6-氟-4-羟基-2-(三氟甲基)喹啉 | 31009-34-4

• 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-氟-4-羟基-2-(三氟甲基)喹啉
• 中文别名: 2-三氟甲基-4-羟基-6-氟喹啉；6-氟--4-羟基-2-(三氟甲基)喹啉；6-氟-4-羟基-2-三氟甲基喹啉
• 英文名称: 6-fluoro-2-(trifluoromethyl)-4-quinolinone
• 英文别名: 6-fluoro-2-trifluoromethyl-4(1H)-quinolinone；6-fluoro-2-trifluoromethyl-4-quinolinone ；6-Fluoro-4-hydroxy-2-(trifluoromethyl)quinoline；6-fluoro-2-(trifluoromethyl)-1H-quinolin-4-one
• CAS: 31009-34-4
• 化学式: C₁₀H₅F₄NO
• mdl: MFCD12147920
• 分子量: 231.149
• InChiKey: FNDABQIPEQHTNR-UHFFFAOYSA-N

物化性质

• 熔点：
  259-263°C
• 沸点：
  302.9±37.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933499090
• WGK Germany：
  3
• 危险标志：
  GHS06
• 危险性描述：
  H301
• 危险性防范说明：
  P301 + P310
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  2811
• 储存条件：
  室温

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 6-Fluoro-4-Hydroxy-2-(Trifluoromethyl)Quinoline
: JRD0217
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 3), H301
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
T Toxic R25
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 231,15 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
6-Fluoro-4-Hydroxy-2-(Trifluoromethyl)Quinoline
Acute Tox. 3; H301 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
6-Fluoro-4-Hydroxy-2-(Trifluoromethyl)Quinoline
T, R25 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Take victim immediately to hospital. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
No data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous
materials causing chronic effects
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use
respirators and components tested and approved under appropriate government standards such
as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour No data available
c) Odour Threshold No data available
d) pH No data available
e) Melting point/freezing No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower No data available
flammability or
explosive limits
k) Vapour pressure No data available
l) Vapour density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient: n- No data available
octanol/water
p) Auto-ignition No data available
temperature
q) Decomposition No data available
temperature
r) Viscosity No data available
s) Explosive properties No data available
t) Oxidizing properties No data available
Other safety information
No data available

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SECTION 10: Stability and reactivity
Reactivity
No data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
No data available
Skin corrosion/irritation
No data available
Serious eye damage/eye irritation
No data available
Respiratory or skin sensitisation
No data available
Germ cell mutagenicity
No data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
No data available
Specific target organ toxicity - single exposure
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
No data available
Persistence and degradability
No data available
Bioaccumulative potential
No data available
Mobility in soil
No data available
Results of PBT and vPvB assessment
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S. (6-Fluoro-4-Hydroxy-2-(Trifluoromethyl)Quinoline)
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (6-Fluoro-4-Hydroxy-2-(Trifluoromethyl)Quinoline)
IATA: Toxic solid, organic, n.o.s. (6-Fluoro-4-Hydroxy-2-(Trifluoromethyl)Quinoline)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
No data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  6-氟-4-羟基-2-(三氟甲基)喹啉 在 三溴氧磷 作用下， 反应 2.0h， 以84%的产率得到4-溴-6-氟-2-(三氟甲基)喹啉
  参考文献：
  名称：

  2-（三氟甲基）喹啉酮的选择性和高效结构制备

  摘要：

  苯胺与 Et 4,4,4-三氟乙酰乙酸酯之间的酸催化环化-缩合反应得到 1,4-二氢-2-三氟甲基-4H-4-喹啉酮，可轻松转化为 4-溴-2-（三氟甲基）喹啉。当用丁基锂处理时，它们进行卤素/金属交换，生成 2-三氟甲基-4-喹啉基锂，和氢/金属交换，当用二异丙基氨基锂处理时生成 4-溴-2-三氟甲基-3-喹啉基锂。后一种中间体的捕获提供了 3 官能化的产物，可以通过溴原子的亲电取代进一步加工。这些调查产生了一些意想不到的发现，最值得注意的是前所未有的支撑效应和违反直觉的卤素反应性。[在 SciFinder (R) 上]

  DOI：

  10.1002/ejoc.200390217
• 作为产物：
  描述：

  4-氟苯胺 在 PPA 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 6-氟-4-羟基-2-(三氟甲基)喹啉
  参考文献：
  名称：

  2-（F-烷基）-4-羟基喹啉的简便合成方法[1]

