1,3-二溴-5-硝基苯 | 6311-60-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 1,3-二溴-5-硝基苯
• 中文别名: 3,5-二溴硝基苯；1,3-二溴硝基苯
• 英文名称: 3,5-dibromonitrobenzene
• 英文别名: 1,3-dibromo-5-nitrobenzene；3,5-Dibromnitrobenzol
• CAS: 6311-60-0
• 化学式: C₆H₃Br₂NO₂
• 分子量: 280.903
• InChiKey: ZWBHGBWABMAWOV-UHFFFAOYSA-N

物化性质

• 熔点：
  103.0 to 107.0 °C
• 沸点：
  290.5°C (rough estimate)
• 密度：
  2.2414 (rough estimate)
• 最大波长(λmax)：
  260nm(Cyclohexane)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• 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
• 危险品标志：
  Xi
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1,3-Dibromo-5-nitrobenzene
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: 1,3-Dibromo-5-nitrobenzene
CAS number: 6311-60-0

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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: C6H3Br2NO2
Molecular weight: 280.9

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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

制备方法与用途

1,3-二溴-5-硝基苯主要用作医药、有机合成及OLED材料的中间体。

反应信息

• 作为反应物：
  描述：

  1,3-二溴-5-硝基苯 在 硫酸 、 铁粉 、 sodium nitrite 作用下， 生成 2,4-二溴硝基苯
  参考文献：
  名称：

  Holleman, Recueil des Travaux Chimiques des Pays-Bas, 1906, vol. 25, p. 202

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二硝基苯 在 ammonium sulfide 作用下， 生成 1,3-二溴-5-硝基苯
  参考文献：
  名称：

  Koerner, Gazzetta Chimica Italiana, 1874, vol. 4, p. 341

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-Bromo-5-(pyridin-3-ylamino)-phenol 、 sodium;hydride 、 叔丁基二苯基氯硅烷 在 氩 、 水 、 Brine 、 magnesium sulfate 、 crude product 、 1,3-二溴-5-硝基苯 、 ethyl acetate heptane 作用下， 以 N,N-二甲基甲酰胺 、 甲基叔丁基醚 为溶剂， 反应 21.0h， 以[3-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amine (21.2 g, 96%) was obtained as a yellow resin的产率得到[3-bromo-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amine
  参考文献：
  名称：

  Anti-cancer agents and uses thereof

  摘要：

  本发明涉及新颖化合物及其盐、合成方法和用作抗癌药物的用途。这些化合物包括公式I的化合物及其溶剂化物、水合物和药学上可接受的盐，其中A1为N或CR1；A3为N或CR3；A5为N或CR5；R1、R3-R6和L在规范中有定义；n为0或1；X为环部分有6-10个碳的可选取代芳基、环部分有1-3个氮原子的可选取代6元杂芳基、环部分有0-4个氮原子且可选取代环部分有1个硫原子或1个氧原子的可选取代5元杂芳基，或者是6元环与5元环或6元环融合的可选取代杂芳基，其中在每种情况下，1、2、3或4个环原子独立选择自氮、氧和硫的杂原子。它们对广泛的癌症有效，特别是对白血病、非小细胞肺癌和结肠癌有效。

  公开号：

  US20060270686A1

文献信息

• Highly Efficient and Chemoselective Hydrogenation of Nitro Compounds into Amines by Nitrogen-Doped Porous Carbon-Supported Co/Ni Bimetallic Nanoparticles
  作者：Zeyu Shen、Lirui Hong、Baishu Zheng、Guanyu Wang、Beibei Zhang、Zhaoxu Wang、Feiyang Zhan、Shaohua Shen、Ruirui Yun

  DOI：10.1021/acs.inorgchem.1c02740

  日期：2021.11.1

  A novel Co/Ni bimetallic nanoparticle supported by nitrogen-doped porous carbon (NPC), Co5/Ni@NPC-700, exhibits high conversion, chemoselectivity, and recyclability in the hydrogenation of 16 different nitro compounds into desired amines with hydrazine hydrate under mild conditions. The synergistic effects of Co/Ni bimetal nanoparticles and the NPC-supported porous honeycomb structure with more accessible

