3-溴-6-甲氧基吡嗪 | 17321-29-8

• 物质功能分类: 医药中间体 - 吡嗪类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-溴-6-甲氧基吡嗪
• 中文别名: 3-溴-6-甲氧基哒嗪
• 英文名称: 3-bromo-6-methoxypyridazine
• 英文别名: 6-Methoxy-3-brom-pyridazin
• CAS: 17321-29-8
• 化学式: C₅H₅BrN₂O
• 分子量: 189.011
• InChiKey: SWXXQESBTCWUIK-UHFFFAOYSA-N

物化性质

• 沸点：
  311.0±22.0 °C(Predicted)
• 密度：
  1.628±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-6-methoxypyridazine
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: 3-Bromo-6-methoxypyridazine
CAS number: 17321-29-8

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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: C5H5BrN2O
Molecular weight: 189.0

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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

应用

3-溴-6-甲氧基吡嗪是一种有机中间体，可通过3,6-二溴哒嗪与甲醇钠的亲核取代反应，在DMSO中于80℃条件下制备得到。据文献报道，这种化合物可用于制备铱金属配合物，并主要应用于实验室有机合成过程中。

制备

3-溴-6-甲氧基吡嗪可通过以下步骤制备：将3,6-二溴哒嗪与甲醇钠在DMSO中于80℃反应即可得到目标产物。

反应信息

• 作为反应物：
  描述：

  3-溴-6-甲氧基吡嗪 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 40.08h， 生成 6-methoxy-N-(pyrazin-2-yl)-N-({5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiophen-2-yl}methyl)pyridazin-3-amine
  参考文献：
  名称：

  [EN] OXADIAZOLYLTHIOPHENE DERIVATIVES USEFUL AS HISTONE DEACETYLASE INHIBITORS
  [FR] DÉRIVÉS D'OXADIAZOLYLTHIOPHÈNE À UTILISER EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE

  摘要：

  一种Formula I的化合物：(I)或其药学上可接受的盐，其中：每个R'是QR1；每个Q独立地选自键，-C1-C10烷基，-C2-C10烯基，-C(O)-，-C(O)O-，-C(O)N(R1)-，-C(O)N(R1)SO2-，-N(R1)C(O)-，-N(R1)-，-N(SO2(R1))，-N(R1)SO2-，-C(O)NR4R5-，-N(R4R5)C(O)-，-N(R4R5)-，-S-，-SO-，-SO2-，-S(O)O-，-SO2N(R1)-和-O-；每个R1独立地选自H，C1-C10烷基，C2-C10烯基，C2-C10炔基，C1-C10卤代烷基，C1-C10杂原子烷基，芳基，杂芳基，C3-C10环烷基，-(C1-C10烷基)-C3-C10环烷基，卤素，氰基，C1-C10烷基-芳基，C1-C10烷基-杂原子芳基，C1-C10杂环烷基和-(C1-C10烷基)-C1-C10杂环烷基。这些化合物是HDAC的抑制剂，因此在治疗包括癌症和炎症在内的多种疾病中具有潜在用途。

  公开号：

  WO2019166824A1
• 作为产物：
  描述：

  3,6-二溴哒嗪 、 sodium methylate 在 甲醇 作用下， 生成 3-溴-6-甲氧基吡嗪
  参考文献：
  名称：

  杂环研究中的化学研究。4. Mitteilung。哒嗪类衍生物

  摘要：

  描述了许多3-和6-位取代的哒嗪和4-甲基哒嗪用于药理研究。某些3,6-二烷氧基-哒嗪具有良好的抗惊厥性质。3,6-二肼基哒嗪在其药理特性上类似于降血压药“ A presoline”和“ Nepresol”。3-氨基-6-氯哒嗪的磺基衍生物具有优异的抗菌作用。

  DOI：

  10.1002/hlca.19540370115

文献信息

• COMPOUNDS AND USES THEREOF
  申请人：Yumanity Therapeutics, Inc.

