3-氟-4-羟基苯甲醛 | 405-05-0

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香醛(含缩醛,半缩醛)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-氟-4-羟基苯甲醛
• 英文名称: 3-fluoro-4-hydroxybenzaldehyde
• 英文别名: 3‐fluoro‐4-hydroxybenzaldehyde
• CAS: 405-05-0
• 化学式: C₇H₅FO₂
• mdl: MFCD00016626
• 分子量: 140.114
• InChiKey: QSBHJTCAPWOIIE-UHFFFAOYSA-N

物化性质

• 熔点：
  121-124°C
• 沸点：
  225.6±20.0 °C(Predicted)
• 密度：
  1.4710 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2913000090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

3-Fluoro-4-hydroxybenzaldehyde Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 3-Fluoro-4-hydroxybenzaldehyde

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 3-Fluoro-4-hydroxybenzaldehyde
Percent: >98.0%(GC)
CAS Number: 405-05-0
Chemical Formula: C7H5FO2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
3-Fluoro-4-hydroxybenzaldehyde

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
3-Fluoro-4-hydroxybenzaldehyde

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Colour: Slightly pale yellow - Reddish yellow
Odour: No data available
pH: No data available
Melting point/freezing point:125°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Hydrogen fluoride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
3-Fluoro-4-hydroxybenzaldehyde

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

3-氟-4-羟基苯甲醛可用于合成3-环丙甲氧基-4-二氟甲氧基苯甲酸，这是制备罗氟司特的关键中间体和杂质。

应用

3-氟-4-羟基苯甲醛可用于制备罗氟司特（Roflumilast）的关键中间体3-环丙甲氧基-4-二氟甲氧基苯甲酸。罗氟司特是由瑞士Nycomed公司和美国Forest公司共同研发的第一个、也是目前唯一的可口服治疗慢性阻塞性肺病(COPD)的选择性磷酸二酯酶-4抑制剂。

2010年5月，欧洲药品管理局(EMEA)批准其用于严重的慢性阻塞性肺病和慢性支气管炎；2011年2月，美国食品和药品监督管理局(FDA)再次批准其用于治疗严重的COPD。该药物作用机制新颖、疗效确切、适用人群广泛，市场前景十分广阔。

制备

将3-氟-4-甲氧基苯甲醛（5.00g，32.5mmol）与48％氢溴酸（30mL）混合，在140℃下加热并用氩气搅拌3小时。然后用水（150mL）稀释，并使用二氯甲烷（2×100mL）萃取混合物。合并的有机层经盐水洗涤后，再经硫酸钠干燥。真空除去溶剂后，得到作为棕色固体的化合物3-氟-4-羟基苯甲醛（4.36g，30.2mmol），产率为97％。

反应信息

• 作为反应物：
  描述：

  3-氟-4-羟基苯甲醛 在 sodium chlorite 、 氨基磺酸 、 potassium tert-butylate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-环丙甲氧基-4-二氟甲氧基苯甲酸
  参考文献：
  名称：

  罗氟司特中间体3-环丙甲氧基-4-二氟甲氧基苯 甲酸的制备

  摘要：

  本发明的主要目的是提供一种制备罗氟司特关键中间体3‑环丙甲氧基‑4‑二氟甲氧基苯甲酸的简便方法。过程中以3‑氟‑4‑羟基苯甲醛作为原料，经醚化反应得到4‑二氟甲氧基‑3‑氟苯甲醛，再经烷氧基对苯环氟的亲电取代得到3‑环丙甲氧基‑4‑二氟甲氧基苯甲醛，最后用亚氯酸钠氧化得到3‑环丙甲氧基‑4‑二氟甲氧基苯甲酸。本发明的第一步反应由于原料底物中羟基单一，不存在选择性醚化的问题，产物单一，收率、纯度均较高，不需要柱层析纯化；本发明的三步反应过程中均没有剧毒、危险品的使用，反应条件温和，操作简便，后处理简单，非常适合工业化大生产，因而是低成本、环境友好型的合成工艺。

  公开号：

  CN103304408B
• 作为产物：
  描述：

  2-氟-4-甲基苯酚 在 氧气 、 cobalt(II) diacetate tetrahydrate 、 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 以85%的产率得到3-氟-4-羟基苯甲醛
  参考文献：
  名称：

