2-碘-5-氯吡啶 | 244221-57-6

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-碘-5-氯吡啶
• 中文别名: 5-氯-2-碘嘧啶；5-氯-2-碘吡啶
• 英文名称: 5-chloro-2-iodopyridine
• 英文别名: 2-iodo-5-chloropyridine
• CAS: 244221-57-6
• 化学式: C₅H₃ClIN
• 分子量: 239.443
• InChiKey: CXWLXKZIXLOBCC-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C(Solv: hexane (110-54-3))
• 沸点：
  237.3±20.0 °C(Predicted)
• 密度：
  2.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn,Xi
• 危险类别码：
  R22
• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：室温、避光、惰性气体环境中保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloro-2-iodopyridine
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-Chloro-2-iodopyridine
CAS number: 244221-57-6

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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: C5H3ClIN
Molecular weight: 239.4

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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 chloride, 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

制备方法

医药生物化工中间体。

用途简介

暂无内容。

反应信息

• 作为反应物：
  描述：

  2-碘-5-氯吡啶 在 吡啶 、 羟胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.83h， 生成 5-chloro-N-hydroxypyridine-2-carboxamidine
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of 3-Aryl-5-aryl-1,2,4-oxadiazoles as a New Series of Apoptosis Inducers and Potential Anticancer Agents

  摘要：

  We have identified 5-(3-chlorothiophen-2-yl)-3-(4-trifluoromethylphenyl)-1,2,4-oxadiazole (1d) as a novel apoptosis inducer through our caspase- and cell-based high-throughput screening assay. Compound 1d has good activity against several breast and colorectal cancer cell lines but is inactive against several other cancer cell lines. In a flow cytometry assay, treatment of T47D cells with 1d resulted in arrest of cells in the G, phase, followed by induction of apoptosis. SAR studies of 1d showed that the 3-phenyl group can be replaced by a pyridyl group, and a substituted five-member ring in the 5-position is important for activity. 5-(3-Chlorothiophen-2-yl)-3-(5-chloropyridin-2-yl)-1,2,4-oxadiazole (41) has been found to have in vivo activity in a MX-1 tumor model. Using a photoaffinity agent, the molecular target has been identified as TIP47, an IGF II receptor binding protein. Therefore, our cell-based chemical genetics approach for the discovery of apoptosis inducers can identify potential anticancer agents as well as their molecular targets.

  DOI：

  10.1021/jm050292k
• 作为产物：
  描述：

  2,5-二氯吡啶 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 various solvent(s) 为溶剂， 反应 96.0h， 以52%的产率得到2-碘-5-氯吡啶
  参考文献：
  名称：

  吡啶和其他杂环中甲硅烷基介导的卤素/卤素置换

  摘要：

  用溴三甲基硅烷加热将 2-氯吡啶转化为 2-溴吡啶，将 2-氯-6-甲基吡啶转化为 2-溴-6-甲基吡啶。2-氯吡啶和2-溴吡啶都得到相应的碘化合物。当用原位生成的碘三甲基硅烷处理时。尽管 3- 和 4- 氯吡啶是完全惰性的，但 2,4- 二氯吡啶在 2- 和 4- 位同时进行卤素/卤素交换。卤素置换仅在 2-位与 2,3-二氯吡啶和 2,5-二氯吡啶发生。与作为发生卤素交换的先决条件的 N-三甲基甲硅烷基吡啶鎓盐的中间体一致，2-氟吡啶和 2-氟-6-甲基吡啶和任何 2,6-二卤代吡啶都不发生反应。最后，溴/氯和碘/氯取代也可以用 2-或 4-氯喹啉、1-氯异喹啉、2-氯嘧啶、氯吡嗪和 2,3-二氯喹喔啉作为底物来完成。[在 SciFinder (R) 上]

  DOI：

  10.1002/1099-0690(200212)2002:24<4181::aid-ejoc4181>3.0.co;2-m

文献信息

• Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water
  作者：Maud Bollenbach、Pedro G. V. Aquino、João Xavier de Araújo-Júnior、Jean-Jacques Bourguignon、Frédéric Bihel、Christophe Salomé、Patrick Wagner、Martine Schmitt

