3,6-二溴吡嗪-2-甲酸甲酯 | 13301-04-7

• 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 - 有机杂环化合物 - 二嗪类
• 中文名称: 3,6-二溴吡嗪-2-甲酸甲酯
• 中文别名: 3,6-二溴吡嗪-2-羧酸甲酯；3,6-二溴-3-羧酸甲酯吡嗪；2,5-二溴-3-羧酸甲酯；3,6-二溴-2-吡嗪羧酸甲酯；3,6-二溴-2-羧酸甲酯吡嗪
• 英文名称: methyl 3,6-dibromopyrazine-2-carboxylate
• 英文别名: 3,6-dibromopyrazine-2-carboxylic acid methyl ester
• CAS: 13301-04-7
• 化学式: C₆H₄Br₂N₂O₂
• 分子量: 295.918
• InChiKey: OHKYQPNNVGHVOT-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68℃
• 沸点：
  304.6±37.0 °C(Predicted)
• 密度：
  2.024

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

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

---

Section 1. Identification of the substance
Product Name: Methyl 3,6-dibromopyrazine-2-carboxylate
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: Methyl 3,6-dibromopyrazine-2-carboxylate
CAS number: 13301-04-7

---

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.
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: C6H4Br2N2O2
Molecular weight: 295.9

---

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

制备方法与用途

应用：3,6-二溴吡嗪-2-甲酸甲酯可作为医药化工合成中的重要中间体。

反应信息

• 作为反应物：
  描述：

  3,6-二溴吡嗪-2-甲酸甲酯 在 水 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以100 %的产率得到3,6-二溴吡嗪-2-甲酸
  参考文献：
  名称：

  Dragmacidins G 和 H 的全合成

  摘要：

  使用适当功能化的吡嗪作为底物，通过亲核芳香取代和位点选择性交叉偶联反应，首次实现了德拉马西丁 G 和 H 的全合成。德拉马西丁 G、德拉马西丁 H 和合成类似物对金黄色葡萄球菌和外排泵缺陷型鼠伤寒沙门氏菌的抗菌活性评估表明，靠近硫化物单元的吲哚环上存在 Br 基团对于提高抗菌活性非常重要。

  DOI：

  10.1021/acs.orglett.3c04039
• 作为产物：
  描述：

  3-氨基吡嗪-2-羧酸 在 硫酸 、 氢溴酸 、 溴 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 3,6-二溴吡嗪-2-甲酸甲酯
  参考文献：
  名称：

  Discovery of a series of imidazopyrazine small molecule inhibitors of the kinase MAPKAPK5, that show activity using in vitro and in vivo models of rheumatoid arthritis

  摘要：

  MAPKAPK5 has been proposed to play a role in regulation of matrix metalloprotease expression and so to be a potential target for intervention in rheumatoid arthritis. We present here the identification of a series of compounds against this target which are effective in both biochemical and cell assays. The expansion of the series is described, along with early SAR and pharmacokinetics for some representative compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.077

文献信息

• [EN] STRAD-BINDING AGENTS AND USES THEREOF<br/>[FR] AGENTS DE LIAISON À STRAD ET LEURS UTILISATIONS
  申请人：UNIV CALIFORNIA

  公开号：WO2021155004A1

  公开（公告）日：2021-08-05

  Disclosed herein, inter alia, are compounds for binding STRAD pseudokinase and uses thereof.

  披露的内容包括，但不限于，用于结合STRAD假激酶的化合物及其用途。
• CARBAMOYLOXYMETHYL TRIAZOLE CYCLOHEXYL ACIDS AS LPA ANTAGONISTS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20170360759A1

  公开（公告）日：2017-12-21

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, pharmaceutically acceptable salts, solvates or prodrugs thereof, wherein all the variables are as defined herein. These compounds are selective LPA receptor inhibitors.

  本发明提供了式(I)的化合物：或其立体异构体、互变异构体、药用盐、溶剂化物或前药，其中所有变量均如本文所述。这些化合物是选择性的LPA受体抑制剂。
• [EN] SHP2 INHIBITORS, COMPOSITIONS AND USES THEREOF<br/>[FR] INHIBITEURS DE SHP2, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：BETTA PHARMACEUTICALS CO LTD

  公开号：WO2021249449A1

  公开（公告）日：2021-12-16

  Provided are compounds of Formula (I), methods of using the compounds as SHP2 inhibitors, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating SHP2-mediated diseases.

  提供的是式（I）的化合物，使用这些化合物作为SHP2抑制剂的方法，以及包含这些化合物的药物组合物。这些化合物在治疗SHP2介导的疾病方面是有用的。
• Efficient Three-Step One-Pot Synthesis of a Novel 2,3,5-Substituted Pyrazine Library
  作者：Christian Delvare、Craig S. Harris、Laurent Hennequin、Patrice Koza、Christine Lambert-van der Brempt、Jacques Pelleter、Olivier Willerval

  DOI：10.1021/co200062n

  日期：2011.9.12

  The partnership between rational synthesis design and mass-triggered preparative LCMS is a powerful one, capable of furnishing very large libraries in a selective manner in a very short space of time. Herein, we communicate one example of possibly a perfect marriage between the synthetic chemistry and the subsequent purification method employed, affording a ∼1000-member library supplying 50 mg on average

  合理的合成设计与大量触发的制备型LCMS之间的合作关系非常强大，能够在很短的时间内以选择性的方式提供非常大的文库。在此，我们提供了一个合成化学方法与随后使用的纯化方法之间可能完美结合的示例，该方法提供了一个〜1000名成员的库，可在不到一个月的时间内平均提供50 mg最终化合物。
• Achieving High ¹ H Nuclear Hyperpolarization Levels with Long Lifetimes in a Range of Tuberculosis Drug Scaffolds
  作者：Philip Norcott、Peter J. Rayner、Gary G. R. Green、Simon B. Duckett

  DOI：10.1002/chem.201703278

  日期：2017.12.1

  The tuberculosis drugs, pyrazinamide, isoniazid and their derivatives have been optimally hyperpolarized using SABRE. Through 2H-labelling the drugs and catalysts T1 lifetimes of over two minutes and ≈20 % polarization have been achieved which opens the door to in vivo assessment.

  结核病药物吡嗪酰胺，异烟肼及其衍生物已使用SABRE进行了最佳超极化。通过2 H标记药物和催化剂，T 1的寿命超过两分钟，极化率约20％，这为体内评估打开了方便之门。