5-三氟甲基-1H-吲唑 | 885271-64-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-三氟甲基-1H-吲唑
• 中文别名: 5-(三氟甲基)-1H-咪唑
• 英文名称: 5-(trifluoromethyl)-1H-indazole
• CAS: 885271-64-7
• 化学式: C₈H₅F₃N₂
• mdl: MFCD08234904
• 分子量: 186.136
• InChiKey: WBHMPANPIGWXQV-UHFFFAOYSA-N

物化性质

• 沸点：
  268.5±35.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 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: 5-(Trifluoromethyl)-1h-indazole
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-(Trifluoromethyl)-1h-indazole
CAS number: 885271-64-7

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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: C8H5F3N2
Molecular weight: 186.1

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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 fluoride.

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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：

  5-三氟甲基-1H-吲唑 在 potassium phosphate 、 1,10-菲罗啉 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 5-(trifluoromethyl)-1-methyl-3-phenyl-1H-indazole
  参考文献：
  名称：

  Palladium-Catalyzed Direct C7-Arylation of Substituted Indazoles

  摘要：

  A novel direct C7-arylation of indazoles with iodoaryls is described using Pd(OAc)2 as catalyst, 1,10-phenanthroline as ligand, and K2CO3 as base in refluxing DMA. Direct C7-arylation of 3-substituted 1H-indazole containing an EWG on the arene ring gave the expected products in good isolated yields. In addition, a one-pot Suzuki-Miyaura/arylation procedure leading to C3,C7-diarylated indazoles has been developed.

  DOI：

  10.1021/jo500876q
• 作为产物：
  描述：

  4-氟三氟甲苯 在 氢氧化钾 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 3.25h， 生成 5-三氟甲基-1H-吲唑
  参考文献：
  名称：

  三甲基甲硅烷基重氮甲烷锂与苯炔的[3 + 2]环加成反应可轻松合成3-三甲基甲硅烷基吲唑

  摘要：

  由卤代苯生成的三甲基硅烷基重氮甲烷甲烷与苯炔的[3 + 2]环加成反应以良好至中等的收率得到了相应的3-三甲基硅烷基吲唑。

  DOI：

  10.1016/j.tetlet.2003.12.086

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。
• New CRTh2 antagonists.
  申请人：Almirall, S.A.

  公开号：EP2548863A1

  公开（公告）日：2013-01-23

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  这项发明涉及到式(I)化合物，制备这种化合物的方法以及它们在治疗病理状况或疾病中的应用，这些病理状况或疾病对CRTh2拮抗活性有改善作用。
• [EN] PYRROLOPYRAZINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE PYRROLOPYRAZINE KINASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013030138A1

  公开（公告）日：2013-03-07

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及式I的新型吡咯并吡嗪衍生物的使用，其中变量如本文所述定义，其抑制JAK和SYK，并可用于治疗自身免疫和炎症性疾病。
• A mild and regioselective Ullmann reaction of indazoles with aryliodides in water
  作者：Xiao Ding、Jingtao Bai、Hailong Wang、Baowei Zhao、Jian Li、Feng Ren

  DOI：10.1016/j.tet.2016.11.066

  日期：2017.1

  A mild and regioselective Ullmann reaction of indazoles with aryliodides has been developed as a general method for the synthesis of 1-aryl-1H-indazoles. Water was used as the solvent wherein Tween 20 (2% w/w) was added to form aqueous micelles to improve solubility of starting materials and accelerate reaction rate. This aqueous protocol allows the Ullmann reaction to proceed at a mild temperature

  已经开发了吲唑与芳基碘化物的温和的区域选择性乌尔曼反应作为合成1-芳基-1 H-吲唑的一般方法。使用水作为溶剂，其中添加吐温20（2％w / w）以形成水性胶束，以改善起始原料的溶解度并加快反应速率。该水性方案允许Ullmann反应在较短的反应时间（2 h）内在温和的温度（60°C）下进行，这通常需要高温（≥100°C）和较长的持续时间（≥24h）。对于所检查的25个实例，该方案证明了广泛的底物范围，具有良好的分离得率和较高的区域选择性（N -1芳基化超过N -2芳基化）。
• A mild and efficient THP protection of indazoles and benzyl alcohols in water
  作者：Yang Zhan、Xiao Ding、Hailong Wang、Haihua Yu、Feng Ren

  DOI：10.1016/j.tetlet.2018.02.061

  日期：2018.5

  A mild and efficient method for THP protection of indazoles and benzyl alcohols has been developed in water, the most environmentally friendly solvent, in which Tween 20 (2% w/w) was added to form aqueous micelles to increase the solubility of starting materials. This aqueous protocol allowed the reaction to proceed smoothly at room temperature and with only 1.2 equiv of DHP, providing moderate to

  在最环保的溶剂水中开发了一种温和有效的THP保护吲唑和苄醇的方法，在其中添加了Tween 20（2％w / w）以形成水性胶束，以提高起始原料的溶解度。该水性方案使反应在室温下仅用1.2当量的DHP即可顺利进行，从而为各种底物提供了中等至良好的THP保护产物收率。此外，该方法在大规模合成中非常实用（例如以1 g的2c合成为例），其中便利的后处理和纯化程序（简单过滤）使该方案更具吸引力。