2,5-二乙基硝基苯 | 119-23-3

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 2,5-二乙基硝基苯
• 中文别名: 1,4-二乙氧基-2-硝基苯；2,5-二乙氧基硝基苯
• 英文名称: 1,4-diethoxy-2-nitrobenzene
• CAS: 119-23-3
• 化学式: C₁₀H₁₃NO₄
• mdl: MFCD00007100
• 分子量: 211.218
• InChiKey: AUCRWWWSFGZHBK-UHFFFAOYSA-N

物化性质

• 熔点：
  48-51 °C(lit.)
• 沸点：
  169 °C13 mm Hg(lit.)
• 密度：
  1.2022 (estimate)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  2

SDS

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Section I.Chemical Product and Company Identification
Chemical Name 1,4-Diethoxy-2-nitrobenzene
Portland OR
Nitrohydroquinone Diethyl Ether
Synonym
NO2C6H3(OC2H5)2
Chemical Formula
CAS Number 119-23-3

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
1,4-Diethoxy-2-nitrobenzene 119-23-3 ---------- Not available. Not available.

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Section III. Hazards Identification
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
Acute Health Effects
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening,
or, occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the
toxic material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
May be combustible at high temperature. Auto-Ignition
Flammability
Flash Points Flammable Limits Not available.
113°C (235.4°F).
Combustion Products These products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media SMALL FIRE: Use DRY chemical powder.
and Instructions LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
1,4-Diethoxy-2-nitrobenzene

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Section VI. Accidental Release Measures
Spill Cleanup Irritating material.
Use a shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
Instructions
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.

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Section VII. Handling and Storage
Handling and Storage IRRITANT. Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in
a dry, cool place. Avoid excessive heat and light. Do not breathe dust.
Information
Always store away from incompatible compounds such as oxidizing agents, alkalis (bases).

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult
a specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Physical state @ 20°C Solid. (Yellow Crystalline Powder.) Solubility Not available.
Not available.
Specific Gravity
Molecular Weight 211.21 Partition Coefficient Not available.
Boiling Point 169°C (336.2°F) @ 13 mmHg Vapor Pressure Not applicable.
Melting Point 48 to 51°C (118.4 to 123.8°F) Vapor Density Not available.
Not available. Volatility Not available.
Refractive Index
Not available.
Critical Temperature Not available. Odor
Not available. Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of Instability
Avoid excessive heat and light.
Incompatibilities
Reactive with strong oxidizing agents, strong alkalis (bases).

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Section XI. Toxicological Information
RTECS Number Not available.
Routes of Exposure Eye Contact. Ingestion. Inhalation.
Not available.
Toxicity Data
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
Acute Toxic Effects
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening,
or, occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Continued on Next Page
1,4-Diethoxy-2-nitrobenzene

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Section XII. Ecological Information
Ecotoxicity Not available.
Not available.
Environmental Fate

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
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 XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
Not applicable.
PIN Number
Proper Shipping Name
Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This compound is ON the EPA Toxic Substances Control Act (TSCA) inventory list.
(EPA)
WHMIS Classification Not controlled under WHMIS (Canada).
On NDSL
(Canada)
EINECS Number (EEC) 204-308-8
EEC Risk Statements
R36/37/38- Irritating to eyes, respiratory system and skin.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,5-二乙基硝基苯 在 aluminum (III) chloride 、 盐酸 、 水 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以87%的产率得到4-ethoxy-2-nitrophenol
  参考文献：
  名称：

  硝基定向选择性脱烷基

  摘要：

  摘要 硝基取代酚醚被成功地选择性脱烷基。出色的区域选择性和良好的产率支持了硝基的导向作用。这些反应表明，AlCl3 与酚硝基的络合比单独与酚醚的络合更强。提出了由硝基引导的选择性脱烷基化机制。

  DOI：

  10.1080/00397910802633439
• 作为产物：
  描述：

  对二乙氧基苯 在 三甲基氯硅烷 、 copper(ll) sulfate pentahydrate 、 硝酸胍 作用下， 以 乙腈 为溶剂， 以99%的产率得到2,5-二乙基硝基苯
  参考文献：
  名称：

  硝酸胍对富电子芳烃的无酸铜催化亲电硝化反应

  摘要：

  报道了一种实用的铜催化富电子芳烃与三甲基氯硅烷和硝酸胍的硝化反应。在无酸、开瓶和操作简单的条件下，在环境温度下以中等至优异的产率 (32–99%) 生成各种硝化产物。

  DOI：

  10.1021/acs.joc.1c03020

文献信息

• A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, <i>N</i>-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
  作者：Anirudhdha G. Kalola、Pratibha Prasad、Jaydeep A. Mokariya、Manish P. Patel

  DOI：10.1080/00397911.2021.1983604

  日期：2021.12.2

  salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without

  摘要 第一个温和、原位、单锅、高收率、筛选良好的铜 (II) 盐基催化剂体系，利用硼氢化钠的氢替代作用，在存在于已经描述了水或甲醇之类的绿色溶剂。此外，该催化体系还可以在短时间内活化各种官能团进行氢化物还原，催化剂负载量低，无需高压或分子氢供应。值得注意的是，该系统探索了替代昂贵的传统加氢方法的巨大潜力，从而在有机合成领域提供了一种更绿色、更简单的加氢策略。
• Hydrazine-mediated Reduction of Nitro and Azide Functionalities Catalyzed by Highly Active and Reusable Magnetic Iron Oxide Nanocrystals
  作者：David Cantillo、Mojtaba Mirhosseini Moghaddam、C. Oliver Kappe

  DOI：10.1021/jo400556g

  日期：2013.5.3

  also successfully applied to the reduction of aliphatic nitro compounds and azides. The iron oxide nanoparticles are generated in a colloidal form, resulting in homogeneous solutions suitable for continuous flow processing. Selected examples of anilines of industrial importance have been prepared in a continuous regime using this protocol.

