甲基-1,3-苯并唑-5-羧酸乙酯 | 924869-17-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 甲基-1,3-苯并唑-5-羧酸乙酯
• 中文别名: 5-苯并恶唑羧酸甲酯
• 英文名称: methyl benzo[d]oxazole-5-carboxylate
• 英文别名: methyl benzoxazole-5-carboxylate；Methyl 1,3-benzoxazole-5-carboxylate
• CAS: 924869-17-0
• 化学式: C₉H₇NO₃
• mdl: MFCD08689687
• 分子量: 177.159
• InChiKey: VHLBJWCXFIGALN-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111
• 沸点：
  272.4±13.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 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：
  52.3
• 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：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 1,3-benzoxazole-5-carboxylate
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: Methyl 1,3-benzoxazole-5-carboxylate
CAS number: 924869-17-0

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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: C9H7NO3
Molecular weight: 177.2

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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：

  甲基-1,3-苯并唑-5-羧酸乙酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Hunashal, Rajesh D.; Kumar, M.R. Pradeep, Indian Journal of Heterocyclic Chemistry, 2016, vol. 26, # 1-2, p. 1 - 6

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸 在 氯化亚砜 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 甲基-1,3-苯并唑-5-羧酸乙酯
  参考文献：
  名称：

  Nocarbenzoxazole G的合成，结构修订和细胞毒性。

  摘要：

  最初从海洋衍生的嗜盐细菌菌株Nocardiopsis lucentensis DSM 44048获得的去甲苯并恶唑F（1）和G（2）的总合成是通过一种简单而通用的方法实现的，该方法涉及微波辅助构建苯并恶唑骨架与相应的芳基溴形成碳-碳键。不幸的是，天然去甲苯并恶唑G的1H和13C NMR光谱与合成化合物的光谱不一致。特别地，分离和合成的化合物的光谱显示出来自芳基中的质子和碳的信号的显着差异。通过实际合成的去甲苯并恶唑G（8c）分子的全合成来验证修订后的结构，该分子是该化合物的区域异构体，之前被报道为去甲苯并恶唑G。

  DOI：

  10.1021/acs.jnatprod.9b00072

文献信息

• Palladium-catalyzed direct arylation of benzoxazoles with unactivated simple arenes
  作者：Ge Wu、Jun Zhou、Min Zhang、Peng Hu、Weiping Su

  DOI：10.1039/c2cc34238c

  日期：——

  Using CuBr(2) as an additive, the Pd-catalyzed intermolecular C-H-C-H cross-coupling between benzoxazoles and unactivated simple arenes has been developed. This protocol provides a straightforward approach for the biological activity of 2-arylbenzoxazole derivatives.

  使用CuBr（2）作为添加剂，已开发了Pd催化的苯并恶唑与未活化的简单芳烃之间的分子间CHCH交叉偶联。这个协议提供了2-arylbenzoxazole衍生物的生物活性的直接的方法。
• Cu-Catalyzed Direct C–P Bond Formation through Dehydrogenative Cross-Coupling Reactions between Azoles and Dialkyl Phosphites
  作者：Soumyadip Hore、Abhijeet Srivastava、Ravi P. Singh

  DOI：10.1021/acs.joc.9b00670

  日期：2019.6.7

  cross-coupling of azoles [C(sp2)–H] with dialkyl phosphites [P(O)–H] to access 2-phosphonated azoles using Cu(I)/Cu(II) as catalyst and K2S2O8/di-tert-butylperoxide as oxidant has been achieved. A remarkable advantage over reported procedures includes that oxazoles, imidazoles, benz(ox/othi/imid)azoles, and indole are found to react under optimized reaction conditions to provide corresponding adducts in

  吡咯[C（sp 2）–H]与亚磷酸二烷基酯[P（O）–H]的直接脱氢交叉偶联，以Cu（I）/ Cu（II）为催化剂和K 2 S来获得2-膦酸化的吡咯已获得2 O 8 /二叔丁基过氧化物作为氧化剂。与报道的方法相比，一个显着的优势包括发现恶唑，咪唑，苯并（ox / othi /咪唑）和吲哚在优化的反应条件下反应，可以高产率提供相应的加合物。通过氘动力学同位素效应研究获得了交叉耦合的机理见解。
• Pd/Cu-Catalyzed C–H/C–H Cross Coupling of (Hetero)Arenes with Azoles through Arylsulfonium Intermediates
  作者：Ze-Yu Tian、Zeng-Hui Lin、Cheng-Pan Zhang

  DOI：10.1021/acs.orglett.1c01322

  日期：2021.6.4

  A highly efficient method for the selective formal C–H/C–H cross-coupling of azoles and (hetero)arenes was established through arylsulfonium intermediates under transition-metal catalysis, which produced a variety of 2-(hetero)aryl azoles in good to excellent yields. Advantages of the reaction included mildness, a good functional group tolerance, a wide range of substrates, a high regio- and chemoselectivity

  在过渡金属催化下，通过芳基锍中间体建立了一种用于唑类和（杂）芳烃的选择性形式 C-H/C-H 交叉偶联的高效方法，该方法可以很好地生产各种 2-（杂）芳基唑类化合物。以优异的产量。该反应的优点包括温和、官能团耐受性好、底物范围广、区域选择性和化学选择性高、一锅法以及不使用氧化剂的复杂分子的后期功能化，提供了一种有前景的策略用于过渡金属催化的唑类的 C-H 芳基化。
• TEMPO-Mediated C–H Amination of Benzoxazoles with N-Heterocycles
  作者：Jian Wang、Jiang-Hua Li、Yidong Guo、Hongbo Dong、Qiang Liu、Xiao-Qi Yu

  DOI：10.1021/acs.joc.0c01921

  日期：2020.10.2

  The direct amination of benzoxazoles at C2 using N-heterocycles as nitrogen sources has been developed for the first time. Several kinds of inexpensive oxidants and also electricity were effective for this transformation in the presence of 2,2,6,6-tetramethylpiperidine-N-oxyl. This metal-free and operationally simple reaction can afford a variety of important C,N′-linked bis-heteocycles in moderate

  首次开发了使用N杂环作为氮源在C2处苯并恶唑的直接胺化反应。在2,2,6,6-四甲基哌啶-N-氧基的存在下，几种廉价的氧化剂以及电对这种转化有效。这种无金属且操作简单的反应可以在非常温和的反应条件下以中等到良好的产率提供各种重要的C，N'-连接的双杂环。事实证明，原位产生的氧铵盐对于这种转化很重要。
• Copper-Catalyzed Three-Component Carboamination of Arynes: Expeditious Synthesis of <i>o</i>-Alkynyl Anilines and <i>o</i>-Benzoxazolyl Anilines
  作者：Sheng-Li Niu、Jiangtao Hu、Kuicheng He、Ying-Chun Chen、Qing Xiao

  DOI：10.1021/acs.orglett.9b01427

  日期：2019.6.7

  reaction conditions, the nucleophiles in this transformation can be extended from terminal alkynes to benzoxazoles. These procedures provide a modular and facile approach to o-alkynyl anilines and o-benzoxazolyl anilines from easily available substrates in only one step.

  已经开发了原位形成的芳烃，末端炔烃和O-苯甲酰基羟胺的铜催化三组分反应。通过调节反应条件，该转化中的亲核试剂可以从末端炔烃延伸至苯并恶唑。这些步骤提供了一种模块化且简便的方法，仅需一步即可从容易获得的底物中获得邻炔基苯胺和邻苯并恶唑基苯胺。