2-甲基-5-硝基-1,3-苯并噁唑 | 32046-51-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 中文名称: 2-甲基-5-硝基-1,3-苯并噁唑
• 中文别名: 2-甲基-5-硝基苯并噁唑；2-甲基-5-硝基-1,3-苯并恶唑；2-甲基-5-硝基-1,3-恶唑
• 英文名称: 2-methyl-5-nitro-1,3-benzoxazole
• 英文别名: 2-methyl-5-nitrobenzo[d]oxazole；2-methyl-5-nitrobenzoxazole；2-Methyl-5-nitro-benzoxazol
• CAS: 32046-51-8
• 化学式: C₈H₆N₂O₃
• mdl: MFCD00466748
• 分子量: 178.147
• InChiKey: UCZSXRHVXKAGFU-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158°C
• 沸点：
  303.1±15.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  存放在2-8°C的环境中，应保持干燥并密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methyl-5-nitro-1,3-benzoxazole
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: 2-Methyl-5-nitro-1,3-benzoxazole
CAS number: 32046-51-8

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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: C8H6N2O3
Molecular weight: 178.1

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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：

  2-甲基-5-硝基-1,3-苯并噁唑 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Gould-Jacobs Reaction of 5- and 6-Amino-2-substituted Benzoxazoles. II. Reaction with 3-Ethoxymethylene-2,4-pentanedione and Ethyl 2-Ethoxymethylene-3-oxobutanoate

  摘要：

  5-氨基和6-氨基-2-取代苯并噁唑醇1和2与3-乙氧基甲烯基-2,4-戊二酮（3）的亲核反应得到化合物5和6。化合物1和2与乙基乙氧基甲烯基-3-氧代丁酸酯（4）反应生成化合物7和8。取代产物7和8在高温下（二苯醚和联苯的沸腾混合物）发生热环化反应，形成5-乙酰基-4-氧代噁唑并[4,5-f]喹啉9和7-乙酰基-8-氧代噁唑并[5,4-g]喹啉10（从7），以及8-乙酰基-9-氧代噁唑并[5,4-f]喹啉11和6-乙酰基-5-氧代噁唑并[4,5-g]喹啉12的角式和线性环化衍生物（从8）。基于它们的谱特性（1H和13C NMR、IR、UV、MS），讨论了取代产物的结构。

  DOI：

  10.1135/cccc19960371
• 作为产物：
  描述：

  2-羟基-5-硝基苯乙酮 在 盐酸羟胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 2-甲基-5-硝基-1,3-苯并噁唑
  参考文献：
  名称：

  Acid Catalyzed Direct-Amidation–Dehydrocyclization of 2-Hydroxy-acetophenones to Benzoxazoles by a One-Pot Sustainable Synthesis

  摘要：

  DOI：

  10.1007/s10562-014-1466-3

文献信息

• Ammonium Chloride-catalyzed Synthesis of Benzo-fused Heterocycles from<i>o</i>-Substituted Anilines and Orthoesters
  作者：Chelsea Fortenberry、Baskar Nammalwar、Richard A. Bunce

  DOI：10.1080/00304948.2013.743751

  日期：2013.1

  mebendazole.10 Similarly, benzoxazole is the core ring structure in the non-steroidal anti-inflammatory drug flunoxaprofen,11 while the benzothiazole unit is found in zopolrestat12 and riluzole,13 which are used to treat diabetes. Current strategies to prepare these ring systems involve oxidative cyclizations of Schiff bases,14–22 metal-catalyzed amide cyclizations23–25 and reaction of o-substituted

  由于苯并咪唑、苯并恶唑和苯并噻唑具有多种生物活性，如抗病毒、1 抗菌、2 抗真菌、3 抗微生物、4 抗帕金森病、5 抗癌 6 和抗8 苯并咪唑支架存在于各种驱虫药中，例如阿苯达唑 9 和甲苯咪唑。 10 同样，苯并恶唑是非甾体类抗炎药氟苯丙胺的核心环结构，11而苯并噻唑单元存在于佐泊司他 12 和利鲁唑 13 中，用于治疗糖尿病。目前制备这些环系统的策略包括席夫碱的氧化环化、14-22 金属催化的酰胺环化 23-25 以及邻取代苯胺与醛的反应、26-29 酰氯、30 酸、31、32 酯、33 酰胺、34 腈、35 或原酸酯。据报道，最后一次转化使用了多种催化剂，包括 HCl、36,37 HOAc、38 H2SO4-硅胶、39 HBF4-硅胶、40 氨基磺酸-甲醇、41 碘、42 1,3dibromo-5,5-二甲基-乙内酰脲、43 三氟甲磺酸镱 (III)、44 三氟甲磺酸铋 45 和八水合氯化锆
• Thermolysis of o-nitro- and 2,4-dinitro-phenoxyacetic acids and related compounds
  作者：R. S. Goudie、P. N. Preston

