。同时具有抗炎和抗微生物活性的化合物7b，应按原样或在衍生后进行研究。