6-碘-4-氧代-4H-苯并吡喃-2-羧酸乙酯 | 35204-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-碘-4-氧代-4H-苯并吡喃-2-羧酸乙酯
• 英文名称: ethyl 6-iodo-4-oxo-4H-chromene-2-carboxylate
• 英文别名: ethyl 6-iodo-4-oxochromene-2-carboxylate
• CAS: 35204-44-5
• 化学式: C₁₂H₉IO₄
• 分子量: 344.106
• InChiKey: HUJFMOAXSPSGDU-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  400.2±45.0 °C(Predicted)
• 密度：
  1.798±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 海关编码：
  2932999099
• 储存条件：
  2-8°C

SDS

Name:	Ethyl 6-iodo-4-oxo-4h-chromene-2-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	35204-44-5

Section 1 - Chemical Product MSDS Name:Ethyl 6-iodo-4-oxo-4h-chromene-2-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
35204-44-5	Ethyl 6-iodo-4-oxo-4H-chromene-2-carbo	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 35204-44-5: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 148 - 150 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H9IO4
Molecular Weight: 344.1

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen iodide, iodine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 35204-44-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 6-iodo-4-oxo-4H-chromene-2-carboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 35204-44-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 35204-44-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 35204-44-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-碘-4-氧代-4H-苯并吡喃-2-羧酸乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride potassium phosphate 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 59.5h， 生成 ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-4-oxo-4H-chromene-2-carboxylate
  参考文献：
  名称：

  WO2008/157270

  摘要：

  公开号：

文献信息

• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。
• Ligand-Promoted<i>meta</i>-C−H Functionalization of Benzylamines
  作者：Peng Wang、Marcus E. Farmer、Jin-Quan Yu

  DOI：10.1002/anie.201701803

  日期：2017.4.24

  Meta‐C−H functionalization of benzylamines has been developed using a PdII/transient mediator strategy. Using 2‐pyridone ligands and 2‐carbomethoxynorbornene (NBE‐CO2Me) as the mediator, arylation, amination, and chlorination of benzylamines are realized. This protocol features a broad substrate scope and is compatible with heterocylic coupling partners. Moreover, the loading of the Pd can be lowered

  使用Pd II /瞬态介质策略开发了苄胺的Meta-C-H功能化。使用2-吡啶酮配体和2-羰甲氧基降冰片烯（NBE-CO 2 Me）作为介体，可以实现苄胺的芳基化，胺化和氯化。该协议具有广泛的底物范围，并与杂环偶联伙伴兼容。此外，通过使用最佳配体，可以将Pd的负载降低至2.5mol％。
• Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry
  作者：Michael Oschmann、Linus Johansson Holm、Monireh Pourghasemi-Lati、Oscar Verho

  DOI：10.3390/molecules25020361

  日期：——

  achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns.

  在此，我们提出了一种简短且高度模块化的合成路线，该路线涉及 8-氨基喹啉定向的 C-H 芳基化和转酰胺化学，并且能够获得各种精细的苯并呋喃-2-甲酰胺。对于定向的 C-H 芳基化反应，使用 Pd 催化在苯并呋喃支架的 C3 位高效安装各种芳基和杂芳基取代基。然后，通过利用一锅两步转酰胺程序，通过中间体 N-酰基-Boc-氨基甲酸酯在单一合成操作中实现 C3-芳基化苯并呋喃产物的定向基团裂解和进一步多样化。鉴于这种合成策略的高效率和模块化，
• Palladium-Catalyzed Arylation of Cyclopropanes via Directing Group-Mediated C(sp³)–H Bond Activation To Construct Quaternary Carbon Centers: Synthesis of <i>cis</i>- and <i>trans</i>-1,1,2-Trisubstituted Chiral Cyclopropanes
  作者：Naoyuki Hoshiya、Takaaki Kobayashi、Mitsuhiro Arisawa、Satoshi Shuto

  DOI：10.1021/ol4030452

  日期：2013.12.20

  Pd(II)-catalyzed tertiary C(sp3)–H arylation of cyclopropanes via directing group-mediated C–H activation for the construction of a chiral quaternary carbon center on cyclopropanes using aryl iodides as a coupling partner is reported. The arylation had a wide substrate scope and good functional group tolerance, including heteroaryl iodides, to provide various chiral arylcyclopropanes with the cis-

  据报道，Pd（II）催化的环丙烷叔C（sp 3）-H芳基化反应是通过基团介导的C-H活化，使用芳基碘化物作为偶联伙伴在环丙烷上构建手性季碳中心。芳基化具有宽的底物范围和良好的官能团耐受性，包括杂芳基碘化物，以提供具有顺式和反式-1,1,2-三取代结构的各种手性芳基环丙烷。
• Convenient Access to Chiral Cyclobutanes with Three Contiguous Stereocenters from Verbenone by Directed C(sp ³ )−H arylation
  作者：Alexander J. Schmitz、Alexander Ricke、Michael Oschmann、Oscar Verho

  DOI：10.1002/chem.201806416

  日期：2019.4.5

  This work demonstrates how a series of complex, chiral cyclobutane derivatives can be accessed in four steps from the terpene verbenone through the application of a directed C−H functionalization approach. The developed synthetic route involved an 8‐aminoquinoline‐directed C(sp3)−H arylation as the key step, and this reaction could be carried out with a wide range of aryl and heteroaryl iodides to

  这项工作演示了如何通过有针对性的CH官能化方法的应用，从萜烯马鞭酮分四步获得一系列复杂的手性环丁烷衍生物。发达的合成路线涉及一个以8-氨基喹啉为导向的C（sp 3）-H芳基化反应的关键步骤，该反应可以在多种芳基和杂芳基碘化物的条件下进行，以提供多种具有三种连续形式的环丁烷产品。立体中心。此外，研究表明，使用基于臭氧分解的裂解方法可以从环丁烷衍生物中有效去除8-氨基喹啉助剂。