1-(4-氯苯基)吡唑-4-甲醛 | 63874-99-7

• 物质功能分类: 有机原料 - 醛类化合物
• 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-氯苯基)吡唑-4-甲醛
• 中文别名: 1-(4-氯苯基)-1H-吡唑-4-甲醛；N-(4-氯苯基)-吡唑-4-甲醛
• 英文名称: 1-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde
• 英文别名: 1-(4-chlorophenyl)pyrazole-4-carbaldehyde
• CAS: 63874-99-7
• 化学式: C₁₀H₇ClN₂O
• mdl: MFCD07643175
• 分子量: 206.631
• InChiKey: VZQVRKCGPMBZQL-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C(Solv: ethanol (64-17-5))
• 沸点：
  339.1±22.0 °C(Predicted)
• 密度：
  1.30±0.1 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：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090
• 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
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(4-Chlorophenyl)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: 1-(4-Chlorophenyl)pyrazole-4-carbaldehyde
CAS number: 63874-99-7

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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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
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：

  1-(4-氯苯基)吡唑-4-甲醛 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.25h， 生成 ethyl 2-((1-(4-chlorophenyl)-1H-pyrazol-4-yl)methoxy)acetate
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new N-phenylpiperazine derivatives designed as homologues of the antipsychotic lead compound LASSBio-579

  摘要：

  In an attempt to increase the affinity of our antipsychotic lead compound LASSBio-579 (1-((1-(4-chlorophenyl)-1H-pyrazol-4-yl)methyl)-4-phenylpiperazine; (2)) for the 5-HT2A receptor, we synthesized five new N-phenylpiperazine derivatives using a linear synthetic route and the homologation strategy. The binding profile of these compounds was evaluated for a series of dopaminergic, serotonergic and alpha-adrenergic receptors relevant for schizophrenia, using classical competition assays. Increasing the length of the spacer between the functional groups of (2) proved to be appropriated since the affinity of these compounds increased 3-10-fold for the 5-HT2A receptor, with no relevant change in the affinity for the D-2-like and 5-HT1A receptors. A GTP-shift assay also indicated that the most promising derivative (1-(4-(1-(4-chlorophenyl)-1H-pyrazol-4-yl) butyl)-4-phenylpiperazine) (LASSBio-1635) (6) has the expected efficacy at the 5-HT2A receptors, acting as an antagonist. Intraperitoneal administration of (6) prevented apomorphine-induced climbing behavior and ketamine-induced hyperlocomotion in mice, in a dose dependent manner. Together, these results show that (6) could be considered as a new antipsychotic lead compound. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.027
• 作为产物：
  描述：

  对氯苯肼盐酸盐 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 13.25h， 生成 1-(4-氯苯基)吡唑-4-甲醛
  参考文献：
  名称：

  PROTEOSTASIS REGULATORS

  摘要：

  本发明涉及具有化学式(Ia-Ie)、(II)、(IIIa-IIId)、(IVa-IVc)、(Va-Vb)、(VIa-VIe)、(VII)、(VIIIa-VIIIc)和(IX)的化合物，以及这些化合物的药用可接受盐、前药和溶剂合物，以及这些化合物的任何组合物，并且用于治疗与蛋白质稳态功能紊乱相关的疾病的方法，包括有效量的这些化合物。

  公开号：

  US20120316193A1

文献信息

• Electrophotocatalytic S _N Ar Reactions of Unactivated Aryl Fluorides at Ambient Temperature and Without Base
  作者：He Huang、Tristan H. Lambert

  DOI：10.1002/anie.201909983

  日期：2020.1.7

  The electrophotocatalytic SN Ar reaction of unactivated aryl fluorides at ambient temperature without strong base is demonstrated.

  证明了在室温下没有强碱的未活化芳基氟化物的电光催化SN Ar反应。
• Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
  作者：He Huang、Zack M. Strater、Michael Rauch、James Shee、Thomas J. Sisto、Colin Nuckolls、Tristan H. Lambert

  DOI：10.1002/anie.201906381

  日期：2019.9.16

  electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron

  可见光光催化和电催化是促进化学反应的两种强大策略。在这里，这两种模式结合在电光催化氧化平台中。该化学过程采用三氨基环丙烯 (TAC) 离子催化剂，通过电化学氧化形成环丙烯自由基阳离子中间体。自由基阳离子在可见光下进行光激发，产生具有氧化能力（3.33 V vs. SCE）的激发态物质，足以通过单电子转移（SET）氧化苯和卤代苯，从而导致 CH/NH 与唑类偶联。提供了光激发物质的强氧化行为的基本原理，同时通过顺式2,6-二甲基哌啶部分的特定构象合理化了催化剂的稳定性。
• Neladenoson Bialanate Hydrochloride: A Prodrug of a Partial Adenosine A₁Receptor Agonist for the Chronic Treatment of Heart Diseases
  作者：Daniel Meibom、Barbara Albrecht-Küpper、Nicole Diedrichs、Walter Hübsch、Raimund Kast、Thomas Krämer、Ursula Krenz、Hans-Georg Lerchen、Joachim Mittendorf、Peter G. Nell、Frank Süssmeier、Alexandros Vakalopoulos、Katja Zimmermann

