2-硝基-4-(三氟甲基)苯甲酸甲酯 | 228418-45-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 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-硝基-4-(三氟甲基)苯甲酸甲酯
• 中文别名: 2-硝基-4-三氟甲基苯甲酸甲酯
• 英文名称: methyl 2-nitro-4-trifluoromethylbenzoate
• 英文别名: Methyl 2-nitro-4-(trifluoromethyl)benzoate
• CAS: 228418-45-9
• 化学式: C₉H₆F₃NO₄
• 分子量: 249.146
• InChiKey: WYTRZKAYPKZGCN-UHFFFAOYSA-N

物化性质

• 沸点：
  272℃
• 密度：
  1.442
• 闪点：
  118℃
• 溶解度：
  乙腈（微溶）、氯仿（微溶）、DMSO（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-nitro-4-(trifluoromethyl)benzoate
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: Methyl 2-nitro-4-(trifluoromethyl)benzoate
CAS number: 228418-45-9

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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.
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: C9H6F3NO4
Molecular weight: 249.1

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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

制备方法与用途

应用

2-硝基-4-三氟甲基苯甲酸甲酯是重要的医药和农药中间体，如尼替西农、异噁唑草酮、TRPV1受体拮抗剂等。

制备方法

一种成本低廉、条件温和、操作简单且收率高的新制备2-硝基-4-三氟甲基苯甲酸甲酯的方法已被研究提供。

步骤 1：

将1克2-硝基-4-三氟甲基苯甲腈（0.023摩尔，等当量）、0.09克NaOH（0.0023摩尔，过量0.1倍）和30毫升水加入反应瓶中。升温至50℃，直至HPLC检测原料完全反应，结束反应后过滤，得到目标产物2-硝基-4-三氟甲基苯甲酰胺4.9克，纯度为99%，产率为90%。

步骤 2：

配置40%硫酸的甲醇溶液。向500毫升单口瓶中加入60克甲醇，冰浴冷却下搅拌，然后缓慢滴加40克98%浓硫酸。在反应瓶中加入含有40%硫酸甲醇溶液12.4克（当量比为5.8倍）、2克2-硝基-4-三氟甲基苯甲酰胺进行回流24小时。HPLC检测显示产物含量大于99%，停止反应，用3×5毫升二氯甲烷洗涤三次有机相，合并后再次用饱和碳酸氢钠洗涤三次。取有机相并旋蒸，最终得到1.9克2-硝基-4-三氟甲基苯甲酸甲酯，纯度高于99%，产率为90%。

反应信息

• 作为反应物：
  描述：

  2-硝基-4-(三氟甲基)苯甲酸甲酯 在 palladium 10% on activated carbon 吡啶 、 盐酸 、 甲醇 、 sodium dithionite 、 硝酸 、 甲酸铵 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 87.5h， 生成 1-tert-butyl 4-methyl 2-oxo-7-(trifluoro-methyl)-2,3-dihydro-1H-benzimidazole-1,4-dicarboxylate
  参考文献：
  名称：

  [EN] FUSED HETEROCYCLIC COMPOUNDS
  [FR] COMPOSES HETEROCYCLIQUES FUSIONNES

  摘要：

  公开号：

  WO2006116412A3
• 作为产物：
  描述：

  2-硝基-4-三氟甲基苯甲酸 在 conc H₂SO₄ 作用下， 以 甲醇 为溶剂， 以98%的产率得到2-硝基-4-(三氟甲基)苯甲酸甲酯
  参考文献：
  名称：

  Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas

  摘要：

  这项发明涉及使用一组芳基脲类化合物治疗细胞因子介导的疾病和蛋白酶酶介导的疾病，以及用于该疗法的药物组合物。

  公开号：

  US20040102636A1
• 作为试剂：
  描述：

  4-溴-3-硝基三氟甲苯 、 三乙胺 、 甲醇 、 sodium thiomethoxide 、 水 在 四丁基溴化铵 、 双三苯基磷二氯化钯 氦气 、 一氧化碳 、 水 、 甲苯 、 盐酸 、 碳酸氢钠 、 2-硝基-4-(三氟甲基)苯甲酸甲酯 、 Sodium sulfate-III 作用下， 反应 40.0h， 以to afford 3.71 g of 6a的产率得到2-甲硫基-4-三氟甲基苯甲酸甲酯
  参考文献：
  名称：

