N-异丙基-4-硝基苯甲酰胺 | 38681-76-4

• 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-异丙基-4-硝基苯甲酰胺
• 英文名称: N-isopropyl-4-nitrobenzamide
• 英文别名: 4-nitro-N-propan-2-ylbenzamide
• CAS: 38681-76-4
• 化学式: C₁₀H₁₂N₂O₃
• mdl: MFCD00779671
• 分子量: 208.217
• InChiKey: YQLNAYKZWIVHIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 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
Product Name: N-Isopropyl-4-nitrobenzamide
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: N-Isopropyl-4-nitrobenzamide
CAS number: 38681-76-4

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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: C10H12N2O3
Molecular weight: 208.2

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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-异丙基-4-硝基苯甲酰胺 在 2-氟吡啶 、 三氟甲磺酸酐 、 1,1,3,3-四甲基二硅氧烷 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.5h， 以82%的产率得到对硝基苯甲醛
  参考文献：
  名称：

  f2O-TMDS组合，可将仲酰胺直接还原转化为醛胺，醛和/或胺

  摘要：

  将高度稳定的仲酰胺直接部分还原为反应性更高的醛亚胺和醛是一项具有挑战性但要求很高的转化。在这种情况下，仅报道了三种方法。我们在此报告Charette方法的改进版本。我们的方案包括用三氟甲磺酸酐/ 2-氟吡啶活化仲酰胺，以及用1,1,3,3-四甲基二硅氧烷（TMDS）部分还原所得的中间体，该中间体在酸性水解后可递送醛胺或醛。芳香酰胺以5％至100％的NMR收率还原为相应的醛亚胺，脂族酰胺的收率（NMR）为72％至86％。通过一锅法对醛亚胺中间体进行酸性水解，可以以80％–96％的产率获得相应的醛。建立了一个简单的协议，以92％–96％的产率分离纯净的不稳定的亚胺。与已知方法相比，改进的方法通常具有更高的产率，并且具有使用更便宜且原子经济性更高的TMDS作为化学选择性还原剂的特征。此外，已经建立了方便的提取方案以允许分离胺，这是一种温和的提取方法。酰胺的N-脱酰基，另一种非常理想的转化。扩展的

  DOI：

  10.1007/s11426-016-0224-5
• 作为产物：
  描述：

  4-硝基苯胺 在 hydrofluoroboric acid 、 水 、 caesium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 0.91h， 生成 N-异丙基-4-硝基苯甲酰胺
  参考文献：
  名称：

  A Transition-Metal-Free Synthesis of Arylcarboxyamides from Aryl Diazonium Salts and Isocyanides

  摘要：

  A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium intermediate.

  DOI：

  10.1021/ol4017244

文献信息

• Isoquinoline-Catalyzed Reaction of Phenacyl Bromide and N,N-Dialkyl­carbodiimides: Novel Synthesis of Azirines
  作者：Abdolali Alizadeh、Atieh Rezvanian

  DOI：10.1055/s-0031-1290487

  日期：2012.4

  A practical and efficient procedure for the synthesis of polysubstituted azirines and in some cases benzamides was developed through reaction of phenacyl bromides and N,N-dialkylcarbodiimides, in the presence of catalytic amount of isoquinoline in dry acetonitrile under mild conditions at ambient temperature. The salient features of this process include operational simplicity, high yields, and easily

  在室温温和条件下，在催化量的异喹啉的干燥乙腈中，通过苯甲酰溴和 N,N-二烷基碳二亚胺的反应开发了一种实用且有效的合成多取代氮丙啶类化合物和在某些情况下苯甲酰胺的方法。该过程的显着特点包括操作简单、产量高和易于获得起始材料。
• Ketone Synthesis by Direct, Orthogonal Chemoselective Hydroacylation of Alkenes with Amides: Use of Alkenes as Surrogates of Alkyl Carbanions
  作者：Hui Geng、Pei‐Qiang Huang

  DOI：10.1002/cjoc.201900252

  日期：2019.8

  and direct transformation of carboxamides are two exciting areas that have attracted considerable attention in recent years. We report herein that secondary amides, the least reactive derivatives of carbonyl compounds, upon activated with triflic anhydride, can serve as effective hydroacylating reagents in partner with alkenes to yield ketones at ambient temperature. The method was applied to the one‐step

  烯烃的直接官能化和羧酰胺的直接转化是近年来令人瞩目的两个令人兴奋的领域。我们在此报道，仲酰胺，即羰基化合物的反应性最低的衍生物，在用三氟甲磺酸酐活化后，可以与烯烃一起作为有效的氢酰化试剂，在环境温度下产生酮。该方法已用于外消旋二氢芳基羟色酮的一步合成。在这种方法中，烯烃用作有机金属试剂的替代物，从而可以进行正交的化学选择性反应。许多烯烃（如camp烯和降冰片烯）的现成性允许一步合成酮，而传统方法则需要几个步骤。
• Versatile and chemoselective transformation of aliphatic and aromatic secondary amides to nitriles
  作者：Hui Geng、Pei-Qiang Huang

  DOI：10.1016/j.tet.2015.03.094

  日期：2015.6

  Triflic anhydride in combination with 2-fluoropyridine effectively dehydrates secondary amides to afford nitriles under mild reaction conditions. The reaction is general in scope and compatible with the use of aliphatic, α,β-unsaturated, aromatic, and heteroaromatic amides bearing either secondary, tertiary, or benzylic N-alkyl groups. The reaction also shows good to excellent chemoselectivity for the

  三氟甲磺酸酐与2-氟吡啶结合可有效地使仲酰胺脱水，在温和的反应条件下提供腈。该反应是一般性的，并且与带有仲，叔或苄基N-烷基的脂族，α，β-不饱和，芳族和杂芳族酰胺的使用相容。该反应还显示出对仲酰胺的良好的化学选择性至优异的化学选择性，并能耐受几个不稳定的官能团。
• Aminobenzamide compounds for the treatment of neurodegenerative disorders
  申请人：Centaur Pharmaceuticals, Inc.

  公开号：US05643965A1

  公开（公告）日：1997-07-01

  A group of benzamide compounds are disclosed which are useful for treating neurodegenerative disorders. Methods for making these compounds are provided. These materials are formed into pharmaceutical compositions for oral or intravenous administration to patients suffering from conditions such as Parkinson's disease which can exhibit themselves as progressive loss of central nervous system function. The compounds can arrest or slow the progressive loss of function.

  一组苯甲酰胺化合物被披露，可用于治疗神经退行性疾病。提供了制备这些化合物的方法。这些材料被制成药物组合物，用于口服或静脉注射给患有帕金森病等疾病的患者，这些疾病可能表现为中枢神经系统功能的进行性丧失。这些化合物可以阻止或减缓功能的进行性丧失。
• Benzamide therapeutics for the treatment of inflammatory bowel disease
  申请人：Centaur Pharmaceuticals, Inc.

  公开号：US06194465B1

  公开（公告）日：2001-02-27

  Benzamides are disclosed to be useful for treating and preventing inflammatory bowel disease.

  苯甲酰胺被披露为治疗和预防炎症性肠病的有用药物。