3-溴-5-硝基苯甲酸甲酯 | 6307-87-5

• 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: 3-溴-5-硝基苯甲酸甲酯
• 英文名称: methyl 3-bromo-5-nitrobenzoate
• CAS: 6307-87-5
• 化学式: C₈H₆BrNO₄
• 分子量: 260.044
• InChiKey: DDJCZBFPZLYREP-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C(Solv: ethanol (64-17-5))
• 沸点：
  326.0±22.0 °C(Predicted)
• 密度：
  1.673±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2916399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-bromo-5-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: Methyl 3-bromo-5-nitrobenzoate
CAS number: 6307-87-5

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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: C8H6BrNO4
Molecular weight: 260.0

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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

制备方法与用途

用途

3-溴-5-硝基苯甲酸甲酯是一种医药中间体。它可用于制备3-酰胺基苯甲酸衍生物，如3-(4-三氟甲基苯甲酰基)氨基-5-(2’，6’-(2H)哌啶基苯基)苯甲酸，这类化合物具有P2Y受体拮抗作用。

制备

首先制备3-硝基-5-溴苯甲酸。在0℃条件下，将3-硝基苯甲酸（5.0g，29.92mmol）溶于浓硫酸（50mL）中，缓慢加入N-溴代琥珀酰亚胺（6.35g，35.90mmol），随后在65℃油浴锅中搅拌反应2小时。反应完全后，将反应液倒入冰水中，搅拌1小时，抽滤、冰水洗涤、干燥，得白色固体产物6.9g，产率约为95%。

接着制备3-溴-5-硝基苯甲酸甲酯。将3-硝基-5-溴苯甲酸（5.0g，23.14mmol）溶于甲醇（25mL）中，在0℃条件下逐滴加入SOCl2（15mL），滴加完毕后移至室温搅拌反应2小时。反应完全后缓慢加入NaHCO3饱和溶液（100mL），继续搅拌30分钟至无气泡产生，乙酸乙酯萃取（3次），有机相用饱和食盐水洗，无水硫酸钠干燥。通过柱层析（石油醚：乙酸乙酯=10:1）得到白色固体约4.6g，产率为86.46%。

反应信息

• 作为反应物：
  描述：

  3-溴-5-硝基苯甲酸甲酯 在 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 3-氨基-5-溴苯甲酸甲酯
  参考文献：
  名称：

  Preparation of Molecular Cage by Coordination of m-Calix[3]amide Bearing Pyridine with Palladium Complex

  摘要：

  通过使用 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS) 环化 3-壬基氨基-5-(吡啶-4-基)苯甲酸甲酯，合成了苯环上有吡啶的间萼[3]酰胺（PyC3A）。分子笼 3Pd-2PyC3A 由 PyC3A 和 [Pd(dppp)(OTf)2] 的 2:3 混合物在 CDCl3/CD3OD （体积比为 5/1）中制备而成。另一方面，在 CDCl3 中，确认了聚合物混合物的形成。

  DOI：

  10.1246/cl.2012.249
• 作为产物：
  描述：

  间硝基苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 草酰氯 、 硫酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 3-溴-5-硝基苯甲酸甲酯
  参考文献：
  名称：

  发现14-3-3蛋白质-蛋白质相互作用抑制剂使多药耐药癌细胞对阿霉素和Akt抑制剂GSK690693敏感

  摘要：

  14-3-3是一类高度保守的衔接蛋白，在药物化学家中引起了极大的兴趣。对14-3-3蛋白-蛋白质相互作用（PPI）的小分子抑制剂的需求量很大，既可以作为工具来增进我们对人类疾病中14-3-3的作用的了解，又可以开发创新的治疗药物。在此，我们通过多学科策略结合分子建模，有机合成，基于图像的报告细胞高含量分析以及使用癌细胞的体外测定方法，提出了新型14-3-3 PPI抑制剂的发现。值得注意的是，两种活性最高的化合物促进c-Abl和FOXO促凋亡因子向核内转移，并使对多药耐药的癌细胞向凋亡诱导剂（如阿霉素和pan-Akt抑制剂GSK690693）敏感，因此成为进一步优化的有价值的潜在候选人。我们的结果强调了14-3-3 PPI抑制剂在抗癌联合疗法中的可能作用。

  DOI：

  10.1002/cmdc.201400044

文献信息

• MACROCYCLIC COMPOUNDS AND THEIR USE AS KINASE INHIBITORS
  申请人：Combs Andrew Paul

  公开号：US20090286778A1

  公开（公告）日：2009-11-19

  The present invention relates to macrocyclic compounds of Formula I: or pharmaceutically acceptable salts thereof or quaternary ammonium salts thereof wherein constituent members are provided hereinwith, as well as their compositions and methods of use, which are JAK/ALK inhibitors useful in the treatment of JAK/ALK-associated diseases including, for example, inflammatory and autoimmune disorders, as well as cancer.