  DOI：10.1002/cmdc.201700151

  日期：2017.5.22

  full A1 R agonists are used, the desired protective and regenerative cardiovascular effects are usually overshadowed by unintended pharmacological effects such as induction of bradycardia, atrioventricular (AV) blocks, and sedation. These unwanted effects can be overcome by using partial A1 R agonists. Starting from previously reported capadenoson we evaluated options to tailor A1 R agonists to a specific

  腺苷已知在多种生理和病理生理条件下释放，以促进受损缺血组织的保护和再生。心肌腺苷A1受体（A1 Rs）的激活已显示可抑制与缺血和再灌注损伤相关的心肌病理，为新的心血管疗法提供了多种选择。当使用完全的A1 R激动剂时，所需的保护性和再生性心血管作用通常会被意想不到的药理作用（如心动过缓，房室传导阻滞和镇静作用）所掩盖。通过使用部分A1 R激动剂可以克服这些不良影响。从先前报道的卡帕狄森菌开始，我们评估了将A1 R激动剂调整到特定部分范围的选项，从而优化治疗窗口。这导致了对强效和选择性激动剂奈拉狄森的鉴定，奈拉狄森显示出对A1 R的所需部分反应，从而在没有镇静作用或心脏房室传导阻滞的情况下实现了心脏保护。为了避免奈拉狄森的溶解度和制剂问题，人们寻求前药方法。口服给药后，二肽酯奈拉德森双丙酸酯盐酸盐显示出显着改善的溶解度和暴露。Neladenoson bialanate hydrochlorid
• Complete assignment of NMR data of 22 phenyl-1<i>H</i> -pyrazoles' derivatives
  作者：Aline Lima de Oliveira、Carlos Henrique Alves de Oliveira、Laura Maia Mairink、Francine Pazini、Ricardo Menegatti、Luciano Morais Lião

  DOI：10.1002/mrc.2773

  日期：2011.8

  Complete assignment of 1H and 13C NMR chemical shifts and J(1H/1H and 1H/19F) coupling constants for 22 1‐phenyl‐1H‐pyrazoles' derivates were performed using the concerted application of 1H 1D and 1H, 13C 2D gs‐HSQC and gs‐HMBC experiments. All 1‐phenyl‐1H‐pyrazoles' derivatives were synthesized as described by Finar and co‐workers. The formylated 1‐phenyl‐1H‐pyrazoles' derivatives were performed under

  22 1-苯基-1H-吡唑衍生物的 1H 和 13C NMR 化学位移和 J（1H/1H 和 1H/19F）耦合常数的完整分配是使用 1H 1D 和 1H、13C 2D gs-HSQC 的协同应用完成的和 gs-HMBC 实验。所有 1-苯基-1H-吡唑衍生物均按照Finar 及其同事的描述合成。甲酰化 1-苯基-1H-吡唑衍生物在达夫条件下进行。版权所有 © 2011 John Wiley & Sons, Ltd.
• Aggregation-induced luminescence enhancement, anion sensing, solvent-selective fluorescence quenching of arylpyrazoline fluorescent probe
  作者：Qiushuo Huang、Tiantian Liu、Danyang Ma、Junxia Liu、Tiegang Ren、Wenpeng Wu、Jinglai Zhang

  DOI：10.1016/j.dyepig.2021.110014

  日期：2022.2

  28 Novel pyrazoline compounds containing pyrazole units have been synthesized and characterized. The crystal structures of C1 and B6 showed that these pyrazoline derivatives could form 3D layered structures through face-to-face stacking of aromatic rings, and they were more inclined to form H-type aggregation in poor solvent. Compound C4 was selected as the standard sample to study their properties

  已合成并表征了 28 种含有吡唑单元的新型吡唑啉化合物。C 1和B 6的晶体结构表明，这些吡唑啉衍生物可以通过芳环的面对面堆叠形成3D层状结构，并且在不良溶剂中更倾向于形成H型聚集体。选择化合物C 4作为标准样品，研究其在THF/环己烷中的聚集诱导发射增强(AIEE)和可逆机械色致发光(MFC)行为。结果表明形成H型聚集，聚集状态下的RIR和RIV现象导致高fc下的强荧光发射行为溶剂。荧光发射光谱分析表明，C 4的荧光发射可以被氯仿选择性猝灭。同时，化合物C 4可以选择性地识别CH 2 Cl 2 中的NO 3 -。荧光猝灭机理研究表明，化合物C 4在CHCl 3溶剂或NO 3 -存在下，可被空气中的氧气氧化生成新的化合物C 4-1，导致C 4的荧光猝灭. 密度泛函理论计算也证实了这一结果。