2,4-二硝基-N-乙基苯胺 | 3846-50-2

• 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: 2,4-二硝基-N-乙基苯胺
• 英文名称: 2,4-dinitro-N-ethylaniline
• 英文别名: N-(2,4-dinitrophenyl)-N-ethylamine；N-(2,4-dinitrophenyl)ethylamine；N-Ethyl-2,4-dinitroaniline；N-ethyl-2,4-dinitro-aniline；N-Aethyl-2,4-dinitro-anilin；N-ethyl-2,4-dinitro-benzenamine
• CAS: 3846-50-2
• 化学式: C₈H₉N₃O₄
• mdl: MFCD00007225
• 分子量: 211.177
• InChiKey: YYOUTZBUOQBAAE-UHFFFAOYSA-N

物化性质

• 熔点：
  110-113 °C(lit.)
• 沸点：
  350.85°C (rough estimate)
• 密度：
  1.4271 (rough estimate)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S23
• 危险类别码：
  R20/21
• 海关编码：
  2921420090

SDS

Name:	2 4-Dinitro-N-Ethylaniline 97% Material Safety Data Sheet
Synonym:	None known
CAS:	3846-50-2

Section 1 - Chemical Product MSDS Name:2 4-Dinitro-N-Ethylaniline 97% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3846-50-2	2,4-Dinitro-N-Ethylaniline	97	223-345-0

Hazard Symbols: XN
Risk Phrases: 20/21

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and in contact with skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Methemoglobinemia is characterized by dizziness, drowsiness, headache, shortness of breath, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), rapid heart rate and chocolate-brown colored blood. Overexposure may cause methemoglobinemia.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Methemoglobinemia is characterized by dizziness, drowsiness, headache, shortness of breath, cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), rapid heart rate and chocolate-brown blood. Inhalation of aniline causes anoxia due to the formation of methemoglobin.
Chronic:
May cause methemoglobinemia, which is characterized by chocolate-brown colored blood, headache, weakness, dizziness, breath shortness, cyanosis (bluish skin due to deficient oxygenation of blood), rapid heart rate, unconsciousness and possible death.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
For methemoglobinemia, administer oxygen alone or with Methylene Blue depending on the methemoglobin concentration in the blood.
Antidote: Methylene blue, alone or in combination with oxygen is indicated as a treatment in nitrite induced methemoglobinemia.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Combustible material; may burn but does not ignite readily.
Extinguishing Media:
Do NOT get water inside containers. For small fires, use dry chemical, carbon dioxide, or water spray. For large fires, use dry chemical, carbon dioxide, alcohol-resistant foam, or water spray.
Cool containers with flooding quantities of water until well after fire is out.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3846-50-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: brown
Odor: aniline-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 110.00 - 113.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H9N3O4
Molecular Weight: 211.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Acid anhydrides, acid chlorides, acids, chloroformates, strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3846-50-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,4-Dinitro-N-Ethylaniline - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21 Harmful by inhalation and in contact with
skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 3846-50-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3846-50-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3846-50-2 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,4-二硝基-N-乙基苯胺 在 palladium on activated charcoal 硫酸 、 氢气 、 铁粉 、 溶剂黄146 、 potassium nitrate 作用下， 生成 7-amino-1-ethyl-6-nitro-2,3(1H,4H)-quinoxalinedione
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3
• 作为产物：
  描述：

  N-乙基苯胺 在 bismuth (III) nitrate pentahydrate 、 palladium diacetate 作用下， 以 2,2,2-三氟乙醇 、 三氟乙酸 为溶剂， 反应 24.0h， 以92%的产率得到2,4-二硝基-N-乙基苯胺
  参考文献：
  名称：

  Pd（OAc）2催化芳香胺的硝化反应

  摘要：

  利用Pd（OAc）2与Bi（NO 3）3 ·5H 2 O在三氟乙醇（TFE）和三氟乙酸（TFA）中催化的硝化反应，我们开发了一种高效且实用的方法来合成仲二硝基-芳香胺。该产品可用于制备5-胺-N-甲基-苯并咪唑酮，具有偶氮染料的经济优势。该方法还扩展到某些叔芳族胺的硝化反应。

  DOI：

  10.1016/j.tet.2015.04.013

文献信息

• Nucleophilic and acid catalyst behavior of a protic ionic liquid in a molecular reaction media. Part 1
  作者：Claudia G. Adam、Graciela G. Fortunato、Pedro M. Mancini

  DOI：10.1002/poc.1501

  日期：2009.5

  achieve this, a kinetic study of nucleophilic aromatic substitution reactions between 1‐fluoro‐2,4‐dinitrobenzene and 1‐butylamine or piperidine was developed in this type of binary mixtures. We have detected nucleophiles competition originated by the presence of the ionic solvent at very low concentrations, observing the ethylamine derivative as the main substitution product. Moreover, in the light

