5-溴-2-碘苯胺 | 64085-52-5

• 物质功能分类: 医药中间体
• 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-碘苯胺
• 中文别名: 2-碘-5-溴苯胺
• 英文名称: 5-bromo-2-iodoaniline
• 英文别名: 2-iodo-5-bromoaniline
• CAS: 64085-52-5
• 化学式: C₆H₅BrIN
• mdl: MFCD09753734
• 分子量: 297.921
• InChiKey: KISIGYZVSJKAEK-UHFFFAOYSA-N

物化性质

• 熔点：
  55 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  309.5±27.0 °C(Predicted)
• 密度：
  2.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  1

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
• 储存条件：
  存于2-8℃环境中，避免光照，保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-iodoaniline
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: 5-Bromo-2-iodoaniline
CAS number: 64085-52-5

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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: C6H5BrIN
Molecular weight: 297.9

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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

制备方法与用途

5-溴-2-碘苯胺可用作医药化工合成中间体。若吸入该物质，请立即将患者移至新鲜空气处；如皮肤接触，应脱去污染的衣物，并用肥皂水和清水彻底清洗皮肤。如有不适，请及时就医。

反应信息

• 作为反应物：
  描述：

  5-溴-2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 dicobalt octacarbonyl 、 四溴化碳 、 四甲基硫脲 、 lithium di-tert-butylbiphenylide 、 四丁基氟化铵 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， -78.0~70.0 ℃ 、101.33 kPa 条件下， 反应 4.84h， 生成 [1-[(3aS,8bR)-3-methyl-4-(3-methylbut-2-enyl)-2-oxo-1,3a-dihydropyrrolo[2,3-b]indol-8b-yl]-3-methylbut-2-enyl] acetate
  参考文献：
  名称：

  基于炔碳二亚胺的Aza-Pauson-Khand型反应合成六氢吡咯并[2,3- b ]吲哚生物碱

  摘要：

  在70°C下用30 mol％的Co 2（CO）8和30 mol％的TMTU在甲苯中处理后，苯桥炔烃二酰亚胺有效地进行闭环反应，得到吡咯并[2,3- b ]吲哚- 2个收率好。这些条件几乎可以抑制脲衍生物的形成，当在苯中使用10 mol％的Co 2（CO）8和60 mol％的TMTU时，可以一致地观察到。八种六氢吡咯并[2,3 - b ]吲哚生物碱的合成是通过用NaBH处理在C 3a-位引入有角取代基从所得到的吡咯并[2,3 - b ]吲哚-2-酮完成的。4/烷基溴是关键步骤。

  DOI：

  10.1021/jo071137b
• 作为产物：
  描述：

  4'-溴乙酰苯胺 在 盐酸 、 氢氧化钾 、 硝酸 、 potassium iodide 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 24.88h， 生成 5-溴-2-碘苯胺
  参考文献：
  名称：

  Sakamoto, Takao; Kondo, Yoshinori; Iwashita, Shigeki, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1823 - 1828

  摘要：

  DOI：

文献信息

• [EN] QUINOLINE DERIVATIVES AS ALPHA4BETA7 INTEGRIN INHIBITORS<br/>[FR] DÉRIVÉS DE QUINOLÉINE UTILISÉS EN TANT QU'INHIBITEURS DE L'INTÉGRINE ALPHA4BÊTA7
  申请人：GILEAD SCIENCES INC

  公开号：WO2020092375A1

  公开（公告）日：2020-05-07

  The present disclosure provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof as described herein. The present disclosure also provides pharmaceutical compositions comprising a compound of Formula (I), processes for preparing compounds of Formula (I), and therapeutic methods for treating inflammatory disease.

