2-乙烯基喹啉 | 772-03-2

• 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: 2-乙烯基喹啉
• 英文名称: 2-vinylquinoline
• 英文别名: 2-ethenylquinoline
• CAS: 772-03-2
• 化学式: C₁₁H₉N
• 分子量: 155.199
• InChiKey: XUGNJOCQALIQFG-UHFFFAOYSA-N

物化性质

• 熔点：
  284-285 °C
• 沸点：
  269.01°C (rough estimate)
• 密度：
  1.0300

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 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：
  1

安全信息

• 安全说明：
  S25,S28,S28A,S36/37/39,S37,S45
• 危险品标志：
  T
• 危险类别码：
  R25
• 储存条件：
  室温

SDS

Name:	2-Vinylquinoline 99% (Titr.) Material Safety Data Sheet
Synonym:	Quinoline, 2-Ethenyl-
CAS:	772-03-2

Section 1 - Chemical Product MSDS Name:2-Vinylquinoline 99% (Titr.) Material Safety Data Sheet
Synonym:Quinoline, 2-Ethenyl-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
772-03-2	Quinoline, 2-Ethenyl-	99	212-246-8

Hazard Symbols: T
Risk Phrases: 25 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic if swallowed. Causes burns.Corrosive.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye burns. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin burns. May cause skin rash (in milder cases), and cold and clammy skin with cyanosis or pale color.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May cause perforation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May cause systemic effects.
Inhalation:
Causes chemical burns to the respiratory tract. The toxicological properties of this substance have not been fully investigated.
Aspiration may lead to pulmonary edema. May cause systemic effects.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Get medical aid. Do NOT allow victim to rub eyes or keep eyes closed. Extensive irrigation with water is required (at least 30 minutes).
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Destroy contaminated shoes.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:

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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. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Do not get on skin or in eyes. Avoid ingestion and inhalation. Do not ingest or inhale. Use with adequate ventilation. Discard contaminated shoes.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area. Keep refrigerated. (Store below 4C/39F.)

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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# 772-03-2: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 71 deg C @ .50mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 128 deg C ( 262.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: 1.0340g/cm3
Molecular Formula: C11H9N
Molecular Weight: 155.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, ignition sources, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 772-03-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Quinoline, 2-Ethenyl- - 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 LIQUID, CORROSIVE, ORGANIC, N.O.S.*
Hazard Class: 6.1 (8)
UN Number: 2927
Packing Group: II
IMO
Shipping Name: TOXIC LIQUID, CORROSIVE, ORGANIC, N.O.S.
Hazard Class: 6.1 (8)
UN Number: 2927
Packing Group: II
RID/ADR
Shipping Name: TOXIC LIQUID, CORROSIVE, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2927
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 25 Toxic if swallowed.
R 34 Causes burns.
Safety Phrases:
S 25 Avoid contact with eyes.
S 28 After contact with skin, wash immediately
with...
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 772-03-2: No information available.
Canada
CAS# 772-03-2 is listed on Canada's NDSL List.
CAS# 772-03-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 772-03-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-乙烯基喹啉 在 硫脲-S,S-二氧化物 、 二氢吡啶 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以69%的产率得到2-乙基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  喹啉、苯并恶嗪和苯并噻嗪转移氢化的有机催化方法

  摘要：

  摘要 本研究报道了二氧化硫脲催化多种含 C=N 杂环化合物以 Hantzsch 酯为氢源的转移氢化。使用这种具有成本效益且易于获得的催化剂，广泛的 2-取代喹啉、3-取代-2H-1,4-苯并恶嗪和 3-取代-2H-1,4-苯并噻嗪被有效地还原为相应的四氢喹啉、二氢-2H-苯并恶嗪和二氢-2H-苯并噻嗪在温和条件下。图形摘要本研究报告了二氧化硫脲催化的 2-取代喹啉、3-取代-2H-1,4-苯并恶嗪和 3-取代-2H-以 Hantzsch 1,4-二氢吡啶为氢源的 1,4-苯并噻嗪。

