4-甲基-5-溴咪唑 | 15813-08-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 4-甲基-5-溴咪唑
• 中文别名: 5-溴-4-甲基咪唑；4-溴-5-甲基咪唑；4(5)-溴-5(4)-甲基-咪唑
• 英文名称: 5-bromo-4-methyl-1H-imidazole
• 英文别名: 5-bromo-4-methyl-imidazole；4-bromo-5-methyl-1H-imidazole
• CAS: 15813-08-8
• 化学式: C₄H₅BrN₂
• 分子量: 161.001
• InChiKey: APWKDMLCPWYWKA-UHFFFAOYSA-N

物化性质

• 熔点：
  140-143
• 沸点：
  328.5±22.0 °C(Predicted)
• 密度：
  1.723±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4(5)-Bromo-5(4)-methyl-imidazole
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4(5)-Bromo-5(4)-methyl-imidazole
CAS number: 15813-08-8

---

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.

---

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.

---

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.

---

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, refrigerated.
Storage:

---

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.

---

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: C4H5BrN2
Molecular weight: 161.0

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-甲基-5-溴咪唑 以 氯仿 为溶剂， 以30 g (55%)的产率得到1-[N-methylcarbamyl]-4-methyl-5-bromoimidazole
  参考文献：
  名称：

  4-alkylimidazole derivatives and their use as nitrification inhibitors

  摘要：

  式I的4-烷基咪唑衍生物，其中R.sup.1是C.sub.1 -C.sub.4-烷基，R.sup.2是氯或溴，R.sup.3是--OR.sup.4或--NR.sup.5R.sup.6基团，其中R.sup.4是C.sub.1 -C.sub.4-烷基，R.sup.5是氢或C.sub.1 -C.sub.4-烷基，R.sub.6是C.sub.1 -C.sub.4-烷基或是苯基，苯基未取代或被1或2个卤素原子取代，及其盐，其制备以及其作为硝化抑制剂的用途。

  公开号：

  US04602927A1
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯仿 、 溴 作用下， 生成 4-甲基-5-溴咪唑
  参考文献：
  名称：

  Pauly; Arauner, Journal fur praktische Chemie (Leipzig 1954), 1928, vol. <2> 118, p. 35,41

  摘要：

  DOI：

文献信息

• Pyridinylimidazoles as GSK3β Inhibitors: The Impact of Tautomerism on Compound Activity via Water Networks
  作者：Fabian Heider、Tatu Pantsar、Mark Kudolo、Francesco Ansideri、Angela De Simone、Letizia Pruccoli、Taiane Schneider、Marcia Inês Goettert、Andrea Tarozzi、Vincenza Andrisano、Stefan A. Laufer、Pierre Koch

  DOI：10.1021/acsmedchemlett.9b00177

  日期：2019.10.10

  GSK3β/p38α mitogen-activated protein kinase inhibitors and identified N-(4-(4-(4-fluorophenyl)-2-methyl-1H-imidazol-5-yl)pyridin-2-yl)cyclopropanecarboxamide (1) as a potent dual inhibitor of both target kinases. In this study, we aimed to design selective GSK3β inhibitors based on our pyridinylimidazole scaffold. Our efforts resulted in several novel and potent GSK3β inhibitors with IC50 values in the

  糖原合酶激酶3β（GSK3β）参与许多病理状况，代表了有吸引力的药物靶标。我们先前曾报道过两种GSK3β/p38α丝裂原活化蛋白激酶抑制剂，并鉴定出N-（4-（4-（4-氟苯基）-2-甲基-1 H-咪唑-5-基）吡啶-2-基）环丙烷甲酰胺（1）作为两种靶激酶的有效双重抑制剂。在这项研究中，我们旨在基于我们的吡啶基咪唑骨架设计选择性GSK3β抑制剂。我们的努力导致了几种新颖且有效的GSK3β抑制剂，其IC 50值在低纳摩尔范围内。5-（2-（环丙烷甲酰胺基）吡啶-4-基）-4-环丙基-1 H-咪唑-2-羧酰胺（6g）在神经元SH-SY5Y细胞中表现出非常好的激酶选择性以及代谢稳定性，并抑制了GSK3β活性。有趣的是，我们观察到了2-甲基咪唑的互变异构状态对于化合物活性的重要性。最后，我们揭示了咪唑-2-羧酰胺如何克服这种关键的互变异构效应，无论它们的互变异构状态如何，咪唑-2-羧酰胺都能通过增强的水网络相互作用来稳定结合。
• [EN] HETEROARYL SUBSTITUTED INDOLE COMPOUNDS USEFUL AS MMP-13 INHIBITORS<br/>[FR] COMPOSÉS INDOLE À SUBSTITUTION HÉTÉROARYLE UTILISÉS COMME INHIBITEURS DE MMP-13
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010045188A1

  公开（公告）日：2010-04-22

  Disclosed are compounds and compositions of the formula I as described herein which are inhibitors of MMP-13. Also disclosed are methods of using and making compounds of the formula I.

