2-氨基-[1,8]萘啶-3-甲腈 | 15935-95-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 2-氨基-[1,8]萘啶-3-甲腈
• 英文名称: 2-amino-3-cyano-1,8-naphthyridine
• 英文别名: 2-amino-[1,8]naphthyridine-3-carbonitrile；2-amino-1,8-naphthyridine-3-carbonitrile；2-Amino-1,8-naphthyridin-3-carbonitril
• CAS: 15935-95-2
• 化学式: C₉H₆N₄
• mdl: MFCD06659014
• 分子量: 170.173
• InChiKey: OAKUSQCSHYQNHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  260-262 °C(Solv: 2-ethoxyethanol (110-80-5))
• 沸点：
  407.0±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090
• WGK Germany：
  3
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-[1,8]naphthyridine-3-carbonitrile
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-Amino-[1,8]naphthyridine-3-carbonitrile
CAS number: 15935-95-2

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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: C9H6N4
Molecular weight: 170.2

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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-氨基-[1,8]萘啶-3-甲腈 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 24.0h， 以85%的产率得到2-oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile
  参考文献：
  名称：

  Shireen Mohammed, Maher Khalid, Indian Journal of Heterocyclic Chemistry, 2019, vol. 29, # 1, p. 21 - 25

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-3-吡啶甲醛 、 丙二腈 在 哌啶 作用下， 以 乙醇 为溶剂， 以95%的产率得到2-氨基-[1,8]萘啶-3-甲腈
  参考文献：
  名称：

  Mogilaiah, K.; Reddy, K. Rajendar; Reddy, K. Vijayender, Journal of the Indian Chemical Society, 1986, vol. 63, p. 345 - 347

  摘要：

  DOI：

文献信息

• Synthesis of carbo- and heterofused 5-amino-2H-1,2-thiazine 1,1-dioxides via the CSIC reaction strategy
  作者：Maksim S. Dyachenko、Yaroslav O. Chuchvera、Alexey V. Dobrydnev、Andriy I. Frolov、Eugeniy N. Ostapchuk、Maria V. Popova、Yulian M. Volovenko

  DOI：10.1016/j.tet.2022.132685

  日期：2022.3

  studies with respect to the synthesis of carbo- and heterofused β-enamino-δ-sultams annelated on face c (3,4-bond). This class of compounds was designed as isomeric counterpart of known pharmacological templates – fused δ-sultams annelated through a face e (5,6-bond) following the principles of bioisosteric replacement. The starting material for this synthesis is cyclic vicinal amino nitriles. In particular

  在这里，我们全面介绍了我们关于合成在面 c（3,4-键）上退火的碳和异质融合的β-烯氨基-δ-磺胺嘧啶核苷的研究。这类化合物被设计为已知药理学模板的异构体对应物——按照生物等排置换原理通过面 e （5,6-键）退火的融合δ-磺胺嘧啶。该合成的起始材料是环状连氨基腈。特别是，根据化学性质和反应性，开发了几种用于 5 元和 6 元碳和杂芳族以及富含 sp 3 的 β-烯氨基腈的甲磺酰化方法。获得的N-单-或/和N,N-二甲磺酸盐被转化为相应的N-甲基甲磺酰胺，对其进行CSIC（碳负离子介导的磺酸盐（磺胺）分子内环化）反应方案，从而提供目标碳和杂稠合的β-烯氨基- δ -苏丹。与碳亲电试剂和异亲电试剂的反应证明了它们的合成效用。
• 2,3-substituted 1,8-naphthyridines, their preparation and their use as
  申请人：BASF Aktiengesellschaft

