2,4-二氟-3-羟基苯甲醛 | 192927-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,4-二氟-3-羟基苯甲醛
• 英文名称: 2,4-difluoro-3-hydroxy-benzaldehyde
• 英文别名: 2,4-difluoro-3-hydroxybenzaldehyde；2,4-difluoro-4-hydroxybenzaldehyde
• CAS: 192927-69-8
• 化学式: C₇H₄F₂O₂
• 分子量: 158.104
• InChiKey: NDEDPHKYSOYQOY-UHFFFAOYSA-N

物化性质

• 沸点：
  204.2±35.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 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：
  4

安全信息

• 海关编码：
  2913000090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  温度：2-8°C，保持在惰性气体氛围中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,4-Difluoro-3-hydroxybenzaldehyde
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: 2,4-Difluoro-3-hydroxybenzaldehyde
CAS number: 192927-69-8

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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: C7H4F2O2
Molecular weight: 158.1

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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, hydrogen fluoride.

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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：

  2,4-二氟-3-羟基苯甲醛 在 吡啶 、 吡啶-N-氧化物 、 盐酸 、 copper diacetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 2-amino-2-(2,4-difluoro-3-phenoxy-phenyl)-acetic acid
  参考文献：
  名称：

  [EN] SUBSTITUTED BENZYLAMINE COMPOUNDS, THEIR USE IN MEDICINE, AND IN PARTICULAR THE TREATMENT OF HEPATITIS C VIRUS (HCV) INFECTION
  [FR] COMPOSÉS DE BENZYLAMINE SUBSTITUÉS, LEUR UTILISATION EN MÉDECINE, EN PARTICULIER DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE C (VHC)

  摘要：

  该发明提供了以下式（I）的化合物，或其盐、N-氧化物或互变异构体，其中A为CH、CF或氮；E为CH、CF或氮；R0为氢或C1-2烷基；R1a选自CONH2；CO2H；一个可选择取代的非环状C1-8碳氢化合物基团；以及一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1、2、3或4个是从O、N和S中选择的杂原子环成员；R2选自氢和一个基团R2a；R2a选自一个可选择取代的非环状d-8碳氢化合物基团；一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1或2个环成员是从O、N和S中选择的杂原子环成员；以及一个可选择取代的含有9或10个环成员的双环杂环基团，其中1或2个环成员是氮原子；其中R1和R2中至少一个不是氢；R3选自一个可选择取代的含有0、1、2或3个从N、O和S中选择的杂原子环成员的3至10个成员的单环或双环碳环或杂环环；R4a选自卤素；氰基；C1-4烷基，可选择取代一个或多个氟原子；C1-4烷氧基，可选择取代一个或多个氟原子；羟基-C1-4烷基；和C1-2烷氧基-C1-4烷基；R5选自氢和一个取代基R5a；R5a选自C1-2烷基，可选择取代一个或多个氟原子；C1-3烷氧基，可选择取代一个或多个氟原子；卤素；环丙基；氰基；和氨基。这些化合物对丙型肝炎病毒具有活性，并可用于预防或治疗丙型肝炎病毒感染。

  公开号：

  WO2013064538A1
• 作为产物：
  描述：

  2,6-二氟苯酚 在 咪唑 、 四丁基氟化铵 、 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,4-二氟-3-羟基苯甲醛
  参考文献：
  名称：

  Songca, Sandile P.; Bonnett, Raymond; Maes, Catherine M., South African Journal of Chemistry, 1997, vol. 50, # 1, p. 40 - 47

  摘要：

  DOI：

文献信息

• ANTI-HIV COMPOUNDS
  申请人：Prosetta Antiviral, Inc.

  公开号：US20160168100A1

  公开（公告）日：2016-06-16

  This invention provides, among other things, tetrahydroisoquinolines useful for treating viral infections, pharmaceutical formulations containing such compounds, as well as methods of inhibiting the replication of a virus, such as HIV, or treating a disease, such as AIDS.

