1-溴-3-甲氧基-5-硝基苯 | 16618-67-0

• 物质功能分类: 化学试剂 - 有机试剂 - 硝基化合物
• 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: 1-溴-3-甲氧基-5-硝基苯
• 中文别名: 3-溴-5-硝基苯甲醚
• 英文名称: 3-bromo-5-nitroanisole
• 英文别名: 1-bromo-3-methoxy-5-nitrobenzene；5-Brom-3-nitro-anisol
• CAS: 16618-67-0
• 化学式: C₇H₆BrNO₃
• mdl: MFCD04112752
• 分子量: 232.034
• InChiKey: MEQKSFQEPDRNEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  86.0 to 90.0 °C
• 沸点：
  295.3±20.0 °C(Predicted)
• 密度：
  1.640±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-5-nitroanisole
Synonyms: 1-Bromo-3-methoxy-5-nitrobenzene

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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: 3-Bromo-5-nitroanisole
CAS number: 16618-67-0

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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: C7H6BrNO3
Molecular weight: 232.0

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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

3-溴-5-硝基苯甲醚的制备

3-溴-5-硝基苯甲醚又称为3-甲氧基-5-硝基溴苯，可通过间二硝基苯为原料经过两步反应制得。它可用于合成吲哚并喹啉类化合物N-(4-碘苯基)10H-吲哚[3,2-b]喹啉。

制备过程

将30.0克间二硝基苯（0.18 mmol）溶解于180毫升浓硫酸中，加热至80℃并保持温度在80-90℃之间。然后分九批加入44.5克NBS（0.25 mol），加完后继续反应30分钟。冷却后倾入600毫升冰水中，析出白色沉淀物，抽滤、水洗、干燥得白色固体3,5-二硝基溴苯41.3克，产率为93.7%。

接着称取1克金属钠（43.4 mmol），溶解于甲醇中配成甲醇钠溶液。将8.7克3,5-二硝基溴苯（35.2 mmol）加入上述甲醇钠溶液中，进行45℃回流反应2小时。冷却至室温后，用50毫升1N盐酸处理，然后使用二氯甲烷萃取。合并有机相并用水洗三次，再用无水硫酸镁干燥，过滤除去溶剂，粗品通过柱分离（石油醚：二氯甲烷=5:1）获得白色粉末状固体3-溴-5-硝基苯甲醚4.6克，产率为56.3%。

反应信息

• 作为反应物：
  描述：

  1-溴-3-甲氧基-5-硝基苯 在 三溴化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 生成 3-溴-5-硝基苯酚
  参考文献：
  名称：

  [EN] 2 -ARYLAMINOQUINAZOLINES FOR TREATING PROLIFERATIVE DISEASES
  [FR] 2 -ARYLAMINOQUINAZOLINES DESTINÉES AU TRAITEMENT DES MALADIES PROLIFÉRATIVES

  摘要：

  这项发明提供了一种抑制PDKI的新型化合物。还提供了包括这些化合物的药物组合物，以及使用这些化合物或组合物治疗增殖性疾病，如癌症的方法。

  公开号：

  WO2009153313A1
• 作为产物：
  描述：

  1,3-二硝基苯 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 1-溴-3-甲氧基-5-硝基苯
  参考文献：
  名称：

  的1,5-双官能有机锂试剂由双定向合成邻-metalation：酯的直接转化为1,8-二甲氧基吖啶盐

  摘要：

  电子和位阻因素对亲电子芳族取代度选择性的影响达到了访问特定取代方式的几个限制。通过定向金属化生成的亲核试剂是制备各种明显取代的芳烃和杂环骨架以克服这些限制的有效替代方法。在此，我们从酯通过加入从双定向1,5-双官能的有机金属试剂报告特定取代的杂环荧光团的直接合成邻-metalation（DD ÒM）。双（3-甲氧基苯基）胺被有效地二锂化，并用于合成具有独特的光物理和电化学性质的1,8-二甲氧基-啶鎓盐。这些新染料的单个还原电势，水溶性和亮度，有望在催化，成像和材料科学中有不同的应用。

  DOI：

  10.1016/j.tet.2018.04.060

文献信息

• IRAK DEGRADERS AND USES THEREOF
  申请人：Kymera Therapeutics, Inc.

  公开号：US20190192668A1

  公开（公告）日：2019-06-27

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• 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。
• KINASE INHIBITORS
  申请人：Topivert Pharma Limited

  公开号：US20140296208A1

  公开（公告）日：2014-10-02

  There are provided compounds of formula I, wherein R 1A to R 1E , R 2 to R 5 , L and X 1 to X 3 have meanings given in the description, which compounds have antiinflammatory activity (e.g. through inhibition of one or more of members of: the family of p38 mitogen-activated protein kinase enzymes; Syk kinase; and members of the Src family of tyrosine kinases) and have use in therapy, including in pharmaceutical combinations, especially in the treatment of inflammatory diseases, including inflammatory diseases of the lung, eye and intestines.

  提供了具有式I的化合物， 其中R 1A至R 1E，R 2至R 5，L和X 1至X 3在描述中给出了含义，这些化合物具有抗炎活性（例如通过抑制p38丝裂原活化蛋白激酶酶家族中的一个或多个成员；Syk激酶；和酪氨酸激酶Src家族的成员之一）并且在治疗中有用，包括在药物组合中，特别是在治疗炎症性疾病，包括肺部、眼睛和肠道的炎症性疾病。
• [EN] UREA DERIVATIVES USEFUL AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS D'URÉE UTILISÉS EN TANT QU'INHIBITEURS DE KINASE
  申请人：RESPIVERT LTD

  公开号：WO2014162126A1

  公开（公告）日：2014-10-09

  There are provided compounds of formula I, wherein R1A to R1E, R2 to R5, L and X1 to X3 have meanings given in the description, which compounds have antiinflammatory activity (e.g. through inhibition of one or more of members of: the family of p38 mitogen-activated protein kinase enzymes; Syk kinase; and members of the Src family of tyrosine kinases) and have use in therapy, including in pharmaceutical combinations, especially in the treatment of inflammatory diseases, including inflammatory diseases of the lung, eye and intestines.

  提供了化学式I的化合物，其中R1A至R1E，R2至R5，L和X1至X3的含义如描述中所示，这些化合物具有抗炎活性（例如通过抑制p38丝裂原活化蛋白激酶酶家族中的一个或多个成员；Syk激酶；和酪氨酸激酶Src家族的成员之一）并且在治疗中有用，包括在药物组合中，特别是用于治疗炎症性疾病，包括肺部、眼睛和肠道的炎症性疾病。
• [EN] HETEROCYCLIC INHIBITORS OF PCSK9<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DE PCSK9
  申请人：CARDIO THERAPEUTICS PTY LTD

  公开号：WO2018165718A1

  公开（公告）日：2018-09-20

  This application relates to chemical compounds which may act as inhibitors of, or which may otherwise modulate the activity of, PCSK9, or a pharmaceutically acceptable salt, solvate, prodrug or polymorph thereof, and to compositions and formulations comprising such compounds, and methods of using and making such compounds. Compounds include compounds of Formula (I): (I) wherein A, D and Q are described herein.

  这种应用涉及可能作为PCSK9的抑制剂或以其他方式调节PCSK9活性的化合物，或其药用可接受的盐、溶剂化合物、前药或多型体，以及包含这些化合物的组合物和配方，以及使用和制备这些化合物的方法。化合物包括式(I)的化合物：(I)其中A、D和Q如本文所述。