3-溴-4-硝基苯胺 | 40787-96-0

• 物质功能分类: 有机原料 - 氨基化合物
• 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: 3-溴-4-硝基苯胺
• 英文名称: 3-bromo-4-nitroaniline
• 英文别名: 3-bromo-4-nitro-aniline；3-Brom-4-nitro-anilin；3-bromo-4-nitro-benzenamine
• CAS: 40787-96-0
• 化学式: C₆H₅BrN₂O₂
• mdl: MFCD07783047
• 分子量: 217.022
• InChiKey: RLAIFIDRVAAEBW-UHFFFAOYSA-N

物化性质

• 熔点：
  259 °C
• 沸点：
  339.3±22.0 °C(Predicted)
• 密度：
  1.812±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  71.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2921420090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromo-4-nitroaniline
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: 3-Bromo-4-nitroaniline
CAS number: 40787-96-0

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H5BrN2O2
Molecular weight: 217

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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：

  3-溴-4-硝基苯胺 生成 2,4-二溴硝基苯
  参考文献：
  名称：

  Lukes; Fragner, Chemicke Listy, vol. 22, p. 324

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-2-硝基苯 在 potassium tert-butylate 、 ammonium pyrrolidinedithiocarbamate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以66%的产率得到3-溴-4-硝基苯胺
  参考文献：
  名称：

  Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen:  Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

  摘要：

  A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The sigma adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkryl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of amination.

  DOI：

  10.1021/jo970582b

文献信息

• [5,6]HETEROCYCLIC COMPOUND
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2565185A1

  公开（公告）日：2013-03-06

  Abstract: An object of the present invention is to provide a novel low molecular weight compound exhibiting an osteogenesis-promoting action. This object is achieved by a compound having the general formula (I) or a pharmacologically acceptable salt thereof. In the general formula (I), R1 and R2 represent hydrogen atoms, and the like; R3 represents a hydrogen atom, and the like; X, Y, and Z represent nitrogen atoms, and the like; A represents a phenylene group, and the like; n represents 1 or 2, and the like; and V and W represent oxygen atoms, and the like.

  摘要：本发明的目的是提供一种表现出促进骨生成作用的新型低分子量化合物。该目的通过具有通式（I）或其药理学可接受的盐的化合物实现。在通式（I）中，R1和R2代表氢原子等；R3代表氢原子等；X、Y和Z代表氮原子等；A代表苯基等；n代表1或2等；V和W代表氧原子等。
• Synthesis of Symmetric Dinitro-Functionalised Tröger's Base Analogues
  作者：M. Delower H. Bhuiyan、Andrew B. Mahon、Paul Jensen、Jack K. Clegg、Andrew C. Try

  DOI：10.1002/ejoc.200801032

  日期：2009.2

  The synthesis of six new examples of 2,8-dinitro-substituted Troger's base analogues are reported, together with the first examples of 1,7-, 3,9- and 4,10-dinitro Troger's base analogues and the first example of a tetranitro Troger's base compound. Several of these dinitro compounds lack substituents at the 2- and 8-positions and therefore provide further examples of Troger's base analogues derived

  报告了 2,8-二硝基取代的 Troger 碱类似物的六个新实例的合成，以及 1,7-、3,9- 和 4,10-二硝基 Troger 碱类似物的第一个实例和 a四硝基 Troger 的碱化合物。这些二硝基化合物中的一些在 2-和 8-位缺少取代基，因此提供了衍生自缺少对位取代基的苯胺的 Troger 碱类似物的进一步实例。
• Synthesis and Pharmacological Evaluation of Isoindolo[1,2-b]quinazolinone and Isoindolo[2,1-a]benzimidazole Derivatives Related to the Antitumor Agent Batracylin
  作者：Sanath K. Meegalla、Gregory J. Stevens、Charlene A. McQueen、Allan Y. Chen、Chiang Yu、Leroy F. Liu、Louis R. Barrows、Edmond J. LaVoie