  DOI：

  10.1007/s10562-017-2061-1
• 作为产物：
  描述：

  2-乙基喹啉 在 chromium oxide bauxit 作用下， 生成 2-乙烯基喹啉
  参考文献：
  名称：

  Production of alkyl quinolines and alkenyl quinolines

  摘要：

  公开号：

  US02592625A1
• 作为试剂：
  描述：

  2-氯喹啉 、 氮气 、 三丁基乙烯基锡 在 四(三苯基膦)钯 silica gel 、 EtOAc hexanes 、 2-乙烯基喹啉 作用下， 以 甲苯 为溶剂， 反应 1.42h， 以700 mg (74%) of a clear oil were obtained的产率得到2-乙烯基喹啉
  参考文献：
  名称：

  Triazolopyridinone PDE10 inhibitors

  摘要：

  本发明涉及三唑吡啶酮化合物，其作为治疗与磷酸二酯酶10（PDE10）相关的中枢神经系统疾病的治疗剂。本发明还涉及使用这种化合物治疗神经系统和精神障碍，例如精神分裂症，精神病或亨廷顿病，以及与纹状体功能不足或基底节功能障碍相关的疾病。

  公开号：

  US09266881B2

文献信息

• Alkenyl Arenes as Dipolarophiles in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides
  作者：Ana Pascual-Escudero、Abel de Cózar、Fernando P. Cossío、Javier Adrio、Juan C. Carretero

  DOI：10.1002/anie.201609187

  日期：2016.12.5

  The use of alkenyl arenes as dipolarophiles in the catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides is reported. Under appropriate reaction conditions with a CuI or AgI catalyst either the exo or the endo adduct was obtained with high stereoselectivity. This process provides efficient access to highly enantiomerically enriched 4‐aryl proline derivatives. The observed results are

  据报道，烯基芳烃在偶氮甲亚胺的催化不对称1,3-偶极环加成反应中用作双极性亲和剂。在适当的反应条件下，用Cu I或Ag I催化剂以高的立体选择性获得外型或内型加合物。此过程可有效获取高度对映体富集的4-芳基脯氨酸衍生物。观察到的结果与1,3-偶极的一个前手性面的阻滞，以及亲电性向亲双性分子的末端碳原子的有效传递是兼容的。这种极化导致从协调机制到逐步机制的转变。
• Water-Sculpting of a Heterogeneous Nanoparticle Precatalyst for Mizoroki–Heck Couplings under Aqueous Micellar Catalysis Conditions
  作者：Haobo Pang、Yuting Hu、Julie Yu、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1021/jacs.0c11484

  日期：2021.3.10

  Powdery, spherical nanoparticles (NPs) containing ppm levels of palladium ligated by t-Bu3P, derived from FeCl3, upon simple exposure to water undergo a remarkable alteration in their morphology leading to nanorods that catalyze Mizoroki–Heck (MH) couplings. Such NP alteration is general, shown to occur with three unrelated phosphine ligand-containing NPs. Each catalyst has been studied using X-ray

  粉末状球形纳米粒子 (NPs) 含有 ppm 级的钯，由来自 FeCl 3的t- Bu 3 P连接，在简单暴露于水中后，其形态发生显着变化，导致纳米棒催化 Mizoroki-Heck (MH) 偶联。这种 NP 改变是普遍的，显示发生在三个不相关的含膦配体的 NP 中。已使用 X 射线光电子能谱 (XPS)、能量色散 X 射线能谱 (EDX)、透射电子显微镜 (TEM) 和低温透射电子显微镜 (cryo-TEM) 分析研究了每种催化剂。专门依赖于含有t- Bu 3 的NPs 的联轴器P-连接的 Pd 在室温至 45 °C 之间的水性胶束催化条件下发生，并显示出广泛的底物范围。与这项新技术相关的其他关键特性包括产品中残留的 Pd 低、水性反应介质的循环利用以及相关的低 E 因子。galipinine 是汉考克生物碱家族的一员，其前体的合成暗示了潜在的工业应用。
• Metal–Organic Framework with Dual Active Sites in Engineered Mesopores for Bioinspired Synergistic Catalysis
  作者：Yangjian Quan、Yang Song、Wenjie Shi、Ziwan Xu、Justin S. Chen、Xiaomin Jiang、Cheng Wang、Wenbin Lin

