5-(4-硝基苯基)-1,3,4-噁二唑-2-醇 | 41125-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(4-硝基苯基)-1,3,4-噁二唑-2-醇
• 中文别名: 5-(4-硝基苯基)-3H-1,3,4-恶二唑-2-酮
• 英文名称: 5-(4-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one
• 英文别名: 2-p-Nitro-phenyl-1,3,4-oxadiazol-5-on；5-(4-nitrophenyl)-3H-1,3,4-oxadiazol-2-one
• CAS: 41125-77-3
• 化学式: C₈H₅N₃O₄
• mdl: MFCD00477935
• 分子量: 207.145
• InChiKey: ADUFTMJBLYUADS-UHFFFAOYSA-N

物化性质

• 熔点：
  249-251 °C
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(4-Nitrophenyl)-3H-1,3,4-oxadiazol-2-one
Synonyms: 5-(4-Nitrophenyl)-2,3-dihydro-1,3,4-oxadiazol-2-one

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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-(4-Nitrophenyl)-3H-1,3,4-oxadiazol-2-one
CAS number: 41125-77-3

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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, refrigerated.
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: C8H5N3O4
Molecular weight: 207.1

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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.

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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-(4-硝基苯基)-1,3,4-噁二唑-2-醇 在 钯 乙醇 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、36.8 MPa 条件下， 反应 1.0h， 以to afford (5-(4-aminophenyl)-1,3,4-oxadiazol-2(3H)-one, 0.46 g, m.p. 172-173° C.的产率得到5-(4-aminophenyl)-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  Thiadiazinones for stimulating cardiac activity

  摘要：

  本发明涉及具有肌力增强、血管扩张和支气管扩张活性的N-苯基吡啶酮衍生物。该发明的一种化合物是5-甲基-6-[4-(4-氧代-1,4-二氢吡啶-1-基)苯基]-4,5-二氢-3(2H)吡啶酮。

  公开号：

  US05246928A1
• 作为产物：
  描述：

  N′-[chloro-(4-nitrophenyl)methylene]-tert-butylcarbazate 在 basic alumina 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以84%的产率得到5-(4-硝基苯基)-1,3,4-噁二唑-2-醇
  参考文献：
  名称：

  Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl-methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition

  摘要：

  The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N'-(chloro-aryl-methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.128

文献信息

• DMF as Methine Source: Copper‐Catalyzed Direct Annulation of Hydrazides to 1,3,4‐Oxadiazoles
  作者：Shoucai Wang、Kai Wang、Xiangfei Kong、Shuhua Zhang、Guangbin Jiang、Fanghua Ji

  DOI：10.1002/adsc.201900395

  日期：2019.9.3

  unprecedented Cu‐catalyzed direct annulation of hydrazides with N,N‐dimethylformamide (DMF) was developed, providing an efficient synthesis of valuable 1,3,4‐oxadiazoles. This process features the short reaction time and can be safely conducted on gram scale. The reaction also facilitated the convenient synthesis of 1,3,4‐oxadiazole‐2(3H)‐ones. Moreover, the mechanistic studies suggest that the source of CH is

  开发了前所未有的Cu催化的N，N-二甲基甲酰胺（DMF）酰肼直接环化反应，可有效合成有价值的1,3,4-恶二唑。该过程的反应时间短，可以安全地以克为单位进行。该反应还促进了1,3,4-恶二唑-2（3 H）-one的便捷合成。此外，机理研究表明，CH的来源是DMF的N-甲基。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：UCL BUSINESS LTD

  公开号：WO2020043866A1

  公开（公告）日：2020-03-05

  A compound for use in the treatment of a disease ameliorated by the inhibition of Notum of formula (I): (I)

  一种用于治疗通过抑制公式（I）中的Notum改善的疾病的化合物：（I）
• N-phenylpyridone type III phosphodiesterases
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04906628A1

  公开（公告）日：1990-03-06

  Phosphodiesterase (type III) inhibitors having the formula: ##STR1## which are useful in stimulating cardiac activity and in treating congestive heart failure and bronchoconstriction, pharmaceutical compositions including these inhibitors, and methods of using these compounds to produce phosphodiesterase (type III) inhibition in mammals.

  磷酸二酯酶（III型）抑制剂具有以下结构式：##STR1##，可用于刺激心脏活动，治疗充血性心力衰竭和支气管痉挛，包括这些抑制剂的药物组合物，以及使用这些化合物在哺乳动物中产生磷酸二酯酶（III型）抑制的方法。
• Synthesis of 5-substituted-3H-[1,3,4]-oxadiazol-2-one derivatives: a carbon dioxide route (CDR)
  作者：M. Brahmayya、Shenghong A. Dai、S.-Y. Suen

  DOI：10.1039/c5ra08910g

  日期：——

  Access to a series of 5-substituted-3(H)-1,3,4-oxadiazole-2-one derivatives is described directly using the greenhouse gas CO₂.

  描述了直接使用温室气体CO₂获得一系列5-取代-3（H）-1,3,4-噁二唑-2-酮衍生物的访问。
• Reaction of 1,3,4-oxadiazolones with free L-<i>α</i>-amino acids: A facile synthesis of novel 3,5-disubstituted hydantoins
  作者：Yasuo Saegusa、Shigeo Harada、Shigeo Nakamura

  DOI：10.1002/jhet.5570270349

  日期：1990.3

  A series of novel 3,5-disubstituted hydantoins 3a-1 were easily synthesized in one-step from the reaction of 2-phenyl-1,3,4-oxadiazolin-5-ones 1a-h with various free L-α-amino acids 2a-e in m-cresol at 150°. An alternative route leading to the formation of 3-benzamido-5-isopropylhydantoin 3c was also developed to make clear the reaction mechanism.

  从2-苯基-1,3,4-恶二唑啉-5-酮1a-h与各种游离L- α-氨基的反应可轻松一步合成一系列新颖的3,5-二取代乙内酰脲3a-1酸2A-E在米甲酚在150℃。还开发了导致3-苯甲酰胺基-5-异丙基乙内酰脲3c形成的替代途径以阐明反应机理。