4-溴-4'-硝基联苯 | 6242-98-4

• 物质功能分类: 化学试剂 - 有机试剂 - 芳烃
• 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-溴-4'-硝基联苯
• 英文名称: 4'-bromo-4-nitrobiphenyl
• 英文别名: 4-bromo-4'-nitro-1,1'-biphenyl；4-Bromo-4'-nitrobiphenyl；1-(4-bromophenyl)-4-nitrobenzene
• CAS: 6242-98-4
• 化学式: C₁₂H₈BrNO₂
• 分子量: 278.105
• InChiKey: LNYRWXNUGZFNIE-UHFFFAOYSA-N

物化性质

• 熔点：
  173 °C
• 沸点：
  386.9±17.0 °C(Predicted)
• 密度：
  1.521±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温下应存于干燥密封的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-4’-nitrobiphenyl
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: 4-Bromo-4’-nitrobiphenyl
CAS number: 6242-98-4

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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: C12H8BrNO2
Molecular weight: 278.1

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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, hydrogen bromide.

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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：

  4-溴-4'-硝基联苯 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 1-乙炔基-4-(4-硝基苯基)苯
  参考文献：
  名称：

  非线性光学的有机金属配合物。X.分子系统改变（环戊二烯基）的平方和立方超极化率双（膦）钌σ-芳基炔阴离子：钌的X射线晶体结构（（Ë）-4,4'--CCC 6 ħ 4 CHC 6 H ^ 4 NO 2）（PPH 3）2（η-C 5 H ^ 5）

  摘要：

  配合物的Ru（4,4'-CCC 6 H ^ 4 Ç 6 ħ 4 NO 2）（PPH 3）2（η-C 5 H ^ 5）和Ru（4,4'-CCC 6 H ^ 4 Ç CC 6 H ^ 4 NO 2（PPH）3）2（η-C 5 H ^ 5）已经准备好，后者的结构特点；它们属于一系列有机金属供体-桥-受体化合物，其中含有（环戊二烯基）双（膦）钌（II）中心作为供体，共轭芳基乙炔桥和硝基受体基团。为系列复合物的Ru（CCR）（PR'电化学数据3）2（η-C 5 H ^ 5）（RPH，4-C 6 H ^ 4 NO 2，R'博士中，Me; R = 4,4'-C 6 H 4 C 6 H 4 NO 2，（E）-4,4'-C 6 H 4 CHCHC 6 H4 NO 2，4,4'--C 6 H ^ 4 ÇCC 6 H ^ 4 NO 2，4,4'--C 6 H ^ 4 ÑCHC 6 H ^ 4 NO

  DOI：

  10.1016/s0022-328x(97)00411-7
• 作为产物：
  描述：

  对溴碘苯 在 lithium chloro-isopropyl-magnesium chloride 、 tetrafluoroboric acid 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 6.0h， 生成 4-溴-4'-硝基联苯
  参考文献：
  名称：

  通过光激活金催化实现芳基锗烷 (C-GeEt3 ) 在 C-Bpin、C-SiR3 和卤素上的模块化和选择性芳基化。

  摘要：

  选择性 C -C偶联是快速、可编程构建双芳基或多芳基的强大策略。为此，合成模块化的下一个前沿可能会产生于利用与强大的 Pd 催化耦合机制正交的耦合空间。该报告详细介绍了这一概念的实现，并提出了在有价值的官能团 C−BPin、C−SiMe 3、C−I、C存在下，芳基锗烷（在 Pd 0 /Pd II催化下呈惰性）的完全选择性芳基化−Br、C−Cl，这反过来又提供了多样化的多样化机会。该方案利用可见光激活与金催化相结合，促进 C−Ge 与芳基重氮盐的选择性偶联。与之前专门针对Ar-N 2 +范围的光/金催化的 Ar-N 2 +偶联相反，我们提出了有效偶联富电子、缺电子、杂环和位阻芳基重氮盐的条件。我们的计算数据表明，虽然缺电子的 Ar-N 2 +盐在蓝光照射下很容易被金激活，但对于激发的富电子 Ar-N 2 +存在竞争性解离失活途径，这需要替代的光-氧化还原方法可实现高效耦合。

  DOI：

  10.1002/anie.202005066

文献信息

• Azo bond formation on metal surfaces
  作者：Xiangzhi Meng、Henning Klaasen、Lena Viergutz、Bertram Schulze Lammers、Melanie C. Witteler、Harry Mönig、Saeed Amirjalayer、Lacheng Liu、Johannes Neugebauer、Hong‐Ying Gao、Armido Studer、Harald Fuchs

