5-溴-2-硝基甲苯 | 52414-98-9

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 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: 5-溴-2-硝基甲苯
• 中文别名: 2-溴-5-硝甲苯；2-溴-5-硝基甲苯；4-溴-3-硝基甲苯
• 英文名称: 5-bromo-2-nitrotoluene
• 英文别名: 4-bromo-2-methyl-1-nitrobenzene；4-bromo-2-methyl nitrobenzene
• CAS: 52414-98-9
• 化学式: C₇H₆BrNO₂
• 分子量: 216.034
• InChiKey: PAHAIHXVVJMZKU-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55℃
• 沸点：
  265℃
• 密度：
  1.615
• 闪点：
  114℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-nitrotoluene
Synonyms: 4-Bromo-2-methyl-1-nitrobenzene

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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: 5-Bromo-2-nitrotoluene
CAS number: 52414-98-9

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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: C7H6BrNO2
Molecular weight: 216

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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：

  5-溴-2-硝基甲苯 在 四氢吡咯 、 锌 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-吲哚甲醛
  参考文献：
  名称：

  Metal-halogen exchange of bromoindoles. A route to substituted indoles

  摘要：

  DOI：

  10.1021/jo00376a010
• 作为产物：
  描述：

  厄多司坦 在 2,6-二叔丁基-4-甲基苯酚 、 copper(ll) bromide 、 Oxone 作用下， 以 乙腈 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 以68%的产率得到5-溴-2-硝基甲苯
  参考文献：
  名称：

  亚硝基卤与铜（II）卤化物的对位选择性卤化

  摘要：

  据报道，亚硝基芳烃与溴化铜（II）和氯化物的对位选择性直接溴化和氯化。在温和的反应条件下，以中等至良好的收率和高的区域选择性获得了一系列卤代芳基亚硝基化合物。另外，通过开发一锅法以获得相应的对卤代苯胺和硝基苯衍生物，证明了该方法的多功能性。

  DOI：

  10.1021/acs.orglett.5b03198

文献信息

• Synthesis of <i>meta</i>-Substituted Anilines via Copper-Catalyzed [1,3]-Methoxy Rearrangement
  作者：Itaru Nakamura、Hiroki Tashiro、Yasuhiro Ishida、Masahiro Terada

  DOI：10.1021/acs.orglett.0c01009

  日期：2020.5.15

  copper-catalyzed [1,3]-methoxy rearrangement of N-methoxyanilines followed by Michael addition of nucleophiles to the in situ generated ortho-quinol imine. The present reaction exhibits excellent applicability of para-substituents, such as vinyl, methylthio, ester, and bromo, and carbon nucleophiles, such as 1,3,5-trimethoxybenzene, N-methylindole, and dimethyl malonate. Thus, the present rearrangement can resolve

  通过铜催化的N-甲氧基苯胺的[1,3]-甲氧基重排，然后将亲核试剂迈克尔加成到原位生成的邻苯二酚亚胺，可以高效地合成间位取代的苯胺。本反应显示出对位取代基如乙烯基，甲硫基，酯和溴的良好适用性，以及碳亲核试剂如1,3,5-三甲氧基苯，N-甲基吲哚和丙二酸二甲酯的优异适用性。因此，本发明的重排可以解决由氧化反应引起的问题，例如使用化学计量的氧化剂和吸电子基团的低相容性。
• Design, synthesis and biological evaluation of biphenylamide derivatives as Hsp90 C-terminal inhibitors
  作者：Huiping Zhao、Gaurav Garg、Jinbo Zhao、Elisabetta Moroni、Antwan Girgis、Lucas S. Franco、Swapnil Singh、Giorgio Colombo、Brian S.J. Blagg

  DOI：10.1016/j.ejmech.2014.10.034

  日期：2015.1

  discovery efforts toward Hsp90 C-terminal inhibition focus on novobiocin, an antibiotic that was transformed into an Hsp90 inhibitor. Based on structural information obtained during the development of novobiocin derivatives and molecular docking studies, scaffolds containing a biphenyl moiety in lieu of the coumarin ring present in novobiocin were identified as new Hsp90 C-terminal inhibitors. Structure–activity

  Hsp90 C端功能的调节代表了一种有前途的治疗方法，用于治疗癌症和神经退行性疾病。目前针对Hsp90 C末端抑制的药物发现工作集中在新霉素（一种转化为Hsp90抑制剂的抗生素）上。根据在开发新霉素衍生物和进行分子对接研究期间获得的结构信息，将含有联苯部分代替新霉素中存在的香豆素环的支架鉴定为新的Hsp90 C末端抑制剂。结构-活性关系研究产生了新的衍生物，它们以纳摩尔浓度抑制乳腺癌细胞系的增殖，这直接与Hsp90抑制作用相对应。
• [EN] BIPHENYLAMIDE DERIVATIVE HSP90 INHIBITORS<br/>[FR] INHIBITEURS DE HSP90 DÉRIVÉS DE BIPHÉNYLAMIDE
  申请人：UNIV KANSAS

  公开号：WO2015070091A1

  公开（公告）日：2015-05-14

  Compounds of the formulas are provided: wherein variables Y1-Y5, X1-X5, A1-A4, x, y, n1, n2, and R1-R15 are as defined herein. Pharmaceutical compositions of the compounds are also provided. In some aspects, these compounds are are useful for the treatment of a disease or disorder, including, for example, a proliferative disease, such as cancer.

  提供具有以下公式的化合物：其中变量Y1-Y5、X1-X5、A1-A4、x、y、n1、n2和R1-R15按本文定义。还提供了这些化合物的药物组合物。在某些方面，这些化合物对于治疗一种疾病或失调，包括例如增殖性疾病（如癌症）是有用的。
• INDOLE DERIVATIVES AS CRAC MODULATORS
  申请人：Alam Muzaffar

  公开号：US20110071150A1

  公开（公告）日：2011-03-24

  Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 and R 4 are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with calcium release-activated calcium channels (CRAC).

  公式I的化合物： 或其药用可接受的盐， 其中R1、R2、R3和R4按本文定义。还公开了制造这些化合物的方法以及使用这些化合物治疗与钙释放激活钙通道（CRAC）相关疾病的用途。
• Nitration of deactivated aromatic compounds via mechanochemical reaction
  作者：Jian-Wei Wu、Pu Zhang、Zhi-Xin Guo

  DOI：10.1016/j.tetlet.2021.153087

  日期：2021.5

  A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

  使用Fe（NO 3）3 ·9H 2 O / P 2 O 5作为硝化剂，在高速球磨条件下，各种失活的芳烃都以极高的收率被硝化为相应的硝基衍生物。针对这种面部，生态友好，安全和有效的硝化反应，提出了一种涉及自由基的机制。