  一种由掺氮多孔碳 (NPC) Co 5 /Ni@NPC-700负载的新型 Co/Ni 双金属纳米颗粒，在 16 种不同的硝基化合物与水合肼加氢成所需胺的过程中表现出高转化率、化学选择性和可回收性条件温和。Co/Ni双金属纳米粒子和具有更易接近的活性位点的NPC支撑的多孔蜂窝结构的协同效应可能是高催化加氢性能的原因。
• Fe/Fe₃C Encapsulated in N-Doped Carbon Tubes: A Recyclable Catalyst for Hydrogenation with High Selectivity
  作者：Ruirui Yun、Shi Zhang、Wanjiao Ma、Xiao Lv、Shoujie Liu、Tian Sheng、Suna Wang

  DOI：10.1021/acs.inorgchem.9b01332

  日期：2019.7.15

  been designed and prepared by grinding a mixture of MIL-88d and melamine, and then the mixture was followed by pyrolysis. An unusual Fe/Fe3C-activated site is uniformly encapsulated in the N-doped carbon tubes obtained by pyrolysis of the film-like nanocrystals of MIL-88d. Experimental characterizations and theoretical calculations demonstrate that the surface N sites can effectively trap the nitrobenzene

  本文中，已经通过研磨MIL-88d和三聚氰胺的混合物来设计和制备一系列Fe基催化剂，然后对该混合物进行热解。一个不寻常的Fe / Fe 3 C活化位点均匀地封装在通过热解MIL-88d的薄膜状纳米晶体而获得的N掺杂碳管中。实验特性和理论计算表明，表面N位可以有效地俘获硝基苯和苯胺的苯基，并形成三个C–N键，这使该催化剂表现出优异的催化活性（周转率≤11268h –1计算）。 （在硝基苯的基础上）和在选择性条件下还原硝基衍生物的化学选择性。
• 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。
• <i>meta</i> ‐Nitration of Arenes Bearing <i>ortho</i> / <i>para</i> Directing Group(s) Using C−H Borylation
  作者：Xuejing Li、Xingwang Deng、Anthony G. Coyne、Rajavel Srinivasan

  DOI：10.1002/chem.201901633

  日期：2019.6.18

  of arenes bearing ortho/para directing group(s) using the iridium‐catalyzed C−H borylation reaction followed by a newly developed copper(II)‐catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one‐pot fashion. This protocol allows the synthesis of meta‐nitrated arenes that are tedious to prepare or require multistep synthesis using the existing

  在本文中，我们报道了荟萃芳烃的-nitration轴承邻/对位用铱催化的C-H硼化反应之后是新开发的铜（II）粗频哪醇的芳基硼酸酯入的催化的变换引导组（多个）以一锅的方式对应的硝基芳烃。该协议允许的合成元-nitrated芳烃是乏味来制备或使用现有的方法需要多步合成。该反应可耐受多种邻位/对位导向基团，例如-F，-Cl，-Br，-CH 3，-Et，-i Pr -OCH 3和-OCF 3。它还提供对π电子缺陷杂环的硝基衍生物（例如吡啶和喹啉衍生物）的区域选择性访问。该方法的应用在复杂分子的后期修饰中以及在以克级制备到FDA批准的药物Nilotinib途中的中间体中得到了证明。最后，我们证明了通过该策略获得的硝基产物也可以通过Baran的胺化方案直接转化为苯胺或受阻胺。
• 1-Aryl-3,3-dialkyltriazenes: A Convenient Synthesis from Dry Arenediazonium o-Benzenedisulfonimides - A High Yield Break Down to the Starting Dry Salts and Efficient Conversions to Aryl Iodides, Bromides and Chlorides
  作者：Margherita Barbero、Iacopo Degani、Nicola Diulgheroff、Stefano Dughera、Rita Fochi

  DOI：10.1055/s-2001-18072

  日期：——

  Synthesis 2001, No. 14, 26 1

  综合 2001, No. 14, 26 1