  原位生成的氧化铁（Fe 3 O 4）纳米晶体从廉价且容易获得的铁源中提取氯代硝基苯可将硝基芳烃还原为苯胺，效率无与伦比。该程序是化学选择性的，避免使用贵金属，可以在温和的回流条件（65或80°C）下使用，也可以在高温状态（150°C）下使用密封容器微波加热进行。利用微波条件，已在150°C下2-8分钟内以几乎定量的产率制备了各种功能化苯胺，该方法也成功地用于还原脂肪族硝基化合物和叠氮化物。氧化铁纳米粒子以胶体形式生成，从而产生适用于连续流处理的均匀溶液。具有工业重要性的苯胺的选定实例已使用该方案以连续方式制备。
• In Situ Generated Iron Oxide Nanocrystals as Efficient and Selective Catalysts for the Reduction of Nitroarenes using a Continuous Flow Method
  作者：David Cantillo、Mostafa Baghbanzadeh、C. Oliver Kappe

  DOI：10.1002/anie.201205792

  日期：2012.10.1

  worlds: The benefits of homogeneous and heterogeneous nanocatalysis are combined, whereby highly reactive colloidal Fe3O4 nanocrystals are generated in situ that remain in solution long enough to allow the efficient and selective reduction of nitroarenes to anilines in continuous‐flow mode (see scheme). After completion of the reaction, the nanoparticles aggregate and can be recovered by a magnet.

  两全其美：结合了均相和非均相纳米催化的优点，从而可以在溶液中原位生成高反应性的胶态Fe 3 O 4纳米晶体，并在溶液中保留足够长的时间，从而可以将硝基芳烃有效地，选择性地还原为连续流动的苯胺。模式（请参阅方案）。反应完成后，纳米颗粒聚集并且可以通过磁体回收。
• 一种富电子芳烃的直接硝化方法
  申请人：中国科学院青岛生物能源与过程研究所

  公开号：CN108530242A

  公开（公告）日：2018-09-14

  本发明公开了一种富电子芳烃的直接硝化合成方法，属于有机合成领域。本发明提供一种新型绿色自由基硝化方法，以芳烃为原料，与绿色硝化试剂叔丁基亚硝酸酯(TBN)在室温条件下，以乙腈、二氯甲烷、氯仿或丙酮作为反应溶剂，发生自由基硝化反应，获得硝基芳烃。本发明不使用金属参与反应，利用亚硝酸叔丁酯直接参与硝化反应。本发明引入供电子基如OMe，提高芳香化合物的电子密度，增加硝化反应的可能性。本发明减少亚硝酸叔丁酯的使用量。本发明反应只生成产物和叔丁醇，减少了环境污染。本发明方法在硝基芳烃合成领域具有重要的应用前景，真正意义上实现了绿色硝化，也为大规模工业化生产硝基芳烃提供了一条新的思路。
• Immobilized Iron Oxide Nanoparticles as Stable and Reusable Catalysts for Hydrazine-Mediated Nitro Reductions in Continuous Flow
  作者：Mojtaba Mirhosseini Moghaddam、Bartholomäus Pieber、Toma Glasnov、C. Oliver Kappe

  DOI：10.1002/cssc.201402455

  日期：2014.11

  alumina‐supported Fe3O4 nanoparticles [(6±1) nm size, 0.67 wt %]and the use of this material in hydrazine‐mediated heterogeneously catalyzed reductions of nitroarenes to anilines under batch and continuous‐flow conditions is presented. The bench‐stable, reusable nano‐Fe3O4@Al2O3 catalyst can selectively reduce functionalized nitroarenes at 1 mol % catalyst loading by using a 20 mol % excess of hydrazine hydrate

  一种实验上易于执行的方法，用于生成氧化铝负载的Fe 3 O 4纳米颗粒[（6±1）nm尺寸，0.67 wt％]，并在肼介导的非均相催化下将硝基芳烃分批还原为苯胺。并给出了连续流动条件。台式稳定，可重复使用的纳米Fe 3 O 4 @Al 2 O 3在升高的温度范围内（150°C，分批反应2至6分钟），使用过量20 mol％的水合肼，催化剂可在1 mol％的催化剂负载量下选择性还原官能化的硝基芳烃。对于连续流处理，将催化剂材料包装到专用滤芯中，并用于市售的高温/高压流送设备中。在连续模式下，在高度强化的过程中，反应时间可以在150°C（30 bar背压）下减少到不到1分钟。纳米Fe 3 O 4 @Al 2 O 3催化剂在生产中以30 mmol h -1的产率显示出硝基苯（0.5 M在MeOH中）稳定还原 超过10 h（每天0.72摩尔）。重要的是，通过电感耦合等离子体MS监测，实际上没有观察到催化活性材料的浸出。

表征谱图