8-氨基-6-甲氧基喹啉 | 90-52-8

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 8-氨基-6-甲氧基喹啉
• 中文别名: 8-氨-6-甲氧基喹啉；6-甲氧基-8-氨基喹啉；6-甲氧基喹啉-8-胺
• 英文名称: 6-methoxyquinolin-8-amine
• 英文别名: 8-amino-6-methoxyquinoline；6-methoxy-8-aminoquinoline；6-Methoxy-quinolin-8-ylamine
• CAS: 90-52-8
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD00672902
• 分子量: 174.202
• InChiKey: YGGTVPCTAKYCSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  41 °C
• 沸点：
  137-138 °C(Press: 1 Torr)
• 密度：
  1.217±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：

  有毒，详细毒性未见报道。操作时应避免直接与人体接触。

  应将有毒物质存放在阴凉通风处，使用铁桶或木桶内衬塑料袋进行包装，并注意防热、防晒、防潮。按有毒化学品规定进行贮存和运输。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封保存，并避免光照。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-Amino-6-methoxyquinoline
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: 8-Amino-6-methoxyquinoline
CAS number: 90-52-8

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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, refrigerated.
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: C10H10N2O
Molecular weight: 174.2

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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

制备方法与用途

合成方法

8-氨基-6-甲氧基喹啉可由6-甲氧基-8-硝基喹啉在盐酸介质中用铁粉还原再经液碱中和而得。具体步骤如下：

将盐酸投入搪玻璃反应锅，升温至50℃，然后加入6-甲氧基-8-硝基喹啉、铁粉。在此条件下，在65-70℃下于3.5小时内分批加入，保温2小时后冷却，过滤得粗品8-氨基-6-甲氧基喹啉盐酸盐。再经盐析精制，并用稀碱中和至pH 7，析出8-氨基-6-甲氧基喹啉，再次过滤得到粗品，使用甲苯进行精制，最终获得产物。

化学性质

8-氨基-6-甲氧基喹啉为白色结晶。熔点为41℃，沸点在137-138℃（133帕）之间。

用途

8-氨基-6-甲氧基喹啉是抗疟类药物磷酸伯氨喹啉、戊喹及扑疟喹的中间体。

反应信息

• 作为反应物：
  描述：

  8-氨基-6-甲氧基喹啉 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 14.5h， 生成 帕马喹
  参考文献：
  名称：

  一种扑疟喹啉的制备方法

  摘要：

  本发明提供了一种扑疟喹啉的制备方法，所述制备方法包括如下步骤：将8‑氨基‑6‑甲氧基喹啉上的氨基取代为卤素，得到8‑卤素‑6‑甲氧基喹啉，而后与5‑二乙氨基‑2‑氨基戊烷偶联，得到所述扑疟喹啉。本发明提供的制备方法以8‑氨基‑6‑甲氧基喹啉和5‑二乙氨基‑2‑氨基戊烷为原料，采用两步合成反应得到产品扑疟喹啉，该制备方法的原料来源广泛、合成路线简单、反应条件温和且易于重现，利用此方法制备得到的扑疟喹啉的产量和纯度均较高，扑疟喹啉的产量为5‑57％，纯度为95‑98％。

  公开号：

  CN111217747B
• 作为产物：
  描述：

  1,2-二硝基-4-甲氧基苯 在 镍 arsenic(V) oxide 、 磷酸 、 氢气 、 铁粉 、 溶剂黄146 作用下， 20.0~118.0 ℃ 、344.74 kPa 条件下， 反应 2.2h， 生成 8-氨基-6-甲氧基喹啉
  参考文献：
  名称：

  8-aminoquinolines as anticoccidials - part III

  摘要：

  Analogues of the antimalarial pentaquine, 1, in which the nature of the side-chain on the 8-amino position was varied, were prepared and evaluated for anticoccidial activity both in vitro and in vivo. Specifically, both the inter-nitrogen distance and the nature of the terminal amino group were investigated. Novel analogues of equal or improved efficacy in vitro and in vivo to pentaquine were discovered. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00393-5

文献信息

• Piperazine-piperidine antagonists and agonists of the 5-HT1A receptor
  申请人：Asselin Magda

  公开号：US20070027160A1

  公开（公告）日：2007-02-01

  The present invention relates to novel piperazine-piperidine compounds. The compounds are useful as 5-HT 1A binding agents, particularly as 5-HT 1A receptor antagonists and agonists. These compounds are useful in treating central nervous system disorders, such as cognition disorders, anxiety disorders, depression and sexual dysfunction.