  公开号：US05059240A1

  公开（公告）日：1991-10-22

  2,3-substituted 1,8-naphthyridines of the general formula I ##STR1## where: R is hydrogen or C.sub.1 -C.sub.4 -alkyl (n=1 or 2) R.sup.1 is amino or substituted amino, XR.sup.5, where X is oxygen or sulfur and R.sup.5 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-((C.sub.1 -C.sub.4)-alkyl, C.sub.5 -C.sub.8 -cycloakyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenyl-(C.sub.1 -C.sub.3)-alkyl, halogen, isothiorhonium halide, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl or phenyl-(C.sub.1 -C.sub.3)-alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl, cyano, carboxyl or a group ##STR2## where X is oxygen or sulfur, B is C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or alkylthio, amino, mono- or dialkylamino, where each alkyl radical is of 1 to 4 carbon atoms, morpholino, piperidyl, chlorine, bromine or substituted or unsubstituted phenyl, D is C.sub.1 -C.sub.4 alkyl or NH.sub.2 and R.sup.6 is hydrogen, C.sub.1 -C.sub.8 -alkyl or alkylcarbonyl, or R.sup.1 and R.sup.2 together are --NH--N.dbd.C(CH.sub.2)--, and their environmentally tolerated salts with the proviso that R.sup.2 is not cyano, carboxyl or a carboxamido or carboxylic ester group when R.sup.1 is methyl, hydroxyl or amino (NH.sub.2), processes for their manufacture, and herbicidal agents containing a naphthyridine I as safener and at least one herbicidal active ingredient selected from the group consisting of a) 2-(4-heteroaryloxy)- or 2-(4-aryloxy)-phenoxyacetic acid derivatives and b) cyclohexenone derivatives.

  通式I为2,3-取代的1,8-萘啶，其中：R为氢或C.sub.1-C.sub.4-烷基（n=1或2），R.sup.1为氨基或取代氨基，XR.sup.5，其中X为氧或硫，R.sup.5为氢，C.sub.1-C.sub.12-烷基，C.sub.1-C.sub.4-烷氧羰基-（C.sub.1-C.sub.4）-烷基，C.sub.5-C.sub.8-环烷基，取代或未取代的苯基，取代或未取代的苯基-（C.sub.1-C.sub.3）-烷基，卤素，异硫蒽铵盐，C.sub.1-C.sub.12-烷基，C.sub.1-C.sub.4-烷氧羰基-C.sub.1-C.sub.4-烷基，取代或未取代的苯基或苯基-（C.sub.1-C.sub.3）-烷基，R.sup.2为C.sub.1-C.sub.4-烷基，氰基，羧基或基团##STR2##其中X为氧或硫，B为C.sub.1-C.sub.6-烷基，C.sub.1-C.sub.6-烷氧基或烷硫基，氨基，单烷基或双烷基氨基，其中每个烷基基团为1至4个碳原子，吗啉基，哌啶基，氯，溴或取代或未取代的苯基，D为C.sub.1-C.sub.4烷基或NH.sub.2，R.sup.6为氢，C.sub.1-C.sub.8-烷基或烷基羰基，或者R.sup.1和R.sup.2在一起为--NH--N.dbd.C(CH.sub.2)--，其环境耐受盐，但R.sup.2不为氰基，羧基或羧酰胺或羧酸酯基团，当R.sup.1为甲基，羟基或氨基（NH.sub.2）时，制造它们的过程，以及含有萘啶I作为安全剂和至少一种除草活性成分的除草剂。所述除草活性成分选自以下组合：a）2-（4-杂环氧基）-或2-（4-芳氧基）-苯氧乙酸衍生物和b）环己酮衍生物。
• Exploring structural effects in a new class of NRF2 inhibitors
  作者：Zhilin Hou、Lizbeth Lockwood、Di Zhang、Christopher J. Occhiuto、Linqing Mo、Kelly E. Aldrich、Hayden E. Stoub、Kathleen A. Gallo、Karen T. Liby、Aaron L. Odom

  DOI：10.1039/d2md00211f

  日期：——

  leads to resistance to chemotherapeutics and promotes metastasis. As a result, inhibition of the NRF2 pathway is a target for new drugs, especially for use in conjunction with established chemotherapeutic agents like carboplatin and 5-fluorouracil. A new class of NRF2 inhibitors has been discovered with substituted nicotinonitriles, such as MSU38225. In this work, the effects on NRF2 inhibition with structural

  NRF2 是一种转录因子，控制细胞对各种应激源（例如活性氧和氮）的反应。因此，它在抑制癌发生方面发挥着关键作用，但癌细胞中的组成型 NRF2 表达会导致对化疗药物的抵抗并促进转移。因此，抑制 NRF2 通路是新药的目标，特别是与卡铂和 5-氟尿嘧啶等现有化疗药物联合使用。已发现一类新的 NRF2 抑制剂，其具有取代的烟腈，例如 MSU38225。在这项工作中，探讨了结构变化对 NRF2 抑制的影响。通过这些研究，我们发现了一些化合物的活性与最初的目标相同或更好，但溶解度大大提高。该合成涉及多种金属催化反应，包括钛多组分偶联反应以及各种Pd和Cu偶联反应。除了抑制 NRF2 活性外，这些新化合物还抑制 NRF2 通路被组成性激活的肺癌细胞的增殖和迁移。
• 2,3-substituierte 1,8-Naphthyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Antidots
  申请人：BASF Aktiengesellschaft