  DOI：10.1002/chem.201700832

  日期：2017.10.4

  A simple, sustainable, efficient, mild, and low‐cost protocol was developed for d‐glucose‐assisted Cu‐catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen‐containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because

  开发了一种简单，可持续，高效，温和且低成本的方案，用于葡萄糖在水中的酰胺，氨基甲酸酯和含氮杂环的d葡萄糖辅助的Ullmann反应。该反应与各种芳基/杂芳基碘化物相容，得到高度取代的吡啶，吲哚或吲唑环。该方法为现有方案提供了一种有吸引力的替代方法，因为该反应在水性介质中进行，在环境温度或接近环境温度的条件下进行，并提供高收率或高收率的N-芳基化产物。
• [EN] NEW BICYCLIC THIOPHENYLAMIDE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS THIOPHÉNYLAMIDE BICYCLIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013189841A1

  公开（公告）日：2013-12-27

  The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, A, E and n are as described herein, compositions including the compounds and use thereof as fatty-acid binding protein (FABP) 4/5 inhibitors in the treatment of e.g. type 2 diabetes, atherosclerosis or cancer.

  这项发明提供了具有一般式（I）的新化合物，其中R1、R2、R3、R4、R5、R6、R7、A、E和n如本文所述，包括这些化合物的组合物以及将其用作脂肪酸结合蛋白（FABP）4/5抑制剂，用于治疗例如2型糖尿病、动脉粥样硬化或癌症。
• Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：——

  公开号：US20030045546A1

  公开（公告）日：2003-03-06

  The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: 1 wherein Ar 1 , Ar 3 , A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代的3-芳基-5-芳基-[1,2,4]-噁二唑及其类似物，由以下式I表示： 1 其中Ar1，Ar3，A，B和D在此处定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生未受控制的异常细胞生长和扩散的细胞死亡。
• Lithium trihydroxy/triisopropoxy-2-pyridylborate salts (LTBS): synthesis, isolation, and use in modified Suzuki–Miyaura cross-coupling reactions
  作者：Kuanchiang Chen、Richard Peterson、Shivanand K. Math、James B. LaMunyon、Charles A. Testa、Dustin R. Cefalo

  DOI：10.1016/j.tetlet.2012.06.145

  日期：2012.9

  and triisopropoxy 2-borate salts (LTBS) for use in modified Suzuki–Miyaura cross-coupling reactions that can be produced in quantities greater than one hundred grams. Pyridyl LTBS provide a viable cross-coupling alternative to unstable 2-pyridylboronic acids, boronates, and trifluoroborate salt derivatives. We also demonstrate the synthesis and cross-coupling of shelf-stable LTBS reagents of other sp2-hybridized

  我们在本文中描述了可用于修饰的Suzuki-Miyaura交叉偶联反应的货架稳定，可分离且可表征的吡啶基锂三羟基和三异丙氧基2-硼酸盐（LTBS），其用量可大于100克。吡啶基LTBS为不稳定的2-吡啶基硼酸，硼酸盐和三氟硼酸盐衍生物提供了可行的交叉偶联选择。我们还证明了其他sp 2-杂化的含氮杂环，包括噻唑，吡嗪，喹啉和异喹啉杂环的货架稳定LTBS试剂的合成和交叉偶联。
• Antiproliferative compounds and therapeutic uses thereof
  申请人：Università Degli Studi Di Milano - Bicocca

  公开号：EP2107054A1

  公开（公告）日：2009-10-07

  Inhibitors of the oncogenic tyrosine kinase ALK and of the Bcr-Abl mutant T315I Bcr-Abl, such as a compound of formula (I): wherein Q, T, W, K, J, Y, X, Z are independently selected from C, N, S, O, provided that the corresponding rings are (hetero)aromatic; n = 0 or 1; q = 1 or 2; pharmaceutical compositions containing the same and their use for the treatment of hyper-proliferative diseases.

  抑制癌基因酪氨酸激酶ALK和Bcr-Abl突变体T315I Bcr-Abl的抑制剂，例如式(I)的化合物： 其中Q、T、W、K、J、Y、X、Z分别独立选择自C、N、S、O，前提是相应的环是(杂)芳香的； n = 0或1； q = 1或2； 含有相同化合物的药物组合物及其用于治疗高增殖性疾病。