3,5-二氟-4-羟基苯甲醛 | 118276-06-5

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,5-二氟-4-羟基苯甲醛
• 中文别名: 3.5二氟4羟氢苯甲醛
• 英文名称: 3,5-difluoro-4-hydroxybenzaldehyde
• 英文别名: 4-hydroxy-3,5-difluorobenzaldehyde；2,6-difluoro-4-formylphenol
• CAS: 118276-06-5
• 化学式: C₇H₄F₂O₂
• 分子量: 158.104
• InChiKey: SKOYTQILPMNZQO-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124°C
• 沸点：
  198.5±35.0 °C(Predicted)
• 密度：
  1.464±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

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
• 危险品标志：
  Xi
• 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

Material Safety Data Sheet

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Section 1. Identification of the substance
3,5-Difluoro-4-hydroxybenzaldehyde
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
3,5-Difluoro-4-hydroxybenzaldehyde
Ingredient name:
CAS number: 118276-06-5

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
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

制备方法与用途

理化性质

3,5-二氟-4-羟基苯甲醛是一种苯甲醛类化合物。由于其苯环上的羟基单元，该物质具有一定的酸性。它可以在中强碱作用下发生碘甲烷类物质的醚化反应；在氧化剂的作用下，则可以转化为相应的苯甲酸类衍生物。此外，在还原剂的作用下，3,5-二氟-4-羟基苯甲醛还可以还原为相应的苄醇类衍生物。

应用

3,5-二氟-4-羟基苯甲醛主要在化学合成领域作为有机合成的中间体使用。通过控制醛基和羟基的反应，可以引入或修饰不同的官能团，用于制备多种化合物。例如，有文献报道该物质可用于制备荧光探针中的苯乙烯基喹啉衍生物，展现了其在合成苯酚类生物活性分子方面的潜力。

反应信息

• 作为反应物：
  描述：

  3,5-二氟-4-羟基苯甲醛 在 caesium carbonate 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 (E)-N²-(4'-cyanophenyl)amino-6-(2'',6''-difluoro-4''-(3-oxobut-1-en-1-yl))phenoxy-3-nitropyridine
  参考文献：
  名称：

  优化作为新型 HIV-1 NNRTIS 的卤化 2,6-二芳基吡啶胺的抗病毒效力和亲脂性

  摘要：

  合成了 19 种在苯氧基 C 环上修饰的新型卤化二芳基吡啶胺 (DAPA) 类似物，并评估了其抗 HIV 活性和某些类药物特性。10 种化合物显示出高抗 HIV 活性（EC 50 <10 n M）。特别是 ( E )-6-(2''-bromo-4''-cyanovinyl-6''-methoxy)phenoxy- N 2- (4'-cyanophenyl)pyridin-2,3-diamine ( 8 c )对带有 E138K 或 K101E 突变的野生型和耐药病毒株显示出低纳摩尔的抗病毒效力 (3-7 n M )，这些突变与对利维匹林的耐药性有关 ( 1b )。化合物8c 的电阻倍数变化 (RFC: 1.1–2.1) 远低于1 b（RFC：11.8–13.0）。化合物8c在人肝微粒体中也表现出比1b更好的代谢稳定性（体外半衰期），具有低亲脂性（clog  D：3.29；测量 log  P：3

  DOI：

  10.1002/cmdc.201400075
• 作为产物：
  描述：

  2,6-二氟苯酚 在 hexamethylenetetramine 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 18.0h， 生成 3,5-二氟-4-羟基苯甲醛
  参考文献：
  名称：

  1,3-Diphenylprop-2-En-1-One Derivative Compounds, Preparation Method Thereof and Uses of Same

  摘要：

  该发明涉及替代的1,3-二苯基丙烯酮衍生物化合物，含有该化合物的药用和/或化妆品组合物，以及在治疗学和化妆品学中的应用。该发明还涉及一种制备上述衍生物的方法。

  公开号：

  US20080058412A1

文献信息

• Propylphosphonic Anhydride (T3P®): A Remarkably Efficient Reagent for the One-Pot Transformation of Aromatic, Heteroaromatic, and Aliphatic Aldehydes to Nitriles
  作者：John Augustine、Rajendra Atta、Balakrishna Ramappa、Chandrakantha Boodappa

  DOI：10.1055/s-0029-1218388

  日期：2009.12

  Propylphosphonic anhydride has been demonstrated to be an efficient reagent for the transformation of aromatic, heteroaromatic, and aliphatic aldehydes to respective nitriles in excellent yields. This procedure offers simple and one-pot access to nitriles and highlights the synthetic utility of T3P® as a versatile reagent in organic chemistry.

