2-氯-6-甲氧基喹啉-3-甲醇 | 92172-83-3

• 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: 2-氯-6-甲氧基喹啉-3-甲醇
• 英文名称: (2-chloro-6-methoxyquinolin-3-yl)methanol
• 英文别名: 2-Chloro-6-methoxyquinoline-3-methanol
• CAS: 92172-83-3
• 化学式: C₁₁H₁₀ClNO₂
• mdl: MFCD02232332
• 分子量: 223.659
• InChiKey: AKKPSGFLKITYGV-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  391.4±37.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  2至8℃，惰性气体

SDS

Name:	2-Chloro-6-methoxyquinoline-3-methanol Material Safety Data Sheet
Synonym:	None Known
CAS:	92172-83-3

Section 1 - Chemical Product MSDS Name:2-Chloro-6-methoxyquinoline-3-methanol Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
92172-83-3	2-Chloro-6-methoxyquinoline-3-methanol	97+	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store protected from moisture. Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 92172-83-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 132-133 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H10ClNO2
Molecular Weight: 223.65

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Moisture sensitive.
Conditions to Avoid:
Dust generation, moisture.
Incompatibilities with Other Materials:
Oxidizing agents, acids, bases, amines, moisture.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 92172-83-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Chloro-6-methoxyquinoline-3-methanol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 92172-83-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 92172-83-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 92172-83-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氯-6-甲氧基喹啉-3-甲醇 在 三溴化磷 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(14-methoxy-8-thia-2,3,5,6,18-pentazatetracyclo[8.8.0.03,7.012,17]octadeca-1(10),4,6,11,13,15,17-heptaen-4-yl)-1H-pyridine-2-thione
  参考文献：
  名称：

  Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies

  摘要：

  The enzymes MetAP-2 and NMT play a crucial role in the process of myristoylation of oncoproteins which is deregulated in many types of cancers. Execution of both these enzymes is considered as strategy for the intervention of various cancers and relative fungal infections, and hence the discovery of novel MetAP-2 and NMT inhibitors necessitate their high relevancy. In this investigation, we have synthesized a series of novel seven-membered triazolothiadiazepinyl quinolines 10(a-m) distinctively under microwave irradiation technique and identified as selective MetAP-2 and NMT inhibitors. Amongst the functionalized derivatives when evaluated for the in vitro antifungal assay, compounds 10b, 10c, 10e and 10f were considered promising due to notable inhibitory effects (MIC = 0.2 mg/mL) on Aspergillus fumigatus. Screening of the anticancer activity against NCI-60 Human tumor cell lines portrayed that conjugates 10b, 10c, 10e and 10f were found to be moderately effective against the Renal Cancer cell line UO-31. The data acquired from biological studies was further validated by molecular docking studies and p harmaco kinetic evaluation. (C) 2019 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2019.127445
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2-氯-6-甲氧基喹啉-3-甲醇
  参考文献：
  名称：

  作为糖尿病 II 抑制剂的新型取代喹啉衍生物的合成及其计算机研究

  摘要：

  本文合成了26种取代喹啉衍生物化合物，并考察了它们对α-葡萄糖苷酶的抑制活性。筛选结果显示，与一线药物阿卡波糖（标准）相比，大多数合成的取代喹啉化合物表现出中等至非常好的 α-葡萄糖苷酶抑制活性。IC 50值在 21.71–375.00 µM 范围内获得。在取代的官能化喹啉衍生物中，化合物10b、10d、11c-11d、17b-17c和18c-18d显示出非常有希望的结果。化合物12的单晶X射线衍射图明确地证实了它的结构。本研究揭示了一系列新的取代喹啉衍生物作为 α-葡萄糖苷酶的良好抑制剂。所有活性命中都停靠在 α-葡萄糖苷酶的活性位点，以研究它们的结合模式。我们得出结论，新引入的取代基对于影响相互作用很重要，因为它们证明了这些化合物对 α-葡萄糖苷酶抑制剂的潜力。

  DOI：

  10.1016/j.molstruc.2022.134560

文献信息

• Synthesis and Antibacterial Evaluation of Some Novel 1,3,4-oxadiazol Derivatives Incorporated with Quinoline Moiety
  作者：Priyanka G. Mandhane、Ratnadeep S. Joshi、Wajid Khan、Charansingh H. Gill

  DOI：10.5012/jkcs.2011.55.4.656

  日期：2011.8.20

  5-(3,4,5-Triethoxyphenyl)-1,3,4-oxadiazole-2-thiol 6을 3-(bromomethyl)-2-chloroquinoline or 2-(p-tolyloxy)-3-(bromomethyl) quinoline 4a-j 화합물과 반응시켜서 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-chloroquinoline 또는 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-(p-tolyloxy)quinoline 7a-j를 합성하였다. 합성한 화합물들에 대한 항균활성을 측정하였으며, 화합물 7d, 7i 및 7j 은 우수한 활성을 나타내었다. 5-(3,4,5-Triethoxyphenyl)-1,3,4-oxadiazole-2-thiol 6 on treatment with substituted 3-(bromomethyl)-2-chloroquinoline or 2-(p-tolyloxy)-3-(bromomethyl)quinoline 4a-j afforded the corresponding 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-chloroquinoline or 3-((5-(3,4,5-triethoxyphenyl)-1,3,4-oxadiazol-2-ylthio)methyl)-2-(p-tolyloxy)quinoline 7a-j, in the presence of $K_2CO_3$ and DMF under stirring at ambient temperature. All the synthesized compounds were further screened for their antibacterial activities. Some of our compounds showed excellent antibacterial activities against test organisms and reference standard.