  本发明涉及以下化学式I的大环化合物： 或其药用可接受盐或季铵盐，其中所述成员在此提供，并且它们的组成物和使用方法，这些JAK/ALK抑制剂在治疗JAK/ALK相关疾病中有用，例如炎症和自身免疫性疾病以及癌症。
• Discovery of 14-3-3 Protein-Protein Interaction Inhibitors that Sensitize Multidrug-Resistant Cancer Cells to Doxorubicin and the Akt Inhibitor GSK690693
  作者：Mattia Mori、Giulia Vignaroli、Ylenia Cau、Jelena Dinić、Richard Hill、Matteo Rossi、David Colecchia、Milica Pešić、Wolfgang Link、Mario Chiariello、Christian Ottmann、Maurizio Botta

  DOI：10.1002/cmdc.201400044

  日期：2014.5

  synthesis, image‐based high‐content analysis of reporter cells, and in vitro assays using cancer cells. Notably, the two most active compounds promoted the translocation of c‐Abl and FOXO pro‐apoptotic factors into the nucleus and sensitized multidrug‐resistant cancer cells to apoptotic inducers such as doxorubicin and the pan‐Akt inhibitor GSK690693, thus becoming valuable lead candidates for further optimization

  14-3-3是一类高度保守的衔接蛋白，在药物化学家中引起了极大的兴趣。对14-3-3蛋白-蛋白质相互作用（PPI）的小分子抑制剂的需求量很大，既可以作为工具来增进我们对人类疾病中14-3-3的作用的了解，又可以开发创新的治疗药物。在此，我们通过多学科策略结合分子建模，有机合成，基于图像的报告细胞高含量分析以及使用癌细胞的体外测定方法，提出了新型14-3-3 PPI抑制剂的发现。值得注意的是，两种活性最高的化合物促进c-Abl和FOXO促凋亡因子向核内转移，并使对多药耐药的癌细胞向凋亡诱导剂（如阿霉素和pan-Akt抑制剂GSK690693）敏感，因此成为进一步优化的有价值的潜在候选人。我们的结果强调了14-3-3 PPI抑制剂在抗癌联合疗法中的可能作用。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2013096153A1

  公开（公告）日：2013-06-27

  The invention is directed to substituted quinoline derivatives. Specifically, the invention is directed to compounds according to Formula I: wherein R, R1, R2, R3 and R4 are defined herein. The compounds of the invention are inhibitors of lactate dehydrogenase A and can be useful in the treatment of cancer and diseases associated with tumor cell metabolism, such as cancer, and more specifically cancers of the breast, colon, prostate and lung. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting lactate dehydrogenase A activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代喹啉衍生物。具体而言，本发明涉及根据公式I的化合物：其中R，R1，R2，R3和R4按如下定义。本发明的化合物是乳酸脱氢酶A的抑制剂，可用于治疗癌症和与肿瘤细胞代谢有关的疾病，例如癌症，更具体地说是乳腺癌、结肠癌、前列腺癌和肺癌。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明的化合物或包含本发明化合物的药物组合物来抑制乳酸脱氢酶A活性和治疗与之相关的疾病的方法。
• <i>meta</i> ‐Nitration of Arenes Bearing <i>ortho</i> / <i>para</i> Directing Group(s) Using C−H Borylation
  作者：Xuejing Li、Xingwang Deng、Anthony G. Coyne、Rajavel Srinivasan

  DOI：10.1002/chem.201901633

  日期：2019.6.18

  of arenes bearing ortho/para directing group(s) using the iridium‐catalyzed C−H borylation reaction followed by a newly developed copper(II)‐catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one‐pot fashion. This protocol allows the synthesis of meta‐nitrated arenes that are tedious to prepare or require multistep synthesis using the existing

  在本文中，我们报道了荟萃芳烃的-nitration轴承邻/对位用铱催化的C-H硼化反应之后是新开发的铜（II）粗频哪醇的芳基硼酸酯入的催化的变换引导组（多个）以一锅的方式对应的硝基芳烃。该协议允许的合成元-nitrated芳烃是乏味来制备或使用现有的方法需要多步合成。该反应可耐受多种邻位/对位导向基团，例如-F，-Cl，-Br，-CH 3，-Et，-i Pr -OCH 3和-OCF 3。它还提供对π电子缺陷杂环的硝基衍生物（例如吡啶和喹啉衍生物）的区域选择性访问。该方法的应用在复杂分子的后期修饰中以及在以克级制备到FDA批准的药物Nilotinib途中的中间体中得到了证明。最后，我们证明了通过该策略获得的硝基产物也可以通过Baran的胺化方案直接转化为苯胺或受阻胺。
• [EN] 1,3,5-SUBSTITUTED PHENYL DERIVATIVE COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE<br/>[FR] DERIVES DE PHENYLE 1,3,5-SUBSTITUES UTILES COMME INHIBITEURS DE LA BETA-SECRETASE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER
  申请人：MERCK & CO INC

  公开号：WO2005103020A1

  公开（公告）日：2005-11-03

  The present invention is directed to 1,3,5-phenyl substituted derivative compounds which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.

  本发明涉及1,3,5-苯基取代衍生物化合物，这些化合物是β-分泌酶的抑制剂，可用于治疗β-分泌酶参与的疾病，例如阿尔茨海默病。该发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在治疗β-分泌酶参与疾病中的用途。