3,5-二溴-6-溴-2-氨基吡嗪 | 566205-01-4

• 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 - 二嗪类
• 中文名称: 3,5-二溴-6-溴-2-氨基吡嗪
• 中文别名: 2-氨基-3,5-二溴-6-氯吡嗪
• 英文名称: 3,5-dibromo-6-chloropyrazin-2-amine
• 英文别名: 2-amino-3,5-dibromo-6-chloropyrazine；3,5-dibromo-6-chloro-pyrazin-2-ylamine
• CAS: 566205-01-4
• 化学式: C₄H₂Br₂ClN₃
• 分子量: 287.341
• InChiKey: KMOICDJWYSOXRT-UHFFFAOYSA-N

物化性质

• 沸点：
  324.0±37.0 °C(Predicted)
• 密度：
  1.237

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 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：
  H302,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: 3,5-Dibromo-6-chloro-2-pyrazinamine
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: 3,5-Dibromo-6-chloro-2-pyrazinamine
CAS number: 566205-01-4

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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, refrigerated.
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: C4H2Br2ClN3
Molecular weight: 287.3

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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 chloride, 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：

  3,5-二溴-6-溴-2-氨基吡嗪 在 aluminum (III) chloride 、 亚硝酸异戊酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到2,6-dibromo-3,5-dichloropyrazine
  参考文献：
  名称：

  钯催化的多个C–S交叉偶联/环化序列的简明合成二噻吩衍生物

  摘要：

  新的含硫稠合杂环的简便合成是通过双重多米诺反应完成的，该反应包括碳硫交叉偶联，然后进行5内挖地环化。使用这种策略，可以得到一系列具有电子中性（-C 6 H 4 - n- Hex），富电子（-C 6 H 4 -NPh 2）和电子-中性的苯并，噻吩，吡啶和吡嗪并二乙炔不足（-C 4 H 3 N 2）取代基以高收率合成。所开发的方法被用于有效合成复杂的供体-受体分子。通过UV-VIS /发光光谱和循环伏安法分析了产物的光物理和电化学性质。

  DOI：

  10.1002/adsc.201600802
• 作为产物：
  描述：

  2-氨基-6-氯吡嗪 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以94.7%的产率得到3,5-二溴-6-溴-2-氨基吡嗪
  参考文献：
  名称：

  黄病毒 NS2B-NS3 蛋白酶变构抑制剂的合成、构效关系和抗病毒活性

  摘要：

  黄病毒，包括寨卡病毒、登革热病毒和西尼罗河病毒，是重要的人类病原体。黄病毒的高度保守的 NS2B-NS3 蛋白酶对于病毒复制是必不可少的，因此是一个有前途的药物靶点。通过化合物筛选和药物化学研究，发现一系列新型 2,5,6-三取代吡嗪化合物是有效的寨卡病毒蛋白酶 (ZVpro) 变构抑制剂，IC 50值低至 130 nM。讨论了它们的结构-活性关系。ZVpro 抑制剂还抑制登革热病毒和西尼罗河病毒的同源蛋白酶，并且它们的抑制活性是相关的。最有效的化合物47和103有效抑制寨卡病毒在 EC 68细胞中的复制值 300-600 nM 和在寨卡病毒感染的小鼠模型中。这些化合物代表了针对黄病毒感染的药物开发的新药理学线索。

  DOI：

  10.1021/acs.jmedchem.0c02070

文献信息

• IMIDAZOPYRAZINES AS LSD1 INHIBITORS
  申请人：Incyte Corporation

  公开号：US20160009720A1

  公开（公告）日：2016-01-14

  The present invention is directed to imidazo[1,2-a]pyrazine derivatives which are LSD1 inhibitors useful in the treatment of diseases such as cancer.

