N,N-二乙基-4-硝基苯甲酰胺 | 5323-47-7

• 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: N,N-二乙基-4-硝基苯甲酰胺
• 英文名称: N,N-diethyl-4-nitrobenzamide
• 英文别名: diethyl 4-nitrobenzamide；4-nitro-N,N-diethylbenzamide；4-Nitro-benzoesaeure-diaethylamid；N.N-Diethyl-p-nitro-benzamid
• CAS: 5323-47-7
• 化学式: C₁₁H₁₄N₂O₃
• mdl: MFCD00454141
• 分子量: 222.244
• InChiKey: JLZWKZDHHREXTA-UHFFFAOYSA-N

物化性质

• 保留指数：
  2071

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N,N-Diethyl-4-nitrobenzamide
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.
N,N-Diethyl-4-nitrobenzamide
Ingredient name:
CAS number: 5323-47-7

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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.

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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: C11H14N2O3
Molecular weight: 222.2

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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.

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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：

  N,N-二乙基-4-硝基苯甲酰胺 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以81%的产率得到对硝基苯甲醛
  参考文献：
  名称：

  A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp₂Zr(H)Cl

  摘要：

  Functional group manipulations continue to play an important role in organic synthesis, and hence the development of new methods to carry out these transformations remains an important part of organic chemistry. The reduction of amides to aldehydes is one such transformation, and although several methods are available,(1) many are substrate specific,(2) the outcome of the reaction being dependent upon the nature of the nitrogen substituent. Problems with existing techniques, which generally require the use of highly reactive reagents such as aluminum and boron hydrides, include low functional group tolerance, over-reduction to amines or alcohols, or the formation of other byproducts. Herein, we report a general procedure for the conversion of tertiary amides to:aldehydes, which employs a commercially available reagent, Cp2Zr(H)Cl (Schwartz reagent(3)) and operates under mild conditions at room temperature (Scheme 1).

  DOI：

  10.1021/ja002149g
• 作为产物：
  描述：

  4-nitro-thiobenzoic acid diethylamide 在 过氧单硫酸 、 silica gel 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以80%的产率得到N,N-二乙基-4-硝基苯甲酰胺
  参考文献：
  名称：

  Caro 酸支持在硅胶上。第 21 部分：硫代酰胺转化为酰胺

  摘要：

  摘要 用硅胶负载的卡罗酸处理，在温和条件下将一系列硫代酰胺化合物转化为相应的酰胺。

  DOI：

  10.1080/00397910008086876

文献信息

• [EN] CONTROLLED RELEASE FROM MACROMOLECULAR CONJUGATES<br/>[FR] LIBÉRATION CONTRÔLÉE À PARTIR DE CONJUGUÉS MACROMOLÉCULAIRES
  申请人：PROLYNX LLC

  公开号：WO2011140393A1

  公开（公告）日：2011-11-10

  The invention relates to conjugates of macromolecular carriers and drugs comprising linkers that release the drug or a prodrug through rate-controlled beta-elimination, and methods of making and using the conjugates.

  这项发明涉及大分子载体和药物的共轭物，包括释放药物或前药的连接剂，通过速率控制的β-消除释放药物，以及制备和使用这些共轭物的方法。
• Pd/C-Catalyzed Aminocarbonylation of Aryl Iodides via Oxidative C–N Bond Activation of Tertiary Amines to Tertiary Amides
  作者：Rajendra S. Mane、Bhalchandra M. Bhanage

  DOI：10.1021/acs.joc.5b02385

  日期：2016.2.5

  This work reports oxidative N-dealkylation/carbonylation of tertiary amines to tertiary amides by using molecular oxygen as a sole oxidant using a Pd/C catalyst. This protocol is free from ligands, additives, bases, and cocatalysts. Different tertiary amines as well as aryl iodides have been examined for this transformation, providing desired products in good to excellent yield.

  这项工作报道了使用Pd / C催化剂将分子氧作为唯一的氧化剂，将叔胺氧化N-脱烷基/羰基化为叔酰胺。该方案不含配体，添加剂，碱和助催化剂。已经研究了不同的叔胺以及碘代芳基化合物的这种转化，从而以良好至优异的产率提供了所需的产物。
• CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in water <i>via</i> benzylic sp³ C–H activation
  作者：Marzieh Rousta、Dariush Khalili、Ali Khalafi-Nezhad、Edris Ebrahimi

  DOI：10.1039/d1nj03982b

  日期：——

  activity of the rGO/Fe3O4–CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals using tert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation

  通过简便的化学方法制备了磁铁矿还原的氧化石墨烯负载的 CuO 纳米复合材料 ( rGO /Fe 3 O 4 –CuO)，并通过傅里叶变换红外光谱 (FTIR)、X 射线衍射 (XRD)、UV-vis光谱、扫描电子显微镜 (SEM)、透射电子显微镜 (TEM)、能量色散光谱 (EDS)、Brunauer-Emmett-Teller (BET) 分析、振动样品磁强计 (VSM) 和热重 (TG) 分析。rGO/Fe 3 O 4的催化活性-CuO纳米复合材料在甲基芳烃与游离胺的直接氧化酰胺化反应中被探测到。使用叔丁基过氧化氢 (TBHP) 作为“绿色”氧化剂和在水中的低毒性 TBAI，在室温下从廉价的原料化学品中有效地制备了各种芳香族和脂肪族酰胺。该方法将甲基芳烃的氧化和酰胺键的形成结合到一个操作中。此外，合成的纳米复合材料可以使用外部磁铁从反应混合物中分离出来，并在连续六次运行中重复使用，催化活性没有明显降低。
• Clickable coupling of carboxylic acids and amines at room temperature mediated by SO₂F₂: a significant breakthrough for the construction of amides and peptide linkages
  作者：Shi-Meng Wang、Chuang Zhao、Xu Zhang、Hua-Li Qin

  DOI：10.1039/c9ob00699k

  日期：——

  carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in

  酰胺键和肽键的构建是所有生命过程和有机合成中最基本的转变之一。结构无处不在的酰胺基序的合成对于许多重要分子（如肽，蛋白质，生物碱，药剂，聚合物，配体和农用化学品）的组装至关重要。开发了一种SO2F2介导的羧酸与胺的直接可点击偶合方法，以简单，温和，高效，稳健和实用的方式合成各种酰胺（> 110例，大多数情况下> 90％的收率） ）。
• A synthesis of sulfonamide analogs of platensimycin employing a palladium-mediated carbonylation strategy
  作者：James McNulty、Jerald J. Nair、Alfredo Capretta

  DOI：10.1016/j.tetlet.2009.04.105

  日期：2009.7

  highly effective in palladium-catalyzed carbonylative cross-coupling. Aryl and vinyl halides were efficiently converted to carboxylic acids, amides and to primary, secondary, and tertiary esters, respectively. Application of the Pd(OAc)2/PA-Ph (1:1) catalyst system proved critical in the methoxycarbonylation of a functionalized nitroresorcinol halide, allowing convenient access to novel platensimycin

  单齿配体1,3,5,7-四甲基-2,4,8-三氧杂-6-苯基-6-磷-金刚烷（PA-Ph）已显示在钯催化的羰基交叉偶联中非常有效。芳基卤化物和乙烯基卤化物分别有效地转化为羧酸，酰胺和伯，仲和叔酯。Pd（OAc）2 / PA-Ph（1：1）催化剂体系的应用在功能化的硝基间苯二酚卤化物的甲氧基羰基化中被证明是至关重要的，从而可以方便地获得新型的板新霉素磺酰胺类似物。