5-溴-2-肼基-3-硝基砒啶 | 15862-42-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 5-溴-2-肼基-3-硝基砒啶
• 英文名称: 5-bromo-2-hydrazino-3-nitropyridine
• 英文别名: 5-Bromo-2-hydrazinyl-3-nitropyridine；(5-bromo-3-nitropyridin-2-yl)hydrazine
• CAS: 15862-42-7
• 化学式: C₅H₅BrN₄O₂
• 分子量: 233.024
• InChiKey: HSSPWVIGDQPZEK-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C(Solv: methanol (67-56-1))
• 沸点：
  252.5±50.0 °C(Predicted)
• 密度：
  2.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-hydrazinyl-3-nitropyridine
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: 5-Bromo-2-hydrazinyl-3-nitropyridine
CAS number: 15862-42-7

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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: C5H5BrN4O2
Molecular weight: 233.0

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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：

  5-溴-2-肼基-3-硝基砒啶 在 silver nitrate 作用下， 以 水 为溶剂， 以84%的产率得到3-溴-5-硝基吡啶
  参考文献：
  名称：

  3-R-5-硝基吡啶与亲核试剂的反应：亲核取代与偶联物加成

  摘要：

  合成了许多3-R-5-硝基吡啶，并研究了它们与各种类型亲核试剂的反应。反应结果取决于亲核试剂的性质：在阴离子O-，N-和S-亲核试剂的情况下，以前未报告的未活化硝基发生取代，而碳亲核试剂经历了吡啶环的脱芳香化反应，形成了1,2-和1,4-加成。

  DOI：

  10.1016/j.tet.2019.130659
• 作为产物：
  描述：

  5-溴-2-氯-3-硝基吡啶 在 一水合肼 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 5-溴-2-肼基-3-硝基砒啶
  参考文献：
  名称：

  （1,2,4）三唑[4,3-a]吡啶衍生物作为伴刀豆球蛋白A诱发肝炎的潜在治疗剂的合成及生物学评价

  摘要：

  已经设计和合成了一系列的（1,2,4）三唑[4,3-a]吡啶（TZP）衍生物。化合物8d被鉴定为对脂多糖（LPS）刺激具有最有效的抑制NO释放的活性，并抑制RAW264.7巨噬细胞上MCP-1蛋白诱导的迁移。基于筛选数据，进行了免疫荧光测定和实时qPCR测定，表明化合物8d通过伴刀豆球蛋白A（Con A）诱导的RAW264.7巨噬细胞抑制了NF-κBp65易位和炎性基因的表达。更重要的是8d还通过在小鼠自身免疫性肝炎（AIH）模型中下调血浆丙氨酸转氨酶（ALT），天冬氨酸转氨酶（AST）和炎性浸润的水平来缓解Con A诱导的肝炎。此外，流式细胞仪（FCM）数据表明化合物8d抑制了Con A诱导的小鼠肝脏中MDSC的积累。这些发现增加了化合物8d可能用作治疗AIH的潜在药物的可能性。

  DOI：

  10.1016/j.ejmech.2019.06.025

文献信息

• Synthesis and biological evaluation of (1,2,4)triazole[4,3-a]pyridine derivatives as potential therapeutic agents for concanavalin A-induced hepatitis
  作者：Yaojie Shi、Qianqian Wang、Juan Rong、Jing Ren、Xuejiao Song、Xiaoli Fan、Mengyi Shen、Yong Xia、Ningyu Wang、Zhihao Liu、Quanfang Hu、Tinghong Ye、Luoting Yu

  DOI：10.1016/j.ejmech.2019.06.025

  日期：2019.10

  A series of (1,2,4)triazole[4,3-a]pyridine (TZP) derivatives have been designed and synthesized. Compound 8d was identified as having the most potent inhibitory activity on NO release in response to lipopolysaccharide (LPS) stimulation and inhibition of the migration induced by MCP-1 protein on RAW264.7 macrophages. Based on the screening data, an immunofluorescence assay and a real-time qPCR assay