  本发明涉及新型哌嗪-哌啶化合物。这些化合物可用作5-HT1A结合剂，特别是作为5-HT1A受体拮抗剂和激动剂。这些化合物在治疗中枢神经系统疾病方面很有用，如认知障碍、焦虑症、抑郁症和性功能障碍。
• Compositions for oxidatively dyeing keratin fibers and methods for using such compositions
  申请人：Lim Mu'Ill

  公开号：US20070209123A1

  公开（公告）日：2007-09-13

  Compositions for dyeing keratin fibers comprise (a) at least one keratin dyeing compound selected from aromatic systems which comprise at least one boronic acid or boronic ester moiety and which are capable of forming upon oxidation a nucleophile or an electrophile, (b) at least one additional keratin dyeing compound selected from the group consisting of auxiliary developers and auxiliary couplers, and (c) a cosmetically suitable medium. Methods for oxidatively dyeing keratin fibers comprise the steps of applying such compositions in the presence of an oxidizing agent and rinsing the hair. A hair coloring product in kit form comprises a first separately packaged container comprising a composition as described above and a second separately packaged container comprising an oxidizing agent.

  用于染色的组合物包括：(a)至少一种选自含有至少一个硼酸或硼酸酯基团的芳香族系统的角蛋白染料化合物，这些化合物在氧化时能够形成亲核物或亲电子物；(b)至少一种额外的角蛋白染料化合物，选自辅助显色剂和辅助偶联剂的组合；(c)一种化妆品适用的介质。氧化染角蛋白纤维的方法包括在氧化剂存在下应用这样的组合物，并冲洗头发。一种套装形式的头发染色产品包括一个第一独立包装容器，其中包含上述描述的组合物，以及一个第二独立包装容器，其中包含氧化剂。
• Merging Annulation with Ring Deconstruction: Synthesis of (<i>E</i>)-3-(2-Acyl-1<i>H</i>-benzo[<i>d</i>]imidazol-4-yl)acrylaldehyde Derivatives via I₂/FeCl₃-Promoted Dual C(sp³)–H Amination/C–N Bond Cleavage
  作者：Cheng Xu、Guodong Yin、Feng-Cheng Jia、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.1c00486

  日期：2021.4.2

  An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic

  前所未有的I 2 / FeCl 3促进的芳基甲基酮与8-氨基喹啉的级联反应，用于方便地合成（E）-3-（2-酰基-1 H-苯并[ d ]咪唑-4-基）丙烯醛。通过将环空和环解构相结合而开发。这种新颖的策略解锁了8-氨基喹啉的新反应性，并为未活化的N-杂芳族化合物的开环提供了一个有吸引力的平台。初步的力学研究表明，双重C（sp 3H-氨基化/ C-N键断裂是关键的反应步骤。此外，所获得产物的后期修饰成功地递送了吡唑和异恶唑衍生物，从而增加了该方法在有机合成中的实用性和应用潜力。
• Metal‐Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions Using <i>N</i> ‐Halosuccinimides
  作者：Jiahao Hou、Kai Wang、Changjun Zhang、Tingting Wei、Renren Bai、Yuanyuan Xie

  DOI：10.1002/ejoc.202001066

  日期：2020.10.31

  A simple electrochemical method for the synthesis of C5 and C7 dihalogenation of quinolines had been developed. The addition of transition metals and oxidants was not required. Compared to previously reported methods, the reaction time was shorter. The desired products were obtained in moderate to excellent yields also on gram scale. The study of the reaction mechanism revealed that a radical step

  已经开发了一种简单的电化学方法，用于合成喹啉的C5和C7二卤代。不需要添加过渡金属和氧化剂。与以前报道的方法相比，反应时间更短。所需产物也以克规模以中等至优异的产率获得。对反应机理的研究表明，这一转化过程涉及一个基本步骤。
• 5-Position-selective C–H trifluoromethylation of 8-aminoquinoline derivatives
  作者：Yoichiro Kuninobu、Mitsumi Nishi、Motomu Kanai

  DOI：10.1039/c6ob01325b

  日期：——

  We developed a copper-catalyzed 5-position-selective C–H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway

  我们开发了8位氨基喹啉衍生物的铜催化5位选择性C–H三氟甲基化。反应在温和条件下以高官能团耐受性进行。对于在喹啉部分的8位带有酰胺，氨基甲酸酯，脲或磺酰胺基的喹啉，自由基清除剂实验表明反应是通过自由基途径进行的。可以通过水解除去8-氨基喹啉衍生物的保护基。另一方面，其他路易斯酸和铜催化剂也促进了8-氨基喹啉的三氟甲基化，甚至在存在自由基清除剂的情况下也进行了。这些结果表明8-氨基喹啉的三氟甲基化通过Friedel-Crafts型反应。有趣的是，根据底物的不同，铜盐既可以充当CF 3自由基形成的催化剂，也可以充当路易斯酸以促进Friedel-Crafts型反应。