4-(三氟甲氧基)苯甲酰基乙腈 | 122454-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-(三氟甲氧基)苯甲酰基乙腈
• 中文别名: 3-氧-3-[4-(三氟甲氧基)苯基]丙腈；beta-氧代-4-(三氟甲氧基)-苯丙腈
• 英文名称: 3-oxo-3-(4-(trifluoromethoxy)phenyl)propanenitrile
• 英文别名: [4-(trifluoromethoxy)benzoyl]acetonitrile；3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile
• CAS: 122454-46-0
• 化学式: C₁₀H₆F₃NO₂
• 分子量: 229.158
• InChiKey: IYZQGBBCANKWMX-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84°C
• 沸点：
  315.4±42.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  TOXIC
• 危险品标志：
  T
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  3439
• 海关编码：
  2926909090
• 危险类别：
  TOXIC
• 安全说明：
  S26,S36/37/39
• 包装等级：
  III
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险性描述：
  H301,H311,H331
• 储存条件：
  存储条件：2-8℃，密封保存，置于干燥处。

SDS

Name:	3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile 97% Material Safety Data Sheet
Synonym:
CAS:	122454-46-0

Section 1 - Chemical Product MSDS Name:3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
122454-46-0	3-Oxo-3-[4-(trifluoromethoxy)phenyl]pr	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 122454-46-0: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 82.5 - 84 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H6F3NO2
Molecular Weight: 229

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Reducing agents, strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 122454-46-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Oxo-3-[4-(trifluoromethoxy)phenyl]propanenitrile - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 122454-46-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 122454-46-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 122454-46-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(三氟甲氧基)苯甲酰基乙腈 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到3-amino-1-(4'-trifluoromethoxyphenyl)propanol
  参考文献：
  名称：

  Arylpropanolamines Incorporating an Antioxidant Function as Neuroprotective Agents

  摘要：

  我们合成了一系列含有二吡咯烷基嘧啶作为抗氧化功能的芳基丙醇胺，并将其评估为具有双重功能的神经保护剂。对它们作为钠通道阻断剂和抗氧化剂的体外功效进行了评估，并将其与乙醇胺衍生物（1）的体外功效进行了比较。研究表明，这些化合物能将 3H-BTX 毒素从大鼠脑膜部分的钠离子通道中置换出来，其能力在很大程度上与芳基环上的取代基无关，这表明这种活性可能主要与氨基嘧啶分子有关。抗氧化功效的结构-活性关系不太明确，但非对称嘧啶的活性始终高于其对称异构体。报告对这一观察结果进行了简要的理论研究。

  DOI：

  10.1071/ch03010
• 作为产物：
  描述：

  丙二腈 、 4-三氟甲氧基苯硼酸 在 4,4'-二甲基-2,2'-联吡啶 、 palladium(II) acetylacetonate 、 对甲苯磺酸 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以88%的产率得到4-(三氟甲氧基)苯甲酰基乙腈
  参考文献：
  名称：

  二腈的催化碳钯催化选择性合成β-乙腈

  摘要：

  已经开发出一种实用，方便且高度选择性的方法，该方法是由Pd催化的向二腈中添加有机硼试剂而合成β-酮腈。该方法提供了优异的官能团耐受性，广泛的基材范围以及使用市售基材的便利性。该方法有望在未来的合成程序中显示出更多的实用性。

  DOI：

  10.1021/acs.joc.0c02388

文献信息

• [EN] SULFONYLAMINOPYRIDINE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS SULFONYLAMINOPYRIDINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2016001341A1

  公开（公告）日：2016-01-07

  Provided are sulfonylaminopyridine compounds that are inhibitors of ITK kinase, compositions containing these compounds and methods for treating diseases mediated by ITK kinase. In particular, provided are compounds of Formula (I), (II) or (III), stereoisomers, tautomers, solvates, prodrugs or pharmaceutically acceptable salts thereof, where n, R1, R2, R3, R6 and R7 are defined herein, pharmaceutical compositions comprising the compound and a pharmaceutically acceptable carrier, adjuvant or vehicle, methods of using the compound or composition in therapy, for example, for treating a disease or condition mediated by ITK kinase in a patient.

