1-苯基-5-三氟甲基-吡唑-4-羧肼 | 175137-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苯基-5-三氟甲基-吡唑-4-羧肼
• 中文别名: 1-苯基-5-(三氟甲基)-1H-吡唑-4-碳酰肼
• 英文名称: 1-phenyl-5-trifluoromethyl-1H-4-pyrazol hydrazide
• 英文别名: 1-phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carbohydrazide；1-phenyl-5-(trifluoromethyl)pyrazole-4-carbohydrazide
• CAS: 175137-32-3
• 化学式: C₁₁H₉F₃N₄O
• mdl: MFCD00068152
• 分子量: 270.214
• InChiKey: HHPIIZJILLCOBV-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155°C
• 密度：
  1.49±0.1 g/cm3(Predicted)
• 溶解度：
  38.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933199090

SDS

Name:	1-Phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carbohydrazide 97% Material Safety Data Sheet
Synonym:	2-Phenyl-3-(trifluoromethyl)pyrazole-4-caroxylic acid hydrazid
CAS:	175137-32-3

Section 1 - Chemical Product MSDS Name:1-Phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carbohydrazide 97% Material Safety Data Sheet
Synonym:2-Phenyl-3-(trifluoromethyl)pyrazole-4-caroxylic acid hydrazid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
175137-32-3	1-Phenyl-5-(trifluoromethyl)-1H-pyrazo	97	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
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.
Store under nitrogen.

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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# 175137-32-3: 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: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 153 - 155 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: C11H9F3N4O
Molecular Weight: 270

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acids, acid chlorides, strong oxidizing agents.
Hazardous Decomposition Products:
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# 175137-32-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Phenyl-5-(trifluoromethyl)-1H-pyrazole-4-carbohydrazide - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 175137-32-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 175137-32-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 175137-32-3 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：

  1-苯基-5-三氟甲基-吡唑-4-羧肼 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 9.0h， 生成 2-allyloxy-5-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  2-（取代醚）-5-（1-苯基-5（三氟甲基）-1H-吡唑-4-基）-1,3,4-恶二唑衍生物的抗菌和抗真菌活性

  摘要：

  通过将酰胺键替换为1,3,4-恶二唑部分，合成了一系列带有1,3,4-恶二唑的1-苯基-5-（三氟甲基）-1H-吡唑衍生物，并评估了它们的抗菌和抗真菌活性。生物测定结果表明，化合物7a和7b对米曲霉黄单胞菌pv表现出最强的抗菌活性。米黄色素的EC50值分别为15.0和6.4 µg / mL；化合物6a对六种真菌表现出全面的抗真菌活性。化合物6f在100 µg / mL的浓缩液中能选择性地抑制菌核菌和茄形丝核菌的生长，抑制率分别为82.5和80.3％。化合物7b对尖孢镰刀菌，曼氏丝孢菌和茄形假丝酵母具有良好的抗真菌活性，抑制率分别为70.8、69.5，和71.5％。结果表明，这类化合物可作为有前途的抗菌剂进行进一步研究。

  DOI：

  10.1002/jhet.2820
• 作为产物：
  描述：

  乙氧基-2-亚甲基三氟乙酰乙酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 1-苯基-5-三氟甲基-吡唑-4-羧肼
  参考文献：
  名称：

  新型2-（硫醚/砜）-5-吡唑基-1,3,4-恶二唑衍生物的合成及生物活性

  摘要：

  摘要通过将吡唑部分引入1,3,4-恶二唑的5-位，合成了一系列新型的2-（硫醚/砜）-5-吡唑基-1,3,4-恶二唑衍生物。初步的生物测定表明，目标化合物对病原菌米氏黄单胞菌PV表现出明显的活性。稻（Xoo）和5种植物致病真菌的体外研究。其中，6c，7a，7b和7c对Xoo的半数最大有效浓度（EC 50）值在16.6μg/ mL和65.7μg/ mL范围内，优于商业化的农业抗菌素比美噻唑（92.6μg/ mL）。 mL）和硫二唑铜（121.8μg/ mL）。化合物7a，7b和7c对五种植物真菌具有全面的抗真菌活性，这与羟甲唑相当。

  DOI：

  10.1016/j.cclet.2016.06.055

文献信息

• 一种1,3,4-噁(噻)二唑基的咪唑类化合物及其制备方法和用途
  申请人：贵州大学

  公开号：CN109942567B

  公开（公告）日：2023-04-07

  本发明涉及一种1,3,4‑噁(噻)二唑基的咪唑类化合物及其制备方法和用途。所述化合物具有如通式(Ⅰ)所示的结构：该化合物对植物致病病原菌，如水稻白叶枯病菌、柑橘溃疡病菌和猕猴桃溃疡病菌具有较好的抑制作用。
• 1-取代-5-三氟甲基-4-吡唑联1,3,4-噁二唑 硫醚或砜类衍生物及其应用
  申请人：贵州大学