  摘要：

  已经开发了一种方便的2-（F-烷基）-4-羟基喹啉的新途径。在三乙胺存在下，在70°C的乙腈中用芳香胺处理2,2-二氢多氟链烷酸乙酯，得到相应的烯胺和亚胺的混合物，将其在170°C的多磷酸（PPA）中环化，得到2 -（F-烷基）-4-羟基喹啉具有良好的收率。

  DOI：

  10.1016/s0022-1139(00)83977-9

文献信息

• Design, Synthesis, and Antifungal Evaluation of Novel Quinoline Derivatives Inspired from Natural Quinine Alkaloids
  作者：Guan-Zhou Yang、Jia-Kai Zhu、Xiao-Dan Yin、Yin-Fang Yan、Yu-Ling Wang、Xiao-Fei Shang、Ying-Qian Liu、Zhong-Min Zhao、Jing-Wen Peng、Hua Liu

  DOI：10.1021/acs.jafc.9b04224

  日期：2019.10.16

  Inspired by quinine and its analogues, we designed, synthesized, and evaluated two series of quinoline small molecular compounds (a and 2a) and six series of quinoline derivatives (3a–f) for their antifungal activities. The results showed that compounds 3e and 3f series exhibited significant fungicidal activities. Significantly, compounds 3f-4 (EC50 = 0.41 μg/mL) and 3f-28 (EC50 = 0.55 μg/mL) displayed

  受奎宁及其类似物的启发，我们设计，合成和评估了两个系列的喹啉小分子化合物（a和2a）和六个系列的喹啉衍生物（3a - f）的抗真菌活性。结果表明，化合物3e和3f系列表现出显着的杀真菌活性。值得注意的是，化合物3f-4（EC 50 = 0.41μg/ mL）和3f-28（EC 50 = 0.55μg/ mL）显示出优异的体外杀真菌活性和对菌核菌的有效体内治疗作用。初步机理研究表明，化合物3f-4和3f-28可能引起细胞膜通透性改变，活性氧的积累，线粒体膜电位的丧失以及有效抑制菌核菌的发芽和形成。这些结果表明，化合物3f-4和3f-28是对抗源自天然产物的核盘菌的新型潜在杀真菌剂。
• Nopol-Based Quinoline Derivatives as Antiplasmodial Agents
  作者：Rogers J. Nyamwihura、Huaisheng Zhang、Jasmine T. Collins、Olamide Crown、Ifedayo Victor Ogungbe

  DOI：10.3390/molecules26041008

  日期：——

  the tropics. In this work, nopol-based quinoline derivatives were investigated for their inhibitory activity against Plasmodium falciparum, one of the parasites that cause malaria. The nopyl-quinolin-8-yl amides (2–4) were moderately active against the asexual blood stage of chloroquine-sensitive strain Pf3D7 but inactive against chloroquine-resistant strains PfK1 and PfNF54. The nopyl-quinolin-4-yl

  疟疾仍然是撒哈拉以南非洲和南亚地区发病和死亡的一个重要原因。虽然根据当地指南使用临床抗疟药是有效的，但对各类抗疟药的耐药性是一个持续存在的问题。人们不断需要新的抗疟疗法来补充寄生虫控制策略以对抗疟疾，特别是在热带地区。在这项工作中，研究了基于诺波尔的喹啉衍生物对恶性疟原虫（引起疟疾的寄生虫之一）的抑制活性。壬基喹啉-8-基酰胺 ( 2 – 4 ) 对氯喹敏感菌株Pf 3D7 的无性血液阶段具有中等活性，但对氯喹抗性菌株Pf K1 和Pf NF54 无活性。 Nopyl-quinolin-4-yl amides 和 nopyl-quinolin-4-yl-acetates 类似物对所有三种菌株的活性通常较低。有趣的是，酰胺8喹啉环 C7 处氯取代基的存在导致Pf K1 菌株中的 EC 50为亚微摩尔。然而， 8 的活性比Pf 3D7 和Pf NF54 低两个数量级以上。总体而言，壬基喹啉-8-基酰胺似乎与先前报道的
• Design and synthesis of ibuprofen-quinoline conjugates as potential anti-inflammatory and analgesic drug candidates
  作者：Amany M. Ghanim、Adel S. Girgis、Benson M. Kariuki、Nermin Samir、Mona F. Said、Anwar Abdelnaser、Soad Nasr、Mohamed S. Bekheit、Mohamed F. Abdelhameed、Ahmad J. Almalki、Tarek S. Ibrahim、Siva S. Panda

