5-氯甲基-3-(4-硝基苯基)-[1,2,4]噁二唑 | 57611-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氯甲基-3-(4-硝基苯基)-[1,2,4]噁二唑
• 中文别名: 3-(4-硝基苯基)-5-(氯甲基)-1,2,4-噁二唑；5-(氯甲基)-3-(4-硝基苯基)-1,2,4-恶二唑
• 英文名称: 5-(chloromethyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
• CAS: 57611-19-5
• 化学式: C₉H₆ClN₃O₃
• mdl: MFCD00452243
• 分子量: 239.618
• InChiKey: DKZJFBGPUIIFGW-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  408.1±55.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(Chloromethyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
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: 5-(Chloromethyl)-3-(4-nitrophenyl)-1,2,4-oxadiazole
CAS number: 57611-19-5

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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: C9H6ClN3O3
Molecular weight: 239.6

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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：

  5-氯甲基-3-(4-硝基苯基)-[1,2,4]噁二唑 在 potassium cyanide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以82%的产率得到5,5',5''-(propane-1,2,3-triyl)tris(3-(4-nitrophenyl)-1,2,4-oxadiazole)
  参考文献：
  名称：

  3-（对-取代-苯基）-5-氯甲基-1,2,4-恶二唑与KCN的反应通过非还原性脱氰途径生成乙腈和烷烃。

  摘要：

  本工作描述了5-（氯甲基）-3-取代的苯基-1,2,4-恶二唑与KCN的不熟悉反应，得到三取代的1,2,4-恶二唑-5-基乙腈及其母体烷烃，即1 ，2，3-三取代-1,2,4-恶二唑-5-基丙烷。据我们所知，就脱氰过程而言，目前导致脱氰产物的合成途径将是第一条途径，该过程允许通过将KCN与原位形成的HCN结合而将三取代的乙腈转化为烷烃。可能是由于挤压出无法检测或分离的氰。此外，两种转化都提出了合理的机制。通过IR，1 H NMR，13 C NMR，2D NMR光谱，TOF-MS和X射线测量来鉴定标题化合物的结构。

  DOI：

  10.3762/bjoc.14.280
• 作为产物：
  描述：

  对硝基苯甲腈 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 、 丙酮 、 甲苯 为溶剂， 生成 5-氯甲基-3-(4-硝基苯基)-[1,2,4]噁二唑
  参考文献：
  名称：

  新型 3,5-二取代-1,2,4-恶二唑衍生物作为碳酸酐酶抑制剂和细胞毒剂的合成、计算机模拟和体外评价

  摘要：

  在这项工作中，高效合成了新的 3,5-二取代-1,2,4-恶二唑，并评估了它们对人碳酸酐酶 (hCA) I 和 II 的抑制作用。它们中的大多数对 hCAs 比乙酰唑胺 (AAZ) 更有效。化合物10d和17d是对 hCA I 最有效的化合物，IC 50值分别为 0.68 和 0.96 µM。化合物7d、17d、10d和3d是最有效的 hCA II 抑制剂，IC 50值为 0.40、0.40、0.65 和 0.71 µM。分子对接研究表明，化合物10d和17d在 hCA I 的活性位点显示出与 Phe91 的 π-π 堆积相互作用。化合物10d和17d能够在 hCA II 的活性位点与 His94 形成 π-π 堆积相互作用，并与 Phe131 形成 π-阳离子相互作用。两种化合物的烷基氨基对 hCA II 活性位点的关键相互作用都有贡献。根据计算机数据，预测所有化合物都具有良好的口服生物

  DOI：

  10.1016/j.molstruc.2022.134699

文献信息

• Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities
  作者：Yaşar DÜRÜST、Hamza KARAKUŞ、Muhsine Zeynep YAVUZ、Ali Akçahan GEPDİREMEN

  DOI：10.3906/kim-1309-59

  日期：——

  1,3-Dipolar cycloaddition of 5-azidomethyl-3-p-substituted phenyl-1,2,4-oxadiazoles to phenyl vinyl sulfone and bismaleimide gives rise straightforwardly to 1-((3-(p-substituted) phenyl-1,2,4-oxadiazol-5-yl)methyl)-4-(phenylsul\-fonyl)-4,5-dihydro-1H-1,2,3-triazoles and bisdihydropyrrolo[3,4-d][1,2,3]triazole-4,6(3aH,5H)-diones. The structures of the new cycloadducts were elucidated by means of IR, NMR (^1H, ^13}C, 2D), mass spectra, and physical characteristics (mp and R_f values). In addition, anticancer activities of the cycloadducts against MCF-7 cells were also investigated.

