6,8-二氟喹啉 | 145241-75-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 6,8-二氟喹啉
• 英文名称: 6,8-Difluoroquinoline
• 英文别名: 6,8-difloroquinoline
• CAS: 145241-75-4
• 化学式: C₉H₅F₂N
• mdl: MFCD03662296
• 分子量: 165.142
• InChiKey: TWMLBTXFCAIQRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  235.0±20.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6,8-Difluoroquinoline
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: 6,8-Difluoroquinoline
CAS number: 145241-75-4

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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: C9H5F2N
Molecular weight: 165.1

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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, hydrogen fluoride.

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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：

  6,8-二氟喹啉 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以42%的产率得到6,8-difluoro-5-nitroquinoline
  参考文献：
  名称：

  硝基喹啉合成多氟氨基喹啉

  摘要：

  在苯部分氟化的14个喹啉转化进行了研究在硝化系统：HNO的混合物3和H 2 SO 4，纳米3 H中2 SO 4，NO 2 BF 3 OH在环丁砜，或纳米3中的发烟硫酸。如果起始化合物中不存在5或8位，则形成5-硝基和/或8-硝基衍生物。否则，无法检测到硝基产物，并且初始化合物被氧化。在某些情况下，邻位的F原子相对于硝基的位置被取代，从而得到羟基硝基喹啉。与在位置2不包含取代基的喹啉相比，多氟2-氯喹啉更容易被硝化。因此，提出了一种方法，用于将硝基喹啉还原为其他方法无法获得的氨基喹啉。

  DOI：

  10.1016/j.jfluchem.2018.04.006
• 作为产物：
  描述：

  2,4-二氟苯胺 、 甘油 在 硫酸 作用下， 反应 1.0h， 以60%的产率得到6,8-二氟喹啉
  参考文献：
  名称：

  甘油和Q管：多官能取代杂芳烃和苯胺的绿色催化剂和合成技术

  摘要：

  研究了甘油作为绿色生物基溶剂、反应物和/或催化剂在压力下合成新型杂环化合物中的作用。证明了使用甘油和压力 Q 管，采用新的改进的 Skraup 合成法以良好的产率合成新型喹啉。新型苯胺三聚体是使用甘油和取代苯胺在压力下、在酸性介质和水中制备的。甘油在新型哒嗪 13a-c 的合成中用作催化剂和绿色溶剂。充分讨论了反应机理以及甘油在质子和非质子介质中的催化作用。通过X射线晶体学和光谱方法确定了合成化合物的结构。

  DOI：

  10.3390/molecules24091806

文献信息

• Transition-metal-free site-selective C–F bond activation for synthesis of 8-aminoquinolines
  作者：Jianping Chen、Dongyang Huang、Yuqiang Ding

  DOI：10.1016/j.tetlet.2017.09.069

  日期：2017.11

  An efficient and general selective method for the synthesis of 8-aminoquinoline derivatives has been disclosed through transition metal direct C–N coupling from fluoroquinolines and arylamines. Significantly, good chemo- and regio-selectivity was observed for polyfluoroquinolines in which only C–F bond on 8-substituted position was broken. Thus, this methodology proves its value as an inexpensive and

  通过过渡金属与氟喹啉和芳胺的直接C–N偶联，已公开了一种有效且通用的8-氨基喹啉衍生物的合成方法。值得注意的是，对于多氟喹啉，只有8位取代基上的CF键被破坏，观察到了良好的化学和区域选择性。因此，该方法论证明了其为以中等至良好收率获得喹啉-8胺衍生物的廉价且有效的合成方法的价值。
• 5-Amino and 5-hydroxy-6,8-difluoroquinolones as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0226961B1

  公开（公告）日：1991-06-12
• Effects of oligofluorine substitution on the mutagenicity of quinoline: a study with twelve fluoroquinoline derivatives
  作者：Taka-aki Kato、Ken-ichi Saeki、Yutaka Kawazoe、Atsushi Hakura

  DOI：10.1016/s1383-5718(98)00188-0

  日期：1999.2

  A total of 12 variously fluorinated derivatives of quinoline (Q) were tested for their mutagenicity in Salmonella typhimurium TA100 in the presence of S9 mix to investigate the structure-mutagenicity relationship in oligofluorinated quinolines. Nine of them, 3,7-di-, 5,6-di-, 6,7-di-, 6,8-di-, 7,8-di-, 3,5,7-tri-, 5,6,8-tri-, 6,7,8-tri-, and 5,6,7,8-tetrafluoroquinolines (FQs), were newly synthesized for this purpose. Those fluorinated at position 3 were all non-mutagenic. Mutagenicity was enhanced by fluorine-substitution at position 5 or 7, but not in 3-FQs (i.e., 3,5-di-, 3,7-di-, and 3,5,7-triFQs). Some of the 6-fluorinated derivatives showed less maximum induced-revertants with more mutagenic potencies in terms of induced-revertants per dose than quinoline. No marked change occurred by fluorine-substitution at position 8. These results show that the effect of di- and trifluoro-substitution on mutagenicity is generally additive, while that of tetrafluorination approaches the deactivating effect of perfluorination. Our study suggests that 3-fluorine-substitution in the pyridine moiety may be a useful means of antimutagenic structural modification in pyridine-fused aromatic chemicals for medicinal and agricultural use. (C) 1999 Elsevier Science B.V. All rights reserved.
• Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide
  作者：Larisa V. Politanskaya、Lyudmila A. Malysheva、Irina V. Beregovaya、Irina Yu. Bagryanskaya、Yuri V. Gatilov、Evgenij V. Malykhin、Vitalij D. Shteingarts

  DOI：10.1016/j.jfluchem.2005.08.010

  日期：2005.12

  Methoxydefluorination of 5,7-, 6,7-, 6,8-, and 5,8-difluoroquinoline (1-4) by the action of sodium methoxide has been studied in liquid ammonia and Me,SO. The regioselectivity of methoxydefluorination of I and 2 in the temperature interval 218-240 K in liquid ammonia and 1 and 4 in the interval 298-378 K in Me2SO as well as the activity correlation of individual reaction centers in different substrates have been established as enthalpically controlled. The overall pattern of relative reactivity is consistent with the ab initio (RHF/6-31G*) calculated relative stabilities and electronic structures of the sigma-complexes formed by the substrates with the hydroxide anion as a model nucleophile. (c) 2005 Elsevier B.V. All rights reserved.
• Novel quinolonecarboxylic acid derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0342675B1

  公开（公告）日：1995-01-25