4-溴-3-硝基苯乙酸乙酯 | 168473-87-8

• 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: 4-溴-3-硝基苯乙酸乙酯
• 英文名称: ethyl 4-bromo-3-nitrobenzoate
• 英文别名: 2-Brom-1-nitro-benzolcarbonsaeure-(5)-aethylester；4-bromo-3-nitro-benzoic acid ethyl ester；4-Brom-3-nitro-benzoesaeure-aethylester
• CAS: 168473-87-8
• 化学式: C₉H₈BrNO₄
• mdl: MFCD09972120
• 分子量: 274.071
• InChiKey: HWABKOBGQZQMAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 4-bromo-3-nitrobenzoate
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: Ethyl 4-bromo-3-nitrobenzoate
CAS number: 168473-87-8

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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.
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: C9H8BrNO4
Molecular weight: 274.1

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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, 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-溴-3-硝基苯乙酸乙酯 在 tin(II) chloride dihdyrate 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以98%的产率得到3-氨基-4-溴苯甲酸乙酯
  参考文献：
  名称：

  Suzuki-Miyaura交叉偶联是2-氨基联苯和2,2'-二氨基联苯合成的关键步骤：在Zn席夫碱配合物合成中的应用

  摘要：

  Suzuki-Miyaura反应被用作合成2-氨基联苯和2,2'-二氨基联苯的关键步骤，而这些反过来又可用于制备Zn的席夫碱配合物。特别强调的是2-溴苯胺与2-硝基取代的芳基硼酸之间的交叉偶联反应，目前尚无此类研究。

  DOI：

  10.1002/ejoc.202000599
• 作为产物：
  描述：

  4-溴苯甲酸乙酯 在 硫酸 、 硝酸 作用下， 反应 3.17h， 以99%的产率得到4-溴-3-硝基苯乙酸乙酯
  参考文献：
  名称：

  Suzuki-Miyaura交叉偶联是2-氨基联苯和2,2'-二氨基联苯合成的关键步骤：在Zn席夫碱配合物合成中的应用

  摘要：

  Suzuki-Miyaura反应被用作合成2-氨基联苯和2,2'-二氨基联苯的关键步骤，而这些反过来又可用于制备Zn的席夫碱配合物。特别强调的是2-溴苯胺与2-硝基取代的芳基硼酸之间的交叉偶联反应，目前尚无此类研究。

  DOI：

  10.1002/ejoc.202000599

文献信息

• Substituted 1,2,4-triazolin-3-one compounds bearing acidic functional
  申请人：Merck & Co., Inc.

  公开号：US05436259A1

  公开（公告）日：1995-07-25

  Novel substituted 1,2,4-triazolin-3-ones of the formula (I) are useful as angiotensin II antagonists. ##STR1##

  小说替代了式(I)的1,2,4-三唑烷酮，可用作血管紧张素II拮抗剂。
• Polyfunctional Lithium, Magnesium, and Zinc Alkenyl Reagents as Building Blocks for the Synthesis of Complex Heterocycles
  作者：Zhi-Liang Shen、Vasudevan Dhayalan、Andreas D. Benischke、Robert Greiner、Konstantin Karaghiosoff、Peter Mayer、Paul Knochel

  DOI：10.1002/anie.201600961

  日期：2016.4.18

  expeditive construction of various polyfunctionalized 5‐, 6‐, and 7‐membered heterocycles, such as furans, pyrroles, quinolines, benzo[b]thieno‐[2,3‐b]pyridine, naphthyridines, fused pyrazoles, and 2,3‐dihydro‐benzo[c]azepines. The latent silyl group has been converted into various carbon–carbon bonds in most heterocycle types.

