5-(3-溴苯基)-1,3,4-噁唑-2(3H)-酮 | 873090-18-7

• 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-(3-溴苯基)-1,3,4-噁唑-2(3H)-酮
• 英文名称: 5-(3-bromophenyl)-3H-1,3,4-oxadiazol-2-one
• 英文别名: 5-(3-bromophenyl)-1,3,4-oxadiazol-2(3H)-one
• CAS: 873090-18-7
• 化学式: C₈H₅BrN₂O₂
• 分子量: 241.044
• InChiKey: ZVWSHDFGLFCEID-UHFFFAOYSA-N

物化性质

• 熔点：
  185.6-186.3 °C
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 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：
  50.7
• 氢给体数：
  1
• 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: 5-(3-Bromophenyl)-3H-1,3,4-oxadiazol-2-one
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-(3-Bromophenyl)-3H-1,3,4-oxadiazol-2-one
CAS number: 873090-18-7

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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.
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: C8H5BrN2O2
Molecular weight: 241.0

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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：

  5-(3-溴苯基)-1,3,4-噁唑-2(3H)-酮 、 4-哌啶基哌啶 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以95%的产率得到1'-[5-(3-bromophenyl)-1,3,4-oxadiazol-2-yl]-1,4'-bipiperidinyl
  参考文献：
  名称：

  Efficient Phosphonium-Mediated Synthesis of 2-Amino-1,3,4-oxadiazoles

  摘要：

  We present an efficient, room temperature procedure for the preparation of 2-amino-1,3,4-oxadiazoles, Oxadiazol-2-ones can be activated for S(N)Ar substitution using phosphonium reagents (e.g., BOP). This approach provides convenient access to N,N-disubstituted 2-amino-1,3,4-oxadiazoles, which are difficult to prepare using existing synthetic strategies.

  DOI：

  10.1021/ol8004084
• 作为产物：
  描述：

  tert-butyl 2-((3-bromophenyl)chloromethylene)hydrazinecarboxylate 在 basic alumina 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以83%的产率得到5-(3-溴苯基)-1,3,4-噁唑-2(3H)-酮
  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

• Parallel Synthesis of a Library of Acylsemicarbazides Using a Solution-Phase One-Pot Method and Their Evaluation as Crop-Protection Agents
  作者：Robert A. Batey、Justyna A. Grzyb、Mark A. Dekeyser

  DOI：10.1055/s-2005-870020

  日期：——

  A solution-phase one-pot synthesis of a 40-member acylsemicarbazide library is outlined. The acylsemicarbazides were prepared by reacting various hydrazides with N,N′-carbonyldiimidazole (CDI) to generate 1,3,4-oxadiazole-2-one intermediates, which were then opened in situ with amines. Purification in the majority of cases was accomplished through filtration of the precipitated product in generally good yields and with ³ 95% purities. An analogous synthesis of acylthiosemicarbazides was accomplished using N,N′-thiocarbonyldiimidazole (TCDI). The library was then assayed for herbicidal, insecticidal, fungicidal and plant growth regulatory behavior.

  本文概述了一种溶液相单锅合成 40 个成员的酰基缩氨基脲库的方法。酰基micarbazides 是通过各种酰肼与 N,N′-羰基二咪唑 (CDI) 反应生成 1,3,4-恶二唑-2-酮中间体，然后用胺原位打开而制备的。大多数情况下，纯化都是通过过滤沉淀产物来完成的，收率普遍较高，纯度达 95%。使用 N,N′-硫代羰基二咪唑 (TCDI) 完成了酰硫代氨基脲的类似合成。然后对该化合物库进行了除草、杀虫、杀真菌和植物生长调节行为的检测。
• SYNTHESIS AND CRYSTALLINE FORMS OF CB-1 ANTAGONIST/INVERSE AGONIST
  申请人：Campos Kevin R.

  公开号：US20100292282A1

  公开（公告）日：2010-11-18

  The present invention relates to a process for producing crystalline 3-[(1S)-1-(1-(S)-(4-chlorophenyl)[3-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]methyl}azetidin-3-yl)-2-fluoro-2-methyl-propyl]-5-fluorobenzonitrile, and novel salts, solvates, hydrates and polymorphs thereof.

  本发明涉及一种生产晶体3-[(1S)-1-(1-(S)-(4-氯苯基)[3-(5-氧代-4,5-二氢-1,3,4-噁二唑-2-基)苯基]甲基}氮杂环己烷-3-基)-2-氟-2-甲基-丙基]-5-氟苯甲腈及其新的盐、溶剂化合物、水合物和多晶形式的方法。
• [EN] SUBSTITUTED AMINOBENZYL HETEROARYL COMPOUNDS AS EGFR AND/OR PI3K INHIBITORS<br/>[FR] COMPOSÉS D'HÉTÉROARYLE D'AMINOBENZYLE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS D'EGFR ET/OU DE PI3K
  申请人：MEKANISTIC THERAPEUTICS LLC

  公开号：WO2022140456A1

  公开（公告）日：2022-06-30

  This disclosure is in the field of medicinal chemistry, and relates to a new class of small-molecules having the Formula I, or a pharmaceutically acceptable salt or solvate thereof, or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof, wherein the variables Ring A, X, R1a, R1b, R2, R3, R4, m, n, and p are described herein, which function as dual inhibitors of EGFR proteins and PI3K proteins. The disclosure further relates to the use of the compounds described herein as therapeutics for the treatment of diseases and conditions mediated by EGFR proteins and/or PI3K proteins, such as cancer and other diseases.

  本公开涉及药物化学领域，涉及一类新的小分子化合物，其具有式I，或其药学上可接受的盐或溶剂化物，或其对映体，对映体混合物，两个或两个以上的非对映异构体混合物，或其同位素变体，其中变量环A、X、R1a、R1b、R2、R3、R4、m、n和p在本文中有所描述，其作为EGFR蛋白和PI3K蛋白的双重抑制剂。本公开进一步涉及将所述化合物用作治疗EGFR蛋白和/或PI3K蛋白介导的疾病和病状的治疗剂，例如癌症和其他疾病。
• [EN] SYNTHESIS AND CRYSTALLINE FORMS OF CB-1 ANTAGONIST/INVERSE AGONIST<br/>[FR] SYNTHÈSE ET FORMES CRISTALLINES D'ANTAGONISTE/AGONISTE INVERSÉ DE CB-1
  申请人：MERCK & CO INC

  公开号：WO2009054923A3

  公开（公告）日：2009-06-18
• 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
  作者：Kamalesh Debnath、Sudipta Pathak、Animesh Pramanik

  DOI：10.1016/j.tetlet.2012.11.128

  日期：2013.2

  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.