  DOI：10.1039/j39710001718

  日期：——

  The products of thermolysis of o-nitro- and 2,4-dinitro-phenoxyacetic acids and their sulphur analogues have been investigated. Predominant products from the former include 2H-1,4-benzoxazin-3(4H)-one and derivatives thereof, benzoxazoles, and related compounds. In general, decomposition of the sulphur analogues follows related pathways. The mechanisms of formation of some of the products are considered

  已经研究了邻-硝基-和2,4-二硝基-苯氧基乙酸及其硫类似物的热解产物。前者的主要产物包括2 H -1,4-苯并恶嗪-3（4 H）-one及其衍生物，苯并恶唑和相关化合物。通常，硫类似物的分解遵循相关途径。考虑了某些产物的形成机理。
• Metal free montmorillonite KSF clay catalyzed practical synthesis of benzoxazoles and benzothiazoles under aerobic conditions
  作者：Vijaya Babu Kummari、Kalavakuntla Chiranjeevi、Alleni Suman Kumar、Rathod Aravind Kumar、Jhillu Singh Yadav

  DOI：10.1080/00397911.2019.1665183

  日期：2019.12.2

  synthesis of benzoxazoles and benzothiazoles via montmorillonite KSF clay catalyzed condensation reaction between 2-aminophenols or 2-aminothiophenols and β-diketones is reported. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on aryls. The reaction is metal free and proceeds without the exclusion of air or moisture, and further the catalyst can

  摘要 报道了一种通过蒙脱石KSF粘土催化2-氨基苯酚或2-氨基苯硫酚与β-二酮之间的缩合反应合成苯并恶唑和苯并噻唑的有效方法。反应的效率反映在广泛的底物范围和芳基上的电子分化。该反应不含金属，在不排除空气或水分的情况下进行，而且催化剂可以循环使用多达 3-5 个催化循环。图形概要
• [EN] SUBSTITUTED BICYCLIC AMINES FOR THE TREATMENT OF DIABETES<br/>[FR] AMINES BICYCLIQUES SUBSTITUÉES POUR LE TRAITEMENT DU DIABÈTE
  申请人：MERCK SHARP & DOHME

  公开号：WO2010056717A1

  公开（公告）日：2010-05-20

  Described herein are substituted bicyclic amines. In particular, described herein are substituted bicyclic amines that are effective as antagonists of SSTR5 and useful for the treatment, control or prevention of disorders responsive to antagonism of SSTR5, such as type 2 diabetes, insulin resistance, lipid disorders, obesity, atherosclerosis, metabolic syndrome, depression, and anxiety.

  本文描述了替代的双环胺。具体来说，本文描述了作为SSTR5拮抗剂有效的替代双环胺，用于治疗、控制或预防对SSTR5拮抗有响应的疾病，如2型糖尿病、胰岛素抵抗、脂质紊乱、肥胖、动脉粥样硬化、代谢综合征、抑郁症和焦虑症。
• Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-<i>b</i>]benzoxazoles
  作者：Ke-Lai Li、Zong-Bo Du、Can-Cheng Guo、Qing-Yun Chen

  DOI：10.1021/jo900267c

  日期：2009.5.1

  o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for

  在已知的化合物2-（苯并恶唑-2'-基）-3-二甲基氨基丙烯醛中，邻乙酰氨基酚（2）与Vilsmeier试剂在Meth-Cohn条件下反应生成2-甲酰基吡啶并[2,1- b ]苯并恶唑（5） （4）。在乙酸酐中回流4得到4-甲酰基吡啶并[2,1- b ]苯并恶唑（6），其为5的异构体。两个图5a和6a中进行了结构表征通过X射线晶体学。5的形成机理 提出了包括顺序氯化，二聚化，分子内去除HCl形成恶唑环，两次甲酰化以及区域选择性分子内亲核环化以构建吡啶酮环的方法。