4-羟基-1H-吲哚 | 81779-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 4-羟基-1H-吲哚
• 中文别名: 4-羟基吲哚-3-甲醛；4-羟基-1H-吲哚-3-甲醛
• 英文名称: 4-hydroxy-1H-indole-3-carbaldehyde
• 英文别名: 4-Hydroxyindole-3-carbaldehyde；4-hydroxy-3-indolecarbaldehyde；4-hydroxyindole-3-carboxaldehyde；4-hydroxy-1H-indole-3-carboxaldehyde
• CAS: 81779-27-3
• 化学式: C₉H₇NO₂
• mdl: MFCD05864721
• 分子量: 161.16
• InChiKey: QLBZIZLLMNWTHG-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  426.3±25.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Hydroxy-1H-indole-3-carbaldehyde
Synonyms: 3-Formyl-4-hydroxy-1H-indole

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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: 4-Hydroxy-1H-indole-3-carbaldehyde
CAS number: 81779-27-3

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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.
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: C9H7NO2
Molecular weight: 161.2

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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.

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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

制备方法与用途

生物活性化合物4-羟基-1H-吲哚-3-碳醛（4-Hydroxy-1H-indole-3-carbaldehyde）是一种植物代谢物，在刺槐（Capparis spinosa L.）中可以分离得到。此外，该化合物还可用于合成荧光探针。

反应信息

• 作为反应物：
  描述：

  4-羟基-1H-吲哚 在 sodium hydroxide 、 乙酸酐 、 copper(II) nitrate 、 sodium chloride 作用下， 生成 4-hydroxy-5-nitroindole
  参考文献：
  名称：

  Preparations of 1-Hydroxyindole Derivatives and Their Potent Inhibitory Activities on Platelet Aggregation

  摘要：

  1-Hydroxymelatonin, 5-bromo- and 5,7-dibromo-1-hydroxytryptamine derivatives, 1,4-dihydroxy-5-nitroindole, 1-hydroxy-3-methylsulfinylmethylindole, and 5-acetyl-1,3,4,5-tetrahydro-1-hydroxypyrrolo[4,3,2-de]quinoline were synthesized for the first time, 1-Hydroxyindoles revealed potent inhibitory activities on platelet aggregation.

  DOI：

  10.3987/com-96-7537
• 作为产物：
  描述：

  (3-formylindol-4-yl)thallium bis-trifluoroacetate 在 copper(II) sulfate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以72.8%的产率得到4-羟基-1H-吲哚
  参考文献：
  名称：

  A Practical and Short Acess to 4-Hydroxy-3-indolecarbaldehyde and Its Application for the Synthesis of Pindolol Analog

  摘要：

  DOI：

  10.3987/r-1986-11-3065

文献信息

• Synthetic Studies of Psilocin Analogs Having Either a Formyl Group or Bromine Atom at the 5- or 7-Position.
  作者：Fumio Yamada、Mayumi Tamura、Atsuko Hasegawa、Masanori Somei

  DOI：10.1248/cpb.50.92

  日期：——

  Psilocin analogs having either a formyl group (9—12) or a bromine atom (13—18) at the 5- or 7-position have been prepared for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25, 29, 30), 4-benzyloxyindole-3-acetonitriles (20, 31), and 4-benzyloxy-N, N-dimethyltryptamine (32, 34, 35) have also been established.

  首次合成了在5位或7位具有甲酰基（9—12）或溴原子（13—18）的Psilocin类似物。此外，还建立了4-羟基（23, 24, 28）和4-苄氧吲哚-3-甲醛（19, 25, 29, 30）、4-苄氧吲哚-3-乙腈（20, 31）以及4-苄氧-N,N-二甲基色氨酸（32, 34, 35）的5-和7-溴衍生物的合成方法。
• Tricylic indole compounds having affinity for serotonin receptor
  申请人：——

  公开号：US20030236295A1

  公开（公告）日：2003-12-25

  Having an affinity against serotonine receptors, compound (I) shown below is useful as a therapeutic agent against various kinds of diseases of central nervous systems. 1 (wherein R 1 is hydrogen; R 2 is hydrogen or lower alkyl; R 3 is hydrogen, —COOR 12 and so on; R 4 is hydrogen, lower alkyl and so on, or R 3 and R 4 taken together may form ═O or ═S; R 5 is hydrogen, or R 3 and R 5 taken together may form a bond; R 6 is hydrogen, —COOR 24 and so on; R 7 is hydrogen, halogen, lower alkyl and so on; R 8 is hydrogen, lower alkyl, cycloalkyl and so on; R 9 , R 10 and R 11 are each independently hydrogen, halogen, lower alkyl and so on)