  提供了一种磺酰氨基吡啶化合物，它们是ITK激酶的抑制剂，包含这些化合物的组合物以及治疗由ITK激酶介导的疾病的方法。具体来说，提供了Formula (I)、(II)或(III)的化合物，立体异构体、互变异构体、溶剂合物、前药或其药用可接受的盐，其中n、R1、R2、R3、R6和R7在此处定义，包括含有该化合物和药用可接受的载体、辅料或载体的药物组合物，使用该化合物或组合物进行治疗的方法，例如，用于治疗患有由ITK激酶介导的疾病或病况的患者。
• Base-Mediated Tunable Synthesis of 2-Trifluoromethylated Furans and Dihydrofuranols: Extraordinary Stable in Sulfuric Acid
  作者：Junwen Wang、Shouxiong Chen、Wei Wu、Shunli Wen、Zhiqiang Weng

  DOI：10.1021/acs.joc.9b02326

  日期：2019.12.6

  2-Trifluoromethylated furans and dihydrofuranols were tunably synthesized from the cyclization of β-ketonitriles with 3-bromo-1,1,1-trifluoroacetone mediated by bases. In addition, dehydration of dihydrofuranol compounds with concentrated sulfuric acid gave another 2-(trifluoromethyl)furans isomer. The developed methodology exhibits an excellent functional group tolerance for both aromatic and aliphatic β-ketonitriles

  由β-乙腈与3-溴-1,1,1-三氟丙酮的碱环合，可将β-酮腈环化而合成2-三氟甲基化的呋喃和二氢呋喃醇。另外，用浓硫酸使二氢呋喃醇化合物脱水，得到另一种2-（三氟甲基）呋喃异构体。所开发的方法对芳香族和脂肪族β-酮腈均具有出色的官能团耐受性。
• 2-三氟甲基取代呋喃化合物及其衍生物的合成方法
  申请人：福州大学

  公开号：CN110272400B

  公开（公告）日：2022-08-23

  本发明公开了一种2‑三氟甲基取代呋喃化合物及其衍生物的合成方法，其是以碱为促进剂，苯甲酰乙腈衍生物为底物，3‑溴‑1,1,1‑三氟丙酮为氟化试剂，在溶剂中，经串联反应得到所述2‑三氟甲基取代呋喃化合物；再经脱水及氰的水解制得2‑三氟甲基取代呋喃衍生物。该反应采用一锅法合成，具有操作步骤简便、原料易制备，反应体系对官能团的普适性较高等优点。所得氟化呋喃化合物对松材线虫等具有很好的杀灭活性，在100 mg/L剂量下，对线虫的死亡率高达87%，可作为一种潜在的含氟杀虫剂。
• [EN] HSP90 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE HSP90 ET LEURS UTILISATIONS
  申请人：UNIV BOSTON

  公开号：WO2020227368A1

  公开（公告）日：2020-11-12

  Herein is described the design and synthesis of resorcylate aminopyrazole compounds. These compounds show broad, potent and fungal-selective Hsp90 inhibitory activity. These compounds also find use in treating Hsp90 related deseases.

  这里描述了对间苯二酚氨基吡唑化合物的设计和合成。这些化合物表现出广泛、强效且对真菌选择性的Hsp90抑制活性。这些化合物还可用于治疗与Hsp90相关的疾病。
• Design and Synthesis of Fungal-Selective Resorcylate Aminopyrazole Hsp90 Inhibitors
  作者：David S. Huang、Emmanuelle V. LeBlanc、Tanvi Shekhar-Guturja、Nicole Robbins、Damian J. Krysan、Juan Pizarro、Luke Whitesell、Leah E. Cowen、Lauren E. Brown

  DOI：10.1021/acs.jmedchem.9b00826

  日期：2020.3.12

  pathogen’s human host, preventing the use of known clinical Hsp90 inhibitors in antifungal applications due to concomitant host toxicity issues. With the goal of developing Hsp90 inhibitors with acceptable therapeutic indices for the treatment of invasive fungal infections, we initiated a program to design and synthesize potent inhibitors with selective activity against fungal Hsp90 isoforms over their

  在所有真核生物中必不可少的分子伴侣Hsp90在促进多种致病真菌物种的存活，毒力和耐药性方面具有多方面的作用。伴侣对病原体的人类宿主也至关重要，由于伴随的宿主毒性问题，防止在抗真菌应用中使用已知的临床Hsp90抑制剂。为了开发具有可接受的治疗指数的Hsp90抑制剂来治疗侵袭性真菌感染，我们启动了一个程序，以设计和合成对人类Hsp90异构体具有选择性的针对真菌Hsp90亚型的选择性活性的有效抑制剂。基于我们先前报道的间苯二酸酯天然产物的衍生化以产生真菌选择性化合物，我们已经开发了一系列具有广泛，有效和真菌选择性Hsp90抑制活性的合成氨基吡唑取代的间苯二酸酰胺。在这里，我们描述了该系列的合成，以及生化结构与活性之间的关系，从而驱动了对Hsp90亚型表达的选择性。新型隐球菌和白色念珠菌是两种具有重要临床意义的致病真菌。