1-甲基-5-三氟甲基苯并咪唑 | 53483-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-甲基-5-三氟甲基苯并咪唑
• 英文名称: 1-methyl-5-(trifluoromethyl)-1H-benzo[d]imidazole
• 英文别名: 1-Methyl-5-trifluoromethylbenzimidazole；1-methyl-5-(trifluoromethyl)benzimidazole
• CAS: 53483-66-2
• 化学式: C₉H₇F₃N₂
• 分子量: 200.163
• InChiKey: FZMXBWXWQILZPU-UHFFFAOYSA-N

物化性质

• 沸点：
  262.4±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Methyl-5-trifluoromethylbenzimidazole
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-Methyl-5-trifluoromethylbenzimidazole
CAS number: 53483-66-2

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H7F3N2
Molecular weight: 200.2

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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：

  1-甲基-5-三氟甲基苯并咪唑 在 2,4-二硝基苯基羟胺 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以13%的产率得到1-amino-3-methyl-6-(trifluoromethyl)benzimidazolium chloride
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724
• 作为产物：
  描述：

  4-氟-3-硝基三氟甲苯 在 盐酸 、 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 1-甲基-5-三氟甲基苯并咪唑
  参考文献：
  名称：

  Cu催化苯并咪唑与艾伦的C-H烯丙基化

  摘要：

  已经描述了 CuH 催化的苯并咪唑与丙二烯的分子内环化和分子间烯丙基化。在Cu(OAc) 2 /Xantphos的催化体系和催化量的(MeO) 2 MeSiH的作用下，反应顺利进行。该协议具有温和的反应条件和对带有吸电子、给电子或电子中性基团的底物的良好耐受性。针对该氢化铜催化体系提出了一种新的催化机理。

  DOI：

  10.1021/acs.orglett.1c02346

文献信息

• C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C–H Activation
  作者：Gaël Tran、Danielle Confair、Kevin D. Hesp、Vincent Mascitti、Jonathan A. Ellman

  DOI：10.1021/acs.joc.7b01723

  日期：2017.9.1

  Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C–H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed

  在本文中，我们报道了Rh（I）/双膦/ K 3 PO 4催化体系，首次使苯并咪唑与Michael受体进行了选择性支链C–H烷基化。用N，N-二甲基丙烯酰胺进行的支化烷基化已成功地用于各种苯并咪唑的烷基化反应，这些苯并咪唑掺入了各种N-取代基，并且在芳烃的不同部位均显示出富电子和贫电子的功能。此外，通过用甲基丙烯酸乙酯进行烷基化来引入季碳。该方法还显示出可用于氮杂苯并咪唑的C 2-选择性支链烷基化。
• Bifurcated Nickel-Catalyzed Functionalizations: Heteroarene C−H Activation with Allenes
  作者：Sachiyo Nakanowatari、Thomas Müller、João C. A. Oliveira、Lutz Ackermann

  DOI：10.1002/anie.201709087

  日期：2017.12.11

  A unified strategy for nickel(0)‐catalyzed C−H allylations, alkenylations, and dienylations has been realized through versatile hydroarylations of allenes with ample scope. Thus, an inexpensive nickel catalyst modified with a N‐heterocyclic carbene ligand enabled the direct transformation of C−H bonds of biologically relevant imidazole and purine derivatives with full control of regio‐ and chemoselectivity

  镍（0）催化的CH烯丙基化，烯基化和二烯基化的统一策略已经通过具有足够范围的多烯键的多用途加氢芳基化实现。因此，一种廉价的用N杂环卡宾配体改性的镍催化剂能够直接控制生物学相关的咪唑和嘌呤衍生物的CH键，并完全控制区域和化学选择性。
• Carbon Chain Rupture: Base-Induced Radical C–C Bond Cleavage of Alkylbenzimidazoles
  作者：Jianhui Huang、Xuegang Fu、Dongyang Guo、Yuting Yan、Timotius Marselo、Mingyu Zhang、Zhenghan Zhang、Siying Li