  A highly efficient approach to vanillin starting from 4-cresol

  摘要：

  一种从4-甲酚出发制备著名香料与香精化合物香兰素的高效方法已被开发，该方法着重于提高所有反应的可持续性。该方法包括三个步骤的序列：准定量的选择性干净氧溴化4-甲酚、高产率的选择性需氧氧化2-溴-4-甲酚，以及定量的3-溴4-羟基苯甲醛甲氧基化并回收纯甲醇。在此，关键的氧化和甲氧基化反应被逻辑上研究和开发成两种简洁的方法。作为一种绿色替代方案，该方法对于香兰素的可持续制造具有重要价值。

  DOI：

  10.1039/c4gc00003j

文献信息

• 크로만 유도체 및 이를 유효성분으로 함유하는 신생혈관성 안질환 또는 암의 예방 또는 치료용 약학적 조성물
  申请人：Gachon University of Industry-Academic cooperation Foundation 가천대학교 산학협력단(220040376324) BRN ▼129-82-07687

  公开号：KR20200124630A

  公开（公告）日：2020-11-03

  본 발명은 크로만 유도체인 하기 화학식 1의 화합물, 이의 수화물, 이의 입체 이성질체, 또는 이의 약학적으로 허용 가능한 염을 포함하는 암 또는 신생혈관과 관련된 질환 치료용 약학적 조성물을 제공한다. [화학식 1] (상기 화학식 1에서 R, R, R, R, R, R, R은 발명의 설명에서 정의한 바와 같다.)

  本发明提供了一种用于治疗与癌症或新生血管有关的疾病的药学组合物，其中包括化学式1的某种克隆衍生物化合物、其水合物、其立体异构体或其药学上可接受的盐。【化学式1】（其中R，R，R，R，R，R，R如上述化学式1中所定义）。
• Discovery of chalcone analogues as novel NLRP3 inflammasome inhibitors with potent anti-inflammation activities
  作者：Cheng Zhang、Hu Yue、Ping Sun、Lei Hua、Shuli Liang、Yitao Ou、Dan Wu、Xinyi Wu、Hao Chen、Ying Hao、Wenhui Hu、Zhongjin Yang

  DOI：10.1016/j.ejmech.2021.113417

  日期：2021.7

  inflammasome activation plays a critical role in inflammation and its related disorders. Herein we report a hit-to-lead effort resulting in the discovery of a novel and potent class of NLRP3 inflammasome inhibitors. Among these, the most potent lead 40 exhibited improved inhibitory potency and almost no toxicity. Further mechanistic study indicated that compound 40 inhibited the NLRP3 inflammasome activation

  NLRP3 炎症小体激活在炎症及其相关疾病中起着关键作用。在此，我们报告了一项领先的努力，导致发现了一类新型有效的 NLRP3 炎症小体抑制剂。其中，最有效的铅40表现出提高的抑制效力并且几乎没有毒性。进一步的机理研究表明，化合物40通过抑制 ROS 的产生来抑制 NLRP3 炎症小体的激活。更重要的是，用40治疗对 LPS 诱导的败血症和 DSS 诱导的结肠炎显示出显着的治疗效果。这项研究鼓励进一步开发基于这种化学支架的更有效的抑制剂，并提供一种化学工具来识别其细胞结合靶点。
• Antagonists of melanin concentrating hormone effects on the melanin concentrating hormone receptor
  申请人：Lynch K. John

  公开号：US20050209274A1

  公开（公告）日：2005-09-22

  The present invention is directed to compounds of formula (I), which antagonize of the effects of melanin-concentrating hormone (MCH) through the melanin concentrating hormone receptor which is useful for the prevention or treatment of eating disorders, weight gain, obesity, abnormalities in reproduction and sexual behavior, thyroid hormone secretion, diuresis and water/electrolyte homeostasis, sensory processing, memory, sleeping, arousal, anxiety, depression, seizures, neurodegeneration and psychiatric disorders.

