1-叔丁氧基-4-硝基苯 | 2109-72-0

• 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: 1-叔丁氧基-4-硝基苯
• 英文名称: 4-tert-butoxy-1-nitrobenzene
• 英文别名: 1-(tert-butoxy)-4-nitrobenzene；4-(tert-Butoxy)nitrobenzene；1-[(2-methylpropan-2-yl)oxy]-4-nitrobenzene
• CAS: 2109-72-0
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD03094683
• 分子量: 195.218
• InChiKey: WQGIOEFHXBODQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-(tert-Butoxy)-4-nitrobenzene
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-(tert-Butoxy)-4-nitrobenzene
CAS number: 2109-72-0

---

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.
Storage: Store in closed vessels, refrigerated.

---

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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H13NO3
Molecular weight: 195.2

---

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：

  1-叔丁氧基-4-硝基苯 在 palladium on activated charcoal 盐酸 、 sodium azide 、 氢气 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 4-tert-butoxyphenyl azide
  参考文献：
  名称：

  对-芳氧基和对烷氧基苯基硝酸re离子的光化学生成及其在水中的寿命

  摘要：

  本文描述了以下4X-C的水溶液照射产品和闪光光解的研究6 ħ 4 Ñ 3 [X =的MeO（12A），环氧乙烷（12B），镨我O（图12C），卜吨O（12D），C 6 H 5 O（12e），4-MeOC 6 H 4 O（12f），F，Cl]和4-甲氧基-1-萘叠氮化物（15）。p苯醌（或1,4-萘），观察到作为产品，与图12a-d，15％，40％与12E，26％，4-F，用4-氯15％的70-90％的产率。醌是通过一种途径产生的，通过溶剂水分子的质子化作用，将最初形成的单线态芳基亚硝烯淬灭，形成亚硝酸根离子。该阳离子在水合处的水合对位通过半缩醛（或卤代醇）到达醌亚胺，后者水解产生最终的醌产物。观察到三个动力学过程，即在µs时间尺度上的nitr水合，在ms时间尺度上的半缩醛分解以及在分钟时间尺度上的亚胺水解。硝酸根离子在水溶液中的寿命为50 ns（4-PhO），70 ns（4-MeOC 6 H

  DOI：

  10.1039/a807567k
• 作为产物：
  描述：

  N,N-二甲基对硝基苯胺 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-叔丁氧基-4-硝基苯
  参考文献：
  名称：

  从苯胺到芳醚：一种温和条件下的简便，高效且多功能的合成方法

  摘要：

  我们通过醇/酚（ROH）与芳基铵盐（ArNMe反应开发了用于芳基醚的合成的简单且直接的方法3 +），它很容易从苯胺制备（ArNR' 2，R'= H或Me） 。该反应在室温下顺利地且快速地进行（在几个小时内）在市售的碱，例如KO的存在吨卜或KHMDS，并具有相对于二者ROH和ArNR'宽的底物范围2。它具有可扩展性，并且与各种功能组兼容。

  DOI：

  10.1002/anie.201712618

文献信息

• Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings
  作者：Noriyasu Kataoka、Quinetta Shelby、James P. Stambuli、John F. Hartwig

  DOI：10.1021/jo025732j

  日期：2002.8.1

  aryl halides coupled with acyclic or cyclic secondary alkyl- and arylamines, with primary alkyl- and arylamines, and with aryl- and primary alkylboronic acids. These last couplings provide the first general procedure for reaction of terminal alkylboronic acids with aryl halides without toxic or expensive bases. The ligand not only generates highly active palladium catalysts, but it is air stable in

  已通过两步合成程序以高收率制备了五苯基二茂铁基二叔丁基膦，并且已研究了由带有该配体的配合物催化的各种交叉偶联过程的范围。该配体为芳基卤化物胺化和Suzuki偶联产生了非常普通的钯催化剂。对于未活化的芳基溴化物或氯化物的胺化，观察到的营业额约为1000。另外，该配体的络合物在温和条件下催化形成选定的芳基醚。反应包括富电子和贫电子的芳基溴化物和氯化物。在含有该配体的催化剂的存在下，这些芳基卤化物与无环或环状仲烷基和芳基胺，伯烷基和芳基胺，以及芳基和伯烷基硼酸偶联。这些最后的偶联为末端烷基硼酸与芳基卤化物的反应提供了第一个通用方法，而没有毒性或昂贵的碱。该配体不仅产生高活性的钯催化剂，而且在溶液和固态中都是空气稳定的。该配体的钯（0）配合物也具有空气稳定性，为固体，仅与溶液中的氧气缓慢反应。
• Catalyst for aromatic C—O, C—N, and C—C bond formation
  申请人：Yale University

