2-溴-1-碘-4-硝基苯 | 7149-14-6

• 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: 2-溴-1-碘-4-硝基苯
• 中文别名: 3-溴-4-碘硝基苯
• 英文名称: 2-bromo-1-iodo-4-nitrobenzene
• 英文别名: 3-bromo-4-iodonitrobenzene；2-bromo-1-iodo-4-nitro-benzene；2-Brom-1-jod-4-nitro-benzol
• CAS: 7149-14-6
• 化学式: C₆H₃BrINO₂
• 分子量: 327.904
• InChiKey: CJUZKENURNQSDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  332.7±27.0 °C(Predicted)
• 密度：
  2.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Bromo-1-iodo-4-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: 2-Bromo-1-iodo-4-nitrobenzene
CAS number: 7149-14-6

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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, refrigerated.
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: C6H3BrINO2
Molecular weight: 327.9

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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, hydrogen Iodide.

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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：

  2-溴-1-碘-4-硝基苯 在 palladium diacetate 、 四(三苯基膦)钯 sodium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 3-(4-硝基苯基)-吡啶
  参考文献：
  名称：

  C−H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions

  摘要：

  [GRAPHICS]Biaryl bromides such as 1 (R=NO2, H, OMe) undergo the Heck reaction to give both the expected products 3 ("retention") as well as "crossover" products 4 derived from a migration of Pd and net transfer of reactivity from one aryl ring to the other. Under the conditions used, crossover is increasingly favored when electron-deficient arenes are involved. Crossover products derived from transfer onto the pyridine ring have also been observed.

  DOI：

  10.1021/ol026426v
• 作为产物：
  描述：

  1,2-二溴-4-硝基苯 在 乙醇 、 氨 作用下， 生成 2-溴-1-碘-4-硝基苯
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• A Pd-catalyzed optional approach for the synthesis of dibenzothiophenes
  作者：Juan Song、Hao Wu、Wei Sun、Songjiang Wang、Haisen Sun、Kang Xiao、Yan Qian、Chao Liu

  DOI：10.1039/c8ob00235e

  日期：——

  A direct and practical approach for the construction of DBTs was developed via a Pd-catalyzed tandem reaction, in which commercially available o-bromo-iodobenzenes combined with benzene thiols or iodobenzenes combined with o-bromo-benzene thiols were applied. These two approaches will provide an alternative for the synthesis of DBT derivatives.

  通过Pd催化的串联反应，开发了一种直接实用的DBT方法，其中应用了可商购的邻溴代碘代苯与苯硫醇结合或碘代苯结合了邻溴代苯硫醇。这两种方法将为DBT衍生物的合成提供替代方法。
• [EN] DIHYDROBENZOXAZINE AND TETRAHYDROQUINOXALINE SODIUM CHANNEL INHIBITORS<br/>[FR] INHIBITEURS DES CANAUX SODIQUES DE TYPE DIHYDROBENZOXAZINE ET TÉTRAHYDROQUINOXALINE
  申请人：AMGEN INC

  公开号：WO2013122897A1

  公开（公告）日：2013-08-22

  The present invention provides compounds of Formula I, or pharmaceutically acceptable salts thereof, that are inhibitors of voltage-gated sodium channels, in particular Nav 1.7. The compounds are useful for the treatment of diseases treatable by inhibition of sodium channels such as pain disorders. Also provided are pharmaceutical compositions containing compounds of the present invention.

  本发明提供了式I的化合物或其药学上可接受的盐，这些化合物是电压门控钠通道的抑制剂，特别是Nav 1.7。这些化合物对于治疗可通过抑制钠通道治疗的疾病，如疼痛障碍，是有用的。还提供了含有本发明化合物的药物组合物。
• Tribromoisocyanuric Acid in Trifluoroacetic Acid: An Efficient System for Smooth Brominating of Moderately Deactivated Arenes
  作者：Marcio de Mattos、Pierre Esteves、Leonardo de Almeida

  DOI：10.1055/s-0032-1317795

  日期：——

  deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48–85% isolated yield. This medium avoids the polybromination of the substrate, ­observed in the same reaction performed in 98% H 2 SO 4 .

  中度失活的芳烃通过与三溴异氰脲酸（0.34 摩尔当量）在室温下在三氟乙酸中反应而被有效溴化，分离产率为 48-85%。这种介质避免了底物的多溴化，在 98% H 2 SO 4 中进行的相同反应中观察到。
• Rhodium-Catalyzed Synthesis and Optical Properties of Silicon-Bridged Arylpyridines
  作者：Ryo Shintani、Nana Misawa、Ryo Takano、Kyoko Nozaki

  DOI：10.1002/chem.201605000

  日期：2017.2.21

  on the benzene ring, as well as through the protonation or alkylation of the nitrogen atom on the pyridine ring. A catalytic asymmetric synthesis of silicon‐centered axially chiral spirocyclic derivatives has also been achieved with high enantioselectivity by using a newly modified MeO‐MOP (MeO‐MOP=2‐(diphenylphosphino)‐2′‐methoxy‐1,1′‐binaphthyl) derivative as the chiral ligand. These spirocyclic compounds

  通过含硅的二炔与腈的铑催化的[2 + 2 + 2]环加成反应，已开发了桥连的4-芳基吡啶的会聚和区域选择性合成方法。已经检查了这些化合物的吸收和发射性质，可以通过改变苯环上的取代基以及通过吡啶环上氮原子的质子化或烷基化来对其进行调节。通过使用新改性的MeO-MOP（MeO-MOP = 2-（二苯基膦基）-2'-甲氧基-1,1'-联萘基），还以高对映选择性实现了以硅为中心的轴向手性螺环衍生物的催化不对称合成。衍生物作为手性配体。发现这些螺环化合物具有CPL活性（CPL =圆偏振发光），
• Pd/Cu-Catalyzed Cascade C(sp³)–H Arylation and Intramolecular C–N Coupling: A One-Pot Synthesis of 3,4-2<i>H</i>-Quinolinone Skeletons
  作者：Han-Zhi Xiao、Wen-Shu Wang、Yu-Song Sun、Hao Luo、Bo-Wen Li、Xiao-Dong Wang、Wei-Li Lin、Fei-Xian Luo

  DOI：10.1021/acs.orglett.9b00214

  日期：2019.3.15

  In this letter, we successfully explored a cascade Pd/Cu-catalyzed intermolecular C(sp3)–H arylation of amides and intramolecular C–N coupling reaction. This method provides a one-pot strategy to synthesize 3,4-2H-quinolinone with good regioselectivity of C–H arylation and C–N coupling from C–I and C–X bonds from readily available starting materials.

  在这封信中，我们成功地探索了级联Pd / Cu催化的酰胺间C（sp 3）-H芳基化和分子内C-N偶联反应。该方法提供了一种一锅法，可从容易获得的起始原料中合成具有良好的C–H芳基化区域选择性和C–N和C–N键的C–N区域选择性的3,4-2 H-喹啉酮。