5,7-二氯-4-羟基喹啉-3-羧酸 | 171850-30-9

• 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: 5,7-二氯-4-羟基喹啉-3-羧酸
• 英文名称: 5,7-Dichloro-4-hydroxyquinoline-3-carboxylic acid
• 英文别名: 5,7-dichloro-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 171850-30-9
• 化学式: C₁₀H₅Cl₂NO₃
• 分子量: 258.061
• InChiKey: DEBOCPZCSPMQBS-UHFFFAOYSA-N

物化性质

• 沸点：
  445.5±45.0 °C(Predicted)
• 密度：
  1.701±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,7-Dichloro-4-hydroxyquinoline-3-carboxylic acid
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5,7-Dichloro-4-hydroxyquinoline-3-carboxylic acid
CAS number: 171850-30-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H5Cl2NO3
Molecular weight: 258.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5,7-二氯-4-羟基喹啉-3-羧酸 在 氢氧化钾 作用下， 以 Therminol VP₁ 、 水 为溶剂， 反应 15.0h， 以70%的产率得到5,7-二氯-4-羟基喹啉
  参考文献：
  名称：

  Method for preparing 4-hydroquinolines and/or tautomeric compounds

  摘要：

  本发明涉及一种制备4-羟基喹啉和/或互变异构体化合物的方法。更具体地，本发明涉及5,7-二氯-4-喹啉和/或其互变异构体化合物。该方法的特点在于，在碱的存在下，将4-羟基喹啉羧酸、其衍生物或前体在不超过200°C的温度下加热。

  公开号：

  US06362340B1
• 作为产物：
  描述：

  3,5-二氯苯胺 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5,7-二氯-4-羟基喹啉-3-羧酸
  参考文献：
  名称：

  作为抗结核药物的新型芳基甲酰胺衍生物的设计、合成和生物学评价

  摘要：

  我们小组之前曾报道过几种表现出强效抗结核活性的吲哚甲酰胺。在这里，我们基于我们之前报道的同源模型和最近发表的分枝杆菌膜蛋白大 3 (MmpL3) 的晶体结构合理地设计了几种芳基甲酰胺。许多类似物对药物敏感 (DS)结核分枝杆菌( M. tb ) 菌株表现出相当大的抗结核活性。萘酰胺衍生物13c和13d是我们研究中最活跃的化合物（MIC：分别为 6.55、7.11 μM），显示出与一线抗结核（抗 TB）药物乙胺丁醇（MIC：4.89 μM）相当的效力。除了萘酰胺衍生物外，我们还确定了喹诺酮-2-甲酰胺和 4-芳基噻唑-2-甲酰胺作为潜在的 MmpL3 抑制剂，其中化合物8i和18b的 MIC 值分别为 9.97 和 9.82 μM。所有四种化合物都保留了对多重耐药 (MDR) 和广泛耐药 (XDR)结核分枝杆菌菌株的高活性。值得注意的是，两种活性最高的化合物13c和13d对 DS、MDR 和

  DOI：

  10.1039/c9ra10663d

文献信息

• Dichloro-4-quinolinol-3-carboxylic acid: Synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA
  作者：Guo-Xiang Li、Zai-Qun Liu、Xu-Yang Luo

  DOI：10.1016/j.ejmech.2010.01.018

  日期：2010.5

  5,7-, 5,8-, 6,8-, 7,8-Dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2′-diphenyl-1-picrylhydrazyl

  5,7-，5,8-，6,8-，7,8-二氯-4-喹啉醇-3-羧酸（5,7-，5,8-，6,8-，7,8-DCQA ）与7-氯-4-喹啉-3-羧酸（7-CQA）和4-喹啉-3-羧酸（QA）一起合成以研究其抗氧化性能。5,7-DCQA表现出最高的清除2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸盐）阳离子自由基（ABTS +。），2,2'-二苯基-1-吡啶并肼基（DPPH）和加尔维氧基自由基的能力。6,8-DCQA具有最高的保护亚油酸甲酯抵抗2,2'-偶氮双（2-ami基丙烷）二盐酸盐（AAPH）诱导的氧化的功效。5,7-，5,8- DCQA和QA能够延缓β胡萝卜素漂在β-胡萝卜素-亚油酸乳液。此外，5,8-和6,8-DCQA有效保护DNA免受羟基自由基（.OH）介导的氧化作用，而5,8-DCQA和7-CQA具有保护DNA免受AAPH诱导的氧化作用的活性。此外，只有7-CQA可以保护DNA免受Cu
• Intermediates for producing 5,7-dichloro-4-hydroxyquinoline
  申请人：Ishihara Sangyo Kaisha Ltd.

  公开号：US05731440A1

  公开（公告）日：1998-03-24

  An industrially advantageous process for producing 5,7-dichloro-4-hydroxyquinoline (DCHQ) useful as an intermediate for agrohorticultural bactericides. The process comprises (i) hydrolyzing 3-cyano- or 3-ethoxycarbonyl-5,7-dichloro-4-hydroxyquinoline into 5,7-dichloro-3-carboxy-4-hydroxyquinoline (DCQA) in the presence of hydrochloric, sulfuric or phosphoric acid and (ii) decarboxylating the formed DCQA into DCHQ in the presence of sulfuric or phosphoric acid. In particular, this process comprises continuously conducting the hydrolysis of 5,7-dichloro-3-ethoxycarbonyl-4-hydroxyquinoline and the decarboxylation of the hydrolyzate in the presence of sulfuric acid having a specified concentration. The invention also relates to a process for producing DCQA by hydrolyzing 3-cyano- or 3-ethoxycarbonyl-5,7-dichloro-4-hydroxyquinoline in the presence of hydrochloric, sulfuric or phosphoric acid and a process for producing DCHQ by decarboxylating DCQA in the presence of sulfuric or phosphoric acid.

