4-氯-6-氟-2-甲基喹啉 | 18529-01-6

• 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: 4-氯-6-氟-2-甲基喹啉
• 英文名称: 4-chloro-6-fluoro-2-methylquinoline
• CAS: 18529-01-6
• 化学式: C₁₀H₇ClFN
• mdl: MFCD00272332
• 分子量: 195.624
• InChiKey: GMMVVJJBQBYMNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  269.9±35.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 安全说明：
  S22,S24,S26,S37/39
• 危险类别码：
  R42/43,R41
• 危险品运输编号：
  3335
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Chloro-6-fluoro-2-methylquinoline
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-Chloro-6-fluoro-2-methylquinoline
Ingredient name:
CAS number: 18529-01-6

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H7ClFN
Molecular weight: 195.6

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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 chloride, 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：

  4-氯-6-氟-2-甲基喹啉 在 sodium tungstate (VI) dihydrate 、 双氧水 、 potassium carbonate 、 苯磺酰氯 、 间氯过氧苯甲酸 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 14.0h， 生成 6-fluoro-2-(((4-fluorobenzyl)sulfonyl)methyl)-N-(3-morpholin-4ylpropyl)quinolin-4-amine
  参考文献：
  名称：

  Design, Synthesis and Antiproliferative Activity of Novel 2-Substituted-4-amino-6-halogenquinolines

  摘要：

  研究人员设计、合成了两个系列的新型 2-取代-4-氨基-6-卤代喹啉类化合物 8a-l 和 13a-h，并在体外评估了它们对 H-460、HT-29、HepG2 和 SGC-7901 癌细胞株的抗增殖活性。药理结果表明，大多数具有 2-芳基乙烯基取代基的化合物都表现出良好至卓越的抗增殖活性。其中，化合物 8e 的 IC50 值分别为 0.03 μM、0.55 μM、0.33 μM 和 1.24 μM，比吉非替尼和化合物 1 的活性高出 2.5 至 186 倍，被认为是有希望进一步进行结构改造的先导化合物。

  DOI：

  10.3390/molecules17055870
• 作为产物：
  描述：

  Ethyl 3-(4-fluorophenyl)iminobutanoate 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 1.0h， 生成 4-氯-6-氟-2-甲基喹啉
  参考文献：
  名称：

  绿色高效合成4-庚基喹啉及其抗菌性能

  摘要：

  已经描述了使用PEG-600作为绿色环保合成绿色高效的4-杂基喹啉（9a，9b，9c，9d），（10a，10b，10c，10d）和（11a，11b，11c，11d）的方法溶剂。最初，在4- ° -2-氯-2-甲基喹啉（5a，5b，5c，5d）与芳族杂环硫醇（6），（7）和（8）在100°C下使用PEG-600反应30–40分钟时产生在（9），（10）和（11）以良好的产率。或者，（9），（10）和（11）也可以在二甲基甲酰胺中，以K2CO3为碱，四丁基溴化铵为相转移催化剂，在100°C下保温1–2小时。合成所有化合物并通过IR，NMR，质谱和13C NMR分析进行表征。筛选所有合成的化合物对临床菌株的抗菌活性，这些菌株包括革兰氏阳性菌（枯草芽孢杆菌MTCC 121，金黄色葡萄球菌MLS-16 MTCC 2940，微球菌MTCC 2470和金黄色葡萄球菌MTCC 96）和革兰氏阴性细菌（白色念珠菌）。

  DOI：

  10.1002/jhet.2698

文献信息

• Microwave-assisted synthesis of 4-quinolylhydrazines followed by nickel boride reduction: a convenient approach to 4-aminoquinolines and derivatives
  作者：Sandra Gemma、Gagan Kukreja、Pierangela Tripaldi、Maria Altarelli、Matteo Bernetti、Silvia Franceschini、Luisa Savini、Giuseppe Campiani、Caterina Fattorusso、Stefania Butini

  DOI：10.1016/j.tetlet.2008.01.128

  日期：2008.3

  Nickel(II) chloride/sodium borohydride combination was employed for the reduction of 4-hydrazinoquinoline derivatives to the corresponding anilines. This reductive protocol was efficiently applied for the reductive cleavage of monosubstituted hydrazines. We described herein the microwave-assisted synthesis of 4-hydrazinoquinolines, which furnished a high yielding and rapid two-step procedure for the

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。
• Efficient 2-sulfolmethyl quinoline formation from 2-methylquinolines and sodium sulfinates under transition-metal free conditions
  作者：Fuhong Xiao、Shuqing Chen、Ya Chen、Huawen Huang、Guo-Jun Deng

  DOI：10.1039/c4cc07546c

  日期：——

  An efficient procedure for 2-sulfolmethyl quinoline preparation from 2-methylquinolines and sodium sulfinates under transition-metal free conditions is described. Halogen functional groups were well tolerated to give the corresponding products in good to high yields.

