3-氟-5-(三氟甲基)苯甲腈 | 149793-69-1

• 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: 3-氟-5-(三氟甲基)苯甲腈
• 中文别名: 3-氟-5-三氟甲基苯腈；3-氟-5-(三氟甲基)苯腈
• 英文名称: 3-fluoro-5-trifluoromethyl-benzonitrile
• 英文别名: 3-Fluoro-5-(trifluoromethyl)benzonitrile
• CAS: 149793-69-1
• 化学式: C₈H₃F₄N
• 分子量: 189.112
• InChiKey: AYNUKEDZAYOEGG-UHFFFAOYSA-N

物化性质

• 沸点：
  179.9±35.0 °C(Predicted)
• 密度：
  1.35
• 闪点：
  65°(149°F)
• 溶解度：
  可溶于氯仿（少量）、乙酸乙酯（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  6.1
• 安全说明：
  S26,S36/37
• 危险品运输编号：
  UN 3276
• 海关编码：
  2926909090
• 危险类别：
  6.1
• 危险品标志：
  Xn,Xi,T
• 危险类别码：
  R20/21/22,R36/38
• 包装等级：
  III
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluoro-5-trifluoromethylbenzonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H331: Toxic if inhaled
H302: Harmful if swallowed
H312: Harmful in contact with skin
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
H227: Combustible liquid
P210: Keep away from heat/sparks/open flames/hot surfaces. No smoking
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluoro-5-trifluoromethylbenzonitrile
CAS number: 149793-69-1

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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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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: C8H3F4N
Molecular weight: 189.1

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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
UN Number: UN3276 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, LIQUID, N.O.S. (3-Fluoro-5-trifluoromethylbenzonitrile)

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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

3-氟-5-(三氟甲基)苯甲腈是一种白色至淡黄色结晶粉末，属于卤代苯腈类化合物。卤代苯腈是重要的有机中间体，广泛用于医药、农药的制备，同时也应用于染料、工程塑料和感光材料的制造过程。

制备

传统合成卤代苯腈的方法包括光卤代法、氨氧化法、相转移催化合成法或羧酸与尿素反应等。本文采用取代苯甲醛为起始物料，经过一系列步骤最终合成了3-氟-5-(三氟甲基)苯甲腈。该路线尽管步骤较多，但每一步的收率都较高，并且产品易于分离纯化，因此是一条可行的合成路径。

合成反应式

图1展示了3-氟-5-(三氟甲基)苯甲腈的合成过程。

步骤如下：

在装有温度计、冷凝管和电搅拌器的三口烧瓶中加入一定物质的量比的3-氟-5-(三氟甲基)苯甲醛与盐酸羟胺，加热保持70~75℃，反应约30分钟。然后，慢慢滴加20%（质量分数）的碳酸钠水溶液，搅拌过程中会观察到气泡产生（可用石灰水检验）。待反应速度减缓后，调节pH值至8～9，并停止加入碳酸钠水溶液。

继续搅拌直至淡红色沉淀逐渐变为乳白色。过滤出沉淀物并用水洗涤2～3次，晾干后得到乳白色的3-氟-5-(三氟甲基)苯甲醛肟粉末，称重备用。将3-氟-5-(三氟甲基)苯甲醛肟与醋酸酐按一定物质的量比加入到烧瓶中，加热至110～120℃反应约3小时。冷却降温后，静置观察到白色晶体出现。抽滤收集晶体，用酒精溶解并进行热过滤以去除不溶物。最后，通过用水萃取分离的方法得到纯净的3-氟-5-(三氟甲基)苯甲腈。

反应信息

• 作为反应物：
  描述：

  3-氟-5-(三氟甲基)苯甲腈 在 氯化亚砜 、 双氧水 、 溴 、 potassium carbonate 、 sodium amide 、 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基乙酰胺 、 水 、 二甲基亚砜 为溶剂， 反应 23.58h， 生成 尼罗替尼
  参考文献：
  名称：

  [EN] AN IMPROVED PROCESS FOR 3-(4-METHYL-1H-IMIDAZOL-1-YL)-5-(TRIFLUOROMETHYL) ANILINE
  [FR] PROCÉDÉ AMÉLIORÉ POUR 3-(4-MÉTHYL-1H-IMIDAZOL-1-YL)-5-(TRIFLUOROMÉTHYL) ANILINE

  摘要：

  本发明涉及一种改进的制备3-(4-甲基-1H-咪唑-1-基)-5-(三氟甲基)苯胺（化学式I）的方法。

  公开号：

  WO2019130254A1
• 作为产物：
  描述：

  3-氨基-5-氰基三氟甲苯 在 iron(III) chloride 、 pyrilium tetrafluoroborate 、 sodium fluoride 作用下， 以 neat (no solvent, solid phase) 为溶剂， 以92 %的产率得到3-氟-5-(三氟甲基)苯甲腈
  参考文献：
  名称：