  5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫醇6与3-(溴甲基)-2-氯喹啉或2-(对甲苯氧基)-3-(溴甲基)喹啉4a-j反应，合成了3-((5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-氯喹啉或3-((5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-(对甲苯氧基)喹啉7a-j。测定了合成的化合物的抗菌活性，化合物7d、7i和7j表现出优秀的活性。在与取代的3-(溴甲基)-2-氯喹啉或2-(对甲苯氧基)-3-(溴甲基)喹啉4a-j反应时，加入K2CO3和DMF，在室温下搅拌，得到了相应的3-((5-(3,4,5-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-氯喹啉或3-((5-(3,4-三乙氧基苯基)-1,3,4-噁二唑-2-硫代)甲基)-2-(对甲苯氧基)喹啉7a-j。所有合成的化合物都进一步进行了抗菌活性筛选，一些化合物对测试生物和参考标准表现出极佳的抗菌活性。
• Synthesis, crystal structure, ABTS radical-scavenging activity, antimicrobial and docking studies of some novel quinoline derivatives
  作者：Sumaiya Tabassum、T.H. Suresha Kumara、Jerry P. Jasinski、Sean P. Millikan、H.S. Yathirajan、P.S. Sujan Ganapathy、H.B.V. Sowmya、Sunil S. More、Gopalpur Nagendrappa、Manpreet Kaur、Gilish Jose

  DOI：10.1016/j.molstruc.2014.04.009

  日期：2014.7

  In this study, a series of nine novel 2-chloroquinolin-3-yl ester derivatives have been synthesized via a two-step protocol from 2-chloroquinoline-3-carbaldehyde. The structures of all these compounds were confirmed by spectral data. The single crystal X-ray structure of two derivatives, (2-chloroquinolin-3-yl)methyl acetate [6a] and (2-chloro-6-methylquinolin-3-yl)methyl acetate [6e] have also been

  在这项研究中，通过两步法从 2-氯喹啉-3-甲醛合成了一系列九种新型 2-氯喹啉-3-基酯衍生物。所有这些化合物的结构都由光谱数据证实。两种衍生物（2-氯喹啉-3-基）乙酸甲酯 [6a] 和（2-氯-6-甲基喹啉-3-基）乙酸甲酯 [6e] 的单晶 X 射线结构也已确定。进一步评估了合成化合物的 ABTS 自由基清除活性和抗菌活性。在所有测试的化合物中，6a 表现出最大的 ABTS 清除活性。关于抗菌和抗真菌活性，发现化合物（2-氯-6-甲氧基喹啉-3-基）甲基 2,4-二氯苯甲酸酯 [6i] 在该系列中对枯草杆菌、金黄色葡萄球菌、大肠杆菌的活性最强。大肠杆菌、肺炎克雷伯菌、C. albicans 和 A. niger 物种。使用 Autodock 研究了这些衍生物的结构-抗菌活性关系。
• IBX works efficiently under solvent free conditions in ball milling
  作者：Tapas Kumar Achar、Saikat Maiti、Prasenjit Mal

  DOI：10.1039/c4ra00415a

  日期：——

  explosiveness at high temperature and poor solubility in common organic solvents except DMSO. Since the discovery of Dess–Martin Periodinane in 1983, several modified IBX systems have been reported. However, under ball milling conditions, IBX works efficiently with various organic functionalities at ambient temperature under solvent free conditions. Also, the waste IBA (2-iodosobenzoic acid) produced

  IBX（2-碘氧基苯甲酸），发现于1893年，是合成化学中的一种氧化剂，由于其在高温下的爆炸性以及在除DMSO之外的普通有机溶剂中的溶解性差而被广泛使用而受到阻碍。自1983年发现Dess-Martin Periodinane以来，已经报道了几种改进的IBX系统。但是，在球磨条件下，IBX可以在环境温度和无溶剂条件下有效地利用各种有机功能。另外，反应产生的废IBA（2-碘代苯甲酸）也就地在接下来的步骤中，使用过硫酸氢钾将其氧化成IBX，因此通过保持其效率（在15个循环后仅损失约6％）而重复用于多个循环。这项工作概述了一种非常经济的合成方法，该方法克服了使用IBX的问题，可以有效地以克为单位且以非爆炸方式进行。
• Methanol as hydrogen source: transfer hydrogenation of aromatic aldehydes with a rhodacycle
  作者：Ahmed H. Aboo、Elliot L. Bennett、Mark Deeprose、Craig M. Robertson、Jonathan A. Iggo、Jianliang Xiao

  DOI：10.1039/c8cc06612d

  日期：——

  A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.

  环金属化铑配合物已显示出高度选择性和有效地还原醛，从而从甲醇中衍生出氢。在温和条件和开放气氛下，使用甲醇作为溶剂和氢供体，在不影响其他官能团的情况下，将大量的芳族醛还原为相应的醇。
• Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents
  作者：Fostino R.B. Bokosi、Richard M. Beteck、Mziyanda Mbaba、Thanduxolo E. Mtshare、Dustin Laming、Heinrich C. Hoppe、Setshaba D. Khanye

  DOI：10.1016/j.bmcl.2021.127855

  日期：2021.4

  Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated

  目前有几类抗疟药可用，但毒性问题和耐药性疟原虫的出现降低了它们的整体治疗效率。基于喹啉的抗疟药已明确存在已久，并继续激发新抗疟药的设计。在此，通过连续步骤合成了一系列单喹啉和双喹啉甲胺衍生物；Vilsmeier-Haack、还原胺化和亲核取代，并以低到极好的收率获得。研究了所得化合物对恶性疟原虫3D7 氯喹敏感菌株以及化合物40和59 的体外抗疟原虫活性。成为最有希望的 IC 50值分别为 0.23 和 0.93 µM。最有前途的化合物还通过分子对接协议在计算机上进行了评估，以了解对血红素晶体模型的 0  0  1} 快速生长面的结合亲和力。