  描述了在无过渡金属的条件下由2-甲基喹啉和亚磺酸钠制备2-巯基甲基喹啉的有效方法。卤素官能团具有良好的耐受性，可以以高至高收率得到相应的产物。
• [EN] POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS<br/>[FR] ANTAGONISTES DE TLR7/8 POLYCYLIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES IMMUNES
  申请人：MERCK PATENT GMBH

  公开号：WO2017106607A1

  公开（公告）日：2017-06-22

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

  本发明涉及式(I)的化合物及其药学上可接受的组合物，作为Toll样受体7/8（TLR7/8）拮抗剂。在式(I)中，环A是芳基或杂芳基；环B是芳基或杂芳基；X是C(R4)2、O、NR4、S、S(R4)或S(R4)2。
• Neue 4-Chinolinol- und 5,6,7,8-Tetrahydro-4-chinolinol-abkömmlinge mit biozider Wirkung
  作者：Horst Gildemeister、Harald Knorr、Hilman Mildenberger、Gerhard Salbeck

  DOI：10.1002/jlac.198219820908

  日期：1982.9.17

  Es wird die Synthese einiger O-substituierter 4-Chinolinole und 5,6,7,8-Tetrahydro-4-chinolinole 7–13 beschrieben. Ausgehend von 2 und 4 gelangt man mit POCl3 zu 4-Chlorchinolinen 14 und 15, welche in die 4-Aryloxychinoline 16 und 17 sowie 4-Alkyl-(Aryl-)thiochinoline 20 bzw. 4-Aminochinoline 21 übergeführt werden.

  描述了一些O-取代的4-喹啉醇和5,6,7,8-四氢-4-喹啉醇7-13的合成。从2和4开始，POCl 3产生4-氯喹啉14和15，它们分别被转化为4-芳氧基喹啉16和17和4-烷基（芳基）硫代喹啉20和4-氨基喹啉21。
• Syntheses and evaluation of new Quinoline derivatives for inhibition of hnRNP K in regulating oncogene c-myc transcription
  作者：Bing Shu、Ping Zeng、Shuangshuang Kang、Peng-Hui Li、Dexuan Hu、Guotao Kuang、Jiaojiao Cao、Xiaoya Li、Meiling Zhang、Lin-Kun An、Zhi-Shu Huang、Ding Li

  DOI：10.1016/j.bioorg.2018.12.020

  日期：2019.4

  Therefore, down-regulation of c-myc transcription by inhibiting hnRNP K through disrupting its binding to c-myc gene promoter is a potential approach for cancer therapy. In the present study, we synthesized and screened a series of Quinoline derivatives and evaluated their binding affinity for hnRNP K. Among these derivatives, (E)-1-(4-methoxyphenyl)-3-(4-morpholino-6-nitroquinolin-2-yl)prop-2-en-1-one (compound

  异质核糖核蛋白K（hnRNP K）的异常过表达是许多人类癌症的发生和发展的关键特征。已发现hnRNP K是上调c-myc基因转录的转录激活因子，c-myc基因转录是调节细胞生长和分化的关键原癌基因。因此，通过破坏hnRNP K破坏其与c-myc基因启动子的结合来抑制c-myc转录是癌症治疗的一种潜在方法。在本研究中，我们合成并筛选了一系列喹啉衍生物，并评估了它们对hnRNP K的结合亲和力。在这些衍生物中，（E）-1-（4-甲氧基苯基）-3-（4-吗啉代-6-硝基喹啉-确定2-（基）丙-2-烯-1-酮（化合物25）是第一个报告的hnRNP K结合配体，其KD值为4.6和2。用SPR和MST分别测得6μM。随后的评估表明，化合物25与hnRNP K的结合可破坏其c-myc启动子i-motif的展开，从而导致c-myc转录的下调。化合物25对人癌细胞系表现出选择性的抗增殖作用，IC50值为1.36至3