2-肼基-3-氯吡啶 | 22841-92-5

• 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 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-肼基-3-氯吡啶
• 中文别名: 3-氯-2-肼基砒啶；3-氯-2-肼基吡啶；3-氯-2-吡啶肼
• 英文名称: (3-chloro-2-pyridyl)hydrazine
• 英文别名: 3-Chloro-2-hydrazinopyridine；3-chloro-2-hydrazinylpyridine；2-hydrazino-3-chloropyridine；(3-chloropyridin-2-yl)hydrazine；3-chloro-2-hydrazylpyridine；3-Chlor-2-hydrazinopyridin
• CAS: 22841-92-5
• 化学式: C₅H₆ClN₃
• mdl: MFCD01936479
• 分子量: 143.576
• InChiKey: XAYCTBDPZIKHCW-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167°
• 沸点：
  247.6±50.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 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：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S45
• 危险类别码：
  R25
• 海关编码：
  2933399090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P301+P310+P330,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301
• 储存条件：
  -20°C，惰性气体，避光

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Chloro-2-hydrazinylpyridine
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-Chloro-2-hydrazinylpyridine
CAS number: 22841-92-5

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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: C5H6ClN3
Molecular weight: 143.6

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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.

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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

制备方法与用途

3-氯-2-肼基砒啶是一种具有抗癌活性的生化制剂。由于它能够与邻氨基苯甲酸和鳞翅目ryanodine受体形成氢键，因此可抑制鳞翅目昆虫（如黑腹果蝇）的蛋白质合成并诱导细胞凋亡。

用途 本品用作农药和医药中间体。

反应信息

• 作为反应物：
  描述：

  2-肼基-3-氯吡啶 在 N-溴代丁二酰亚胺(NBS) 、 双氧水 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.25h， 生成 methyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate
  参考文献：
  名称：

  含取代吡唑的新型色酮衍生物的合成，杀线虫活性和对接研究

  摘要：

  摘要设计合成了一系列含取代吡唑的色酮衍生物。初步的生物测定表明，大多数合成的化合物在体内对10 mg / L的根结线虫都有良好的杀线虫活性。在测试的化合物中，A10和A11表现出100％的抑制率。此外，分子对接结果表明，化合物A10和A11都通过氢键和π-π堆积与AChE的氨基酸残基Tyr121，Trp279，Tyr70，Trp84和Phe330相互作用。这项研究表明，可以进一步优化含有色酮的取代吡唑支架，以探索新型的，具有高生物活性的杀线虫剂。

  DOI：

  10.1016/j.cclet.2017.10.011
• 作为产物：
  描述：

  2,3,6-三氯吡啶 在 四丁基氯化铵 、 氢气 、 一水合肼 作用下， 以 甲醇 为溶剂， 108.0~110.0 ℃ 、1.4 MPa 条件下， 反应 11.0h， 生成 2-肼基-3-氯吡啶
  参考文献：
  名称：

  一种氯虫苯甲酰胺的制备方法

  摘要：

  本发明涉及杀虫剂合成领域，公开了一种氯虫苯甲酰胺的制备方法，包括中间体一的合成步骤、中间体二的合成步骤和氯虫苯甲酰胺的合成步骤。本发明以2,3,6‑三氯吡啶为原料，在催化剂A作用下与水合肼反应得到3,6‑二氯‑2‑肼基吡啶，然后在催化剂B的作用下，加氢还原反应得到中间体一，中间体一与马来酸二乙酯，在催化剂C的作用下制得2‑(3‑氯吡啶‑2‑基)‑5‑羟基吡唑‑3‑甲酸乙酯，溴化后水解得到中间体二，再由中间体二制得氯虫苯甲酰胺。本发明中，采用2,3,6‑三氯吡啶替代2,3‑二氯吡啶为原料制备中间体一，避免了2,3‑二氯吡啶原料难得及其合成条件苛刻和收率低等缺点，提高了中间体一的反应总收率，实现一锅法制备中间体二，减少后处理操作，降低了氯虫苯甲酰胺的合成成本。

  公开号：

  CN112552284B

文献信息

• Copper(<scp>i</scp>)-catalyzed benzylation of triazolopyridine through direct C–H functionalization
  作者：Madhava Reddy Lonka、Jinquan Zhang、Thirupathi Gogula、Hongbin Zou

  DOI：10.1039/c9ob01433k

  日期：——

  A general and efficient copper-catalyzed benzylation reaction of triazolopyridine with N-tosylhydrazones was developed. This reaction forms a C(sp2)-C(sp3) bond through cross-coupling, and represents an exceedingly practical method to afford 3-benzylated triazolopyridines in moderate to good yields. A proposed mechanistic pathway underlying this reaction was outlined. This catalytic transformation

