2-氨基-3,5-二硝基-6-甲基砒啶 | 25864-34-0

• 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-氨基-3,5-二硝基-6-甲基砒啶
• 中文别名: 2-氨基-3,5-二硝基-6-甲基吡啶
• 英文名称: 2-amino-3,5-dinitro-6-methylpyridine
• 英文别名: 2-amino-6-methyl-3,5-dinitropyridine；6-Methyl-3,5-dinitropyridin-2-amine
• CAS: 25864-34-0
• 化学式: C₆H₆N₄O₄
• mdl: MFCD00091867
• 分子量: 198.138
• InChiKey: KWYALJWSYDOZON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-3,5-dinitro-6-methylpyridine
Synonyms: 6-Methyl-3,5-dinitropyridin-2-amine

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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-Amino-3,5-dinitro-6-methylpyridine
CAS number: 25864-34-0

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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: C6H6N4O4
Molecular weight: 198.1

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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-氨基-3,5-二硝基-6-甲基砒啶 在 盐酸 、 potassium permanganate 、 五氯化磷 、 硫酸 、 magnesium sulfate 、 tin(ll) chloride 、 sodium nitrite 、 三氯氧磷 作用下， 以 水 为溶剂， 反应 1.5h， 生成 3,5-diacetylamino-6-chloropyridine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger

  摘要：

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00022-6
• 作为产物：
  描述：

  6-甲基-N-硝基-2-吡啶胺 在 硫酸 作用下， 生成 2-氨基-3,5-二硝基-6-甲基砒啶
  参考文献：
  名称：

  Synthesis and biological evaluation of aroylguanidines related to amiloride as inhibitors of the human platelet Na+/H+ exchanger

  摘要：

  Pyridine and benzene bioisosteres of amiloride were synthesized and evaluated for their inhibitory Potency against the sodium-hydrogen exchanger (NHE) involved in intracellular pH regulation. The inhibition of NHE was determined by using the platelet swelling assay (PSA) in which the swelling of human platelets was induced by their incubation in an acid buffer (pH 6.7). Additionally, the inhibitory potency of the most active compounds was assessed by measuring the inhibition of the EIPA-sensitive Na-22 (+) uptake (UIA) by human platelets after intracellular acidosis. The results indicated that several benzene derivatives and compounds bearing an carbonylguanidine moiety in the meta position of the pyridine nitrogen were much more potent than amiloride (PSA:IC50 = 43.5 muM, UIA:IC50 = 100.1 muM), but less than EIPA, a pyrazine NHE inhibitor (PSA:IC50=0.08 muM, UIA: IC50 - 0.5 muM). In both biological assays (2-amino-5-bromo-pyridine-3-carbonyl)guanidine (32) was the most active molecule (PSA: IC50 = 0.8 muM, UIA : IC50 = 0.8 muM). Our investigations demonstrated that the replacement of the pyrazine ring of amiloride e by a pyridine ora phenyl ring improved the NHE inhibitory potency (phenyl >pyridine >pyrazine). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00022-6

文献信息

• Theoretical and experimental NMR data of 3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and of its 4- and 6-methyl derivatives
  作者：M. Wandas、Z. Talik

  DOI：10.1016/j.molstruc.2013.03.052

  日期：2013.7

  Abstract 3,5-Dinitro-2-(2-phenylhydrazinyl)pyridine and its methyl derivatives: 4-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine and 6-methyl-3,5-dinitro-2-(2-phenylhydrazinyl)pyridine were synthesized and characterized by 1 H NMR and 13 C NMR. Calculations were also performed where the above molecules were optimized using the methods of density functional theory (DFT) with 6-31G(d,p) and 6-311G(d,p) basis

  摘要 3,5-二硝基-2-(2-苯基肼基)吡啶及其甲基衍生物：4-甲基-3,5-二硝基-2-(2-苯基肼基)吡啶和6-甲基-3,5-二硝基-2 -(2-苯基肼基)吡啶被合成并通过1 H NMR和13 C NMR表征。还进行了计算，其中使用密度泛函理论 (DFT) 和 6-31G(d,p) 和 6-311G(d,p) 基组优化了上述分子。对于所有研究的分子，最低能量是使用 6-311G(d,p) 基组获得的。对 6-311G 和 6-311++G 和 6-311G ** 基组进行了 GIAO/DFT（规范不变原子轨道/密度泛函理论）计算，以确定质子和碳的化学位移，并发现它们是接近实验值。还发现氢原子（在2-NH基团中）和氧原子（吡啶-3-NO 2 ）之间存在分子内氢键。此外，吡啶环和吸电子 3-硝基之间的共振以及该环和 NH 基团的孤电子对之间的共振有利于结构的共面性；这意味着由上述分子内氢键形成的螯合环几乎与吡啶环共面。
• Discovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists
  作者：Santosh S. Kulkarni、Amy Hauck Newman

  DOI：10.1016/j.bmcl.2007.03.066

  日期：2007.6

  Investigation of a series of heterobicyclic compounds with essential pharmacophoric features of the metabotropic glutamate receptor 5 (mGluR5) antagonists MPEP and MTEP provided novel structural templates with sub-micromolar affinities at the mGluR5.

  对一系列具有代谢型谷氨酸受体 5 (mGluR5) 拮抗剂 MPEP 和 MTEP 基本药效特征的杂双环化合物的研究提供了在 mGluR5 上具有亚微摩尔亲和力的新型结构模板。
• 6-amino substituted imidazo[4,5-bipyridines as angiotensin II antagonists
  申请人：Merck & Co., Inc.

  公开号：US05223499A1

  公开（公告）日：1993-06-29

  Substituted imidazo[4,5-b]pyridines of structural formula: ##STR1## are angiotensin II antagonists useful in the treatment of hypertension and congestive heart failure.

  结构式为：##STR1## 的取代咪唑[4,5-b]吡啶类化合物是用于治疗高血压和充血性心力衰竭的血管紧张素II拮抗剂。
• Substituted heteroaromatic 5-HT 1F agonists
  申请人：ELI LILLY AND COMPANY

  公开号：EP0875513A1

  公开（公告）日：1998-11-04

  This invention provides novel 5-HT1F agonists of the Formula in which X, Y, E, R, A, B, and n are as defined in the specification, which are useful for the treatment of migraine and associated disorders.

  这项发明提供了一种新型的5-HT1F激动剂，其化学式为X、Y、E、R、A、B和n如规范中所定义，可用于治疗偏头痛及相关疾病。
• Synthesis of New Nebularine Analogues and Their Inhibitory Activity against Adenosine Deaminase
  作者：Nikolaos Lougiakis、Panagiotis Marakos、Nicole Pouli、Elisabeth Fragopoulou、Roxane Tenta

  DOI：10.1248/cpb.c14-00731

  日期：——

  A number of new 2,6-disubstituted-1-deazanebularine analogues as well as two structurally related pyrazole-fused tricyclic nucleosides were prepared. Their synthesis was carried out by the conversion of 6-amino-2-picoline to a suitable 1-deazapurine, followed by a Vorbrüggen type glycosylation and subsequent elaboration of the condensed pyrazole ring. The synthesized nebularine analogues proved to be weak adenosine deaminase inhibitors.

  本研究制备了一些新的 2,6-二取代-1-脱氮鸟嘌呤类似物以及两种结构相关的吡唑融合三环核苷。它们的合成是通过将 6-氨基-2-甲基吡啶转化为合适的 1-脱氮杂环嘌呤，然后进行沃布吕根式糖基化和随后的缩合吡唑环精制而完成的。事实证明，合成的奈布林类似物是一种弱的腺苷脱氨酶抑制剂。