  公开号：EP0387582A1

  公开（公告）日：1990-09-19

  2,3-substituierte 1,8-Naphthyridine der allgemeinen Formel I in der die Substituenten die folgende Bedeutung haben: R Wasserstoff oder C1-C4-Alkyl (n = 1 oder 2) R1 Amino, substituiertes Amino XR5, worin X Sauerstoff oder Schwefel bedeutet und R5 für Wasserstoff, C1-C12-Alkyl, C1-C4-Alkoxicarbonyl-(Ci-C4)-alkyl, C5-C8-Cycloakyl, ggf. substituiertes Phenyl, ggf. substituiertes Phenyl(C1-C3)-alkyl, Halogen, Isothiorhoniumhalogenid, C1-C12-Alkyl, C1-C4-Alkoxycarbonyl-C1-C4-alkyl, ggf. substituiertes Phenyl oder Phenyl-(Ci-C3)-alkyl, R2 C1-C4-Alkyl, Cyano, Carboxyl, eine Gruppe B oder worin x Sauerstoff oder Schwefel, B Ci-C6-Alkyl, C1-C6-Alkoxy oder Alkylthio, Amino, Mono- oder Dialkylamino mit 1 bis 4 C-Atomen je Alkylrest, Morpholino, Piperidyl, Chlor, Brom oder ggf. substituiertes Phenyl, D C1-C4-Alkyl oder NH2 und R6 Wasserstoff, C1-C8-Alkyl oder Alkylcarbonyl bedeuten oder R1 und R2 gemeinsam -NH-N = C(CH2)-, sowie deren pflanzenverträgliche Salze mit der Maßgabe, daß wenn R1 Methyl, Hydroxyl oder Amino (NH2) bedeutet, R2 nicht für Cyano, Carboxyl, eine Carbonsäureamid- oder -estergruppe steht, Verfahren zu ihrer Herstellung und herbizide Mlttel die mindestens ein Naphthyridin I als Antidot sowie mindestens einen herbiziden Wirkstoff aus der Gruppe der a) 2-(4-Heteroaryloxy)- oder 2-(4-Aryloxy)-phenoxyessigsäurederivate oder b) Cyclohexenonderivate enthalten.

  通式 I 的 2,3-取代的 1,8-萘啶化合物 其中取代基的含义如下： R 氢或 C1-C4 烷基（n = 1 或 2） R1 氨基、取代氨基 XR5，其中 X 为氧或硫，R5 为氢、C1-C12-烷基、C1-C4-烷氧羰基-(Ci-C4)-烷基、C5-C8-环烷基、任选取代的苯基、任选取代的苯基(C1-C3)-烷基、 卤素 异噻吩卤化物、 C1-C12 烷基 C1-C4-烷氧基羰基-C1-C4-烷基、 任选取代的苯基或苯基-(Ci-C3)-烷基、 R2 C1-C4 烷基、氰基、羧基、 基团 B或 其中 x 氧或硫、 B 是 C1-C6 烷基、C1-C6 烷氧基或硫代烷基、氨基、每个烷基含有 1 至 4 个碳原子的单烷基或二烷基氨基、吗啉基、哌啶基、氯基、溴基或任选取代的苯基、 D C1-C4 烷基或 NH2，以及 R6 是氢、C1-C8 烷基或烷基羰基 或 R1 和 R2 同为-NH-N = C（CH2）-、 以及它们的植物相容盐 但当 R1 是甲基、羟基或氨基（NH2）时，R2 不是氰基、羧基、羧酸酰胺基或酯基，其制备方法和除草组合物含有至少一种作为解毒剂的萘啶 I 和至少一种来自以下组别的除草活性化合物： 1. a) 2-(4-杂芳基氧基)-或 2-(4-芳基氧基)-苯氧基乙酸衍生物或 b) 环己烯酮衍生物。
• Mogilaiah; Reddy, N. Vasudeva, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 1, p. 215 - 217
  作者：Mogilaiah、Reddy, N. Vasudeva

  DOI：——

  日期：——