8-甲基-1,2,3,4-四氢喹啉 | 52601-70-4

• 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-甲基-1,2,3,4-四氢喹啉
• 中文别名: 8-甲基-1,2,3,4-氢喹啉
• 英文名称: 8-methyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 8-methyltetrahydroquinoline；1,2,3,4-tetrahydro-8-methylquinoline
• CAS: 52601-70-4
• 化学式: C₁₀H₁₃N
• mdl: MFCD00218100
• 分子量: 147.22
• InChiKey: YIIPMCFBCZKCFB-UHFFFAOYSA-N

物化性质

• 沸点：
  255 °C
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险类别码：
  R20/21/22
• 海关编码：
  2933499090
• 安全说明：
  S24/25
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C

SDS

Name:	8-Methyl-1 2 3 4-tetrahydroquinoline 97% Material Safety Data Sheet
Synonym:	1,2,3,4-Tetrahydro-8-methylquinolin
CAS:	52601-70-4

Section 1 - Chemical Product MSDS Name:8-Methyl-1 2 3 4-tetrahydroquinoline 97% Material Safety Data Sheet
Synonym:1,2,3,4-Tetrahydro-8-methylquinolin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52601-70-4	8-Methyl-1,2,3,4-tetrahydroquinoline	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 52601-70-4: Personal Protective Equipment Eyes: Not available.
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: Liquid
Color: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 120 - 125 deg C @10mmHg
Freezing/Melting Point: Not available.
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: C10H13N
Molecular Weight: 147

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 52601-70-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
8-Methyl-1,2,3,4-tetrahydroquinoline - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 52601-70-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 52601-70-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 52601-70-4 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：

  8-甲基-1,2,3,4-四氢喹啉 在 叔丁基过氧化氢 作用下， 以 氘代二甲亚砜 、 水 、 重水 、 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到8-甲基喹啉
  参考文献：
  名称：

  基于具有酸碱依赖性电荷可调性的有机顶点的氧化还原活性超分子 Fe4L6 笼用于脱氢催化

  摘要：

  超分子笼化学具有持久的意义，因为作为天然酶的人工蓝图，自组装笼结构不仅提供了底物承载的仿生环境，而且可以在受限的纳米空间中整合活性位点以实现功能协同。在此，我们展示了一种顶点定向的有机夹螯合组装策略，以构建金属-有机笼 Fe 4 L 6 8+ (MOC-63)，在八面体中包含 12 个咪唑质子供体 - 受体基序和四个氧化还原活性 Fe 中心协调纳米空间。与常规的以配位金属顶点组装的超分子笼不同，MOC-63 包含六个双位有机夹配体作为顶点和四个三螯合 Fe(N∩N) 3部分作为面，从而通过溶液中的笼稳定动力学提高其酸、碱和氧化还原稳定性。MOC-63 改进了 1,2,3,4-四氢喹啉衍生物的脱氢催化，这是由于超分子笼效应可协同多个 Fe​​ 中心和自由基物种，以加速笼受限纳米空间中多步反应的中间转化。酸碱缓冲咪唑基序在调节总电荷状态以抵抗 pH 变化和调节不同溶剂之间的溶解度方面发挥着至关

  DOI：

  10.1021/jacs.2c02692
• 作为产物：
  描述：

  2-甲基-3-氨基苯酚 在 indium(III) triflate 、 吡啶 、 萘 、 palladium on activated charcoal 、 ammonium acetate 、 sodium 、 magnesium 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 8-甲基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  氧杂环丁烷的异常骨架重组，用于合成1,2-二氢喹啉。

  摘要：

  骨骼重组由于其有趣的机制和在复杂分子合成中的实用性而成为一种引人入胜的转化。然而，对于大多数官能团而言，仅有限数量的实例是已知的。在此，我们描述了氧杂环丁烷的这种异常过程。在In（OTf）3作为催化剂的存在下，氧杂环丁烷系苯胺意外反应形成1,2-二氢喹啉。该方法不仅提供了方便的二氢喹啉的途径，而且代表了氧杂环丁烷的新反应。从机理上讲，据信反应是通过最初的氮攻击而不是芳烃攻击进行的，随后是一系列的键断裂和形成事件。对照实验提供了对该机理的重要见解。

  DOI：

  10.1002/anie.201916727

文献信息

• Flavin/I₂ -Catalyzed Aerobic Oxidative C-H Sulfenylation of Aryl-Fused Cyclic Amines
  作者：Xinpeng Jiang、Zongchen Zhao、Zhifeng Shen、Keda Chen、Liyun Fang、Chuanming Yu

  DOI：10.1002/ejoc.202000508

  日期：2020.7.7

  A metal‐free aerobic oxidative C–H sulfenylation of aryl‐fused cyclic amines with various thiols was developed with excellent functional compatibility. While flavin I catalyzed the C–H sulfenylation of indolines to afford 3‐sulfenylindoles, flavin II enabled transformations resulting in substitution at the position para to the N atom on the aryl ring to obtain 6‐sulfenylquinolines.

