1-溴-3-氯-5-碘苯 | 13101-40-1

• 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: 1-溴-3-氯-5-碘苯
• 英文名称: 1-bromo-3-chloro-5-iodobenzene
• 英文别名: 3-bromo-5-chloroiodobenzene；3-chloro-5-bromoiodobenzene；3-iodo-5-bromochlorobenzene；3-bromo-5-chloro-1-iodobenzene
• CAS: 13101-40-1
• 化学式: C₆H₃BrClI
• 分子量: 317.351
• InChiKey: RSGRRCWDCXLEHS-UHFFFAOYSA-N

物化性质

• 熔点：
  85.8℃
• 沸点：
  280.4±25.0℃ (760 Torr)
• 密度：
  2.272±0.06 g/cm3 (20 ºC 760 Torr)
• 闪点：
  123.4±23.2℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 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：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Bromo-3-chloro-5-iodobenzene
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-Bromo-3-chloro-5-iodobenzene
CAS number: 13101-40-1

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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: C6H3BrClI
Molecular weight: 317.3

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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, hydrogen chloride, 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：

  1-溴-3-氯-5-碘苯 在 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 为溶剂， 生成 5′-chloro-3,4″-dinitro-m-terphenyl
  参考文献：
  名称：

  合成和双阳离子的抗原虫活性米三联苯和1,3- Dipyridylbenzene衍生物

  摘要：

  4,4“-Diamidino-米-三联苯（1制备并在体外测定对抗T）和36类似物rypanosoma布氏罗得西亚，克氏锥虫，疟原虫和利什曼原虫亚马孙。23种化合物对T. b具有很高的活性。罗得西亚或恶性疟原虫。最值得注意的是脒1，10，和11与IC 50 4nM的反对的布氏锥虫 罗得香和二甲基四氢嘧啶类似物4和9（IC 50）对恶性疟原虫的值≤3 nM 。双吡啶基酰亚胺酰胺衍生物31对T的效力是苯并咪唑的25倍。克鲁氏菌对亚马逊乳酸杆菌的杀伤力比两性霉素B强。三联苯二胺1和二吡啶基苯类似物23和25分别治愈了感染T.b的4/4小鼠。罗得西亚STIB900具有四个每日5mg / kg的腹膜内剂量，以及与单次剂量的≤10毫克/公斤。衍生物5和28（前药1和25）每只治愈3/4只小鼠，每天四次口服25 mg / kg口服剂量。

  DOI：

  10.1021/jm400508e
• 作为产物：
  描述：

  间氯溴苯 在 喹喔啉 、 palladium(II) trifluoroacetate 、 2-硝基碘苯 、 N-乙酰甘氨酸 、 silver(l) oxide 作用下， 以21 %的产率得到1-溴-3-氯-5-碘苯
  参考文献：
  名称：

  芳烃的空间控制等渗晚期 C-H 碘化

  摘要：

  芳基碘化物是有机化学中的关键基序，因为它们在金属介导的交叉偶联反应中作为关键的多功能性，用于合成和药物发现。这些支架通常由预功能化起始材料间接制备或通过亲电芳香族碘化协议。这些方法因其固有的选择性和/或所需起始材料的可用性而限于特定的区域异构体。在此，我们描述了通过基于双配体的双配体催化剂实现的等距 C-H/C-I 键复分解方法对芳烃进行空间控制的碘化，以实现芳烃限制的非定向 C-H 活化。该协议允许直接访问与传统方法相关的互补产品谱。它的合成效用通过广泛的范围和后期修饰的适用性得到证明。

  DOI：

  10.1039/d3sc00801k

文献信息

• 2-Aminomethylene-5-sulfonylthiazole Inhibitors of Lysyl Oxidase (LOX) and LOXL2 Show Significant Efficacy in Delaying Tumor Growth
  作者：Deborah A. Smithen、Leo M. H. Leung、Mairi Challinor、Rae Lawrence、HaoRan Tang、Dan Niculescu-Duvaz、Simon P. Pearce、Robert Mcleary、Filipa Lopes、Mohammed Aljarah、Michael Brown、Louise Johnson、Graeme Thomson、Richard Marais、Caroline Springer

  DOI：10.1021/acs.jmedchem.9b01112

  日期：2020.3.12

  The lysyl oxidase (LOX) family of extracellular proteins plays a vital role in catalyzing the formation of cross-links in fibrillar elastin and collagens leading to extracellular matrix (ECM) stabilization. These enzymes have also been implicated in tumor progression and metastatic disease and have thus become an attractive therapeutic target for many types of invasive cancers. Following our recently

  细胞外蛋白的赖氨酰氧化酶（LOX）家族在催化原纤维弹性蛋白和胶原蛋白的交联形成中起着至关重要的作用，从而导致细胞外基质（ECM）稳定。这些酶也与肿瘤进展和转移性疾病有关，因此已经成为许多类型的浸润性癌症的有吸引力的治疗靶标。继我们最近发表的发现氨基亚甲基噻吩（AMT）作为有效的口服生物利用LOX / LOXL2抑制剂的工作之后，我们在此报告了一系列双重LOX / LOXL2抑制剂以及一系列LOXL2选择性抑制剂的发现，氨基亚甲基噻唑（AMTz）支架。噻唑核心的掺入通过不可逆的抑制结合模式导致对LOXL2抑制的效力提高。SAR研究使得发现预测性3DQSAR模型成为可能。领先的AMTz抑制剂在自发性乳腺癌基因工程小鼠模型中显示出改善的药代动力学特性和出色的抗肿瘤功效，并显着降低了肿瘤的生长。
• Modular and Selective Arylation of Aryl Germanes (C−GeEt ₃ ) over C−Bpin, C−SiR ₃ and Halogens Enabled by Light‐Activated Gold Catalysis
  作者：Grant J. Sherborne、Avetik G. Gevondian、Ignacio Funes‐Ardoiz、Amit Dahiya、Christoph Fricke、Franziska Schoenebeck