  DOI：10.1016/j.bioorg.2021.105557

  日期：2022.2

  properties in the carrageenan-induced rat paw edema test without showing any ulcerogenic liability. In addition, most conjugates showed promising peripheral analgesic activity in the acetic acid-induced writhing test as well as central analgesic properties in the in vivo hot plate test. The most promising conjugates were the unsubstituted and 6-substituted fluoro- and chloro-derivatives of 2-(trifl

  利用分子杂交方法中的优化反应程序，以良好的收率合成了一组新的布洛芬-喹啉共轭物，包括通过烷基链连接的喹啉基杂环和布洛芬部分，以克服当前非甾体类抗炎药的缺点。筛选合成的缀合物的抗炎和致溃疡特性。在角叉菜胶诱导的大鼠爪水肿试验中发现几种缀合物具有显着的抗炎特性，而没有显示出任何致溃疡的倾向。此外，大多数缀合物在乙酸诱导的扭体试验中显示出有希望的外周镇痛活性以及在体内的中枢镇痛特性热板测试。最有希望的缀合物是通过丙基链与布洛芬连接的 2-(三氟甲基)喹啉的未取代和 6-取代的氟代和氯代衍生物。针对 RAW264.7 小鼠巨噬细胞中 LPS 刺激的炎症反应评估了它们的抗炎活性。在这方面，发现大多数缀合物能够显着减少LPS刺激的巨噬细胞中一氧化氮的释放和产生。促炎细胞因子 IL-6、TNF-α 和诱导型一氧化氮合酶 (iNOS) 的分泌和表达也被显着抑制。
• New quinoline-triazole conjugates: Synthesis, and antiviral properties against SARS-CoV-2
  作者：Israa A. Seliem、Siva S. Panda、Adel S. Girgis、Yassmin Moatasim、Ahmed Kandeil、Ahmed Mostafa、Mohamed A. Ali、Eman S. Nossier、Fatma Rasslan、Aladdin M. Srour、Rajeev Sakhuja、Tarek S. Ibrahim、Zakaria K.M. Abdel-samii、Amany M.M. Al-Mahmoudy

  DOI：10.1016/j.bioorg.2021.105117

  日期：2021.9

  limited. We designed and synthesized three sets of small molecules using quinoline scaffolds. A series of quinoline conjugates (10a-l, 11a-c, and 12a-e) by incorporating 1,2,3-triazole were synthesized via a modified microwave-assisted click chemistry technique. Among the synthesized conjugates, 4-((1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-fluoro-2-(trifluoromethyl)quinoline (10g) and 6-fluor

  目前，严重急性呼吸系统综合症冠状病毒 2 (SARS-CoV-2) 的治疗选择非常有限。我们使用喹啉支架设计并合成了三组小分子。通过改进的微波辅助点击化学技术合成了一系列通过掺入 1,2,3-三唑的喹啉偶联物（10a-l、11a-c 和 12a-e） 。在合成的缀合物中，4-((1-(2-氯苯基)-1 H -1,2,3-三唑-4-基)甲氧基)-6-氟-2-(三氟甲基)喹啉 (10g) 和 6 -fluoro-4-(2-(1-(4-methoxyphenyl)-1 H -1,2,3-triazol-4-yl)ethoxy)-2-(trifluoromethyl)quinoline (12c) 对 SARS 表现出高效能-冠状病毒-2。化合物 10g 和 12c 的选择性指数 (SI) 也表明与参考药物相比具有显着的功效。
• Novel compounds and methods of treating cell proliferative diseases, retinopathies and arthritis
  申请人：Leblond Bertrand

  公开号：US20060183749A1

  公开（公告）日：2006-08-17

  The present invention relates to compounds and their uses, particularly in the pharmaceutical industry. The invention discloses compounds having anti-proliferative and antiangiogenic activities, as well as methods for treating various diseases associated with abnormal cell proliferation, including cancer, or associated with unregulated angiogenesis including growth and metastasis of solid tumors, ocular diseases and especially retinopathies, or arthritis, by administering said compounds. It further deals with pharmaceutical compositions comprising said compounds, more particularly useful to treat cancers (such as leukemia), ocular diseases and arthritis.

  本发明涉及化合物及其用途，特别是在制药工业中的应用。该发明揭示了具有抗增殖和抗血管生成活性的化合物，以及治疗与异常细胞增殖相关的各种疾病的方法，包括癌症，或与非调节性血管生成相关的疾病，包括实体肿瘤的生长和转移、眼部疾病，特别是视网膜病变或关节炎，通过给予这些化合物进行治疗。它还涉及包含这些化合物的制药组合物，更具体地用于治疗癌症（如白血病）、眼部疾病和关节炎。