  已经制备了新的Li，Mg和Zn的β-甲硅烷基化有机金属试剂，并将其用于快速构建各种多官能化的5、6和7元杂环，例如呋喃，吡咯，喹啉，苯并[ b ]噻吩并[2,3- b ]吡啶，萘啶，稠合吡唑和2,3-二氢-苯并[ c ]氮杂s。在大多数杂环类型中，潜在的甲硅烷基已转化为各种碳-碳键。
• Presence versus Proximity: The Role of Pendant Amines in the Catalytic Hydrolysis of a Nerve Agent Simulant
  作者：Timur Islamoglu、Manuel A. Ortuño、Emmanuel Proussaloglou、Ashlee J. Howarth、Nicolaas A. Vermeulen、Ahmet Atilgan、Abdullah M. Asiri、Christopher J. Cramer、Omar K. Farha

  DOI：10.1002/anie.201712645

  日期：2018.2.12

  Amino‐functionalized zirconium‐based metal‐organic frameworks (MOFs) have shown unprecedented catalytic activity compared to non‐functionalized analogues for hydrolysis of organophosphonate‐based toxic chemicals. Importantly, the effect of the amino group on the catalytic activity is significantly higher in the case of UiO‐66‐NH2, where the amino groups reside near the node, compared to UiO‐67‐m‐NH2, where

  氨基官能化的锆基金属有机骨架（MOF）与非官能化的类似物相比，水解基于有机膦酸酯的有毒化学物质表现出空前的催化活性。重要的是，该氨基上的催化活性的作用是显著高于UIO-66-NH的情况下2，其中所述氨基基团所在的节点附近，相对于UIO-67-米-NH 2，它们被引导远离节点。本文中，我们证明了氨基的邻近对于快速催化基于有机膦酸酯的神经毒剂的水解具有至关重要的作用。已在具有不同拓扑结构的两个不同的MOF系统上测试了观察到的胺邻近性催化活性的一般性。DFT计算表明，所有研究的MOF上的氨基都不是布朗斯台德碱。相反，它们控制Zr 6节点活性位点的微溶剂化环境，因此提高了总催化速率。
• Synthesis of ortho-substituted nitroaromatics via improved Negishi coupling conditions
  作者：Jamison B. Tuttle、Joseph M. Azzarelli、Bruce M. Bechle、Amy B. Dounay、Edelweiss Evrard、Xinmin Gan、Somraj Ghosh、Jaclyn Henderson、Ji-Young Kim、Vinod D. Parikh、Patrick R. Verhoest

  DOI：10.1016/j.tetlet.2011.07.083

  日期：2011.10

  We describe modified Negishi coupling conditions that allow improved access to ortho-nitrophenylalanine derivatives. These useful amino acid intermediates can be further elaborated into biologically active lactams and cyclic hydroxamic acid targets.

  我们描述了改良的Negishi偶联条件，可以改善对邻硝基硝基苯丙氨酸衍生物的访问。这些有用的氨基酸中间体可以进一步加工成具有生物活性的内酰胺和环状异羟肟酸靶标。
• Closing the Cycle as It Begins: Synthesis of <i>ortho</i> ‐Iodobiaryls via Catellani Reaction
  作者：Vinayak Botla、Marco Fontana、Aleksandr Voronov、Raimondo Maggi、Elena Motti、Giovanni Maestri、Nicola Della Ca'

  DOI：10.1002/anie.202218928

  日期：——

  A new strategy based on the Catellani reactions has enabled the one-pot synthesis of ortho-iodobiaryls starting from aryl iodides and bromides. Beyond the synthetic utility of this transformation (32 examples and 6 subsequent derivatizations), a DFT study provides insights on the mechanism of the reductive elimination step, which is driven by an original transmetallation between palladium(II)-halide

  一种基于Catellani 反应的新策略使得能够从芳基碘化物和芳基溴化物开始一锅法合成邻碘二芳基化合物。除了这种转化的综合效用（32 个例子和 6 个后续衍生化）之外，DFT 研究还提供了对还原消除步骤机制的见解，该步骤由钯 (II)-卤化物络合物之间的原始金属转移作用驱动。