2-碘-5-三氟甲基苯甲酸 | 702641-04-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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-碘-5-三氟甲基苯甲酸
• 中文别名: 2-碘-5-(三氟甲基)苯甲酸
• 英文名称: 2-iodo-5-(trifluoromethyl)benzoic acid
• CAS: 702641-04-1
• 化学式: C₈H₄F₃IO₂
• 分子量: 316.018
• InChiKey: NRBYTEOMUOSDNU-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  301.4±42.0 °C(Predicted)
• 密度：
  2.005

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Iodo-5-(trifluoromethyl)benzoic acid
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-Iodo-5-(trifluoromethyl)benzoic acid
CAS number: 702641-04-1

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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: C8H4F3IO2
Molecular weight: 316.0

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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 fluoride, 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-碘-5-三氟甲基苯甲酸 在 硼烷四氢呋喃络合物 、 四溴化碳 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Biphenyl-Substituted Oxazolidinones as Cholesteryl Ester Transfer Protein Inhibitors: Modifications of the Oxazolidinone Ring Leading to the Discovery of Anacetrapib

  摘要：

  The development of the structure-activity studies leading to the discovery of anacetrapib is described. These studies focused on varying the substitution of the oxazolidinone ring of the 5-aryloxazolidinone system. Specifically, it was found that substitution of the 4-position with a methyl group with the cis-stereochemistry relative to the 5-aryl group afforded compounds with increased cholesteryl ester transfer protein (CETP) inhibition potency and a robust in vivo effect on increasing HDL-C levels in transgenic mice expressing cynomolgus monkey CETP.

  DOI：

  10.1021/jm200484c
• 作为产物：
  描述：

  4-氨基-3-碘三氟甲苯 在 氢氧化钾 、 亚硝酸特丁酯 、 二碘甲烷 、 水 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 、 乙腈 为溶剂， 反应 16.0h， 生成 2-碘-5-三氟甲基苯甲酸
  参考文献：
  名称：

  WO2007/79186

  摘要：

  公开号：

文献信息

• One-Pot C–H Arylation/Lactamization Cascade Reaction of Free Benzylamines
  作者：Pratibha Chand-Thakuri、Vinod G. Landge、Mohit Kapoor、Michael C. Young

  DOI：10.1021/acs.joc.0c00542

  日期：2020.5.15

  ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized

  已经开发出一种有效的方法，用于合成七元联芳基内酰胺，涉及钯催化的，天然胺导向的苄胺的正芳基化，然后进行原位内酰胺化。通过使用2-碘代苯甲酸酯使该级联序列成为可能，其在通常需要改进的导向基团方法的条件下促进游离胺的CH芳基化。该反应的特征在于底物范围广，具有良好的官能团耐受性。还探索了对酯对羧酸官能化的偶合剂的需求，以及合成八元联芳基内酰胺的潜力。还研究了各种应用，包括使用氮杂-油菜素内酯核心。
• Base- and Additive-Free Ir-Catalyzed <i>ortho</i>-Iodination of Benzoic Acids: Scope and Mechanistic Investigations
  作者：Elis Erbing、Amparo Sanz-Marco、Ana Vázquez-Romero、Jesper Malmberg、Magnus J. Johansson、Enrique Gómez-Bengoa、Belén Martín-Matute

  DOI：10.1021/acscatal.7b02987

  日期：2018.2.2

  A protocol for the C–H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture

  已经开发了一种由简单铱络合物催化的苯甲酸的C–H活化/碘化的方案。本文描述的方法允许在非常温和的条件下，在没有任何添加剂或碱的情况下，在1,1,1,3,3,3-六氟异丙醇作为溶剂中对多种苯甲酸进行邻位碘化。所用的铱催化剂可耐受空气和湿气，并选择性地以高转化率得到邻碘苯甲酸。机理研究表明，Ir（III）/ Ir（V）催化循环起作用，并且HFIP的独特性质使得能够使用羧基作为引导基团进行C-H碘化。
• Mizoroki–Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers
  作者：Jose M. Medina、Jesus Moreno、Sophie Racine、Shuaijing Du、Neil K. Garg

  DOI：10.1002/anie.201703174

  日期：2017.6

  report non-decarbonylative Mizoroki–Heck reactions of amide derivatives. The transformation relies on the use of nickel catalysis and proceeds using sterically hindered tri- and tetrasubstituted olefins to give products containing quaternary centers. The resulting polycyclic or spirocyclic products can be obtained in good yields. Moreover, a diastereoselective variant of this method gives access to an

  我们报告了酰胺衍生物的非脱羰基Mizoroki-Heck反应。该转化依赖于镍催化的使用，并使用空间受阻的三和四取代的烯烃进行，以得到含有季中心的产物。可以高收率获得所得的多环或螺环产物。而且，该方法的非对映选择性变体使得能够接近带有邻近的，高度取代的sp 3立体中心的加合物。这些结果表明，酰胺衍生物可以用作组装复杂支架的基础。
• Monoacylglycerol Lipase Modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US20200102311A1

  公开（公告）日：2020-04-02

  Bridged compounds of Formula (I) and Formula (II), pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with MGL modulation, such as those associated with pain, psychiatric disorders, neurological disorders (including, but not limited to major depressive disorder, treatment resistant depression, anxious depression, bipolar disorder), cancers and eye conditions. wherein R 2 , R 3 R 4 , R 5 and R 6 are defined herein.

  桥接化合物，其结构式为(I)和(II)，包含它们的药物组合物，制造它们的方法，以及使用它们的方法，包括用于治疗与MGL调节相关的疾病状态、障碍和状况的方法，如与疼痛、精神障碍、神经障碍（包括但不限于重性抑郁障碍、难治性抑郁、焦虑性抑郁、双相情感障碍）、癌症和眼科疾病相关的方法。 其中R2、R3、R4、R5和R6的定义如下。
• Novel piperazine based benzamide derivatives as potential anti-glioblastoma agents inhibiting cell proliferation and cell cycle progression
  作者：Yingmei Lu、Yiyue Feng、Zhao Li、Junfang Li、Honghua Zhang、Xiaoling Hu、Weifan Jiang、Tao Shi、Zhen Wang

  DOI：10.1016/j.ejmech.2021.113908

  日期：2022.1

  Highly efficacious and tolerable agents for the treatment of glioblastoma (GBM), the most common and aggressive primary brain tumor, are urgently needed. Herein, we reveal the design, synthesis and biological evaluation of several piperazine based benzamide derivatives, which are based on the non-classical isostere principle and combination principle for GBM therapy. After structure-activity relationship

  迫切需要用于治疗最常见和最具侵袭性的原发性脑肿瘤胶质母细胞瘤 (GBM) 的高效和耐受药物。在此，我们揭示了几种基于哌嗪的苯甲酰胺衍生物的设计、合成和生物学评价，这些衍生物基于 GBM 治疗的非经典等排原理和组合原理。经过构效关系 (SAR) 研究，化合物L19被证明是最有希望的化合物，其对 GBM C6、U87-MG、U251 细胞的 IC 50值分别为 0.15 μM、0.29 μM、1.25 μM。此外，化合物L19在体外可抑制GBM细胞系的增殖、迁移和侵袭，诱导细胞凋亡和细胞周期停滞。. 从机制上看，通过蛋白质印迹实验，化合物L19可以调节细胞周期相关蛋白并影响p16 INK4a -CDK4/6-pRb通路。值得一提的是，化合物L19可以穿透血脑屏障 (BBB)，在体内具有 1.07 的出色脑浆比。此外，在U87-MG-异种移植模型上鉴定出化合物L19在体内具有优异的抗胶质母细胞瘤