4-氟-3-硝基苯甲酸乙酯 | 367-80-6

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氟-3-硝基苯甲酸乙酯
• 中文别名: 3-硝基-4-氟苯甲酸乙酯
• 英文名称: ethyl 4-fluoro-3-nitrobenzoate
• 英文别名: 4-fluoro-3-nitrobenzoic acid ethyl ester
• CAS: 367-80-6
• 化学式: C₉H₈FNO₄
• mdl: MFCD03428515
• 分子量: 213.165
• InChiKey: YONVBKVUSUGBQR-UHFFFAOYSA-N

物化性质

• 熔点：
  45.3 °C
• 沸点：
  312.3±22.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2916399090
• 储存条件：
  存放条件：室温、密封、干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 4-fluoro-3-nitrobenzoate
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: Ethyl 4-fluoro-3-nitrobenzoate
CAS number: 367-80-6

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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: C9H8FNO4
Molecular weight: 213.2

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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, 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：

  4-氟-3-硝基苯甲酸乙酯 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-氨基-3-硝基苯甲酸乙酯
  参考文献：
  名称：

  Discovery of a potent and highly fluorescent sirtuin inhibitor

  摘要：

  一种高度荧光的去乙酰化酶抑制剂被发现对多种癌细胞系具有生长抑制作用。

  DOI：

  10.1039/c5md00307e
• 作为产物：
  描述：

  对氟苯甲酸乙酯 在 硫酸 、 sodium nitrate 作用下， 以95 %的产率得到4-氟-3-硝基苯甲酸乙酯
  参考文献：
  名称：

  具有 ABCB1 抑制作用的新型 1,2,5-三取代苯并咪唑衍生物的分子设计、合成和生物学评价，以克服癌细胞的多药耐药性

  摘要：

  摘要 多药耐药性（MDR）是癌症患者治疗失败的主要原因。MDR 的原因之一是真核细胞中 ATP 结合盒 (ABC) 转运蛋白特别是 ABCB1（P-糖蛋白）中的药物流出。在本研究中，利用基于配体的药效团方法设计了某些新型 1,2,5-三取代苯并咪唑衍生物。合成并评估了设计的苯并咪唑对多柔比星敏感细胞系（CCRF/CEM 和 MCF7）以及对多柔比星耐药癌细胞（CEM/ADR 5000 和 Caco-2）的细胞毒活性。特别是，化合物VIII在所有先前提到的细胞系中显示出显着的细胞毒性作用，尤其是在多柔比星抗性 CEM/ADR5000 细胞中（IC 50= 8.13 µM）。此外，测试了最有希望的衍生物VII、VIII和XI在多柔比星抗性 CEM/ADR 5000 亚系中的 ABCB1 抑制作用，该亚系以 ABCB1 转运蛋白的过表达而闻名。结果表明，与作为参照ABCB1抑制剂的维拉帕米相比，化合物VII在三个测试浓度（22

  DOI：

  10.1080/14756366.2022.2127700

文献信息

• Efficient and highly selective boron-doped carbon materials-catalyzed reduction of nitroarenes
  作者：Yangming Lin、Shuchang Wu、Wen Shi、Bingsen Zhang、Jia Wang、Yoong Ahm Kim、Morinobu Endo、Dang Sheng Su

  DOI：10.1039/c5cc01963j

  日期：——

  Boron-doped carbon materials are demonstrated to be excellent catalysts in nitroarene reduction reactions.

  硼掺杂的碳材料被证明在硝基芳烃还原反应中是优秀的催化剂。
• Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles
  作者：Natarajan Arumugam、Aisyah Saad Abdul Rahim、Shafida Abd Hamid、Hasnah Osman

  DOI：10.3390/molecules17089887

  日期：——

  series of novel 1-(2'-α-O-D-glucopyranosyl ethyl) 2-arylbenzimidazoles has been prepared via one-pot glycosylation of ethyl-1-(2'-hydroxyethyl)-2-arylbenzimidazole-5-carboxylate derivatives. Synthesis of the 2-arylbenzimidazole aglycones from 4-fluoro-3-nitrobenzoic acid was accomplished in four high-yielding steps. The reduction and cyclocondensation steps for the aglycone synthesis proceeded efficiently