  公开号：US06562989B2

  公开（公告）日：2003-05-13

  The present invention is directed to a transition metal catalyst, comprising a Group 8 metal and a ligand having the structure wherein R, R′ and R″ are organic groups having 1-15 carbon atoms, n=1-5, and m=0-4. The present invention is also directed to a method of forming a compound having an aromatic or vinylic carbon-oxygen, carbon-nitrogen, or carbon-carbon bond using the above catalyst. The catalyst and the method of using the catalyst are advantageous in preparation of compounds under mild conditions of approximately room temperature and pressure.

  本发明涉及一种过渡金属催化剂，包括一种第8族金属和具有结构的配体 其中R、R'和R"是具有1-15个碳原子的有机基团，n=1-5，m=0-4。本发明还涉及一种利用上述催化剂形成具有芳香性或乙烯基碳-氧、碳-氮或碳-碳键的化合物的方法。该催化剂和使用该催化剂的方法在大约室温和压力下的温和条件下制备化合物具有优势。
• Boron-Promoted Ether Interchange Reaction: Synthesis of Alkyl Nitroaromatic Ethers from Methoxynitroarenes
  作者：Zhenwei Liu、Nannan Luan、Hongtao Lu、Apeng Liang、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1002/ejoc.201901779

  日期：2020.2.14

  for boron‐promoted ether interchange reaction of methoxynitroarenes is reported. A series of methoxynitroarenes and alcohols, including primary, secondary, as well as tertiary alcohols, reacted smoothly in moderate to good yields under the optimized reaction conditions. This protocol is an operationally simple and scalable strategy for the synthesis of alkyl nitroaromatic ethers.

  报道了第一个硼促进甲氧基硝基芳烃的醚交换反应的方案。在优化的反应条件下，一系列的甲氧基硝基芳烃和醇，包括伯醇，仲醇和叔醇，以中等至良好的收率平稳反应。该协议是用于烷基硝基芳族醚合成的操作简单且可扩展的策略。
• Room Temperature, Metal-Free Arylation of Aliphatic Alcohols
  作者：Raju Ghosh、Erik Lindstedt、Nazli Jalalian、Berit Olofsson

  DOI：10.1002/open.201402006

  日期：2014.4

  are demonstrated as efficient arylating agents of aliphatic alcohols under metal‐free conditions. The reaction proceeds at room temperature within 90 min to give alkyl aryl ethers in good to excellent yields. Aryl groups with electron‐withdrawing substituents are transferred most efficiently, and unsymmetric iodonium salts give chemoselective arylations. The methodology has been applied to the formal

  在无金属条件下，二芳基碘盐被证明是脂肪醇的有效芳基化剂。反应在室温下在 90 分钟内进行，以良好至极好的收率得到烷基芳基醚。具有吸电子取代基的芳基转移最有效，不对称碘盐会产生化学选择性芳基化。该方法已应用于丁氧卡因的正式合成。
• Efficient Methods for the Preparation of Alkyl−Aryl and Symmetrical or Unsymmetrical Dialkyl Ethers between Alcohols and Phenols or Two Alcohols by Oxidation−Reduction Condensation
  作者：Taichi Shintou、Teruaki Mukaiyama

  DOI：10.1021/ja0487877

  日期：2004.6.1

  generated in situ from chlorodiphenylphosphine (2) and alcohols, 2,6-dimethyl-1,4-benzoquinone (3), and phenols proceeds smoothly to afford alkyl-aryl ethers in good to high yields under neutral conditions. In a similar fashion, a new and efficient method for the preparation of symmetrical or unsymmetrical dialkyl ethers in good to high yields is established via tetrafluoro-1,4-benzoquinone (fluoranil) (4)

  通过烷氧基二苯基膦（二苯基亚膦酸酯）（1）进行氧化还原缩合，由氯二苯基膦（2）和醇、2,6-二甲基-1,4-苯醌（3）原位生成，苯酚顺利进行，得到烷基芳基醚在中性条件下产量良好。以类似的方式，通过四氟-1,4-苯醌（荧苯胺）（4）、醇类和 1 由（ n) BuLi 处理的醇和 2. 该方法也适用于具有保留或反转构型的手性仲醇或叔醇的醚化。通过处理手性烷氧基二苯基膦和非手性醇得到反相醚，