  5-叠氮甲基-3-对取代苯基-1,2,4-嗯二唑与苯基乙烯砜和双马来酰亚胺的1,3-偶极环加成反应，直接生成1-((3-(对取代)苯基-1,2,4-嗯二唑-5-基)甲基)-4-(苯磺酰基)-4,5-二氢-1H-1,2,3-三唑和双二氢吡咯并[3,4-d][1,2,3]三唑-4,6(3aH,5H)-二酮。通过红外、核磁共振(^1H、^13C、2D)、质谱和物理性质(熔点和R_f值)阐明了新环加合物的结构。此外，还研究了这些环加合物对MCF-7细胞的抗癌活性。
• Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties
  作者：B. Özer、Y. Dürüst

  DOI：10.1134/s1070428020040193

  日期：2020.4

  from 1,4,9,12-tetraazacyclohexadecane-2,11-dione and subjected to 1,3-cycloaddition reaction with 5-(azidomethyl)-3-(4-R-phenyl)-1,2,4-oxadiazoles which were prepared by acylation of the corresponding para-substituted benzamidoximes with chloroacetyl chloride, followed by azidation. In this way, a series of azacrown ethers bearing 1,2,4-oxadiazole and 1,2,3-triazole rings were successfully obtained

  摘要从1,4开始合成了一个在两个氮原子上带有炔丙基的四氮杂row醚4,9-二（prop-2-yn-1-yl）-1,4,9,12-四氮杂环十六烷-2,11-二酮，9，12-四氮杂环十六烷-2，11-二酮并与通过酰化制备的5-（叠氮甲基）-3-（4-R-苯基）-1，2，4-恶二唑进行1，3-环加成反应。将相应的对位取代的苯甲酰胺肟与氯乙酰氯混合，然后进行叠氮化。以这种方式，成功地获得了一系列带有1,2,4-恶二唑和1,2,3-三唑环的氮杂皇冠醚，并通过光谱/物理数据阐明了它们的结构。
• Synthesis and anti-protozoal activity of novel dihydropyrrolo[3,4-d][1,2,3]triazoles
  作者：Yaşar Dürüst、Hamza Karakuş、Marcel Kaiser、Deniz Tasdemir

  DOI：10.1016/j.ejmech.2011.12.028

  日期：2012.2

  containing heterocyclic compounds continue to gain interest in synthesis of chemical entities and exhibit various biological activities as anti-protozoal and anti-cancer agents. By using the principle of bioisosterism, a series of novel oxadiazolyl pyrrolo triazole diones; namely, (3aS,6aR)-1-((3-(4-substituted phenyl)-1,2,4-oxadiazol-5-yl)methyl)-5-phenyl-1,6a-dihydropyrrolo[3,4-d][1,2,3] triazole-4,6(3aH

  含1,2,4-恶二唑和1,2,3-三唑的杂环化合物继续引起化学实体合成的兴趣，并表现出各种作为抗原生动物和抗癌剂的生物学活性。利用生物立体异构原理，合成了一系列新型的恶二唑基吡咯并三唑二酮；即（3a S，6a R）-1-（（（3-（4-取代苯基）-1,2,4-恶二唑-5-基）甲基）-5-苯基-1,6a-二氢吡咯[3，通过新型5-叠氮基甲基3-的1,3-偶极环加成反应设计合成了4-d] [1,2,3]三唑-4,6（3a H，5 H）-二酮（5a - k）。芳基取代的1,2,4-恶二唑（4a – k）与N-苯基马来酰亚胺。通过光谱方法和物理特性阐明了所有环加合物的结构。的体外抗原生动物和这些新的杂环化合物的细胞毒活性进行了研究。
• A metal-free isoamyl nitrite mediated efficient synthesis of 1,2,4-oxadiazoles
  作者：Sharad A. Galave、Kishorkumar S. Kadam、Amol D. Sonawane、Vaibhav R. Pansare、Dinesh R. Garud

  DOI：10.1016/j.tetlet.2023.154616

  日期：2023.7

  We report herein, a metal-free isoamyl nitrite mediated efficient synthesis of 1,2,4-oxadiazoles by one-pot cycloaddition reaction of aldoximes with nitriles. The structure of the 1,2,4-oxadiazole derivatives was confirmed by studies of spectral analysis. Current methodology provides a novel pathway to access 1,2,4-oxadiazole derivatives.

  我们在此报道了一种无金属亚硝酸异戊酯介导的通过醛肟与腈的一锅环加成反应有效合成 1,2,4-恶二唑的方法。1,2,4-恶二唑衍生物的结构通过光谱分析研究得到证实。目前的方法提供了获取 1,2,4-恶二唑衍生物的新途径。
• Novel benzodioxatriaza and dibenzodioxadiazacrown compounds carrying 1,2,4-oxadiazole moiety
  作者：Besra Özer、Yaşar Dürüst

  DOI：10.1515/hc-2022-0150

  日期：2022.9.27

  A series of benzo (dibenzo)dioxadiaza and triazamacrocyclic ether compounds carrying 1,2,4-oxadiazole group has been successfully synthesized through N-substitution with 3-p-phenylsubstituted-5-chloromethyl-1,2,4-oxadiazoles. The structures of all the novel macrocycles were confirmed by spectral/physical data including HRMS measurements.

  摘要 通过与 3-对苯代-5-氯甲基-1,2,4-恶二唑进行 N-取代，成功合成了一系列带有 1,2,4-恶二唑基团的苯（二苯并）二噁二唑和三氮杂环醚化合物。通过光谱/物理数据（包括 HRMS 测量）证实了所有新型大环的结构。