  已经设计和合成了一系列的（1,2,4）三唑[4,3-a]吡啶（TZP）衍生物。化合物8d被鉴定为对脂多糖（LPS）刺激具有最有效的抑制NO释放的活性，并抑制RAW264.7巨噬细胞上MCP-1蛋白诱导的迁移。基于筛选数据，进行了免疫荧光测定和实时qPCR测定，表明化合物8d通过伴刀豆球蛋白A（Con A）诱导的RAW264.7巨噬细胞抑制了NF-κBp65易位和炎性基因的表达。更重要的是8d还通过在小鼠自身免疫性肝炎（AIH）模型中下调血浆丙氨酸转氨酶（ALT），天冬氨酸转氨酶（AST）和炎性浸润的水平来缓解Con A诱导的肝炎。此外，流式细胞仪（FCM）数据表明化合物8d抑制了Con A诱导的小鼠肝脏中MDSC的积累。这些发现增加了化合物8d可能用作治疗AIH的潜在药物的可能性。
• 1,2,4-三氮唑并[4,3-a]吡啶类衍生物及其制 备方法和用途
  申请人：四川大学

  公开号：CN112079829B

  公开（公告）日：2021-11-26

  本发明公开了一种1,2,4‑三氮唑并[4,3‑a]吡啶类衍生物及其制备方法和用途，属于化学医药领域。本发明提供了式Ⅰ所示的化合物或其药学上可接受的盐。本发明还提供了所述化合物的制备方法和用途。生物学实验表明，这类化合物对细胞释放NO具有明显的抑制作用，能够明显改善自身免疫性肝炎引起的病变，为抗肝损伤，特别是抗自身免疫性疾病的药物开发和应用提供了新的选择。
• FUSED HETEROCYCLIC COMPOUNDS AS ION CHANNEL MODULATORS
  申请人：Corkey Britton

  公开号：US20110021521A1

  公开（公告）日：2011-01-27

  The present invention relates to compounds that are sodium channel inhibitors and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula I: wherein W 1 , W 2 , W 3 , R 1 , Q, X 1 , X 2 and X 3 are as described herein, to methods for the preparation and use of the compounds and to pharmaceutical compositions containing the same.

  本发明涉及一类钠通道抑制剂化合物，以及它们在治疗各种疾病状态中的应用，包括心血管疾病和糖尿病。具体实施例中，该化合物的结构由下式给出：其中W1、W2、W3、R1、Q、X1、X2和X3如本文所述，以及制备和使用该化合物的方法，以及含有该化合物的药物组合物。
• Fused heterocyclic compounds as ion channel modulators
  申请人：Corkey Britton

  公开号：US08952034B2

  公开（公告）日：2015-02-10

  The present invention relates to compounds that are sodium channel inhibitors and to their use in the treatment of various disease states, including cardiovascular diseases and diabetes. In particular embodiments, the structure of the compounds is given by Formula I: wherein W1, W2, W3, R1, Q, X1, X2 and X3 are as described herein, to methods for the preparation and use of the compounds and to pharmaceutical compositions containing the same.

  本发明涉及化合物，它们是钠通道抑制剂，并且用于治疗各种疾病状态，包括心血管疾病和糖尿病。在特定实施例中，该化合物的结构由公式I给出：其中W1、W2、W3、R1、Q、X1、X2和X3如本文所述，本发明还涉及制备和使用该化合物的方法以及含有该化合物的制药组合物。
• Reactions of 3-R-5-nitropyridines with nucleophiles: Nucleophilic substitution vs conjugate addition
  作者：Maxim A. Bastrakov、Vladislav V. Nikol’skiy、Alexey M. Starosotnikov、Ivan V. Fedyanin、Svyatoslav A. Shevelev、Daniil A. Knyazev

  DOI：10.1016/j.tet.2019.130659

  日期：2019.11

  A number of 3-R-5-nitropyridines were synthesized and their reactions with various types of nucleophiles were investigated. The reaction outcome depends on the nature of a nucleophile: in case of anionic O-, N- and S-nucleophiles the previously unreported substitution of non-activated nitro group occurred while carbon nucleophiles underwent dearomatization of the pyridine ring with the formation of

  合成了许多3-R-5-硝基吡啶，并研究了它们与各种类型亲核试剂的反应。反应结果取决于亲核试剂的性质：在阴离子O-，N-和S-亲核试剂的情况下，以前未报告的未活化硝基发生取代，而碳亲核试剂经历了吡啶环的脱芳香化反应，形成了1,2-和1,4-加成。