8-羟基喹啉-2-甲醛 | 14510-06-6

• 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: 8-羟基喹啉-2-甲醛
• 中文别名: 8-羟基-2-喹啉甲醛
• 英文名称: 2-formyl oxine
• 英文别名: 8-hydroxyquinoline-2-carboxaldehyde；8-hydroxyquinoline-2-carbaldehyde；2-formyl-8-hydroxyquinoline；8-hydroxy-2-quinolinecarbaldehyde；8-hydroxyquinoline-2-aldehyde；8-hydroxy-2-quinolinecarboxaldehyde；8-Hydroxy-chinolin-2-carbaldehyd；2-aldehyde-8-hydroxyquinoline；8-hydroxy-2-quinolinaldehyde；2-formyl-8-quinolinol；8-hydroxyquinoline-2-formaldehyde；8-hydroxyquinolin-2-carbaldehyde
• CAS: 14510-06-6
• 化学式: C₁₀H₇NO₂
• mdl: MFCD00168962
• 分子量: 173.171
• InChiKey: SLBPIHCMXPQAIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  97-100 °C
• 沸点：
  392.2±22.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933499090
• 危险品运输编号：
  NONH for all modes of transport
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  存于阴凉干燥处

SDS

Name:	8-Hydroxyquinoline-2-carboxaldehyde Material Safety Data Sheet
Synonym:	None Known
CAS:	14510-06-6

Section 1 - Chemical Product MSDS Name:8-Hydroxyquinoline-2-carboxaldehyde Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14510-06-6	8-Hydroxyquinoline-2-carboxaldehyde	98	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
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.

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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# 14510-06-6: 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: Crystalline powder
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 97 - 100 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: C10H7NO2
Molecular Weight: 173.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14510-06-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
8-Hydroxyquinoline-2-carboxaldehyde - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 14510-06-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14510-06-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14510-06-6 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

制备方法与用途

用途

8-羟基喹啉-2-甲醛是一种有用的研究化学品，常作为合成络合剂的结构单元。

反应信息

• 作为反应物：
  描述：

  8-羟基喹啉-2-甲醛 在 甲酸 、 双氧水 作用下， 反应 12.0h， 生成 8-羟基喹啉-2-羧酸
  参考文献：
  名称：

  新型8-取代喹啉-2-羧酰胺类碳酸酐酶抑制剂的合成及生物学评价

  摘要：

  抽象的 通过使8-羟基-N-（4-氨磺酰基苯基）喹啉-2-羧酰胺与烷基和苄基卤反应，合成了一系列新型的8-取代-N-（4-氨磺酰基苯基）喹啉-2-羧酰胺。测定化合物对四种hCA同工型，hCA I，hCA II，hCA IV和hCA IX的碳酸酐酶（CA）抑制活性。除非hCA IX，所有同工型都被抑制了从低到高的纳摩尔范围。hCA I的抑制范围为61.9-8126 nM，化合物5h的抑制常数为K I  = 61.9 nM。hCA II被抑制的范围为33.0-8759 nM，化合物5h的抑制常数为33.0 nM，化合物5a和5b具有分别为88.4和85.7nM的抑制常数。hCA IV被抑制在657.2-6757 nM的范围内。因此，可以选择具有低纳摩尔hCA I和II抑制作用的化合物5h作为设计新型CA I和II抑制剂的先导。

  DOI：

  10.1080/14756366.2019.1626376
• 作为产物：
  描述：

  8-羟基喹啉 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以60%的产率得到8-羟基喹啉-2-甲醛
  参考文献：
  名称：

  一种识别和检测草酸的荧光分子探针及其制备方法和应用

  摘要：

  一种识别和检测草酸的荧光分子探针及其制备方法和应用，明涉及识别和检测草酸的探针及其制备方法和应用。本发明是要解决现有的利用荧光法识别和检测草酸的荧光探针无法实现定量检测，而且选择性差、易受其它有机酸干扰的技术问题。本发明的荧光分子探针的结构式为：制法：一、水杨酸、浓硫酸、甲醇反应制备中间体I；二、中间体I与水合肼制备中间体Ⅱ；三、8‑羟基喹哪啶、二氧化硒、1,4‑二氧六环反应制备中间体Ⅲ；四、中间体Ⅲ与中间体Ⅱ反应得到中间体Ⅳ；五、向中间体Ⅳ与Fe3+反应，得到探针。它通过荧光增强对草酸进行识别和检测，选择性高且不受其它有机酸的干扰，检出限为1.3×10‑7mol/L。可用于环境、食品领域。

  公开号：

  CN111518026A

文献信息

• Investigation of the Biological Properties of (Hetero)Aromatic Thiosemicarbazones
  作者：Maciej Serda、Anna Mrozek-Wilczkiewicz、Josef Jampilek、Matus Pesko、Katarina Kralova、Marcela Vejsova、Robert Musiol、Alicja Ratuszna、Jaroslaw Polanski