  这项发明提供了用于治疗病毒感染的四氢异喹啉等化合物，含有这类化合物的药物配方，以及抑制病毒（如HIV）复制或治疗疾病（如艾滋病）的方法。
• Indole derivatives as mcp-1 receptor antagonists
  申请人：——

  公开号：US20030144339A1

  公开（公告）日：2003-07-31

  A compound of formula (I) wherein: R 1 is hydrogen, halo or methoxy; R 2 is hydrogen, halo, methyl, ethyl or methoxy; R 3 is a halo group or a trifluoromethyl group; R 4 is a halo group or a trifluoromethyl group; R 5 is hydrogen or halo; R 6 is hydrogen or halo; provided that when R 5 and R 6 are both hydrogen, and one of R 3 or R 4 is chloro or fluoro, then the other is not chloro or fluoro; or a pharmaceutically acceptable salt or prodrug thereof. These compounds have useful activity for the treatment of inflammatory disease, specifically in antagonising an MCP-1 mediated effect in a warm-blooded animal such as a human being.

  一种化合物的化学式（I），其中：R1为氢、卤素或甲氧基；R2为氢、卤素、甲基、乙基或甲氧基；R3为卤素基团或三氟甲基基团；R4为卤素基团或三氟甲基基团；R5为氢或卤素；R6为氢或卤素；但是当R5和R6都为氢，并且R3或R4中的一个为氯或氟时，则另一个不是氯或氟；或其药用可接受的盐或前药。这些化合物对于治疗炎症性疾病具有有用活性，特别是在拮抗MCP-1介导的效应方面，在温血动物（如人类）中。
• The structure of β-diketones related to curcumin determined by X-ray crystallography, NMR (solution and solid state) and theoretical calculations
  作者：Carla I. Nieto、Pilar Cabildo、Rosa M. Claramunt、Pilar Cornago、Dionisia Sanz、M. Carmen Torralba、M. Rosario Torres、Marta B. Ferraro、Ibon Alkorta、Marta Marín-Luna、José Elguero

  DOI：10.1007/s11224-015-0704-7

  日期：2016.4

  Structural data are reported on sixteen ketoenols of β-diketones: solution NMR, solid-state NMR (CPMAS and MAS) and X-ray crystallography (four compounds, where three are new). The emphasis is on the tautomerism between both ketoenols, in solution and in the solid state. GIAO/B3LYP/6-311++G(d,p) and Quantum ESPRESSO (QE) calculations were used and compared. For average values, the GIAO/DMSO-PCM is enough

  报告了 16 种 β-二酮酮烯醇的结构数据：溶液 NMR、固态 NMR（CPMAS 和 MAS）和 X 射线晶体学（四种化合物，其中三种是新化合物）。重点是在溶液和固态两种酮烯醇之间的互变异构。使用并比较了 GIAO/B3LYP/6-311++G(d,p) 和 Quantum ESPRESSO (QE) 计算。对于平均值，GIAO/DMSO-PCM 就足够了，但只能通过使用 QE 来实现拆分。分析了一个旋转障碍的案例。已经检测到一些与 C-F 键和 C-CF3 基团相关的异常。
• Evaluation of the Antioxidant and Neuroprotectant Activities of New Asymmetrical 1,3-Diketones
  作者：Carla Nieto、María Cornago、María Cabildo、Dionisia Sanz、Rosa Claramunt、María Torralba、María Torres、Diana Martínez Casanova、Yaiza Sánchez-Alegre、Esther Escudero、José Lavandera

  DOI：10.3390/molecules23081837

  日期：——

  A series of fourteen new asymmetrical 1,3-diketone derivatives have been synthesized and evaluated in the ABTS, FRAP and DPPH assays as a new chemotype with antioxidant and drug-like properties. All the compounds displayed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH-SY5Y cell line. Among them, (3Z,5E)-6-(2,5-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (6b) and (3Z,5E)-6-(2,3-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (7b) with excellent solubility and chemical stability in biorelevant media, have also shown a similar Fe+2 chelation behavior to that of curcumin. Additionally, both derivatives 6b and 7b have afforded good neuroprotection activity against H2O2 induced oxidative stress in the same neuronal cell line, with a significant reduction of intracellular ROS levels, in parallel with a good recovery of the Mitochondrial Membrane Potential (ΔΨm). Compounds 6b and 7b with a promising antioxidant and drug-like profile, with low cytotoxic and good neuroprotectant activity, constitute a new interesting chemical class with high potential as new therapeutic agents against neurodegenerative diseases.