  纳米纤维素作为 FeCl3 介导的（杂）芳香胺机械化学脱氨氟化反应介质

  摘要：

  开发一种有效替代广泛使用的 Balz-Schiemann 脱氨基氟化方法（即不使用芳基重氮四氟硼酸盐）是一项具有挑战性的任务。在此，我们报道了一种方便的一锅法，用于 FeCl3-纳米纤维素介导的氟代芳烃的机械化学合成，通过使用四氟硼酸吡喃鎓 (Pyry-BF4) 和氟化钠 (NaF) 原位形成，用氟基团选择性取代芳香氨基吡啶鎓盐中间体。本协议的范围包括通过氟选择性取代（SNAr）氨基以优异的产率合成二十八种有机氟化合物。所提出的简洁方法为制药行业后期功能化开辟了进入新化学空间的途径。

  DOI：

  10.1002/adsc.202400303

文献信息

• Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)
  申请人：Madar J. David

  公开号：US20050215784A1

  公开（公告）日：2005-09-29

  The present invention relates to compounds that inhibit dipeptidyl peptidase IV (DPP-IV) and are useful for the prevention or treatment of diabetes, especially type II diabetes, as well as hyperglycemia, Syndrome X, hyperinsulinemia, obesity, atherosclerosis, and various immunomodulatory diseases.

  本发明涉及抑制二肽基肽酶IV（DPP-IV）的化合物，用于预防或治疗糖尿病，特别是II型糖尿病，以及高血糖、X综合征、高胰岛素血症、肥胖、动脉粥样硬化和各种免疫调节性疾病。
• ALDH-2 INHIBITORS IN THE TREATMENT OF DRUG ADDICTION
  申请人：Zablocki Jeff

  公开号：US20080032995A1

  公开（公告）日：2008-02-07

  Disclosed are novel isoflavone derivatives having the structure of Formula I which are useful as ALDH-2 inhibitors for treating mammals for dependence upon drugs of addiction, for example addiction to dopamine-producing agent such as cocaine, morphine, amphetamines, nicotine, and alcohol.

  揭示了具有以下结构的新型异黄酮衍生物，其可用作ALDH-2抑制剂，用于治疗哺乳动物对成瘾药物的依赖，例如对多巴胺类药物如可卡因、吗啡、安非他命、尼古丁和酒精的依赖。
• [EN] AZAINDOLE DERIVATIVES AS MULTI KINASE INHIBITORS<br/>[FR] DÉRIVÉS AZA-INDOLIQUES UTILISÉS COMME INHIBITEURS DE MULTIPLES KINASES
  申请人：ORIBASE PHARMA

  公开号：WO2014102377A1

  公开（公告）日：2014-07-03

  The present invention relates to compounds of the following formula (I) and/or the pharmaceutically acceptable addition salts, solvates, enantiomers, diastereoisomers thereof, as well as mixtures thereof. The subject matter of the present invention thus also includes the preparation of compounds of formula (I), their uses, in particular in the inhibition of protein kinases which are implicated for example in numerous diseases such as cancers or immune system disorders.

  本发明涉及式(I)化合物和/或其药用可接受的增加盐、溶剂化物、对映异构体、非对映异构体，以及它们的混合物。因此，本发明的主题还包括式(I)化合物的制备、用途，特别是在抑制涉及多种疾病（如癌症或免疫系统疾病）的蛋白激酶方面的用途。
• ALDH-2 INHIBITORS IN THE TREATMENT OF PSYCHIATRIC DISORDERS
  申请人：Diamond Ivan

  公开号：US20090124672A1

  公开（公告）日：2009-05-14

  Disclosed are isoflavone derivatives having the structure of Formula I which are useful as ALDH-2 inhibitors for use treating in mammals suffering from psychiatric disorders such as, for example, depression, generalized anxiety, social phobia, panic disorder, and sleep disorders.

  披露的是具有公式I结构的异黄酮衍生物，它们作为ALDH-2抑制剂，用于治疗遭受精神疾病困扰的哺乳动物，例如抑郁症、广泛性焦虑症、社交恐惧症、恐慌症和睡眠障碍。
• [EN] RAF-DEGRADING CONJUGATE COMPOUNDS<br/>[FR] COMPOSÉS CONJUGUÉS DE DÉGRADATION DE RAF
  申请人：QUARTZ THERAPEUTICS INC

  公开号：WO2018200981A1

  公开（公告）日：2018-11-01

  The present disclosure provides, inter alia, RAF-Degrading Conjugate Compounds that are useful in the treatment of cancer and other RAF related diseases. Also provided are, pharmaceutical compositions, methods of treatment, and kits comprising a RAF- Degrading Conjugate Compound.

  本公开提供了用于治疗癌症和其他与RAF相关疾病的RAF降解共轭化合物。还提供了药物组合物、治疗方法和包含RAF降解共轭化合物的试剂盒。

表征谱图