  本发明涉及式(I)的化合物，通过对抗黑素浓集激素（MCH）的作用，通过对抗黑素浓集激素受体，有助于预防或治疗进食障碍、体重增加、肥胖、生殖和性行为异常、甲状腺激素分泌、利尿和水/电解质稳态、感觉处理、记忆、睡眠、觉醒、焦虑、抑郁、癫痫、神经退行性疾病和精神障碍。
• Synthesis and biological evaluation of novel fluorinated anticancer agents incorporating the indolin-2-one moiety
  作者：Shuai-Yu Wang、Li-Jun Wang、Bo Jiang、Ning Wu、Xiang-Qian Li、Jiao Luo、Bao-Cheng Wang、Ren-Shuai Zhang、Qi Xu、Da-Yong Shi

  DOI：10.1039/c5ra19617e

  日期：——

  A series of novel fluorinated anticancer agents containing the indolin-2-one moiety were designed, synthesized and evaluated for their anticancer activities in vitro.

  一系列含有吲哚啉-2-酮基团的新型氟化抗癌药物被设计、合成并在体外评估其抗癌活性。
• Discovery of novel isoliquiritigenin analogue ISL-17 as a potential anti-gastric cancer agent
  作者：Fengchang Huang、Jin Wang、Yi Xu、Yunfei Zhang、Ning Xu、Liang Yin

  DOI：10.1042/bsr20201199

  日期：2020.6.26

  Isoliquiritigenin (ISL), a natural product isolated from licorice root, exhibits anti-gastric cancer effects. However, applications of ISL are still limited in clinical practice due to its poor bioavailability. To discovery of more effective anti-gastric cancer agents based on ISL, aldol condensation reaction was applied to synthesize the ISL analogues. MTS assay was used to evaluate the inhibitory activities of ISL analogues against SGC-7901, BGC-823 and GES-1 cells in vitro. Cell cycle distribution, apoptosis and reactive oxygen species (ROS) generation were detected by flow cytometry. Western blot assay was used to analyze the expression levels of related proteins. The drug-likeness and pharmacokinetic properties were predicted with Osiris property explorer and PreADMET server. As a result, 18 new ISL analogues (ISL-1 to ISL-18) were synthesized. Among these analogues, ISL-17 showed the strongest inhibitory activities against SGC-7901 and BGC-823 cells, and could induce G2/M cell cycle arrest and apoptosis in these two cell lines. Treatment with ISL-17 resulted in increased ROS production and elevated autophagy levels in SGC-7901 cells. The PI3K/AKT/mTOR signaling pathway was down-regulated after treatment with ISL-17 in SGC-7901 cells. The results of drug-likeness and pharmacokinetic prediction indicated that all the ISL analogues complied with Lipinski's rule of five and Veber rule and had a favorable ADME character. Overall, our results attest that ISL-17 holds promise as a candidate agent against gastric cancer.

  摘要 Isoliquiritigenin (ISL) 是一种从甘草根中分离出来的天然产物，具有抗胃癌作用。然而，由于 ISL 的生物利用度较低，其在临床上的应用仍然有限。为了发现基于 ISL 的更有效的抗胃癌药物，研究人员采用醛醇缩合反应合成了 ISL 类似物。采用 MTS 法评估 ISL 类似物对 SGC-7901、BGC-823 和 GES-1 细胞的体外抑制活性。流式细胞仪检测细胞周期分布、细胞凋亡和活性氧（ROS）生成。用 Western 印迹法分析了相关蛋白的表达水平。利用 Osiris Property explorer 和 PreADMET 服务器预测了药物相似性和药代动力学特性。结果合成了 18 种新的 ISL 类似物（ISL-1 至 ISL-18）。在这些类似物中，ISL-17 对 SGC-7901 和 BGC-823 细胞具有最强的抑制活性，能诱导这两种细胞系的 G2/M 细胞周期停滞和细胞凋亡。用 ISL-17 处理 SGC-7901 细胞会导致 ROS 生成增加和自噬水平升高。用 ISL-17 处理 SGC-7901 细胞后，PI3K/AKT/mTOR 信号通路下调。药物相似性和药代动力学预测结果表明，所有 ISL 类似物都符合利宾斯基五法则和维伯法则，具有良好的 ADME 特性。总之，我们的研究结果证明 ISL-17 有希望成为一种抗胃癌的候选药物。