  一系列新的不对称1,3-二酮衍生物已经合成并在ABTS、FRAP和DPPH测定中作为具有抗氧化和药物样性质的新化学类型进行评估。所有化合物与对人类神经母细胞瘤SH-SY5Y细胞系的曲马多相比显示出低细胞毒性。其中，(3Z,5E)-6-(2,5-二氟-4-羟基苯基)-1,1,1-三氟-4-羟基己-3,5-二烯-2-酮（6b）和(3Z,5E)-6-(2,3-二氟-4-羟基苯基)-1,1,1-三氟-4-羟基己-3,5-二烯-2-酮（7b）在生物相关介质中具有良好的溶解性和化学稳定性，且表现出与曲马多相似的Fe+2螯合行为。此外，这两种衍生物6b和7b在相同的神经元细胞系中对H2O2诱导的氧化应激具有良好的神经保护作用，与细胞内ROS水平的显著降低以及线粒体膜电位（ΔΨm）的良好恢复相平行。化合物6b和7b具有有前途的抗氧化和药物样特性，低细胞毒性和良好的神经保护活性，构成了一种新的有趣的化学类别，具有作为治疗神经退行性疾病的新药物候选剂的高潜力。
• Fluorination Effects on NOS Inhibitory Activity of Pyrazoles Related to Curcumin
  作者：Carla Nieto、María Cabildo、María Cornago、Dionisia Sanz、Rosa Claramunt、María Torralba、María Torres、José Elguero、José García、Ana López、Darío Acuña-Castroviejo

  DOI：10.3390/molecules200915643

  日期：——

  A series of new (E)-3(5)-[β-(aryl)-ethenyl]-5(3)-phenyl-1H-pyrazoles bearing fluorine atoms at different positions of the aryl group have been synthesized starting from the corresponding β-diketones. All compounds have been characterized by elemental analysis, DSC as well as NMR (1H, 13C, 19F and 15N) spectroscopy in solution and in solid state. Three structures have been solved by X-ray diffraction analysis, confirming the tautomeric forms detected by solid state NMR. The in vitro study of their inhibitory potency and selectivity on the activity of nNOS and eNOS (calcium-calmodulin dependent) as well as iNOS (calcium-calmodulin independent) isoenzymes is presented. A qualitative structure–activity analysis allowed the establishment of a correlation between the presence/ absence of different substituents with the inhibition data proving that fluorine groups enhance the biological activity. (E)-3(5)-[β-(3-Fluoro-4-hydroxyphenyl)-ethenyl]-5(3)-phenyl-1H-pyrazole (13), is the best inhibitor of iNOS, being also more selective towards the other two isoforms.

  从相应的 β-二酮开始，合成了一系列在芳基的不同位置含有氟原子的 (E)-3(5)-[β-(aryl)-ethenyl]-5(3)-phenyl-1H-pyrazoles 新化合物。所有化合物都通过元素分析、DSC 以及溶液和固态核磁共振（1H、13C、19F 和 15N）光谱进行了表征。通过 X 射线衍射分析解决了三种化合物的结构，证实了固态核磁共振检测到的同分异构形式。对它们对 nNOS 和 eNOS（依赖于钙-钙调蛋白）以及 iNOS（独立于钙-钙调蛋白）同工酶活性的抑制效力和选择性进行了体外研究。通过结构-活性定性分析，可以建立不同取代基的存在/不存在与抑制数据之间的相关性，证明氟基增强了生物活性。(E)-3(5)-[β-(3-氟-4-羟基苯基)-乙烯基]-5(3)-苯基-1H-吡唑 (13) 是 iNOS 的最佳抑制剂，而且对其他两种同工酶具有更高的选择性。