  三丙基膦酐已被证明是一种高效的试剂，可将芳香族、杂芳香族和脂肪族醛分别转化为相应的腈，产率极佳。这一过程提供了简单且一步制备腈的方法，并强调了T3P®作为一种多功能试剂在有机化学中的合成应用价值。
• [EN] IMIDAZO [2, 1-F] [1, 2, 4] TRIAZIN-4-AMINE DERIVATIVES AS TLR7 AGONIST<br/>[FR] DÉRIVÉS D'IMIDAZO[2,1-F] [1, 2, 4] TRIAZIN-4-AMINE UTILISÉS EN TANT QU'AGONISTES DE TLR7
  申请人：BEIGENE LTD

  公开号：WO2020160711A1

  公开（公告）日：2020-08-13

  Disclosed herein is an imidazo [2, 1-f] [1, 2, 4] triazin-4-amine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as a TLR7 agonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the imidazo [2, 1-f] [1, 2, 4] triazin-4-amine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as TLR7 agonist.

  披露的是一种咪唑[2,1-f][1,2,4]三嗪-4-胺衍生物或其立体异构体，或其药用可接受盐，用作TLR7激动剂，以及包含该化合物的药物组合物。还披露了一种使用咪唑[2,1-f][1,2,4]三嗪-4-胺衍生物或其立体异构体，或其药用可接受盐作为TLR7激动剂来治疗癌症的方法。
• Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors
  作者：Koichiro Harada、Hideki Kubo、Jun Abe、Mari Haneta、Arnel Conception、Shinichi Inoue、Satoshi Okada、Kazuhiko Nishioka

  DOI：10.1016/j.bmc.2012.03.052

  日期：2012.5

  and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg

  先前我们已经报道了衍生自亚苄基恶唑烷二酮和噻唑烷二酮支架的新型3类有效的17β-羟类固醇脱氢酶抑制剂（17β-HSD3）的发现。在这项研究中，这些类似物是在基于人类细胞的分析中进行设计，合成和评估的。建立了围绕该药效团的详细的结构-活性关系（SAR），因此，该系列化合物中的许多化合物在体外均表现出一位数的纳摩尔17β-HDS3抑制活性。为改善口服生物利用度而进行的后续优化工作已通过基于磷酸酯的前药策略针对这些17β-HSD3抑制剂进行了体内概念验证。当以100 mg / kg的高剂量口服磷酸酯16时，图16显示，在促黄体生成激素释放激素（LH-RH）诱导的T产生测定中，相对于阳性对照，有效的睾丸激素（T）降低作用大约两倍。给药后4小时，降低T的作用持续在对照的约10％水平。基于该系列的非甾体分子具有为治疗前列腺癌提供独特而有效的临床机会的潜力。
• [EN] ASPARAGINE DERIVATIVES AND METHODS OF USING SAME<br/>[FR] DÉRIVÉS D'ASPARAGINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SENDA BIOSCIENCES INC

  公开号：WO2021252640A1

  公开（公告）日：2021-12-16

  The present disclosure relates to compounds of formulas (A) and (I), pharmaceutically acceptable salts thereof, and solvates of any of the foregoing, pharmaceutical compositions comprising the same, methods of preparing the same, intermediate compounds useful for preparing the same, and methods for treating or prophylaxis of diseases, in particular cancer, such as colorectal cancer, using the same.

  本公开涉及式（A）和（I）的化合物，其药学上可接受的盐，以及任何上述化合物的溶剂化合物，包括相同的药物组合物，制备相同的方法，用于制备相同的中间化合物，以及使用相同的方法治疗或预防疾病，特别是癌症，如结直肠癌。
• An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P®)
  作者：John Kallikat Augustine、Rajesha Kumar、Agnes Bombrun、Ashis Baran Mandal

  DOI：10.1016/j.tetlet.2010.12.090

  日期：2011.3

  An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P®) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include

  描述了一种由催化量（15摩尔％）的丙基膦酸酐介导的将酮肟的贝克曼重排成酰胺的有效方法。Aldoximes在室温下与T3P（15 mol％）反应后，进行了二阶Beckmann重排，从而以优异的产率提供了相应的腈。这种环境友好协议的主要优点包括程序简单，尤其是产品隔离容易。