4-氯 3-碘-苯甲酸甲酯 | 132244-31-6

• 物质功能分类: 医药中间体
• 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: 4-氯 3-碘-苯甲酸甲酯
• 中文别名: 5-溴苯并恶唑；4-氯3-碘-苯甲酸甲酯；5-溴苯并噁唑；5-溴-苯并异恶唑
• 英文名称: 5-bromo-1,3-benzoxazole
• 英文别名: 5-bromobenzo[d]oxazole；5-bromobenzoxazole；5-bromobenzooxazole
• CAS: 132244-31-6
• 化学式: C₇H₄BrNO
• 分子量: 198.019
• InChiKey: PGOGTWDYLFKOHI-UHFFFAOYSA-N

物化性质

• 熔点：
  38-40°
• 沸点：
  251.2±13.0 °C(Predicted)
• 密度：
  1.710±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090
• 储存条件：
  存储条件：室温、密封保存，并保持干燥环境。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromobenzooxazole
Synonyms: 5-Bromobenzo[d]oxazole

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Bromobenzooxazole
CAS number: 132244-31-6

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels, refrigerated.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H4BrNO
Molecular weight: 198.0

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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：

  4-氯 3-碘-苯甲酸甲酯 在 2,3,4,5,6-五氟碘苯 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 以43 %的产率得到5-bromo-2-iodobenzo[d]oxazole
  参考文献：
  名称：

  Copper‐Catalyzed Aryne Insertion into the Carbon‐Iodine Bond of Heteroaryl Iodides

  摘要：

  摘要 首次实现了在杂芳基碘化物的碳-碘键中插入丙烯。这一新型反应为从杂芳基碘化物和邻硅芳基三酸酯合成有价值的 2-iodoheterobiaryls 构建模块提供了一条高效途径，且具有极佳的区域选择性。铜（I）催化剂带有 N-杂环碳烯（NHC）配体，对完成反应至关重要。对照反应和 DFT 计算表明，作为路易斯酸的铜与杂芳基碘化物的氮原子配位介导了芳基插入杂芳基碳-碘键。

  DOI：

  10.1002/anie.202305146
• 作为产物：
  描述：

  2-溴苯酚 在 硝酸 、 铁粉 、 氯化铵 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 8.08h， 生成 4-氯 3-碘-苯甲酸甲酯
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS

  摘要：

  提供了氨基吡嗪化合物作为腺苷受体的调节剂。这些化合物可能作为治疗经由G蛋白偶联受体信号通路介导的疾病的治疗剂，并且可能在肿瘤学中发挥特定作用。

  公开号：

  US20190023666A1

文献信息

• Copper-Catalyzed Oxidative Amination of Benzoxazoles via C−H and C−N Bond Activation: A New Strategy for Using Tertiary Amines as Nitrogen Group Sources
  作者：Shengmei Guo、Bo Qian、Yinjun Xie、Chungu Xia、Hanmin Huang

  DOI：10.1021/ol1030298

  日期：2011.2.4

  method for oxidative amination of azoles with tertiary amines via copper-catalyzed C−H and C−N bond activation has been developed. This protocol can be performed in the absence of external base and only requires atmospheric oxygen as oxidant. The catalyst system is very simple and efficient, which opens a new way for using tertiary amines as nitrogen group sources for C−N bond formation reactions.

  通过铜催化的CH和CN键活化作用，开发了一种高效，概念上新颖的用叔胺氧化唑类胺的方法。该方案可以在不存在外部碱的情况下进行，并且仅需要大气中的氧气作为氧化剂。催化剂体系非常简单和高效，这为使用叔胺作为C-N键形成反应的氮源提供了新途径。
• Highly Stereospecific Cross-Coupling Reactions of Anomeric Stannanes for the Synthesis of C-Aryl Glycosides
  作者：Feng Zhu、Michael J. Rourke、Tianyi Yang、Jacob Rodriguez、Maciej A. Walczak

  DOI：10.1021/jacs.6b07891

  日期：2016.9.21

  We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross-coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrate scope (>40 examples), this reaction eliminates critical problems inherent to nucleophilic displacement methods and is applicable to (hetero)aromatics

  我们证明，在具有极高立体控制水平的钯催化剂存在下，构型稳定的异头锡烷与芳族卤化物发生立体定向交叉偶联反应。除了广泛的底物范围（> 40 个例子）之外，该反应消除了亲核置换方法固有的关键问题，适用于（杂）芳烃、肽、药物、常见单糖和含有游离羟基的糖类。
• [EN] HETEROCYCLIC KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE HÉTÉROCYCLIQUES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2016022312A1

  公开（公告）日：2016-02-11

  The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

  本公开内容通常涉及能够抑制AAK1（适配器相关激酶1）的化合物、包含该化合物的组合物以及抑制AAK1的方法。
• Cobalt-catalyzed synthesis of N-containing heterocycles <i>via</i> cyclization of <i>ortho</i>-substituted anilines with CO₂/H₂
  作者：Zhengang Ke、Bo Yu、Huan Wang、Junfeng Xiang、Juanjuan Han、Yunyan Wu、Zhenghui Liu、Peng Yang、Zhimin Liu

  DOI：10.1039/c9gc00095j

  日期：——

  The CO2-involved synthesis of chemicals is of great significance from the green and sustainable chemistry viewpoint. Herein, we report a non-noble metal catalytic system composed of CoF2, CsF and P(CH2CH2PPh2)3 (denoted as PP3) for the synthesis of N-containing heterocycles from ortho-substituted anilines and CO2/H2. Mechanism investigation indicates that [Co(PP3)H(CO2)]+ is a catalytically active

  从绿色和可持续的化学观点来看，涉及CO 2的化学合成具有重要意义。本文中，我们报道了由CoF 2，CsF和P（CH 2 CH 2 PPh 2）3（表示为P P 3）组成的非贵金属催化体系，用于由邻位取代的苯胺和CO合成含氮杂环2 / H 2。机理研究表明[Co（P P 3）H（CO 2）] +是在工作条件下具有催化活性的中间体；CsF和CsF在通过氢键相互作用活化邻位取代的苯胺中起重要作用，从而促进最终产物的形成。该催化体系是高效的，并且允许宽范围的邻位取代的苯胺，以及优异的官能团耐受性，以良好至优异的产率提供各种含氮杂环。
• [EN] INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF<br/>[FR] INHIBITEURS DE LA PROTÉINE TYROSINE PHOSPHATASE DE FAIBLE POIDS MOLÉCULAIRE (LMPTP) ET UTILISATIONS ASSOCIÉES
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2019136093A1

  公开（公告）日：2019-07-11

  Protein tyrosine phosphatases (PTPs) are key regulators of metabolism and insulin signaling. As a negative regulator of insulin signaling, the low molecular weight protein tyrosine phosphatase (LMPTP) is a target for insulin resistance and related conditions. Described herein are compounds capable of modulating the level of activity of LMPTP, compositions, and methods of using these compounds and compositions.

  蛋白酪氨酸磷酸酶（PTPs）是代谢和胰岛素信号传导的关键调节因子。作为胰岛素信号传导的负调节因子，低分子量蛋白酪氨酸磷酸酶（LMPTP）是胰岛素抵抗和相关疾病的靶点。本文描述了能够调节LMPTP活性水平的化合物、组合物以及使用这些化合物和组合物的方法。