2-(2-硝基苯胺基)乙酸乙酯 | 5428-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(2-硝基苯胺基)乙酸乙酯
• 英文名称: n-(2-nitrophenyl)glycine ethyl ester
• 英文别名: 2-Nitro-phenylglycin-aethylester；N-(2-Nitro-phenyl)-glycin-aethylester；Ethyl 2-[(2-nitrophenyl)amino]acetate；ethyl 2-(2-nitroanilino)acetate
• CAS: 5428-05-7
• 化学式: C₁₀H₁₂N₂O₄
• mdl: MFCD00455119
• 分子量: 224.216
• InChiKey: GDBQBQLTUSNRBO-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84 °C(Solv: isopropanol (67-63-0))
• 沸点：
  351.8±22.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2922499990

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-[(2-nitrophenyl)amino]acetate
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 2-[(2-nitrophenyl)amino]acetate
CAS number: 5428-05-7

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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: C10H12N2O4
Molecular weight: 224.2

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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：

  2-(2-硝基苯胺基)乙酸乙酯 在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 氯磷酸二乙酯 作用下， 以 甲醇 为溶剂， -78.0~25.0 ℃ 、241.32 kPa 条件下， 反应 5.0h， 生成 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4,5-dihydroimidazo<1,5-a>quinoxaline
  参考文献：
  名称：

  通过GABAA /苯并二氮杂receptor受体起作用的咪唑并[1,5-a]喹喔啉酰胺和氨基甲酸酯的拮抗剂，部分激动剂和完全激动剂。

  摘要：

  （4RS）-1-（5-环丙基-1,2-，4-恶二唑-3-基）-12,12a-二羟基咪唑并[1,5-a]吡咯并[2,1-c]喹喔啉-10（11H） ）-一（1a），5-苯甲酰基-3-（5-环丙基-1,2,4-恶二唑-3-基）-4,5-二氢咪唑并[1,5-a]喹喔啉（13b）和叔叔（4S）-12,12a-二氢咪唑并[1,5-a]吡咯并[2,1-c]喹喔啉-1-羧酸（1e）以及其他咪唑并[1,5-a]喹喔啉酰胺和氨基甲酸酯代表了一系列与GABAA /苯并二氮杂receptor受体具有高亲和力的化合物。通过[35S] TBPS结合比测量，这些化合物具有广泛的内在功效。1a的合成开始于将DL-谷氨酸添加到1-氟-2-硝基苯中，然后还原硝基并随后闭环形成3-（羧乙氧基甲基）-1,2,3,4-四氢喹喔啉-2-one，然后进行第二个环闭合，得到（4RS）-1，以5-二氧-1,2,3,4,5,6-六氢吡咯并[1

  DOI：

  10.1021/jm00032a008
• 作为产物：
  描述：

  1-氟-2-硝基苯 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(2-硝基苯胺基)乙酸乙酯
  参考文献：
  名称：

  Harvey, Ian W.; McFarlane, Michael D.; Moody, David J., Journal of the Chemical Society. Perkin transactions I, 1988, p. 681 - 690

  摘要：

  DOI：

文献信息

• Palladium-catalyzed direct Hiyama arylation of quinoxalin-2(1H)-ones with aryl siloxanes in water
  作者：Xinya Liu、Zhenwei Liu、Yingying Xue、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1016/j.tetlet.2020.152612

  日期：2020.12

  An efficient method for palladium-catalyzed direct Hiyama coupling of various quinoxalin-2(1H)-ones with aryl siloxanes has been developed. The protocol provides a convenient access to a variety of useful C3-arylated 1-methylquinoxalin-2(1H)-one derivatives in reasonable yields by using low cost water as a solvent and oxygen as an oxidant.

  已开发出一种有效的方法，用于钯催化的各种喹喔啉-2（1H）-与芳基硅氧烷的直接Hiyama偶联。该协议通过使用低成本的水作为溶剂和氧气作为氧化剂，以合理的产率方便地获得了各种有用的C3芳基化的1-甲基喹喔啉-2（1H）-衍生物。
• Microwave-assisted Synthesis of N-Arylglycines: Improvement of Sydnone Synthesis
  作者：Davood Azarifar、Hassan Ghasemnejad Bosra、Mohammad-Ali Zolfigol、Mahmood Tajbaksh

  DOI：10.3987/com-05-10574

  日期：——

  Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.
• 1-Methylimidazolium tetrafluoroborate [Hmim][BF4]: an efficient acidic ionic liquid catalyst for insertion of α-diazo compounds into the N–H bonds of amines
  作者：Jafar Akbari、Ali Ebrahimi、Akbar Heydari

  DOI：10.1016/j.tetlet.2014.08.013

  日期：2014.10

  The reusable acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [Hmim][BF4], was found to be an effective catalyst for the insertion of alpha-diazoacetate into the N-H bonds of amines. The corresponding products were obtained in good yields and short reaction times via a simple procedure. The catalyst could be recycled and reused without any noticeable decrease in its activity. (C) 2014 Elsevier Ltd. All rights reserved.
• 681. The structures of some supposed azetid-2 : 4-diones. Part II. Derivatives of tartronic acid
  作者：F. E. King、J. W. Clark-Lewis

  DOI：10.1039/jr9510003077

  日期：——
• HARVEY, IAN W.;MCFARLANE, MICHAEL D.;MOODY, DAVID J.;SMITH, DAVID M., J. CHEM. SOC. PERKIN TRANS.,(1988) N 3, 681-689
  作者：HARVEY, IAN W.、MCFARLANE, MICHAEL D.、MOODY, DAVID J.、SMITH, DAVID M.

  DOI：——

  日期：——