  公开号：US20190330198A1

  公开（公告）日：2019-10-31

  The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本发明涉及用于治疗神经系统疾病的化合物。本发明的化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• Synthesis of Isomerically Pure (<i>Z</i>)-Alkenes from Terminal Alkynes and Terminal Alkenes: Silver-Catalyzed Hydroalkylation of Alkynes
  作者：Mitchell T. Lee、Madison B. Goodstein、Gojko Lalic

  DOI：10.1021/jacs.9b09336

  日期：2019.10.30

  molecules and often are used as intermediates in organic synthesis. Many alkenes exist in two stereoisomeric forms (E and Z), which have different structures and different properties. The selective formation of the two isomers is an important synthetic goal that has long inspired the development of new synthetic methods. However, the efficient synthesis of diastereopure, thermodynamically less stable, Z-alkenes

  烯烃是一类重要的化合物，常见于生物活性分子中，常被用作有机合成的中间体。许多烯烃以两种立体异构形式（E 和 Z）存在，它们具有不同的结构和不同的性质。两种异构体的选择性形成是一个重要的合成目标，长期以来一直激励着新合成方法的发展。然而，非对映纯、热力学稳定性较差的 Z-烯烃的有效合成仍然具有挑战性。在这里，我们展示了通过银催化的末端炔烃加氢烷基化，使用烷基硼烷作为偶联伙伴，有效合成非对映纯 Z-烯烃（Z:E > 300:1）。我们还描述了对底物范围的探索，这揭示了新方法的广泛官能团兼容性。
• [EN] MAP4K4 INHIBITORS<br/>[FR] INHIBITEURS DE MAP4K4
  申请人：IMPERIAL COLLEGE SCI TECH & MEDICINE

  公开号：WO2020115481A1

  公开（公告）日：2020-06-11

  This invention relates to compounds that may be useful as inhibitors of Mitogen-activated Protein Kinase Kinase Kinase Kinase-4 (MAP4K4). The invention also relates to the use of these compounds, for example in a method of treatmentof cardiac conditions.In particular, the present invention relates to compounds of formula (I):

  这项发明涉及可能作为Mitogen-activated Protein Kinase Kinase Kinase Kinase-4（MAP4K4）抑制剂有用的化合物。发明还涉及这些化合物的使用，例如在治疗心脏疾病的方法中。特别是，本发明涉及公式（I）的化合物：
• Stereospecific Synthesis of <i>E</i>-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes
  作者：Avijit Hazra、Jason Chen、Gojko Lalic

  DOI：10.1021/jacs.9b04800

  日期：2019.8.14

  We have developed a method for stereospecific synthesis of E-alkenes from terminal alkynes and alkyl iodides. The hydroalkylation reaction is enabled by a cooperative action of copper and nickel catalysts and proceeds with excellent anti-Markovnikov selectivity. We demonstrate the broad scope of the reaction, which can be accomplished in the presence of esters, nitriles, aryl bromides, ethers, alkyl

  我们开发了一种从末端炔烃和烷基碘立体有择合成 E-烯烃的方法。加氢烷基化反应是通过铜和镍催化剂的协同作用实现的，并以优异的抗马尔科夫尼科夫选择性进行。我们展示了该反应的广泛范围，该反应可以在酯类、腈类、芳基溴化物、醚类、烷基氯、苯胺和各种含氮杂芳族化合物的存在下完成。机理研究提供的证据表明，铜催化剂通过氢铜作用活化炔烃，从而控制整个反应的区域选择性和非对映选择性。镍催化剂活化烷基碘并促进与烯基铜中间体的交叉偶联。
• [EN] 5-PHENOXY-3H-PYRIMIDIN-4-ONE DERIVATIVES AND THEIR USE AS HIV REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] DÉRIVÉS DE 5-PHÉNOXY-3H-PYRIMIDIN-4-ONE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA TRANSCRIPTASE INVERSE DU VIH
  申请人：MERCK SHARP & DOHME

  公开号：WO2014058747A1

  公开（公告）日：2014-04-17

  Compounds of Formula (I) are HIV reverse transcriptase inhibitors, wherein R1, R2, RE, L, M and Z are defined herein. The compounds of Formula (I) and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

  化合物（I）的化学式是HIV反转录酶抑制剂，其中R1、R2、RE、L、M和Z在此处定义。化合物（I）及其药学上可接受的盐在抑制HIV反转录酶、预防和治疗HIV感染以及预防、延缓艾滋病发病或进展和治疗方面是有用的。这些化合物及其盐可作为药物组合物中的成分，可选择性地与其他抗病毒药物、免疫调节剂、抗生素或疫苗结合使用。