2-(4-溴-2-硝基苯基)乙酸甲酯 | 100487-82-9

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-溴-2-硝基苯基)乙酸甲酯
• 中文别名: 4-溴-2-硝基苯乙酸甲酯
• 英文名称: 4-bromo-2-nitro-benzoic acid methyl ester
• 英文别名: methyl 2-(4-bromo-2-nitrophenyl)-acetate；Methyl 2-(4-bromo-2-nitrophenyl)acetate
• CAS: 100487-82-9
• 化学式: C₉H₈BrNO₄
• 分子量: 274.071
• InChiKey: KHXUTOLCCFWPDH-UHFFFAOYSA-N

物化性质

• 沸点：
  331.7±27.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温下，应保持干燥和密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-(4-bromo-2-nitrophenyl)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: Methyl 2-(4-bromo-2-nitrophenyl)acetate
CAS number: 100487-82-9

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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：

  2-(4-溴-2-硝基苯基)乙酸甲酯 在 potassium phosphate 、 四(三苯基膦)钯 、 potassium tert-butylate 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 对二甲苯 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 48.5h， 生成 (E)-6'-((3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)methyl)-2'-oxospiro[cyclohexane-1,3'-indoline]-4-carbonitrile
  参考文献：
  名称：

  确认螺螺吲哚和二苯并氮杂pine基序为有效的盐皮质激素受体拮抗剂

  摘要：

  盐皮质激素受体（MR）拮抗剂继续是制药行业研究的主要领域。在本文中，我们报道了作为有效的MR拮抗剂的各种螺氧杂吲哚和二苯并x庚因构建物的发现。SAR分析我们的螺氧杂吲哚导致了含有极性增溶基团的高效化合物，这些基团与MR配体结合域（LBD）的11螺旋区域相互作用。为了替代已知的与MR LBD的疏水区相互作用的二苯并庚烷体系，还制备了各种二苯并x庚因部分。另外，从高效化合物获得了X射线晶体结构，该化合物显示出针对MR的部分激动剂和拮抗剂作用模式。

  DOI：

  10.1016/j.bmc.2016.02.014
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 sodium hydride 、 lithium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 5.17h， 生成 2-(4-溴-2-硝基苯基)乙酸甲酯
  参考文献：
  名称：

  A General Oxindole Synthesis

  摘要：

  一种针对吲哚-2(3H)-酮（氧吲哚）的整体合成方法被开发，该方法基于二甲基马来酸酯与可商业获得的卤代硝基苯的加成。这条路线相较于许多其他氧吲哚合成方法的优势在于对芳香环取代模式的区域化学控制。

  DOI：

  10.1055/s-1993-25790
• 作为试剂：
  描述：

  2-(4-溴-2-硝基苯基)丙二酸二甲酯 、 氯化锂 、 水 在 2-(4-溴-2-硝基苯基)乙酸甲酯 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 生成 2-(4-溴-2-硝基苯基)乙酸甲酯
  参考文献：
  名称：

  Heterocyclic compounds and their uses

  摘要：

  含有替代双环杂环芳基的化合物及其组合物，用于治疗一般性炎症、关节炎、风湿性疾病、骨关节炎、炎症性肠病、炎症性眼疾、炎症性或不稳定的膀胱疾病、牛皮癣、含有炎症成分的皮肤疾病、慢性炎症性疾病，包括但不限于自身免疫性疾病，如系统性红斑狼疮（SLE）、重症肌无力、类风湿性关节炎、急性播散性脑脊髓炎、特发性血小板减少性紫癜、多发性硬化症、Sjogren综合症和自身免疫性溶血性贫血，包括所有形式的过敏反应。本发明还提供了用于治疗介导、依赖或与p110活性相关的癌症的方法，包括但不限于白血病，如急性髓系白血病（AML）、骨髓增生异常综合征（MDS）、骨髓增生性疾病（MPD）、慢性髓性白血病（CML）、T细胞急性淋巴细胞白血病（T-ALL）、B细胞急性淋巴细胞白血病（B-ALL）、非霍奇金淋巴瘤（NHL）、B细胞淋巴瘤和实体瘤，如乳腺癌。

  公开号：

  US08765940B2

文献信息

• N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and
  申请人：Pfizer Inc.

  公开号：US04569942A1

  公开（公告）日：1986-02-11

  Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also further substituted on the carboxamide nitrogen by an alkyl, cycloalkyl, phenyl or substituted phenyl group, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and antiinflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for ameliorating pain in human patients recovering from surgery or trauma, and alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having a substituent on the carboxamide nitrogen, are useful as intermediates to the analgesic and antiinflammatory agents of the invention.

