4-氟-3-三氟甲基苯腈 | 67515-59-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯腈系列
• 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: 4-氟-3-三氟甲基苯腈
• 中文别名: 4-氟-3-(三氟甲基)苯腈；5-氰基-2-氟三氟甲苯；3-三氟甲基-4-氟苯腈；4-氟-3-三氟甲基苯甲腈；4-氟-3-三氟甲基苄腈；4-氟-3-(三氟甲基)苯甲腈；4-氟-3-(三氟甲基)苯甲腈, 98+%；4-氟-3-(三氟甲基)苄腈
• 英文名称: 4-Fluoro-3-(trifluoromethyl)benzonitrile
• 英文别名: 3-trifluoromethyl-4-fluorobenzonitrile
• CAS: 67515-59-7
• 化学式: C₈H₃F₄N
• mdl: MFCD00061284
• 分子量: 189.112
• InChiKey: CQZQCORFYSSCFY-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C
• 沸点：
  194°C
• 密度：
  1,323 g/cm
• 闪点：
  193-195°C
• 稳定性/保质期：
  远离氧化物。

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：
  0.125
• 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
• 危险品标志：
  Xn,Xi,T
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2926909090
• 危险品运输编号：
  3276
• 危险类别：
  6.1
• 包装等级：
  III
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。请确保存储地点远离氧化剂。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Fluoro-3-trifluoromethylbenzonitrile
Synonyms: 4-Fluoro-3-(trifluoromethyl)benzonitrile; 5-cyano-2-fluorobenzotrifluoride

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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
Causes skin irritation
H315:
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Fluoro-3-trifluoromethylbenzonitrile
CAS number: 67515-59-7

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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
Not specified
Appearance:
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: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (4-Fluoro-3-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

简介

4-氟-3-三氟甲基苯腈是一种3-三氟甲基4-卤苯腈化合物。这类化合物是许多染料、除草剂、医药品和天然化合物的重要组成部分，同时也是重要的有机合成中间体。其氰基可以转化为酮、酰胺、羧酸、亚胺酯、羧酸酯、硫代酰胺等一系列化合物。

制备

将10 mmol的3-三氟甲基-4-卤苯胺溶解于10 mL微热冰乙酸中，缓慢加入2.5 mL 12 mol·L-1硫酸溶液，搅拌直至完全溶解，形成焦黄色溶液。然后将其置于冰盐浴中冷却至0～5℃，搅拌成白色膏状物。接下来，将已冷却到0～5℃的10 mL 2 mol·L-1 NaNO2溶液在剧烈搅拌下滴入白色膏状物中（约30分钟），直至淀粉碘化钾试纸检测溶液显蓝色为止。最后用Na2CO3中和冰乙酸至pH=7.0，不经分离析出直接用于目标化合物的合成。

将0.84 g(2 mmol) K3[Fe(CN)6]溶解于20 mL蒸馏水中，向其中加入4.5 mmol乙二胺和1.5 mmol Cu(OAc)2，在室温下搅拌1小时后转入冰盐浴冷却至0-5℃。将上述重氮盐溶液滴加到K3[Fe(CN)6]溶液中（约1小时），在冰盐浴下持续搅拌2小时，出现红棕色沉淀。过滤除去沉淀，固体用二氯甲烷洗涤，收集有机相；水相用1/3体积的二氯甲烷萃取两次，合并有机相，减压浓缩后上柱分离，洗脱（石油醚：乙酸乙酯=20:1）得到产物。

用途

用于医药中间体

反应信息

• 作为反应物：
  描述：

  4-氟-3-三氟甲基苯腈 在 水 、 sodium hydride 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 17.5h， 生成 5-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  [EN] COMPOUNDS AS AGONISTS OF S1P1 RECEPTORS
  [FR] COMPOSÉS COMME AGONISTES DE RÉCEPTEURS DE S1P1

  摘要：

  式(I)的化合物，其制备方法，含有它们的药物组合物以及它们在通过S1P1受体介导的疾病治疗中的应用。

  公开号：

  WO2011134280A1
• 作为产物：
  描述：

  4-氟-3-三氟甲基苯胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 碳酸氢钠 、 sodium nitrite 作用下， 生成 4-氟-3-三氟甲基苯腈
  参考文献：
  名称：

  Synthesis of 3-Trifluoromethyl-4-halobenzonitriles

  摘要：

  The practical synthetic method for a series of substantially novel fluorine-containing polyfunctional aromatic compounds, 3-trifluoromethyl-4-halobenzonitriles [halo = Cl, Br, and F], was established by using copper-cyano complexes as effective Sandmeyer cyanating reagents.

  DOI：

  10.1080/00397919608003525

文献信息

• Npy antagonists, preparation and uses
  申请人：Botez Iuliana

  公开号：US20090233910A1

  公开（公告）日：2009-09-17

  The present invention concerns novel compounds, their preparation and their uses, therapeutic uses in particular. More specifically it concerns derivative compounds having at least two aromatic cycles, their preparation and their uses, in particular in the area of human or animal health. These compounds have an affinity for the biological receptors of neuropeptide Y, NPY, present in the central and peripheral nervous systems. The compounds of the invention are preferably NPY antagonists, and more particularly antagonists of sub-type NPY Y1, and can therefore be used for the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also concerns pharmaceutical compositions containing said compounds, their preparation and their uses, as well as treatment methods using said compounds.