  一种工业上有利的生产5,7-二氯-4-羟基喹啉（DCHQ）的过程，用作农业植物保护杀菌剂的中间体。该过程包括（i）在盐酸、硫酸或磷酸的存在下，将3-氰基或3-乙酰氧基羰基-5,7-二氯-4-羟基喹啉水解成5,7-二氯-3-羧基-4-羟基喹啉（DCQA），以及（ii）在硫酸或磷酸的存在下，将形成的DCQA脱羧成DCHQ。具体而言，该过程包括在具有指定浓度的硫酸存在下连续进行5,7-二氯-3-乙酰氧基羰基-4-羟基喹啉的水解和水解产物的脱羧。本发明还涉及一种通过在盐酸、硫酸或磷酸的存在下水解3-氰基或3-乙酰氧基羰基-5,7-二氯-4-羟基喹啉来生产DCQA的过程，以及一种通过在硫酸或磷酸的存在下脱羧DCQA来生产DCHQ的过程。
• Noncatalyzed synthesis of 4-hydroxyquinolines and/or tautomers thereof
  申请人：——

  公开号：US20020007067A1

  公开（公告）日：2002-01-17

  The 4-hydroxyquinoline compounds and/or tautomers thereof, notably 4-hydroxy-5,7-dichchloroquinoline, are synthesized in very high yields by hydrolyzing/decarboxylating a 4-hydroxyquinolinecarboxylic acid ester in the presence of water, whether in liquid or vapor state, but in the absence of any catalyst for such reaction(s).

  4-羟基喹啉化合物及其互变异构体，特别是4-羟基-5,7-二氯喹啉，通过在水的存在下水解/脱羧4-羟基喹啉羧酸酯而高产合成，无需任何催化剂。水可以是液态或气态。
• Process for the preparation of halo-4-phenoxyquinolines
  申请人：——

  公开号：US05973153A1

  公开（公告）日：1999-10-26

  The present invention relates to a new improved, simplified process for the preparation of halo-4-phenoxyquinolines, whereby thionyl chloride is used as the chlorinating agent to prepare the corresponding chloroquinoline intermediate prior to the final coupling reaction, and a single, inert high boiling polyether solvent is used throughout the entire reaction procedure.

  本发明涉及一种新的改良、简化的工艺，用于制备卤代4-苯氧基喹啉。在最终的偶联反应之前，使用亚磺酰氯作为氯化试剂制备相应的氯代喹啉中间体，并在整个反应过程中使用单一的惰性高沸点聚醚溶剂。
• PROCESS FOR PRODUCING 5,7-DICHLORO-4-HYDROXYQUINOLINE
  申请人：ISHIHARA SANGYO KAISHA, LTD.

  公开号：EP0748799A1

  公开（公告）日：1996-12-18

  An industrially advantageous process for producing 5,7-dichloro-4-hydroxyquinoline (DCHQ) useful as an intermediate for agrohorticultural bactericides. The process comprises (i) hydrolyzing 3-cyano- or 3-ethoxycarbonyl-5,7-dichloro-4-hydroxyquinoline into 5,7-dichloro-3-carboxy-4-hydroxyquinoline (DCQA) in the presence of hydrochloric, sulfuric or phosphoric acid and (ii) decarboxylating the formed DCQA into DCHQ in the presence of sulfuric or phosphoric acid. In particular, this process comprises continuously conducting the hydrolysis of 5,7-dichloro-3-ethoxycarbonyl-4-hydroxyquinoline and the decarboxylation of the hydrolyzate in the presence of sulfuric acid having a specified concentration. The invention also relates to a process for producing DCQA by hydrolyzing 3-cyano- or 3-ethoxycarbonyl-5,7-dichloro-4-hydroxyquinoline in the presence of hydrochloric, sulfuric or phosphoric acid and a process for producing DCHQ by decarboxylating DCQA in the presence of sulfuric or phosphoric acid.

  一种具有工业优势的生产 5,7-二氯-4-羟基喹啉（DCHQ）的工艺，可用作农业园艺杀菌剂的中间体。该工艺包括：(i) 在盐酸、硫酸或磷酸存在下，将 3-氰基或 3-乙氧羰基-5,7-二氯-4-羟基喹啉水解为 5,7-二氯-3-羧基-4-羟基喹啉（DCQA）；(ii) 在硫酸或磷酸存在下，将形成的 DCQA 脱羧为 DCHQ。具体而言，该工艺包括在具有特定浓度的硫酸存在下，连续进行 5,7-二氯-3-乙氧羰基-4-羟基喹啉的水解和水解产物的脱羧。本发明还涉及一种在盐酸、硫酸或磷酸存在下通过水解 3-氰基或 3-乙氧羰基-5,7-二氯-4-羟基喹啉生产 DCQA 的工艺，以及一种在硫酸或磷酸存在下通过脱羧 DCQA 生产 DCHQ 的工艺。