  某些在3位上具有酰基取代基，并且在羧酰胺氮上进一步被烷基、环烷基、苯基或取代苯基基团取代的2-噁嗪-1-羧酰胺化合物是环氧合酶（CO）和脂氧合酶（LO）酶的抑制剂，并且在哺乳动物主体中作为镇痛和抗炎药物是有用的。这些2-噁嗪-1-羧酰胺化合物对于缓解人类手术或创伤康复患者的疼痛以及减轻人类主体中慢性疾病的症状，如类风湿性关节炎和骨关节炎，具有特殊价值。某些在C-3位未取代的2-噁嗪-1-羧酰胺化合物，但在羧酰胺氮上具有取代基，作为本发明的镇痛和抗炎药物的中间体是有用的。
• 1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
  申请人：Pfizer Inc.

  公开号：US04721712A1

  公开（公告）日：1988-01-26

  Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also on the carboxamide nitrogen atom, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and anti-inflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis. Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having an acyl substituent on the carboxamide nitrogen atom, are useful as intermediates to the aforementioned analgesic and anti-inflammatory agents.

  某些在3位上具有酰基取代基，并且在羧酰胺氮原子上也有取代基的2-噁嗪-1-羧酰胺化合物是环氧合酶（CO）和脂氧合酶（LO）酶的抑制剂，并且在哺乳动物体内作为镇痛剂和抗炎剂具有用途。这些2-噁嗪-1-羧酰胺化合物对于急性给药用于缓解手术或创伤后人类患者的疼痛，以及对于慢性给药用于减轻慢性疾病症状，如类风湿性关节炎和骨关节炎的人类患者，具有特殊价值。某些在C-3位未取代的2-噁嗪-1-羧酰胺化合物，但在羧酰胺氮原子上具有酰基取代基，可作为上述镇痛剂和抗炎剂的中间体。
• Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
  申请人：Pfizer Inc.

  公开号：US04690943A1

  公开（公告）日：1987-09-01

  Certain novel 2-oxindole compounds, having an acyl substituent at both the 1-position and the 3-position, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic agents and antiinflammatory agents in mammalian subjects. These 1,3-diacyl-2-oxindole compounds are of particular value for acute administration for ameliorating pain in human patients recovering from surgery or trauma, and also for chronic administration to human subjects for alleviating the symptoms of chronic diseases such as rheumatoid arthritis and osteoarthritis.

  某些新型的2-噁嗪酮化合物，在1-位置和3-位置都有酰基取代基，是环氧合酶（CO）和脂氧合酶（LO）酶的抑制剂，并且在哺乳动物主体中作为镇痛剂和抗炎剂是有用的。这些1,3-二酰基-2-噁嗪化合物对于急性给药在减轻人类手术或创伤恢复中的疼痛方面具有特殊价值，也对于慢性给药给予人类主体以减轻类风湿性关节炎和骨关节炎等慢性疾病症状方面是有益的。
• Iron(II) Bromide-Catalyzed Intramolecular C–H Bond Amination [1,2]-Shift Tandem Reactions of Aryl Azides
  作者：Quyen Nguyen、Tuyen Nguyen、Tom G. Driver

  DOI：10.1021/ja3113565

  日期：2013.1.16

  Iron(II) bromide catalyzes the transformation of ortho-substituted aryl azides into 2,3-disubstituted indoles through a tandem ethereal C-H bond amination [1,2]-shift reaction. The preference for the 1,2-shift component of the tandem reaction was established to be Me < 1° < 2° < Ph.

  溴化铁 (II) 通过串联醚 CH 键胺化 [1,2] 转移反应催化邻位取代的芳基叠氮化物转化为 2,3-二取代的吲哚。对串联反应的 1,2-转变组分的偏好确定为 Me < 1° < 2° < Ph。
• 1,3-dicarboxamide-oxindoles as antiinflammatory agents
  申请人：Pfizer Inc.

  公开号：US04725616A1

  公开（公告）日：1988-02-16

  1,3-Dicarboxamidooxindoles as antiinflammatory agents prepared by reaction of the 1-carbamoyloxindole with an isocyanate or by aminolysis of the corresponding alkyl 1-carbamoyloxindole-3-carboxylate.

  1,3-二羧酰胺基吲哚作为抗炎药物，通过1-羰胺氧吲哚与异氰酸酯的反应或通过相应的烷基1-羰胺氧吲哚-3-羧酸酯的氨解反应制备。

表征谱图