  DOI：10.1021/jm00046a028

  日期：1994.9

  The synthesis and pharmacological activity of isoindolo[1,2-b]quinazolin-12(10H)-ones and isoindolo[2,1-a]benzimidazoles related to batracylin are described. The acute toxicity of batracyclin has been associated with the formation of its N-acetyl metabolite which is a potent inducer of unscheduled DNA synthesis in rat hepatocytes. The desamino derivative and the 8-aza analog of batracylin retained

  描述了与batracylin有关的异吲哚并[1,2-b]喹唑啉-12（10H）-one和异吲哚并[2,1-a]苯并咪唑的合成及其药理活性。Batracyclin的急性毒性与其N-乙酰代谢产物的形成有关，N-乙酰代谢产物是大鼠肝细胞中非计划DNA合成的有效诱导剂。batracylin的脱氨基衍生物和8-氮杂类似物保留了抑制拓扑异构酶II的能力，但没有诱导计划外的DNA合成。这些类似物虽然不如batracylin活性强，但对CCRF CEM白血病细胞具有细胞毒性。异吲哚并[2，1-a]苯并咪唑衍生物作为拓扑异构酶II抑制剂是无活性的，并且通常不能表现出可比的抗肿瘤活性或无法诱导计划外的DNA合成。
• Discovery of benzophosphadiazine drug candidate IDX375: A novel hepatitis C allosteric NS5B RdRp inhibitor
  作者：Jean-Laurent Paparin、Agnès Amador、Eric Badaroux、Stéphanie Bot、Catherine Caillet、Thierry Convard、Daniel Da Costa、David Dukhan、Ludovic Griffe、Jean-François Griffon、Massimiliano LaColla、Frédéric Leroy、Michel Liuzzi、Anna Giulia Loi、Joe McCarville、Valeria Mascia、Julien Milhau、Loredana Onidi、Claire Pierra、Rachid Rahali、Elodie Rosinosky、Efisio Sais、Maria Seifer、Dominique Surleraux、David Standring、Cyril B. Dousson

  DOI：10.1016/j.bmcl.2017.01.017

  日期：2017.6

  mammalian cells, and as a consequence is an attractive target for selective inhibition. This paper describes the discovery of a novel family of HCV NS5B non-nucleoside inhibitors inspired by the bioisosterism between sulfonamide and phosphonamide. Systematic structural optimization in this new series led to the identification of IDX375, a potent non-nucleoside inhibitor that is selective for genotypes

  丙型肝炎病毒 (HCV) NS5B RNA 依赖性 RNA 聚合酶 (RdRp) 在病毒复制中起核心作用。NS5B 在哺乳动物细胞中没有功能等效物，因此是一个有吸引力的选择性抑制靶标。本文描述了一种新的 HCV NS5B 非核苷抑制剂家族的发现，其灵感来自磺胺和膦酰胺之间的生物等排性。这个新系列的系统结构优化导致了 IDX375 的鉴定，这是一种对基因型 1a 和 1b 具有选择性的强效非核苷抑制剂。IDX375的结构和结合域通过X射线共结晶研究得到证实。
• Synthesis of amino-substituted indoles using the Bartoli reaction
  作者：Laura Wylie、Paolo Innocenti、Daniel K. Whelligan、Swen Hoelder

  DOI：10.1039/c2ob25256b

  日期：——

  We report herein the concise preparation of a range of functionalised aminoindoles via a new application of the Bartoli reaction. Scope and limitations of the methodology have been extensively studied to reveal the importance of protecting groups and substitution patterns. The use of amino substituted nitroanilines for the Bartoli reaction is to our knowledge unprecedented. Our work thus represents

  我们在此报告了通过Bartoli 反应的新应用来简明制备一系列功能化氨基吲哚。该方法的范围和局限性已被广泛研究，以揭示保护基团和取代模式的重要性。据我们所知，使用氨基取代的硝基苯胺进行 Bartoli 反应是前所未有的。因此，我们的工作代表了一种新的进入取代氨基吲哚的方法，它是精细化工和制药行业的相关构件。