  本发明涉及新颖化合物，它们的制备和用途，特别是在治疗方面的用途。更具体地说，它涉及至少具有两个芳香环的衍生化合物，它们的制备和用途，特别是在人类或动物健康领域。这些化合物对存在于中枢和外周神经系统中的神经肽Y（NPY）的生物受体具有亲和力。本发明的化合物优选为NPY拮抗剂，更具体地说是NPY Y1亚型的拮抗剂，因此可用于治疗或预防涉及NPY的任何疾病。本发明还涉及含有所述化合物的药物组合物，其制备和用途，以及使用所述化合物的治疗方法。
• [EN] SPHINGOSINE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA SPHINGOSINE KINASE
  申请人：LYNCH KEVIN

  公开号：WO2016054261A1

  公开（公告）日：2016-04-07

  Sphingosine kinases are enzymes that catalyze the biosynthesis of sphingosine-1-phosphate. The invention provides compounds that are effective for inhibition of sphingosine kinase type 1, sphingosine kinase type 2, or both. Certain compounds are selective for sphingosine kinase type 2 relative to sphingosine kinase type 1. Compounds of the invention can be used in treatment of a range of diseases wherein increasing the level of sphingosine-1-phosphate in blood is medically indicated. Diseases that can be treated by administration of an effective dose of a compound of the invention include a neoplastic disease that involves excess vascular growth; macular degeneration or diabetic retinopathy; an allergic disease such as asthma, an inflammatory disease of the eye such as uveitis, scleritis, or vitritis; an inflammatory disease of the kidney; a fibrotic disease; atherosclerosis; or pulmonary arterial hypertension. A compound of the invention can be used to improve the integrity of a vascular barrier in a disease where the vascular barrier is disrupted, such as cancer or Alzheimer's disease.

  鞘氨醇激酶是催化鞘氨醇-1-磷酸酯生物合成的酶。该发明提供了对鞘氨醇激酶1型、鞘氨醇激酶2型或两者均具有效抑制作用的化合物。某些化合物相对于鞘氨醇激酶1型具有选择性作用于鞘氨醇激酶2型。该发明的化合物可用于治疗一系列疾病，其中增加血液中鞘氨醇-1-磷酸酯水平在医学上是指示的。通过给予该发明的化合物有效剂量可以治疗的疾病包括涉及过度血管生长的肿瘤性疾病；黄斑变性或糖尿病视网膜病变；哮喘等过敏性疾病，眼部炎症性疾病如葡萄膜炎、巩膜炎或玻璃体炎；肾脏炎症性疾病；纤维化疾病；动脉粥样硬化；或肺动脉高压。该发明的化合物可用于改善血管屏障的完整性，在血管屏障受损的疾病中，如癌症或阿尔茨海默病。
• Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
  申请人：——

  公开号：US20040157849A1

  公开（公告）日：2004-08-12

  Compounds of formula (I) 1 are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.

  式（I）的化合物是新颖的VR1拮抗剂，可用于治疗疼痛、炎症性热性过敏、尿失禁和膀胱过度活动。
• Structure-activity relationship of new antimalarial 1-aryl-3-susbtituted propanol derivatives: Synthesis, preliminary toxicity profiling, parasite life cycle stage studies, target exploration, and targeted delivery
  作者：Miguel Quiliano、Adriana Pabón、Ernest Moles、Leonardo Bonilla-Ramirez、Isabelle Fabing、Kim Y. Fong、Diego A. Nieto-Aco、David W. Wright、Juan C. Pizarro、Ariane Vettorazzi、Adela López de Cerain、Eric Deharo、Xavier Fernández-Busquets、Giovanny Garavito、Ignacio Aldana、Silvia Galiano

  DOI：10.1016/j.ejmech.2018.04.038

  日期：2018.5

  Design, synthesis, structure-activity relationship, cytotoxicity studies, in silico drug-likeness, genotoxicity screening, and in vivo studies of new 1-aryl-3-substituted propanol derivatives led to the identification of nine compounds with promising in vitro (55, 56, 61, 64, 66, and 70-73) and in vivo (66 and 72) antimalarial profiles against Plasmodium falciparum and Plasmodium berghei. Compounds

  设计，合成，构效关系，细胞毒性研究，计算机模拟药物，遗传毒性筛选以及新的1-芳基-3-取代丙醇衍生物的体内研究导致了九种化合物的体外鉴定（55， 56、61、64、66和70-73）和体内（66和72）针对恶性疟原虫和柏氏疟原虫的抗疟药谱。化合物55、56、61、64、66和70-73对抗氯喹菌株FCR-3（IC50s <0.28μM）表现出强大的抗疟原虫活性，化合物55、56、64、70、71和72显示出强大的生物活性在对氯喹敏感和耐多药的菌株中的活性（3D7，D6，FCR-3和C235的IC50 <0.7μM）。所有这些化合物均具有适当的药物相似性和适当的选择性指数（77
• Inhibitors of c-Jun N-terminal kinases
  申请人：Liu Gang

  公开号：US20060173050A1

  公开（公告）日：2006-08-03

  The present invention relates to compounds that are inhibitors of c-jun N-terminal kinase 1, 2, or 3 (JNK1, JNK2, or JNK3), compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by the activation of JNK1, JNK2 and JNK3.

  本发明涉及作为c-jun N-末端激酶1、2或3（JNK1、JNK2或JNK3）抑制剂的化合物，包含这些化合物的组合物以及这些化合物在预防或治疗由JNK1、JNK2和JNK3激活调控的疾病中的用途。

表征谱图