2-肼基-5-甲基-3-硝基砒啶 | 21901-25-7

• 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: 2-肼基-5-甲基-3-硝基砒啶
• 中文别名: 2-肼基-5-甲基-3-硝基吡啶
• 英文名称: 2-Hydrazino-5-methyl-3-nitro-pyridin
• 英文别名: 2-Hydrazinyl-5-methyl-3-nitropyridine；(5-methyl-3-nitropyridin-2-yl)hydrazine
• CAS: 21901-25-7
• 化学式: C₆H₈N₄O₂
• 分子量: 168.155
• InChiKey: XDMWWISPNLFVGD-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C(Solv: ethanol (64-17-5))
• 沸点：
  293.9±43.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  96.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Hydrazinyl-5-methyl-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: 2-Hydrazinyl-5-methyl-3-nitropyridine
CAS number: 21901-25-7

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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: C6H8N4O2
Molecular weight: 168.2

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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.

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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：

  2-肼基-5-甲基-3-硝基砒啶 在 盐酸 、 4-二甲氨基吡啶 、 palladium on activated charcoal 、 氢气 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 74.5h， 生成 6-methyl-8-(3-pyridin-2-ylpropylamino)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one
  参考文献：
  名称：

  作为氨基糖原合酶激酶3（GSK-3）抑制剂的8-氨基-[1,2,4]三唑并[4,3 - a ]吡啶-3（2 H）-one衍生物的合成与评价

  摘要：

  通过建模，合成设计了新的强力糖原合酶激酶3（GSK-3）抑制剂8-氨基-[1,2,4]三唑并[4,3 - a ]吡啶-3（2 H）-one衍生物。并进行了体外评价。化合物17c在基于酶和细胞的测定中显示出良好的效价（IC 50  = 111 nM，EC 50  = 1.78μM）。此外，已证明其具有理想的水溶性，PK曲线和适度的大脑渗透能力。

  DOI：

  10.1016/j.bmcl.2013.03.119
• 作为产物：
  描述：

  2-羟基-5-甲基嘧啶 在 氯化亚砜 、 硫酸 、 硝酸 、 一水合肼 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 2-肼基-5-甲基-3-硝基砒啶
  参考文献：
  名称：

  作为氨基糖原合酶激酶3（GSK-3）抑制剂的8-氨基-[1,2,4]三唑并[4,3 - a ]吡啶-3（2 H）-one衍生物的合成与评价

  摘要：

  通过建模，合成设计了新的强力糖原合酶激酶3（GSK-3）抑制剂8-氨基-[1,2,4]三唑并[4,3 - a ]吡啶-3（2 H）-one衍生物。并进行了体外评价。化合物17c在基于酶和细胞的测定中显示出良好的效价（IC 50  = 111 nM，EC 50  = 1.78μM）。此外，已证明其具有理想的水溶性，PK曲线和适度的大脑渗透能力。

  DOI：

  10.1016/j.bmcl.2013.03.119

文献信息

• Syntheses and Decarboxylation of the Isomeric Nitropyridinecarboxylic Acids
  作者：Ellis V. Brown

  DOI：10.1021/ja01641a016

  日期：1954.6
• Conformation of azo-bridge in 3,3′-dinitro-2,2′-azobipyridine and its 4,4′(or 5,5′ or 6,6′)-dimethyl-derivatives: Vibrational studies and DFT quantum chemical calculations
  作者：E. Kucharska、J. Hanuza、J. Lorenc

  DOI：10.1016/j.saa.2014.02.050

  日期：2014.6

  Syntheses of 3,3'-dinitro-2,2'-azobipyridine and 4,4' (or 5,5' or 6,6')-dimethyl-3,3'-dinitro-2,2'-azobipyridine have been described. Molecular structures of these compounds have been determined and compared, to the basic compound, azobipyridine, reported by us earlier. The conformation of the azo-bond and other structural data are discussed in terms of substitution place of methyl chromophore. Fourier transform IR and Raman spectra of these compounds have been measured and analysed. The 6-311G (2d,2p) basis set with the B3LYP functional have been used to discuss the space conformation and dynamics of the studied compounds. (C) 2014 Elsevier B.V. All rights reserved.
• [EN] NOBLE TRIAZOLOPYRIDINE DERIVATIVE OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PRODUCTION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION INCLUDING SAME<br/>[FR] DÉRIVÉ DE TRIAZOLOPYRIDINE NOBLE OU SELS PHARMACEUTIQUEMENT ACCEPTABLES DE CELUI-CI, PROCÉDÉ DE PRODUCTION DE CELUI-CI, ET COMPOSITION PHARMACEUTIQUE COMPRENANT CELUI-CI
  申请人：JEIL PHARMACEUTICAL CO LTD

  公开号：WO2012150829A2

  公开（公告）日：2012-11-08

  본 발명은 신규한 트리아졸로피리딘 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 약학적 조성물에 관한 것이다. 본 발명의 신규한 트리아졸로피리딘 유도체는 GSK-3를 억제함으로써, 치매, 알츠하이머 병, 파킨슨 병, 전두측두(Frontotemporal) 치매 파킨슨 유형, 괌(Guam) 파킨슨 치매 복합증, HIV 치매 또는 신경섬유 얽힘 병리학과 관련된 질환을 예방 또는 치료하는데 유용하게 사용될 수 있다.
• Synthesis and evaluation of 8-amino-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives as glycogen synthase kinase-3 (GSK-3) inhibitors
  作者：Kwangwoo Chun、Ji-Seon Park、Han-Chang Lee、Young-Ha Kim、In-Hea Ye、Kang-Jeon Kim、Il-Whea Ku、Min-Young Noh、Goang-Won Cho、Heejaung Kim、Seung Hyun Kim、Jeongmin Kim

  DOI：10.1016/j.bmcl.2013.03.119

  日期：2013.7

  New potent glycogen synthase kinase-3 (GSK-3) inhibitors, 8-amino-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives, were designed by modeling, synthesized and evaluated in vitro. Compound 17c showed good potency in enzyme and cell-based assays (IC50 = 111 nM, EC50 = 1.78 μM). Moreover, it has demonstrated desirable water solubility, PK profile, and moderate brain penetration.

  通过建模，合成设计了新的强力糖原合酶激酶3（GSK-3）抑制剂8-氨基-[1,2,4]三唑并[4,3 - a ]吡啶-3（2 H）-one衍生物。并进行了体外评价。化合物17c在基于酶和细胞的测定中显示出良好的效价（IC 50  = 111 nM，EC 50  = 1.78μM）。此外，已证明其具有理想的水溶性，PK曲线和适度的大脑渗透能力。