  本公开提供了如下所述的化合物的化学式(I)或其药用可接受的盐。本公开还提供了包含化合物的药物组合物的制备方法，制备化合物的方法以及治疗炎症性疾病的治疗方法。
• Palladium-Catalyzed Aminocyclization–Coupling Cascades: Preparation of Dehydrotryptophan Derivatives and Computational Study
  作者：Belén Vaz、Claudio Martínez、Francisco Cruz、J. Gabriel Denis、Ángel R. de Lera、José M. Aurrecoechea、Rosana Álvarez

  DOI：10.1021/acs.joc.1c00636

  日期：2021.7.2

  Dehydrotryptophan derivatives have been prepared by palladium-catalyzed aminocyclization-Heck-type coupling cascades starting from o-alkynylaniline derivatives and methyl α-aminoacrylate. Aryl, alkyl (primary, secondary, and tertiary), and alkenyl substituents have been introduced at the indole C-2 position. Further variations at the indole benzene ring, as well as the C-2-unsubstituted case, have

  从邻炔基苯胺衍生物和α-氨基丙烯酸甲酯开始，通过钯催化的氨基环化-Heck型偶联级联制备了脱氢色氨酸衍生物。芳基、烷基（伯、仲和叔）和烯基取代基已在吲哚 C-2 位引入。吲哚苯环的进一步变化以及 C-2-未取代的情况均已得到证明。在 C-2 芳基取代的情况下，通过 Sonogashira 偶联制备邻炔基苯胺底物以及随后的环化-偶联级联是使用单一催化剂的一锅法进行的。 DFT 计算揭示了这些反应的反应曲线相对于丙烯酸甲酯或甲基丙烯酸酯的反应以及游离苯胺与其相应氨基甲酸酯的反应之间存在显着差异。这些计算表明，在 C-C 键形成之前的 HX/烯烃交换步骤中释放的烯烃和酸 HX 的性质可能是实验观察到的反应效率差异的原因。
• Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid
  作者：Hiroshi Miyamoto、Tomohiro Hirano、Yoichiro Okawa、Atsuo Nakazaki、Susumu Kobayashi

  DOI：10.1016/j.tet.2013.08.057

  日期：2013.11

  efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic

  已经开发了从碘吲哚合成螺环氧吲哚的有效且方便的方法。该方法最显着的特征是，分子内乌尔曼偶合和克莱森重排以一锅法进行，从而以良好的非对映选择性很好地提供了3-螺-2-氧吲哚。一锅法反应在手性非外消旋叔醇底物上的应用导致手性完全转移到螺环季碳上。使用该方法，完成了（-）-去溴氟乙胺B的不对称全合成。
• Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides
  作者：Shuo Yuan、Dan-Qing Zhang、Jing-Ya Zhang、Bin Yu、Hong-Min Liu

  DOI：10.1021/acs.orglett.9b04241

  日期：2020.2.7

  heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1'-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably

  吲哚和邻苯二甲酸酯是众多天然产物和生物活性分子中的特权杂环骨架。很少有报道结合这两种支架的化合物的合成和生物学评估。在这里，我们提出了第一个无钯催化的无配体双环化反应，该反应能够在温和条件下有效合成3-（1'-吲哚基）-邻苯二甲酸酯（42个实例，产率高达96％）。值得注意的是，仅使用1.0摩尔％的催化剂负载，表明高效率。后期精巧可提供高度功能化的类似物。
• [EN] PYRAZOLE-CONTAINING MACROPHAGE MIGRATION INHIBITORY FACTOR INHIBITORS<br/>[FR] INHIBITEURS DU FACTEUR INHIBITEUR DE MIGRATION DES MACROPHAGES CONTENANT DU PYRAZOLE
  申请人：UNIV YALE

  公开号：WO2019178480A1

  公开（公告）日：2019-09-19

  In one aspect, the invention comprises compounds that bind and inhibit macrophage migration inhibitory factor. In another aspect, the invention provides methods of treating inflammatory disease, neurological disorders and cancer using the compounds of the invention.

  在一个方面，该发明涉及结合并抑制巨噬细胞迁移抑制因子的化合物。在另一个方面，该发明提供使用该发明的化合物治疗炎症性疾病、神经系统疾病和癌症的方法。