  通过1-(2'-羟乙基)-2-芳基苯并咪唑-5-羧酸酯衍生物的一锅糖基化制备了一系列新型1-(2'-α-OD-吡喃葡萄糖基乙基)2-芳基苯并咪唑。由 4-氟-3-硝基苯甲酸合成 2-芳基苯并咪唑苷元通过四个高产步骤完成。糖苷配基合成的还原和环缩合步骤在微波辐射下有效进行，在 2-3 分钟内以优异的产率提供合适的苯并咪唑。用过苯甲基化 1-羟基-吡喃葡萄糖对羟乙基苷元进行糖基化，用 Appel-Lee 试剂进行预处理，然后进行催化氢解，以简单的方法得到所需的 1-(2'-α-OD-吡喃葡萄糖基乙基) 2-芳基-苯并咪唑和直接的方式。
• Unprecedented alkylation of carboxylic acids by boron trifluoride etherate
  作者：N. D. Jumbam、Y. Maganga、W. Masamba、N. I. Mbunye、E. Mgoqi、S. Mtwa

  DOI：10.4314/bcse.v32i2.16

  日期：——

  investigated were not affected by alkylation, those of meta - and para -substituted carboxylic acids were partially etherified. Furthermore, the alkylation reaction was found to be compatible with a range of functional groups such as halogens, amino and nitro groups except for the alkene function of undecylenic acid that underwent polymerisation with concomitant alkylation of its carboxylic acid function

  在不存在来自反应体系的乙醇的情况下，由三氟化硼醚化物的乙基部分进行的羧酸烷基化是出乎意料且新颖的。芳香族和脂肪族羧酸都被清楚地烷基化，在短的反应时间内提供了良好的收率，但烟酸需要进行过夜反应。注意到尽管所研究的羧酸的邻位取代的羟基不受烷基化的影响，但是间位和对位取代的羧酸的那些被部分醚化。此外，发现烷基化反应与一系列官能团如卤素，氨基和硝基相容，除了十一碳烯酸的烯烃官能团伴随其羧酸官能团的烷基化而聚合。关键词：羧酸，烷基化，醚化，官能团，三氟化硼醚醚。化学 Soc。埃塞俄比亚。2018，32（2），387-392。DOI：https：//dx.doi.org/10.4314/bcse.v32i2.16
• Microwave-assisted synthesis of <i>sec/tert</i>-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells
  作者：Aisyah Saad Abdul Rahim、Salizawati Muhamad Salhimi、Natarajan Arumugam、Lim Chung Pin、Ng Shy Yee、Nithya Niranjini Muttiah、Wong Boon Keat、Shafida Abd. Hamid、Hasnah Osman、Ishak b. Mat

  DOI：10.3109/14756366.2012.729828

  日期：2013.12.1

  using (1)H NMR, (13)C NMR, high resolution MS and melting points. Evaluation of antiproliferative activity of the benzimidazole analogues against MCF-7 and MDA-MB-231 revealed several compounds with unexpected selective inhibitions of MDA-MB-231 in micromolar range. All analogues were found inactive towards MCF-7. The most potent inhibition against MDA-MB-231 human breast cancer cell line came from the

  在聚焦微波辐射下，通过将3-氨基-4-丁基氨基苯甲酸乙酯与苯甲醛的各种取代的亚硫酸氢盐加合物缩合，在2-3.5分钟内以85-96％的产率合成了一系列新的N-仲/叔丁基2-芳基苯并咪唑衍生物。 。苯并咪唑类似物使用（1）H NMR，（13）C NMR，高分辨率MS和熔点进行表征。苯并咪唑类似物对MCF-7和MDA-MB-231的抗增殖活性的评估显示了几种化合物在微摩尔范围内具有意想不到的选择性抑制MDA-MB-231的作用。发现所有类似物对MCF-7无活性。对MDA-MB-231人乳腺癌细胞系最有效的抑制作用来自未取代的2-苯基苯并咪唑10a。
• [EN] 1,2,3-BENZOTRIAZOLE DERIVATIVES AS ROR GAMMA T MODULATORS<br/>[FR] DÉRIVÉS DE 1,2,3-BENZOTRIAZOLE EN TANT QUE MODULATEURS DE ROR GAMMA T
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2018042342A1

  公开（公告）日：2018-03-08

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, G, L, R1, Rx, Ry, X1, X2, X3, X4, n, p, q and t are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORyt). These compounds prevent, inhibit, or suppress the action of RORyt and are therefore useful in the treatment of RORyt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer (I).

  本公开涉及式(I)的化合物及其药用可接受的盐，其中环A、G、L、R1、Rx、Ry、X1、X2、X3、X4、n、p、q和t如本文所定义，这些化合物作为视黄醇相关孤儿受体γt（RORγt）的调节剂具有活性。这些化合物可以预防、抑制或抑制RORγt的作用，因此在治疗RORγt介导的疾病、紊乱、综合症或症状方面具有用处，例如疼痛、炎症、慢性阻塞性肺病（COPD）、哮喘、类风湿性关节炎、结肠炎、多发性硬化症、牛皮癣、神经退行性疾病和癌症。