3-(4-溴苯基)-5-苯基-1,2,4-噁二唑 | 65004-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(4-溴苯基)-5-苯基-1,2,4-噁二唑
• 英文名称: 3-(4-bromophenyl)-5-phenyl-1,2,4-oxadiazole
• CAS: 65004-19-5
• 化学式: C₁₄H₉BrN₂O
• 分子量: 301.142
• InChiKey: GLBNCUMZRRDBRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

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: 3-(4-Bromophenyl)-5-phenyl-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: 3-(4-Bromophenyl)-5-phenyl-1,2,4-oxadiazole
CAS number: 65004-19-5

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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: C14H9BrN2O
Molecular weight: 301.1

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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, hydrogen bromide.

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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-溴苯基)-5-苯基-1,2,4-噁二唑 、 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  蓝色荧光分子及制备方法和应用

  摘要：

  本申请公开了蓝色荧光分子，具有D‑π‑A结构，包含作为受体基团的噁二唑和作为给体基团的苯基咔唑，以具有热激子能级排布特征的芳环作为π桥连接受体基团和给体基团。本申请还提供了蓝色荧光分子的制备方法和应用。本申请以具有热激子能级排布特征的芳环作为π桥，通过引入给受体合理调控其高能激发态，激活分子的热激子通道，突破荧光材料25％的激子利用率限制从而获得对激子利用率的提升。

  公开号：

  CN116283949A
• 作为产物：
  描述：

  对溴苯甲醛 在 吡啶 、 potassium phosphate 、 N-氯代丁二酰亚胺 、 盐酸羟胺 、 四丁基高氯酸铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 14.0h， 生成 3-(4-溴苯基)-5-苯基-1,2,4-噁二唑
  参考文献：
  名称：

  偕胺肟脱氢环化电化学合成1,2,4-恶二唑

  摘要：

  为从N-苄基偕胺肟合成 3,5-二取代的 1,2,4-恶二唑，开发了一种通过阳极氧化生成亚胺氧基自由基的简便有效的方法。转化通过 1.5-氢原子转移 (1,5-HAT) 和分子内环化进行。该工艺操作简单、条件温和、底物范围广、官能团相容性高，为1,2,4-恶二唑的制备提供了一条简便实用的途径。

  DOI：

  10.1039/d1ob02040d

文献信息

• A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes
  作者：Wei Guo、Kunbo Huang、Fanghua Ji、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c5cc02110c

  日期：——

  Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with...

  各种3,5-二取代-1,2,4-恶二唑是通过铜催化的am和甲基芳烃的级联环化反应顺利形成的。这种串联的氧化-胺化-环化反应代表了一种简单的方法，可以从容易获得的起始原料中制备1,2,4-恶二唑，并采用...
• NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N‒O bond formation
  作者：Ertong Li、Manman Wang、Zhen Wang、Wenquan Yu、Junbiao Chang

  DOI：10.1016/j.tet.2018.07.036

  日期：2018.8

  A reaction involving an efficient NBS-mediated oxidative N‒O bond formation has been established for the synthesis of 1,2,4-oxadiazoles from readily accessible N-acyl amidines. The features of this synthetic method include simplicity of operation, mild reaction conditions, short reaction times, high yields, and eco-friendliness. The reaction also works well with crude N-acyl amidines obtained by amidation

  已经建立了涉及有效的NBS介导的氧化N ＝ O键形成的反应，用于由容易获得的N-酰基am合成1,2,4-恶二唑。这种合成方法的特点包括操作简单，反应条件温和，反应时间短，产率高和环保。该反应还适用于通过简单的苯甲酸和mid酰胺化而获得的粗制N-酰基s，以可扩展的方式生产生物学上相关的1,2,4-恶二唑。
• Base-mediated one-pot synthesis of 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride without addition of extra oxidant
  作者：Wei Wang、Hao Xu、Yuanqing Xu、Tao Ding、Wenkai Zhang、Yanrong Ren、Haibo Chang

  DOI：10.1039/c6ob01794k

  日期：——

  A simple base-mediated one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles, aldehydes and hydroxylamine hydrochloride has been developed, in which the aldehydes act as both substrates and oxidants. The reactions include three sequential procedures: base-promoted intermolecular addition of hydroxylamine to nitrile to lead to amidoxime, treatment of the amidoxime with an aldehyde to

  已经开发了由腈，醛和盐酸羟胺形成的简单的碱介导的一锅法合成3,5-二取代的1,2,4-恶二唑，其中醛既充当底物又充当氧化剂。反应包括三个顺序程序：碱促进的羟胺分子间加成到腈中以生成a胺肟；用醛处理the胺肟以形成4,5-二氢-1,2,4-恶二唑；以及氧化4， 5-二氢-1,2,4-恶二唑通过使用另一种醛得到1,2,4-恶二唑。该方法代表了合成3,5-二取代的1,2,4-恶二唑的直接而简单的方法。
• Orthogonal aerobic conversion of N-benzyl amidoximes to 1,2,4-oxadiazoles or quinazolinones
  作者：Feng-Lian Zhang、Yi-Feng Wang、Shunsuke Chiba

  DOI：10.1039/c3ob41393d

  日期：——

  Concise synthesis of 1,2,4-oxadiazoles was achieved by heating N-benzyl amidoximes with K3PO4 in DMF at 60 °C under an O2 atmosphere via benzylic C–H oxygenation. On the other hand, aerobic treatment of N-benzyl amidoximes with Cs2CO3 in DMSO at 100 °C could result in oxidative skeletal rearrangement to deliver quinazolinones as a major product. This orthogonal product selectivity could be realized by difference of the reaction temperature as well as selection of the solvents and inorganic bases.

  通过在60°C下，在O2气氛中使用K3PO4作为催化剂，将N-苄基脒肟在DMF中加热，实现了1,2,4-噁二唑的简洁合成，这一过程涉及苄基C-H氧合作用。另一方面，在100°C下，使用Cs2CO3作为催化剂，在DMSO中对N-苄基脒脟进行需氧处理，可能导致骨架氧化重排，主要产物为喹唑啉酮。这种正交的产品选择性可以通过反应温度、溶剂和无机碱的选择来实现。
• Oxidative cyclization of amidoximes and thiohydroximic acids: A facile and efficient strategy for accessing 3,5-disubstituted 1,2,4-oxadiazoles and 1,4,2-oxathiazoles
  作者：Jatin J. Lade、Bhausaheb N. Patil、Kamlesh S. Vadagaonkar、Atul C. Chaskar

  DOI：10.1016/j.tetlet.2017.04.045

  日期：2017.5

  A facile and practical protocol has been developed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 1,4,2-oxathiazoles through oxidative cyclization of amidoximes and thiohydroximic acids, respectively at room temperature. Use of mild reaction conditions, inexpensive reagents, broad substrate scope and good to excellent yield of the products are the salient features of this protocol.

  已经开发了一种简便实用的方案，分别通过室温下mid胺肟和硫代氢肟酸的氧化环化反应来合成3,5-二取代的1,2,4-恶二唑和1,4,2-恶二唑。使用温和的反应条件，廉价的试剂，广泛的底物范围以及良好至优异的产物收率是该方案的主要特征。