(4-硝基苯基)-氨基甲酸苯甲酯 | 53821-12-8

• 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-硝基苯基)-氨基甲酸苯甲酯
• 英文名称: benzyl 4-(nitro)phenylcarbamate
• 英文别名: benzyl N-(4-nitrophenyl)carbamate
• CAS: 53821-12-8
• 化学式: C₁₄H₁₂N₂O₄
• mdl: MFCD00429113
• 分子量: 272.26
• InChiKey: CCBJUOVCMNSVPT-UHFFFAOYSA-N

物化性质

• 熔点：
  155 °C
• 沸点：
  402.8±38.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、DMSO（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: Benzyl N-(4-nitrophenyl)carbamate
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: Benzyl N-(4-nitrophenyl)carbamate
CAS number: 53821-12-8

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C14H12N2O4
Molecular weight: 272.3

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (4-硝基苯基)-氨基甲酸苯甲酯 在 1,1,3,3-四甲基二硅氧烷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到n-(4-氨基苯基)氨基甲酸苄酯
  参考文献：
  名称：

  A magnetically separable gold catalyst for chemoselective reduction of nitro compounds

  摘要：

  制备了一种磁性可分离的金纳米粒子催化剂，并显示出对硝基苯与氢硅烷进行化学选择性还原的优异活性。

  DOI：

  10.1039/c2ob27025k
• 作为产物：
  描述：

  N-(苄羰氧基)羟基胺 在 potassium tert-butylate 作用下， 生成 (4-硝基苯基)-氨基甲酸苯甲酯
  参考文献：
  名称：

  Sheradsky,T.; Salemnick,G., Israel Journal of Chemistry, 1972, vol. 10, p. 857 - 866

  摘要：

  DOI：

文献信息

• Palladium/Phosphorus-Doped Porous Organic Polymer as Recyclable Chemoselective and Efficient Hydrogenation Catalyst under Ambient Conditions
  作者：Zong-Cang Ding、Cun-Yao Li、Jun-Jia Chen、Jia-Hao Zeng、Hai-Tao Tang、Yun-Jie Ding、Zhuang-Ping Zhan

  DOI：10.1002/adsc.201700374

  日期：2017.7.3

  A new type of phosphorus‐doped porous organic polymer (POP) has been readily synthesized through a Heck reaction, which could be used not only as a support but also a ligand for palladium nanoparticles. The dual‐functional material supported palladium nanocatalyst was used for the efficient and chemoselective hydrogenation of varieties of nitroarenes and α,β‐unsaturated compounds, as well as for the

  通过Heck反应很容易地合成了一种新型的掺磷多孔有机聚合物（POP），它不仅可以用作载体，而且可以用作钯纳米粒子的配体。双功能材料负载的钯纳米催化剂可用于多种硝基芳烃和α，β-不饱和化合物的高效化学选择加氢，以及在室温下于绿色溶剂中于1atm氢气下由2-硝基苯基乙腈合成吲哚。 。在反应进行十次后，没有观察到新纳米催化剂的明显聚集和催化活性的损失。
• Simple one-pot synthesis of Rh–Fe3O4 heterodimer nanocrystals and their applications to a magnetically recyclable catalyst for efficient and selective reduction of nitroarenes and alkenes
  作者：Youngjin Jang、Seyoung Kim、Samuel Woojoo Jun、Byung Hyo Kim、Sunhwan Hwang、In Kyu Song、B. Moon Kim、Taeghwan Hyeon

  DOI：10.1039/c0cc04816j

  日期：——

  A simple synthesis of Rh–Fe3O4 heterodimer nanocrystals was achieved by controlled one-pot thermolysis. The nanocrystals exhibited excellent activities for the selective reduction of nitroarenes and alkenes. Furthermore the nanocrystal catalyst could be easily separated by a magnet, and recycled eight times without losing the catalytic activity.

  通过控制一步热解法，成功合成了Rh–Fe3O4异二聚体纳米晶。这些纳米晶对硝基苯和烯烃的选择性还原表现出优异的活性。此外，纳米晶催化剂可以通过磁铁轻松分离，并且在不损失催化活性下可以循环使用八次。
• Fe3O4 Nanoparticles: A Conveniently Reusable Catalyst for the Reduction of Nitroarenes Using Hydrazine Hydrate
  作者：Seyoung Kim、Eunsuk Kim、B. Moon Kim

  DOI：10.1002/asia.201100311

  日期：2011.8.1

  A magnetic personality: Commercially available Fe3O4 nanoparticles were utilized for efficient nitroarene reductions, and could be recycled up to 10 times using magnetic separation, whilst retaining activity (99 % aniline yield in each case without any side‐products). Excellent chemoselectivity for reduction of the nitro versus other functional groups, such as halogen, ester, O‐benzyl, and N‐Cbz groups

  磁性：可利用市售的Fe 3 O 4纳米颗粒有效地还原硝基芳烃，并通过磁分离可回收多达10次，同时保持活性（在每种情况下苯胺产率均为99％，无任何副产物）。观察到与硝基，卤素，酯，O-苄基和N- Cbz基等其他官能团相比，还原硝基具有出色的化学选择性。
• Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids
  作者：Ali Reza Sardarian、Iman DindarlooInaloo、Milad Zangiabadi

  DOI：10.1007/s10562-017-2277-0

  日期：2018.2

  An efficient, selective and cost-effective procedure has been developed for mono N-arylation of primary alkyl and benzyl carbamates with aryl iodides and bromides by incorporating CuI as an inexpensive and commercially available catalyst. Despite previous reports on C–N coupling reactions, this process does not need expensive ligands and takes advantage of readily available and inexpensive ethylenediamine

  通过引入 CuI 作为廉价且市售的催化剂，已开发出一种高效、选择性和成本效益高的程序，用于伯烷基和苄基氨基甲酸酯与芳基碘化物和溴化物的单 N-芳基化。尽管之前有关于 C-N 偶联反应的报道，但该过程不需要昂贵的配体，并且利用容易获得且价格低廉的乙二胺 (EDA) 作为配体。反应时间相对较短，并且以极好的收率获得了相关的 N-芳基化氨基甲酸酯。有趣的是，用 Cu(OAc)2 代替 CuI 使我们能够使用芳基硼酸作为该反应的偶联伙伴。所有产品均通过 1H- 和 13C-NMR、MS、熔点、IR 和 CHNS 技术进行了充分表征。图形摘要
• Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI
  作者：Ralph N Salvatore、Feixia Chu、Advait S Nagle、Elona A Kapxhiu、Richard M Cross、Kyung Woon Jung

  DOI：10.1016/s0040-4020(02)00286-7

  日期：2002.4

  Novel solution and solid-phase methods for the synthesis of carbonates and carbamates were developed using cesium bases and TBAI via a three-component coupling. Cesium carbonate not only promoted successful carbonylations of alcohols and carbamations of amines, but also suppressed common side reactions traditionally seen using existing protocols. Various alcohols and amines were examined, using a wide

  利用铯碱和TBAI，通过三组分偶联，开发了用于合成碳酸盐和氨基甲酸酯的新型溶液和固相方法。碳酸铯不仅可以促进醇的成功羰基化和胺的氨基甲酸酯化，而且还可以抑制传统上使用现有方案观察到的常见副反应。使用各种各样的烷基卤化物检查了各种醇和胺，结果表明该方法具有高度的化学选择性。特别地，使用对空间有要求的底物或氨基酸衍生物只能提供相应的产物，从而提供了广泛的应用，例如新颖的保护基和拟肽合成。