  DOI：10.1021/jacs.0c02966

  日期：2020.5.13

  strong Lewis acid and photoredox sites in engineered mesopores. Al-MOF (1) with mixed 2,2'-bipyridyl-5,5-dicarboxylate (dcbpy) and 1,4-benzenediacrylate ligands was oxidized with ozone and then tiflated to generate strongly Lewis acidic Al-OTf sites in the mesopores, followed by the installation of [Ir(ppy)2(dcbpy)]+ (ppy = 2-phenylpyridine) sites to afford 1-OTf-Ir with both Lewis acid and photoredox

  在这里，我们通过在工程介孔中安装强路易斯酸和光氧化还原位点来报告模拟酶的金属有机框架 (MOF) 1-OTf-Ir 的设计。具有混合 2,2'-联吡啶-5,5-二羧酸酯 (dcbpy) 和 1,4-苯二丙烯酸酯配体的 Al-MOF (1) 用臭氧氧化，然后 tiflated 以在介孔中生成强路易斯酸性 Al-OTf 位点，然后安装 [Ir(ppy)2(dcbpy)]+ (ppy = 2-苯基吡啶) 位点以提供具有路易斯酸和光氧化还原位点的 1-OTf-Ir。1-OTf-Ir 有效地催化 N-羟基邻苯二甲酰亚胺酯或芳基溴甲基酮与乙烯基或炔基氮杂芳烃的还原交叉偶联，以提供新的氮杂芳烃衍生物。1-OTf-Ir 能够催化合成抗胆碱能药物苯那敏和氯苯那敏。
• Development of Brønsted Base–Photocatalyst Hybrid Systems for Highly Efficient C–C Bond Formation Reactions of Malonates with Styrenes
  作者：Sebastian Baś、Yasuhiro Yamashita、Shu̅ Kobayashi

  DOI：10.1021/acscatal.0c02716

  日期：2020.9.18

  developed for reactions of malonates with styrene derivatives. The concept of this process lies in the photo-oxidation of catalytic amounts of the enolate to form reactive radicals that react with alkene double bonds under mild reaction conditions. This is an example of visible-light-activated C–C bond formation reactions of malonates with alkenes to realize high atom economy under very mild reaction conditions

  已开发出布朗斯台德碱-光催化剂混合体系，用于丙二酸酯与苯乙烯衍生物的反应。该方法的概念在于催化量的烯醇化物的光氧化以形成在温和的反应条件下与烯烃双键反应的反应性自由基。这是丙二酸酯与烯烃的可见光活化C–C键形成反应的一个示例，该反应在非常温和的反应条件下无需使用任何过渡金属催化剂即可实现高原子经济性。
• The photoredox-catalyzed hydrosulfamoylation of styrenes and its application in the novel synthesis of naratriptan
  作者：Mingjun Zhang、Miaomiao Chen、Xin Ding、Jin Kang、Yongyue Gao、Xingxing He、Ziwen Wang、Aidang Lu、Qingmin Wang

  DOI：10.1039/d1cc04225d

  日期：——

  The hydrosulfamoylation of diverse aryl olefins provides facile access to alkylsulfonamides. Here we report a novel protocol utilizing radical-mediated addition and a thiol-assisted strategy to achieve the hydrosulfamoylation of diverse styrenes in modest to excellent yields under mild and economic reaction conditions. The methodology was found to provide an efficient and convenient approach for the

  多种芳基烯烃的氢氨磺酰化提供了容易获得烷基磺酰胺的途径。在这里，我们报告了一种新的协议，利用自由基介导的加成和硫醇辅助的策略，在温和和经济的反应条件下以适度到优异的产率实现各种苯乙烯的氢氨磺酰化。该方法被发现为合成抗偏头痛药物那拉曲坦提供了一种高效便捷的方法，也可用于天然产物或药物的后期功能化。