  这项工作提出了一种使用离子液体的新方法，即硝酸乙铵。目的是分析向纯分子溶剂中添加少量质子离子液体如何改变反应介质的微观特性。为了实现这一目标，在这种二元混合物中，进行了1-氟-2,4-二硝基苯与1-丁胺或哌啶之间亲核芳香取代反应的动力学研究。我们已经观察到亲核试剂的竞争是由于以非常低的浓度存在离子溶剂而引起的，观察到乙胺衍生物是主要的取代产物。此外，根据先前的结果，我们已经确认质子离子液体可以同时充当布朗斯台德酸和/或亲核试剂。在这方面，我们选择了胺向羰基化合物的亲核加成作为反应模型。质子离子液体在存在被供电子基团取代的芳族醛的情况下，可能以高收率形成相应的亚胺。结果表明，质子离子液体的影响在两个反应体系中都非常重要。版权所有©2008 John Wiley＆Sons，Ltd.
• The mechanistic origin of regiochemical changes in the nitrosative N-dealkylation of N,N-dialkyl aromatic amines
  作者：Emma L. Teuten、Richard N. Loeppky

  DOI：10.1039/b418457b

  日期：——

  mechanistic pathways, two of which give the nitrosamine through the iminium ion, and one leads to the formation of C-nitro compounds. The competing pathways to nitrosamine formation involve NOH elimination from a nitrosammonium ion and deprotonation of the radical cation to give an alpha-amino radical which rapidly oxidized to the iminium ion. Predominant, but not highly regioselective demethylation occurs by

  亚硝酸介导的4-取代的-N-乙基-N-甲基苯胺的去烷基化的区域选择性是反应混合物酸度的函数。在高酸度下，脱乙基化占主导，而脱甲基化是在pH 2及以上的亚硝胺形成过程中的主要反应。在某些情况下，亚硝化脱烷基反应的区域选择性随运行的进行而改变。通过使用相应的4-硝基苯胺作为主要底物，CIDNP，动力学，动力学氘同位素效应以及涉及非质子溶剂中与NO2或NOBF4亚硝化的其他转化，推导了叔胺亚硝化的新机理，并提出了解释区域选择性的新方法。脱乙基。该机理涉及通过NO +将底物氧化成胺自由基阳离子。随后，通过NO 2从与胺氮相邻的碳中抽出氢原子，生成亚胺离子，该亚胺离子进一步反应生成相应的醛和亚硝胺。取决于酸度，该过程与其他三个机理途径竞争，其中两个通过亚胺离子产生亚硝胺，一个导致C-硝基化合物的形成。亚硝胺形成的竞争途径涉及从亚硝铵离子中去除NOH和使自由基阳离子去质子化，从而产生迅速氧化为亚胺离子
• A New Leaving Group in Nucleophilic Aromatic Substitution Reactions (S_NAr)
  作者：Mehdi Bakavoli、Mehdi Pordel、Mohammad Rahimizadeh、Pooneh Jahandari

  DOI：10.3184/030823408x338693

  日期：2008.8

  Nucleophilic aromatic substitution of a 2,4-dinitrophenyl substituted pyrazole 1 with primary amines leads to substitution of the pyrazolo substituent. In these nucleophilic aromatic substitution reactions (SNAr), 5-amino-1H-4-pyrazolecarbonitrile (3) acts as a new leaving group.

  2,4-二硝基苯基取代的吡唑 1 与伯胺的亲核芳族取代导致吡唑基取代基的取代。在这些亲核芳香取代反应 (SNAr) 中，5-氨基-1H-4-吡唑甲腈 (3) 作为新的离去基团。
• Sulfonamide derivatives
  申请人：Sumitomo Chemical Takeda Agro Company, Limited

  公开号：US06586617B1

  公开（公告）日：2003-07-01

  The present invention relates to microbicides for agricultural or horticultural use containing a sulfonamide derivative.

  本发明涉及包含磺酰胺衍生物的用于农业或园艺的杀微生物剂。
• Cobalt-based molecular electrocatalysis of nitrile reduction: evolving sustainability beyond hydrogen
  作者：Simon N. Child、Radoslav Raychev、Nathan Moss、Benjamin Howchen、Peter N. Horton、Christopher C. Prior、Vasily S. Oganesyan、John Fielden

  DOI：10.1039/c9dt00773c

  日期：——

  Two complexes, designed as hydrogen evolution catalysts, are shown to be the first earth-abundant molecular electrocatalysts for reduction of acetonitrile to ethylamine.

  两种设计为氢进化催化剂的复合物被证明是第一批用于将乙腈还原为乙胺的丰富地球元素分子电催化剂。

表征谱图