  芳基稠合的环胺与各种硫醇的无金属好氧氧化C–H亚磺酰化反应具有出色的功能相容性。虽然黄素我催化的二氢吲哚的C-H亚磺酰化，得到3- sulfenylindoles，黄素II启用导致取代在位置变换对位到Ñ在芳环上原子，得到6- sulfenylquinolines。
• Tuning the chemoselective hydrogenation of aromatic ketones, aromatic aldehydes and quinolines catalyzed by phosphine functionalized ionic liquid stabilized ruthenium nanoparticles
  作者：He-yan Jiang、Xu-xu Zheng

  DOI：10.1039/c5cy00293a

  日期：——

  Ruthenium nanoparticles (Ru NPs) stabilized by phosphine-functionalized ionic liquids (PFILs) were synthesized in an imidazolium-based ionic liquid using H2 as a reductant. Characterization showed well-dispersed particles of about 2.2 nm (TEM) and confirmed the PFIL stabilization of the Ru NPs (NMR). The Ru NPs stabilized by PFILs exhibited excellent activity and switchable chemoselectivity in the

  使用H 2作为还原剂，在咪唑基离子液体中合成了由膦官能化离子液体（PFIL）稳定的钌纳米粒子（Ru NPs）。表征显示出约2.2 nm（TEM）的分散良好的颗粒，并证实了Ru NPs的PFIL稳定（NMR）。PFILs稳定的Ru NPs在温和条件下在芳香族酮，芳香族醛和喹啉的非均相选择性加氢中表现出出色的活性和可切换的化学选择性。
• Highly Selective Hydrogenation with Ionic Liquid Stabilized Nickel Nanoparticles
  作者：He-yan Jiang、Si-shi Zhang、Bin Sun

  DOI：10.1007/s10562-018-2361-0

  日期：2018.5

  Nickel nanoparticles (Ni NPs) were conveniently synthesized from the reduction of nickel(II) salt with NaBH4 or hydrazine in the presence of the ionic liquid 1-butyl-2,3-dimethylimidazolium (S)-2-pyrrolidinecarboxylic acid salt. UV/Vis spectroscopy, thermogravimetric analysis, and X-ray photoelectron spectroscopy were employed to characterize the interaction between the metal and the ionic liquid.

  在离子液体 1-丁基-2,3-二甲基咪唑鎓（S）-2-吡咯烷羧酸盐存在下，通过用 NaBH4 或肼还原镍（II）盐，方便地合成镍纳米颗粒（Ni NPs）。紫外/可见光谱、热重分析和 X 射线光电子能谱被用来表征金属和离子液体之间的相互作用。Ni NPs(0) 的面心立方结构通过 X 射线衍射表征得到证实。透射电子显微镜图像显示平均直径约为 5.1 nm 的分散良好的 Ni 颗粒。在温和的反应条件下，离子液体固定的 Ni NPs 被用作高效催化剂，用于喹啉和相关化合物以及芳香硝基化合物的化学选择性加氢。
• Cobalt-Catalyzed Selective Functionalization of Aniline Derivatives with Hexafluoroisopropanol
  作者：He Zhao、Shuo Zhao、Xiu Li、Yinyue Deng、Huanfeng Jiang、Min Zhang

  DOI：10.1021/acs.orglett.8b03666

  日期：2019.1.4

  A cobalt-catalyzed site-selective functionalization of aniline derivatives with hexafluoroisopropanol, which enables the synthesis of a wide array of fluoroalkylated anilines, a class of highly valuable building blocks for further preparation of fluorinated functional products, is reported. The developed transformation proceeds with operational simplicity, use of earth-abundant metal catalyst, broad

  报道了用六氟异丙醇对苯胺衍生物进行钴催化的位点选择性官能化，这使得能够合成各种各样的氟代烷基化苯胺，这是一类非常有价值的用于进一步制备氟化功能产物的结构单元。所开发的转化过程将以操作简便，使用富含地球的金属催化剂，广泛的底物范围，良好的官能团耐受性和温和的反应条件进行。
• Heteroaryl hydroxamic acid derivatives and their use in the treatment, amelioration or prevention of a viral disease
  申请人：F. HOFFMANN-LA ROCHE LTD

  公开号：US20130102600A1

  公开（公告）日：2013-04-25

  The present invention relates to a compound having the general formula I, optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

  本发明涉及一种具有通式I的化合物，可选地以药物可接受的盐、溶剂化物、多晶型、前药、互变异构体、外消旋体、对映体、非对映体或其混合物的形式，该化合物在治疗、改善或预防病毒性疾病方面有用。此外，还公开了特定的组合疗法。