  本发明涉及咪唑并[1,2-a]吡嗪衍生物，这些衍生物是LSD1抑制剂，可用于治疗癌症等疾病。
• [EN] IMIDAZO[1,2-A]PYRAZINE MODULATORS OF THE ADENOSINE A2A RECEPTOR<br/>[FR] MODULATEURS DE 5,6-BICYCLO-IMIDAZO[1,2-A]PYRAZINE DU RÉCEPTEUR A2A DE L'ADÉNOSINE
  申请人：SELVITA S A

  公开号：WO2019002606A1

  公开（公告）日：2019-01-03

  The present invention relates to the compound of formula (I) and salts, stereoisomers, tautomers, isotopologues,or N-oxides thereof. The present invention is further concerned with the use of such a compound or salt, stereoisomer, tautomer, isotopologues,or N-oxide thereof as medicament and a pharmaceutical composition comprising said compound.

  本发明涉及式(I)的化合物及其盐、立体异构体、互变异构体、同位素同分异构体或N-氧化物。本发明进一步涉及将该化合物或盐、立体异构体、互变异构体、同位素同分异构体或N-氧化物用作药物的用途，以及包含该化合物的药物组合物。
• Facile Synthesis of Tetraarylpyrazines by Sequential Cross-coupling Approach
  作者：Yoshitake Nishiyama、Kei Akiyama、Yuki Sakata、Takamitsu Hosoya、Suguru Yoshida

  DOI：10.1246/cl.200715

  日期：2021.1.5

  A facile synthetic method for unsymmetric tetraarylpyrazines by sequential cross-couplings is disclosed. This 5-step synthesis was achieved from 2-amino-3,5-dibromo-6-chloropyrazine through four-fold cross-coupling and diazotization. Dibenzo-fused quinoxaline synthesis was also accomplished by further intramolecular coupling.

  摘要 本发明公开了一种通过连续交叉偶联合成不对称四芳基吡嗪的简便方法。该方法由 2-氨基-3,5-二溴-6-氯吡嗪通过四次交叉偶联和重氮化实现五步合成。通过进一步的分子内偶联，还完成了二苯并融合喹喔啉的合成。
• Regioselective synthesis of dipyrrolopyrazine (DPP) derivatives via metal free and metal catalyzed amination and investigation of their optical and thermal properties
  作者：Puttavva Meti、Eun-Sil Lee、Jung-Won Yang、Young-Dae Gong

  DOI：10.1039/c7ra01795b

  日期：——

  Pyrazine is an important molecular scaffold employed in organic optoelectronic materials. Here we report efficient methods for the synthesis of dipyrrolopyrazine, and pyrrolothieno-pyrazine derivatives that involve regio-selective amination reactions of dihalo-pyrrolopyrazines. The developed protocol readily affords either 2-amino- or 3-amino-pyrrolopyrazines from the corresponding 2-bromo-3-chloro-5H-pyrrolo[2

  吡嗪是有机光电材料中使用的重要分子支架。在这里，我们报告有效的方法来合成二吡咯并吡嗪和吡咯并噻吩并吡嗪衍生物，其中涉及二卤代吡咯并吡嗪的区域选择性胺化反应。所开发的方案容易从相应的2-溴-3-氯-5 H-吡咯并[2,3- b ]吡嗪提供2-氨基-或3-氨基-吡咯并吡嗪。当胺化反应在不含金属的微波辐射下进行时，仅获得3-氨基-吡咯并吡嗪。相反，2-溴-3-氯-5 H-吡咯并[2,3- b]吡嗪仅提供2-氨基-吡咯并吡嗪。使用Sonogashira反应将吡咯并吡嗪支架转化为相应的1,7-和1,5-二氢二吡咯并[2,3- b ]吡嗪衍生物。对合成化合物的光学性质，热性质和分子堆积进行了全面的研究。结果表明，1,7衍生物可能是有前途的有机材料，可用于光电应用。
• [EN] SULPHONAMIDE COMPOUNDS THAT MODULATE CHEMOKINE RECEPTOR ACTIVITY (CCR4)<br/>[FR] COMPOSES SULFAMIDES MODULANT L'ACTIVITE DES RECEPTEURS DES CHIMIOKINES (CCR4)
  申请人：ASTRAZENECA AB

  公开号：WO2004108692A1

  公开（公告）日：2004-12-16

  The invention relates to sulphonamide compounds, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明涉及磺胺化合物、用于其制备的工艺和中间体、含有它们的药物组合物以及它们在治疗中的用途。