  DOI：10.1002/anie.202011858

  日期：2021.1.18

  precursors containing both an amino and a nitro functionality, azo polymers are prepared on surface via highly efficient nitro‐amino cross‐coupling. Experiments conducted on other substrates and surface orientations reveal that the metal surface has a significant effect on the reaction efficiency. The reaction was further found to proceed from partially oxidized/reduced precursors in dimerization reactions

  通过硝基芳烃和芳胺的氧化还原交叉偶联形成偶氮化合物，这对溶液相化学具有挑战性，这是通过表面化学实现的。反应产物用低温扫描隧道显微镜（STM）和X射线光电子能谱（XPS）进行分析。通过使用精心设计的同时包含氨基和硝基官能团的前体，可通过高效的硝基-氨基交叉偶联在表面制备偶氮聚合物。在其他基材和表面取向上进行的实验表明，金属表面对反应效率有重大影响。进一步发现该反应是由二聚反应中的部分氧化/还原的前体进行的，从而阐明了通过DFT计算研究的机理。
• Synthesis, characterization and catalytic performance of palladium supported on pyridine‐based covalent organic polymer for Suzuki‐Miyaura reaction
  作者：Yi Han、Jia‐Qi Di、Ai‐Dong Zhao、Zhan‐Hui Zhang

  DOI：10.1002/aoc.5172

  日期：2019.10

  bipyridine‐based covalent organic polymer (COP) was successfully synthesized by condensation of trimesoyl chloride (TMC) and 2,2′‐bipyridine‐5,5′‐diamine (Bpy) under ambient conditions. This material was modified by coordination of PdCl2 to COP framework, affording a hybrid material, Pd@TMC‐Bpy COP, which was applied as a highly efficient heterogeneous catalyst for Suzuki‐Miyaura reaction under ligand‐free conditions

  在环境条件下，通过偏苯三酰氯（TMC）和2,2'-联吡啶-5,5'-二胺（Bpy）的缩合成功合成了基于联吡啶的共价有机聚合物（COP）。该材料通过将PdCl 2与COP框架配位而改性，提供了一种杂合材料Pd @ TMC-Bpy COP，可作为高效的非均相催化剂用于Suzuki-Miyaura在无配体条件下在乳酸乙酯中的反应。该催化剂可以重复使用五次而不会明显丧失其活性。
• Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides
  作者：Margherita Barbero、Stefano Dughera

  DOI：10.1016/j.tet.2018.08.018

  日期：2018.9

  Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further

  Arenediazonzon邻苯二磺酰亚胺已被用作Au（I）催化的Suzuki偶联反应中的有效亲电子伙伴。合成规程是通用的，容易的并且以高收率生产联芳基或杂芳基芳烃（51个阳性实例，平均收率80％）。在反应结束时回收邻苯二甲磺酰亚胺，并重新用于制备起始盐以用于进一步的反应。机械学的见解表明，邻苯二磺酰亚胺阴离子起电子转移剂的作用，并促进了不需要光催化剂或外部氧化剂存在的催化循环。
• The nitration of substituted ethylbenzenes and substituted biphenyls
  作者：AH Clemens、MP Hartshorn、KE Richards、GJ Wright

  DOI：10.1071/ch9770103

  日期：——

  Nitration occurs ipso to the ethyl group for p-ethyltoluene, p- diethylbenzene and ethylmesitylene. No evidence was found for ipso- nitration for 2,4,6-trimethyl-, 4-methoxy-, 4-bromo- and 2,2',4,4',6,6'-hexamethoxy-biphenyls.

  对乙基甲苯、对二乙基苯和乙基甲苯胺 对乙基甲苯、对二乙基苯和乙基甲苯乙基。没有发现 4-溴联苯和 2,2',4,4',6,6'-六甲氧基联苯的异硝化。
• Selective Suzuki-Miyaura Monocouplings with Symmetrical Dibromoarenes and Aryl Ditriflates for the One-Pot Synthesis of Unsymmetrical Triaryls
  作者：Corinne Minard、Carole Palacio、Kevin Cariou、Robert H. Dodd

  DOI：10.1002/ejoc.201400090

  日期：2014.5

  parameters that would permit selective Suzuki–Miyaura monocouplings of symmetrical dihaloarenes were studied. High selectivity and efficiency can be obtained for a broad range of substrates by using operationally simple conditions and widely available reagents. The 38 different examples described provide a valuable toolbox for the rapid access to unsymmetrical triaryls, as illustrated by the preparation

  研究了允许对称二卤芳烃选择性 Suzuki-Miyaura 单偶联的各种参数。通过使用操作简单的条件和广泛可用的试剂，可以获得对广泛底物的高选择性和效率。所描述的 38 个不同的例子为快速获取不对称三芳基提供了一个有价值的工具箱，如二芳基吡啶 8、三联苯 9 和二芳基吡咯 10 的制备所示。