3-溴咪唑[1,2-A]吡嗪 | 57948-41-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡嗪类
• 中文名称: 3-溴咪唑[1,2-A]吡嗪
• 中文别名: 3-溴咪唑并[1,2-a]吡嗪
• 英文名称: 3-bromoimidazo[1,2-a]pyrazine
• 英文别名: 3-bromoimidazo<1,2-a>pyrazine；3-Brom-imidazo<1,2-a>pyrazin
• CAS: 57948-41-1
• 化学式: C₆H₄BrN₃
• 分子量: 198.022
• InChiKey: OZNGJOXLTIENCF-UHFFFAOYSA-N

物化性质

• 熔点：
  191-196 °C
• 密度：
  1.89±0.1 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H315,H318,H335
• 危险性防范说明：
  P261,P280,P305 + P351 + P338
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromoimidazo[1,2-a]pyrazine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Bromoimidazo[1,2-a]pyrazine
CAS number: 57948-41-1

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H4BrN3
Molecular weight: 198.0

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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

反应信息

• 作为反应物：
  描述：

  3-溴咪唑[1,2-A]吡嗪 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(imidazo[1,2-a]pyrazin-3-ylethynyl)-4-methylbenzamide
  参考文献：
  名称：

  [EN] METHODS AND COMPOSITIONS FOR RAF KINASE MEDIATED DISEASES
  [FR] PROCÉDÉS ET COMPOSITIONS POUR LE TRAITEMENT DE MALADIES MÉDIÉES PAR LA KINASE RAF

  摘要：

  该发明揭示了通过给予化合物Formula 1或其药学上可接受的盐、溶剂或水合物来治疗或预防由RAF激酶介导的疾病或症状的方法和组合物，其中变量如本文所定义。

  公开号：

  WO2013162727A1
• 作为产物：
  描述：

  吲哚[1,2-A]吡嗪 在 溴 、 sodium acetate 、 potassium bromide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 3-溴咪唑[1,2-A]吡嗪
  参考文献：
  名称：

  [EN] 5,6,7,8-TETRAHYDROIMIDAZO[1,2-A]PYRAZINE DERIVATIVES AS P2X7 MODULATORS
  [FR] DÉRIVÉS DE 5,6,7,8-TÉTRAHYDROIMIDAZO[1,2-A]PYRAZINE COMME MODULATEURS DE P2X7

  摘要：

  本发明提供了一种具有以下式（I）的化合物或其药学上可接受的盐：其中A为氢、C1-4烷基、C3-6环烷基、C1-3烷氧基、C1-3烷氧基C1-4烷基、C1-2氟代烷基、卤素、NR6R7可选择地取代的杂芳基（Het）或可选择地取代的苯基，R1、R2、R3、R4、R5、R6和R7如描述中所定义。认为这些化合物或盐能够调节P2X7受体功能，并能够拮抗P2X7受体上ATP的作用。本发明还提供了该化合物或盐在治疗或预防炎症性疼痛、神经病性疼痛、内脏疼痛、类风湿性关节炎或骨关节炎或神经退行性疾病等疾病中的用途。

  公开号：

  WO2010125101A1

文献信息

• Catalyst shuttling enabled by a thermoresponsive polymeric ligand: facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium
  作者：Erfei Wang、Mao Chen

  DOI：10.1039/c9sc02171j

  日期：——

  A polymeric monophosphine ligand WePhos has been synthesized and complexed with palladium(II) acetate [Pd(OAc)2] to generate a thermoresponsive pre-catalyst that can shuttle between water and organic phases, with the change being regulated by temperature. The structure of the polymeric ligand was confirmed with matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) mass spectrometry

  合成了一种聚合单膦配体WePhos，并与乙酸钯( II )[Pd(OAc) 2 ]络合，生成一种热响应性预催化剂，可以在水相和有机相之间穿梭，其变化受温度调节。通过基质辅助激光解吸/电离飞行时间（MALDI-TOF）质谱和尺寸排阻色谱（SEC）分析以及核磁共振（NMR）测量证实了聚合物配体的结构。这种聚合物金属配合物能够使用 50 至 500 ppm 的钯实现高效的 Pd 催化交叉偶联和串联反应，这可以促进对广谱（杂）芳基底物和官能团具有耐受性的反应，如 73 个示例所示分离收率高达 99%。值得注意的是，经过 10 轮催化剂回收实验后，97% 的钯仍保留在水相中，通过电感耦合等离子体原子发射光谱 (ICP-AES) 测量确定，这表明催化剂转移效率很高。此外，基于流动化学与催化剂穿梭行为相结合，已经成功开发出连续催化剂回收方法，使得铃木-宫浦耦合能够以克级进行，钯负载量低至 10 ppm。
• [EN] GCN2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE GCN2 ET LEURS UTILISATIONS
  申请人：MERCK PATENT GMBH

  公开号：WO2019148132A1

  公开（公告）日：2019-08-01

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

  本发明提供了化合物、其组合物以及使用它们的方法。
• HPK1 ANTAGONISTS AND USES THEREOF
  申请人：Nimbus Saturn, Inc.

  公开号：US20210078996A1

  公开（公告）日：2021-03-18

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of HPK1, and the treatment of HPK1-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物用于抑制HPK1和治疗HPK1介导的疾病的方法。
• Imidazo-pyrazine derivatives as ligands for gaba receptors
  申请人：——

  公开号：US20040019057A1

  公开（公告）日：2004-01-29

  A class of imidazo[1,2-&agr;]pyrazine analogues substituted in the 3-position by a substituted phenyl ring, being selective ligands for GABAA receptors which interact more favourably with the &agr;2 and/or &agr;3 subunit than with the &agr;1 subunit, are accordingly of benefit in the treatment and/or prevention of a variety of disorders of the central nervous system, including anxiety and convulsions, with a reduced propensity to cause sedation.

  一类在3位被取代的苯环所取代的咪唑[1,2-α]吡嗪类似物，作为GABAA受体的选择性配体，与α2和/或α3亚单位相比，与α1亚单位更有利的相互作用，因此在治疗和/或预防包括焦虑和惊厥在内的多种中枢神经系统疾病方面具有益处，且减少引起镇静的倾向。
• Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles
  作者：Xi-Jie Dai、Oliver D. Engl、Thierry León、Stephen L. Buchwald

  DOI：10.1002/anie.201814331

  日期：2019.3.11

  heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium‐ring dibenzo‐fused nitrogen heterocycles.

  本文中，我们报告了通过Suzuki-Miyaura交叉偶联和对映选择性铜催化的分子内加氢胺化反应制备α-芳基吡咯烷的实用两步合成路线。出色的立体选择性和药物相关杂芳烃转化底物的广泛范围使该方法成为吡咯烷合成的实用且通用的方法。此外，这种分子内加氢胺化策略促进了四氢异喹啉和中环二苯并稠合氮杂环的不对称合成。