  DOI：10.1002/anie.202005066

  日期：2020.9

  rapid and programmable construction of bi‐ or multiaryls. To this end, the next frontier of synthetic modularity will likely arise from harnessing the coupling space that is orthogonal to the powerful Pd‐catalyzed coupling regime. This report details the realization of this concept and presents the fully selective arylation of aryl germanes (which are inert under Pd0/PdII catalysis) in the presence of

  选择性 C -C偶联是快速、可编程构建双芳基或多芳基的强大策略。为此，合成模块化的下一个前沿可能会产生于利用与强大的 Pd 催化耦合机制正交的耦合空间。该报告详细介绍了这一概念的实现，并提出了在有价值的官能团 C−BPin、C−SiMe 3、C−I、C存在下，芳基锗烷（在 Pd 0 /Pd II催化下呈惰性）的完全选择性芳基化−Br、C−Cl，这反过来又提供了多样化的多样化机会。该方案利用可见光激活与金催化相结合，促进 C−Ge 与芳基重氮盐的选择性偶联。与之前专门针对Ar-N 2 +范围的光/金催化的 Ar-N 2 +偶联相反，我们提出了有效偶联富电子、缺电子、杂环和位阻芳基重氮盐的条件。我们的计算数据表明，虽然缺电子的 Ar-N 2 +盐在蓝光照射下很容易被金激活，但对于激发的富电子 Ar-N 2 +存在竞争性解离失活途径，这需要替代的光-氧化还原方法可实现高效耦合。
• Sterically Controlled Iodination of Arenes via Iridium-Catalyzed C–H Borylation
  作者：Benjamin M. Partridge、John F. Hartwig

  DOI：10.1021/ol303164h

  日期：2013.1.4

  to prepare aryl and heteroaryl iodides by sequential C–H borylation and iodination is reported. The regioselectivity of this process is controlled by steric effects on the C–H borylation step and is complementary to existing methods to form aryl iodides. The iodination of boronic esters has potential for the synthesis of radiolabeled aryl iodides, as demonstrated by the concise synthesis of a potential

  报道了一种通过连续的C–H硼化和碘化制备芳基和杂芳基碘化物的温和方法。该过程的区域选择性由C–H硼化步骤中的空间效应控制，是对现有形成芳基碘化物的方法的补充。硼酸酯的碘化具有放射性标记的芳基碘化物的合成潜力，正如SPECT成像的潜在示踪剂的简明合成所证明的那样。
• Pd ^II ‐Catalyzed Enantioselective C(sp ³ )–H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group
  作者：Li‐Jun Xiao、Kai Hong、Fan Luo、Liang Hu、William R. Ewing、Kap‐Sun Yeung、Jin‐Quan Yu

  DOI：10.1002/anie.202000532

  日期：2020.6.8

  mixture of reactive complexes. We report a PdII‐catalyzed enantioselective β‐C(sp 3)−H arylation reaction of aliphatic ketones using a chiral TDG. A chiral trisubstituted cyclobutane was efficiently synthesized from a mono‐substituted cyclobutane through sequential C−H arylation reactions, thus demonstrating the utility of this method for accessing structurally complex products from simple starting materials

  使用手性瞬态导向基团 (TDG) 是开发 Pd II催化的对映选择性 C(sp 3 )−H 活化反应的一种有前途的方法。然而，这种策略具有挑战性，因为 TDG 上的立体中心通常远离 C−H 键，并且共价连接到底物上的 TDG 和游离 TDG 都能够与 Pd II中心配位，这可能导致混合反应复合物。我们报道了使用手性 TDG 的 Pd II催化的脂肪族酮的对映选择性 β-C( sp 3 )−H 芳基化反应。通过连续的 C-H 芳基化反应，由单取代环丁烷有效合成了手性三取代环丁烷，从而证明了该方法从简单起始原料获得结构复杂产物的实用性。缺电子吡啶酮配体的使用对于观察到的对映选择性至关重要。有趣的是，使用不同的银盐可以逆转对映选择性。
• Chemoselective and Diastereoselective Synthesis of <i>C</i> ‐Aryl Nucleoside Analogues by Nickel‐Catalyzed Cross‐Coupling of Furanosyl Acetates with Aryl Iodides
  作者：Yuxi Li、Zheng Wang、Luyang Li、Xiaoying Tian、Feng Shao、Chao Li

  DOI：10.1002/anie.202110391

  日期：2022.1.3

  The facile synthesis of C-aryl nucleoside analogues from readily available furanose acetates and aryl iodides is disclosed. This nickel-catalyzed cross-electrophile coupling showed good functional-group compatibility and excellent β-selectivity. The high chemoselectivity with respect to aryl iodides enabled the efficient preparation of a variety of C-aryl halide furanosides suitable for various po

  公开了从容易获得的呋喃糖乙酸酯和芳基碘化物轻松合成C-芳基核苷类似物。这种镍催化的交叉亲电偶联表现出良好的官能团相容性和优异的β-选择性。对芳基碘化物的高化学选择性使得能够有效制备适用于各种后官能化反应的各种C-芳基卤化物呋喃糖苷。