  针对5-羟色胺受体具有亲和力的化合物(I)，如下所示，可用作治疗中枢神经系统各种疾病的治疗剂。其中R1为氢；R2为氢或较低的烷基；R3为氢，—COOR12等；R4为氢，较低的烷基等，或者R3和R4一起可能形成═O或═S；R5为氢，或者R3和R5一起可能形成键；R6为氢，—COOR24等；R7为氢，卤素，较低的烷基等；R8为氢，较低的烷基，环烷基等；R9、R10和R11各自独立地为氢，卤素，较低的烷基等。
• A single fluorescent probe for imaging ribonucleic acid and sulfur dioxide in living systems and its unique application in tumor and normal cells
  作者：Weishan Wang、Yong Liu、Jie Niu、Weiying Lin

  DOI：10.1039/c8tb02144a

  日期：——

  unique interrelation of ribonucleic acid (RNA) and sulfur dioxide (SO2) in living systems, it is necessary to construct novel molecular tools that could detect RNA and SO2 in living cancer cells and animals. Herein, we have constructed a unique fluorescent probe, EPI-RS, for imaging RNA and SO2 with distinct fluorescence signals in living systems. This type of probe shows a series of advantages, such

  为了研究核糖核酸（RNA）和二氧化硫（SO 2）在生命系统中的独特相互关系，有必要构建能够检测活癌细胞和动物中RNA和SO 2的新型分子工具。本文中，我们构建了独特的荧光探针EPI-RS，用于在活体系统中对具有不同荧光信号的RNA和SO 2进行成像。这种类型的探针具有一系列优点，例如在纯水系统中具有较高的光稳定性，较大的斯托克斯位移，较高的选择性和灵敏度。鉴于这些优点，采用探针EPI-RS对RNA和SO 2进行成像通过“打开”和“关闭”活细胞，组织，斑马鱼和小鼠中的荧光信号。有趣的是，探针EPI-RS在正常细胞和肿瘤细胞中表现出不同的体内成像特性。
• 一种识别纯水体系内二氧化硫的荧光探针及 其应用
  申请人：济南大学

  公开号：CN108640902B

  公开（公告）日：2020-08-21

  本发明公开了一种在纯水相识别二氧化硫的荧光探针EPI‑RS，其化学结构式如式（I）所示。本发明还公开了所述荧光探针在检测过程中荧光变化及选择性等光谱性质。实验证明：本发明的荧光探针通过荧光淬灭不仅能识别检测二氧化硫，而且其选择性好，最后该探针在活细胞靶标分子的标记领域具有潜在的应用价值。
• Tricyclic indole compounds having an affinity against serotonin receptors
  申请人：Fukui Yoshikazu

  公开号：US20050043387A1

  公开（公告）日：2005-02-24

  Having an affinity against serotonine receptors, compound (I) shown below is useful as a therapeutic agent against various kinds of diseases of central nervous systems. (wherein R 1 is hydrogen; R 2 is hydrogen or lower alkyl; R 3 is hydrogen, —COOR 12 and so on; R 4 is hydrogen, lower alkyl and so on, or R 3 and R 4 taken together may form ═O or ═S; R 5 is hydrogen, or R 3 and R 5 taken together may form a bond; R 6 is hydrogen, —COOR 24 and so on; R 7 is hydrogen, halogen, lower alkyl and so on; R 8 is hydrogen, lower alkyl, cycloalkyl and so on; R 9 , R 10 and R 11 are each independently hydrogen, halogen, lower alkyl and so on)

  以下化合物（I）具有对5-羟色胺受体的亲和性，因此可用作治疗中枢神经系统各种疾病的治疗剂。（其中R1为氢；R2为氢或低碳基；R3为氢，-COOR12等；R4为氢，低碳基等，或R3和R4可共同形成═O或═S；R5为氢，或者R3和R5共同形成键；R6为氢，-COOR24等；R7为氢，卤素，低碳基等；R8为氢，低碳基，环烷基等；R9，R10和R11各自独立地为氢，卤素，低碳基等）