  Preparation of substituted aromatic carboxylic acid esters

  摘要：

  本发明描述了制备取代芳香族羧酸酯的方法。特别地，本发明涉及一种制备硝基取代的芳香族羧酸酯的方法：1此外，本发明还涉及一种制备硫醚取代的芳香族羧酸酯的方法：2这种芳香族酯在制备各种农药和农药中间体方面非常有用。

  公开号：

  US20020040159A1

文献信息

• Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas
  申请人：Miller Scott

  公开号：US20080269265A1

  公开（公告）日：2008-10-30

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及用于该疗法的药物组合物。
• Inhibition of raf kinase using symmetrical and unsymmetrical substituted diphenyl ureas
  申请人：Bayer Corporation

  公开号：EP1449834A3

  公开（公告）日：2004-12-22

  This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.

  这项发明涉及使用一组芳基脲类化合物治疗raf介导的疾病，以及用于该疗法的药物组合物。
• [EN] COMPOUNDS AND METHODS FOR TREATING DYSLIPIDEMIA<br/>[FR] COMPOSES ET METHODES DE TRAITEMENT DE LA DYSLIPIDEMIE
  申请人：LILLY CO ELI

  公开号：WO2006002342A1

  公开（公告）日：2006-01-05

  Compounds of Formula (I): wherein n, m, p, q, Y, R1 R2, R3a, R3b, R4, R5, and R6 are as defined herein and their pharmaceutical compositions and methods of use are disclosed.

  式(I)的化合物：其中n、m、p、q、Y、R1、R2、R3a、R3b、R4、R5和R6如本文所定义，并且其药物组合物和使用方法已被披露。
• Quinoxaline compounds
  申请人：Allison D. Brett

  公开号：US20050038032A1

  公开（公告）日：2005-02-17

  Certain amidophenyl-sulfonylamino-quinoxaline compounds are CCK2 modulators useful in the treatment of CCK2 mediated diseases.

  某些氨基苯磺酰胺基喹喔啉化合物是CCK2调节剂，可用于治疗CCK2介导的疾病。
• Novel Heterocyclidene Acetamide Derivative
  申请人：Uchida Hideharu

  公开号：US20080287428A1

  公开（公告）日：2008-11-20

  A compound represented by formula (I′): (wherein m, n, and p each represent 0 to 2; q represents 0 or 1; R 1 represents halogen, a hydrocarbon group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, a sulfamoyl group, a CN group, an NO 2 group, or the like; R 2 represents halogen, amino, a hydrocarbon group, an aromatic heterocyclic group, or an oxo group; X 1 represents O, —NR 3 —, or —S(O)r-; X 2 represents a methylene group, O, —NR 3 —, or —S(O)r-; Q′ represents a heteroaryl group, a heteroarylalkyl group, a substituted aryl group, or an aralkyl group; Cycle moiety represents an aryl ring or a heteroaryl ring; and the wavy line represents an E-isomer or a Z-isomer), a salt of the compound, or a solvate of the compound or the salt. A pharmaceutical composition and a transient receptor potential type I (TRPV1) receptor antagonist each contain, as an active ingredient, at least one of the compound, a salt of the compound, and a solvate of the compound or the salt.

  一个由式(I′)表示的化合物：（其中m、n和p分别表示0到2；q表示0或1；R1表示卤素、烃基、杂环基、烷氧基、烷氧羰基、磺酰胺基、CN基团、NO2基团等；R2表示卤素、氨基、烃基、芳香杂环基或醛基；X1表示O、—NR3—或—S(O)r-；X2表示亚甲基、O、—NR3—或—S(O)r-；Q′表示异芳基基团、异芳基烷基基团、取代芳基基团或芳基烷基基团；Cycle moiety代表芳基环或杂芳基环；波浪线表示E异构体或Z异构体），该化合物的盐，或该化合物或其盐的溶剂络合物。一种药物组合物和一种瞬时受体电位类型I（TRPV1）受体拮抗剂，每种包含至少一种该化合物、该化合物的盐，或该化合物或其盐的溶剂络合物作为活性成分。