  DOI：10.3390/molecules171113483

  日期：——

  Two series of thiosemicarbazone-based iron chelators (twenty-seven compounds) were designed and synthesized using a microwave-assisted approach. Quinoline and halogenated phenyl were selected as parent scaffolds on the basis of a similarity search. The lipophilicity of the synthesized compounds was measured using HPLC and then calculated. Primary in vitro screening of the synthesized compounds was performed against eight pathogenic fungal strains. Only a few compounds showed moderate activity against fungi, and (E)-2-(quinolin-2-ylvinyl)-N,N-dimethylhydrazine-carbothioamide appeared to be more effective than fluconazole against most of the fungal strains tested. Antiproliferative activity was measured using a human colon cancer cell line (HCT-116). Several of the tested compounds showed submicromolar antiproliferative activity. Compounds were also tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The structure-activity relationships are discussed for all of the compounds.

  采用微波辅助法设计并合成了两系列基于硫代 semicarbazone 的铁螯合剂（共 27 个化合物）。根据相似性搜索，以喹啉和卤代苯为母体骨架。通过 HPLC 测量并计算所合成化合物的亲脂性。对所合成的化合物进行了针对八种病原真菌的初级体外筛选。仅有少数化合物显示出中等的抗真菌活性，其中(E)-2-(喹啉-2-基乙烯基)-N,N-二甲基胼硫代卡巴脒对大部分测试的真菌株的抗真菌活性均优于氟康唑。采用人结肠癌细胞系(HCT-116) 测量其抗增殖活性。部分测试化合物显示出亚微摩尔级的抗增殖活性。此外，还测试了它们抑制菠菜（Spinacia oleracea L.）叶绿体中光合电子传递（PET）的能力。对于所有化合物，讨论了其结构-活性关系。
• Aminopiperidine quinolines and their azaisosteric analogues with antibacterical activity
  申请人：——

  公开号：US20040038998A1

  公开（公告）日：2004-02-26

  Aminopiperidine derivatives of formula (I) and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly in man. 1

  氨基哌啶衍生物的公式(I)及其药物可接受的衍生物，用于治疗哺乳动物，特别是人类的细菌感染。
• Pyrimidine Derivatives Which Are Antagonists Of Vitronectin Receptor
  申请人：Lefrancois Jean-Michel

  公开号：US20080058348A1

  公开（公告）日：2008-03-06

  A subject of the invention is the compounds of formula (I); in which R 1 , R 2 , R 3 , R 4 and R have the meanings indicated in the description, their preparation process, their use as medicaments having an antagonist activity on the vitronectin receptor and the pharmaceutical compositions containing them.

  本发明的主题是公式(I)的化合物；其中R1、R2、R3、R4和R具有说明书中指出的含义，它们的制备过程，它们作为对玻连蛋白受体具有拮抗活性的药物的使用以及包含它们的药物组合物。
• [EN] SUBSTITUTED 6,7-DIALKOXY-3-ISOQUINOLINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE10A)<br/>[FR] DÉRIVÉS DE 6,7-DIALCOXY-3-ISOQUINOLINE SUBSTITUÉS À TITRE D'INHIBITEURS DE PHOSPHODIESTÉRASE 10 (PDE10A)
  申请人：ALLERGAN INC

  公开号：WO2014071044A1

  公开（公告）日：2014-05-08

  The invention relates to compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R', R1 through R7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.

  本发明涉及公式（I）的化合物或其药用可接受盐，其中R'，R1至R7和Ar如本文所述定义。这些化合物作为磷酸二酯酶10（PDE10A）的抑制剂，可用于治疗中枢神经系统疾病，如精神疾病，也可用于治疗例如肥胖、II型糖尿病、代谢综合征、葡萄糖不耐症、疼痛和眼科疾病。
• Cathepsin B inhibitors: Further exploration of the nitroxoline core
  作者：Izidor Sosič、Ana Mitrović、Hrvoje Ćurić、Damijan Knez、Helena Brodnik Žugelj、Bogdan Štefane、Janko Kos、Stanislav Gobec

  DOI：10.1016/j.bmcl.2018.02.042

  日期：2018.4

  their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline

  人组织蛋白酶B是一种半胱氨酸蛋白酶，具有许多看家功能，例如溶酶体内的细胞内蛋白水解。它增加的活性和表达与包括癌症在内的许多病理过程密切相关。我们在这里介绍设计​​和合成作为组织蛋白酶B抑制剂的新的硝基氧代林衍生物。这些衍生物可通过省略吡啶部分或修饰硝基氧代林的2、7和8位来制备。评估了所有化合物抑制组织蛋白酶B的内肽酶和外肽酶活性的能力。对于最有希望的抑制剂，确定了减少细胞外和细胞内胶原IV降解的能力，然后在基于细胞的体外进行了评估肿瘤侵袭模型。所提供的数据表明，我们进一步确定了氮氧杂环丁烷衍生物抑制组织蛋白酶B的结构要求，并提供了可能导致非肽类化合物对抗肿瘤进展的其他知识。

表征谱图