  DOI：10.1055/a-1883-1357

  日期：2022.10

  A base-mediated aerobic oxidation of alkylbenzimidazoles for the preparation of carboxylic acids is described. A number of aliphatic carboxylic acids have been prepared in good to excellent yields via a C–C bond rupture process. Preliminary mechanistic studies suggest the reaction undergoes a radical pathway initiated by strong bases such as potassium amide. This type of transformation provides an

  描述了用于制备羧酸的烷基苯并咪唑的碱介导有氧氧化。许多脂肪族羧酸已经通过 C-C 键断裂过程以良好至优异的产率制备。初步机理研究表明，该反应经历了由强碱（如氨基钾）引发的自由基途径。这种类型的转化为获取重要的羧酸部分提供了一种替代策略。
• <i>n</i>Bu₄N⁺[Ag^I(CF₃)₂]⁻: Trifluoromethylated Argentate Derived from Fluoroform and Its Reaction with (Hetero)Aryl Diazonium Salts
  作者：Zehai Lu、Linhua Wang、Matthew Hughes、Stephen Smith、Qilong Shen

  DOI：10.1021/acs.orglett.3c02804

  日期：2024.4.12

  argentate nBu4N+[Ag(CF3)2]− 1 from fluoroform was described. The complex was stable in the solid state and in solution under an inert atmosphere. Treatment of a variety of (hetero)aryl diazonium tetrafluoroborates with nBu4N+[Ag(CF3)2]− 1 generated trifluoromethylated (hetero)arenes in good to excellent yields. Preliminary experiments were conducted, and a reasonable mechanism of the reaction was proposed

  描述了从氟仿制备明确的三氟甲基化银酸盐n Bu 4 N + [Ag(CF 3 ) 2 ] - 1 。该配合物在惰性气氛下在固态和溶液中均稳定。用n Bu 4 N + [Ag(CF 3 ) 2 ] - 1处理各种（杂）芳基重氮四氟硼酸盐，生成三氟甲基化（杂）芳烃，收率良好至优异。进行了初步实验，提出了合理的反应机理。
• MEDICINAL COMPOSITION FOR PREVENTION OR TREATMENT OF PARASITIC PROTOZOAN INFECTION
  申请人：Japan Science and Technology Agency

  公开号：EP1800682A1

  公开（公告）日：2007-06-27

  The present invention is to provide a medicinal composition for preventing or treating parasitic protozoan infections, having a high selective toxicity against parasitic protozoan infection, and a superior preventive or treating effect. A medicinal composition for preventing or treating parasitic protozoan infections comprises a compound shown by the following general formula (1) as an active ingredient (wherein R represents an alkyl group, aryl group or heterocyclic group; A and B each independently represents a 5- or 6-membered ring containing at least one hetero atom, or a condensation ring wherein 1 or more 3- to 8-membered ring is condensed thereto; Y represents S, 0, Se, or -NR1-(R1 represents an alkyl group, aryl group or heterocyclic group); L1, L2, L3, L4 and L5 each independently represents a methine group; Q represents a physiologically acceptable anion; k represents an integer of 0 to 2, necessary to make the electric charge of the whole molecule 0; p and q each represents an integer of 0 to 3, wherein the sum of p and q is 1 or more, and 6 or less.)

  本发明旨在提供一种用于预防或治疗寄生性原虫感染的药物组合物，该组合物对寄生性原虫感染具有较高的选择性毒性，并具有优异的预防或治疗效果。一种用于预防或治疗寄生性原生动物感染的药物组合物由以下通式（1）所示的化合物作为活性成分组成 (其中 R 代表烷基、芳基或杂环基团；A 和 B 各自独立地代表含有至少一个杂原子的 5 或 6 元环，或其上缩合有一个或多个 3 至 8 元环的缩合环；Y 代表 S、0、Se 或 -NR1-（R1 代表烷基、芳基或杂环基团）；L1、L2、L3、L4 和 L5 各自独立地代表一个甲基； Q 代表生理上可接受的阴离子； k 代表 0 至 2 的整数，是使整个分子的电荷为 0 所必需的； p 和 q 各自代表 0 至 3 的整数，其中 p 和 q 的和为 1 或以上，6 或以下。)