  披露了公式I的化合物和组合物，如本文所述，它们是MMP-13的抑制剂。还披露了使用和制造公式I化合物的方法。
• [EN] MACROCYCLIC AZOLOPYRIDINE DERIVATIVES AS EED AND PRC2 MODULATORS<br/>[FR] DÉRIVÉS D'AZOLOPYRIDINE MACROCYCLIQUES UTILISÉS EN TANT QUE MODULATEURS EED ET PRC2
  申请人：FULCRUM THERAPEUTICS INC

  公开号：WO2020190754A1

  公开（公告）日：2020-09-24

  The invention relates to modulators of Embryonic Ectoderm Development (EED) and/or Polycomb Repressive Complex 2 (PRC2) useful in the treatment of disorders and diseases associated with EEC and PRC2, being macrocyclic azolopyridine derivatives and compositions thereof of Formula (I), or a pharmaceutically acceptable salt, prodrug, solvate, hydrate, enantiomer, isomer, or tautomer thereof, wherein X1, X2, X3, A1, A2, Y, R1, R2, R3, and R4 are as described herein.

  本发明涉及用于治疗与Embryonic Ectoderm Development (EED)和/或Polycomb Repressive Complex 2 (PRC2)相关的疾病和障碍的调节剂，是式(I)所示的宏环唑啉衍生物及其组合物，或其药用可接受的盐、前药、溶剂化物、水合物、对映体、异构体或互变异构体，其中X1、X2、X3、A1、A2、Y、R1、R2、R3和R4如本文所述。
• TRICYCLIC ASK1 INHIBITORS
  申请人：Terns, Inc.

  公开号：US20190315767A1

  公开（公告）日：2019-10-17

  Provided herein are compounds, preferably ASK1 inhibitor compounds, compositions thereof, and methods of their preparation, and methods of inhibiting ASK1 and methods for treating disorders mediated by ASK1.

  本文提供了化合物，最好是ASK1抑制剂化合物，其组成物，以及它们的制备方法，抑制ASK1的方法以及治疗由ASK1介导的疾病的方法。
• Synthesis of a Nonhydrolyzable Nucleotide Phosphoroimidazolide Analogue That Catalyzes Nonenzymatic RNA Primer Extension
  作者：Chun Pong Tam、Lijun Zhou、Albert C. Fahrenbach、Wen Zhang、Travis Walton、Jack W. Szostak

  DOI：10.1021/jacs.7b11623

  日期：2018.1.17

  nonenzymatic RNA primer extension. The addition of a 2-MeImpN monomer to a primer is catalyzed by the presence of a downstream activated monomer, yet the three nonhydrolyzable analogues do not show catalytic effects under standard mildly basic primer extension conditions. Surprisingly, ICG, which has a pKa similar to that of 2-MeImpG, is a modest catalyst of nonenzymatic primer extension at acidic pH.

  我们报告了鸟苷 5'-（4-甲基咪唑基）膦酸酯（ICG）的合成，这是一系列不可水解的核苷 5'-磷酸-2-甲基咪唑化物（2-MeImpN）类似物的第三个成员，设计用于非酶 RNA 引物的机械研究扩大。将 2-MeImpN 单体添加到引物是由下游活化单体的存在催化的，但三种不可水解的类似物在标准的温和碱性引物延伸条件下不显示催化作用。令人惊讶的是，ICG 具有与 2-MeImpG 相似的 pKa，是酸性 pH 下非酶促引物延伸的适度催化剂。在这里，我们表明 ICG 与 2-MeImpC 反应形成稳定的 5'-5'-咪唑桥连鸟苷-胞嘧啶二核苷酸，在中央咪唑桥两侧有一个不稳定的氮-磷和一个稳定的碳-磷键。同源 RNA 引物-模板复合物通过攻击 5'-5'-咪唑桥活化 N-P 侧的引物 3'-羟基与该 GC-二核苷酸反应。这些观察结果支持这样的假设，即 5'-5'-咪唑桥接二核苷酸可以与同源 RNA