  开发了一种通用且有效的铜催化的三唑并吡啶与N-甲苯磺酰azo的苄基化反应。该反应通过交叉偶联形成C（sp2）-C（sp3）键，并且代表一种非常实用的方法，以中等至良好的产率提供3-苄基化的三唑并吡啶。概述了该反应基础的拟议的机理途径。这种催化转化应能在官能化化学中实现广泛的合成应用，从而可以合成新的药学上相关的三唑并吡啶衍生物。
• Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives. III. Synthesis and Antitumor Activity of 3-Phenylpiperazinyl-1-trans-propenes
  作者：Hiroyuki Naito、Satoru Ohsuki、Ryo Atsumi、Megumi Minami、Mineko Mochizuki、Kenji Hirotani、Eiji Kumazawa、Akio Ejima

  DOI：10.1248/cpb.53.153

  日期：——

  A series of novel 3-[4-phenyl-1-piperazinyl]-1-[5-methyl-1-(2-pyrimidinyl)-4-pyrazolyl]-1-trans-propenes and related compounds were synthesized and evaluated by their cytotoxic activity against several tumor cell lines in vitro and in vivo antitumor activity against some tumor models when administered both intraperitoneally and orally. Compounds with the 3-chloropyridin-2-yl group (9g) and the 3-fluoro-5-substituted phenylpiperazinyl group (29b, c, and e) showed significantly potent cytotoxicity by in vitro testing. Among them, the 3-cyano-5-fluorophenyl derivative (29b) exhibited potent antitumor activity against several tumor cells including human carcinoma without causing undesirable effects in mice.

  一系列新型的3-[4-苯基-1-哌嗪基]-1-[5-甲基-1-(2-嘧啶基)-4-吡唑基]-1-反式丙烯及其相关化合物被合成，并通过其对几种肿瘤细胞系的体外细胞毒性活性和对某些肿瘤模型的体内抗肿瘤活性进行了评估，这些化合物既可以通过腹腔注射给药，也可以口服给药。具有3-氯吡啶-2-基团（9g）和3-氟-5-取代苯基哌嗪基团（29b、c和e）的化合物在体外测试中显示出显著的细胞毒性。其中，3-氰基-5-氟苯基衍生物（29b）表现出对包括人癌在内的几种肿瘤细胞的强效抗肿瘤活性，且在老鼠中没有引起不良反应。
• 一种含氯虫苯甲酰胺的杀虫剂
  申请人：江苏腾龙生物药业有限公司

  公开号：CN111134128A

  公开（公告）日：2020-05-12

  本发明公开了一种含氯虫苯甲酰胺的杀虫剂，该杀虫剂由氯虫苯甲酰胺、甲氧虫酰肼及茚虫威为有效成分复配而成，其中，按质量比计氯虫苯甲酰胺：甲氧虫酰肼：茚虫威=2:1:1；该杀虫剂增效作用显著，杀虫效果好，成本低廉。
• Retracted: Synthesis of 2‐Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4‐Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy
  作者：Wei Yao、Chenyang Ge、Yilin Zhang、Xiao‐Feng Xia、Long Wang、Dawei Wang

  DOI：10.1002/chem.201904095

  日期：2019.12.13

  2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited

  1,2,4-三唑铱配合物与介孔 MCM-41 的共价连接产生了一种非均相催化剂，该催化剂被发现可通过级联借用有效合成 2-芳基异二氢吲哚、喹啉、环胺和对称仲胺氢战略。有趣的是，由 1,2,4-三唑铱络合物和介孔 MCM-41 制备的负载型多相铱催化剂在制备 2-芳基异二氢吲哚衍生物和对称仲胺方面表现出高催化活性。催化剂系统至少可循环使用五次。除了三唑的重要作用外，接枝在硅质载体上的铱位点可以作为多功能催化中心，从而大大提高催化剂的催化活性。此外，机械实验表明，该反应由初始醇脱氢引发，并由氢化铱中间体促进。重要的是，对诊断性氢化铱信号的直接检测证实了 2-芳基异二氢吲哚的合成是通过借氢过程发生的。这项工作为通过借氢策略合成异二氢吲哚提供了一个有效的例子。
• 6-Arylmethyl-substituted pyrazolopyrimidines
  申请人：Hendrix Martin

  公开号：US20070161662A1

  公开（公告）日：2007-07-12

  The invention relates to novel 6-arylmethyl-substituted pyrazolopyrimidines, process for their preparation and their use for producing medicaments for improving perception, concentration, learning and/or memory.

  这项发明涉及新型的6-芳基甲基取代的吡唑吡嘧啶化合物，其制备方法以及它们用于生产用于改善感知、集中力、学习和/或记忆的药物。