  公开号：CN104829605B

  公开（公告）日：2018-03-23

  本发明公开了一类1‑取代‑5‑三氟甲基‑4‑吡唑联1,3,4‑噁二唑硫醚或砜类衍生物及其应用，其结构式如A，B所示，以三氟乙酰乙酸乙酯为原料，经酯化、闭环、肼解、闭环、取代5步反应合成了1‑取代‑5‑三氟甲基‑4‑吡唑联1,3,4‑噁二唑类化合物。该类化合物对植物细菌或植物真菌病害具有一定的抑制作用，可作防治植物细菌病或植物真菌病的农药和农药添加剂。
• 吡唑酰胺类衍生物、其制备方法及应用
  申请人：沈阳万菱生物技术有限公司

  公开号：CN114181150A

  公开（公告）日：2022-03-15

  本发明公开了一种具有抑制植物生长及体外HPPD靶标酶的1‑取代基‑5‑取代基‑N'‑(1‑双取代基)‑1H‑吡唑‑4‑甲酰肼衍生物(通式Ⅰ)和1‑甲基‑5‑取代基‑1H‑吡唑‑4‑甲酰氨基酸甲酯衍生物(通式Ⅱ)的制备及应用。本发明涉及化工和农药技术领域，具体技术是此类化合物可以有效的抑制阔叶杂草马齿苋根茎的生长且对HPPD酶也显示出优秀的抑制活性。本发明1‑甲基‑5‑取代基‑1H‑吡唑‑4‑甲酰氨基酸甲酯衍生物中的化合物B7在100μg/mL剂量下对马齿苋根及茎皆有100％抑制率，甚至在10μg/mL剂量下，B7仍对马齿苋根及茎存在77.39％和64.93％抑制率，优于苯唑草酮(53.96％和43.0％)。本发明所述化合物可作为潜在的HPPD抑制剂及阔叶杂草苗前除草剂开发使用，其结构和制备工艺简单，生产成本低，应用前景广阔。
• Novel Pyrazole Amides as Potential 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors
  作者：Huanan Zeng、Wei Zhang、Zhengxing Wang、Wang Geng、Gang Feng、Xiuhai Gan

  DOI：10.1021/acs.jafc.2c02123

  日期：2022.6.22

  4-Hydroxyphenylpyruvate dioxygenase (HPPD) is an important target for the development of new herbicides. HPPD inhibitors can hinder photosynthesis and induce weed death with bleaching symptoms. To explore the novel skeleton of HPPD inhibitors, a series of novel pyrazole amide derivatives were synthesized and evaluated for their inhibitory effects on Arabidopsis thaliana HPPD (AtHPPD) and herbicidal

  4-羟基苯丙酮酸双加氧酶（HPPD）是开发新型除草剂的重要靶点。HPPD 抑制剂会阻碍光合作用并导致杂草死亡并出现白化症状。为探索HPPD抑制剂的新骨架，合成了一系列新型吡唑酰胺衍生物，并对其对拟南芥HPPD（At HPPD）的抑制作用和除草活性进行了评价。一些化合物对At HPPD具有优异的抑制活性。其中，化合物B5对At HPPD的抑制活性位居前列，IC 50值为0.04 μM，明显优于topramezone（IC 50值为 0.11 μM）。此外，化合物B2和B7在 100 μg/mL的培养皿试验中对马齿苋和三色苋具有 100% 的除草活性。特别是化合物B7不仅具有很强的At HPPD抑制活性，而且表现出显着的芽前除草活性。然而，化合物B7对大豆、棉花和小麦完全无害。此外，分子对接和微尺度热泳测量实验验证了化合物可以通过以下途径与At HPPD很好地结合。π-π 相互作用。目前的工作为合理设计更有效的
• Design, Synthesis and Bioactivity Evaluation of Novel 2-(pyrazol-4-yl)-1,3,4-oxadiazoles Containing an Imidazole Fragment as Antibacterial Agents
  作者：Hongwu Liu、Shan Yang、Ting Li、Siyue Ma、Peiyi Wang、Guoqing Wang、Shanshan Su、Yue Ding、Linli Yang、Xiang Zhou、Song Yang

  DOI：10.3390/molecules28062442

  日期：——

  antibacterial compounds, a series of novel imidazole-fragment-decorated 2-(pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized based on our previous works via the active substructure splicing principle, and their bioactivities were systematically evaluated both in vitro and in vivo. The bioassays showed that some of the target compounds displayed excellent in vitro antibacterial activity toward

  咪唑生物碱是一类常见的五元芳杂环化合物，广泛存在于植物、动物和海洋生物中。由于咪唑具有广泛而优异的生物学和药理活性，一直是研究人员关注的热点，被广泛用作寻找生物活性分子的活性基团。为了寻找更有效的抗菌化合物，基于我们以前的工作，通过活性亚结构剪接原理设计合成了一系列新型咪唑片段修饰的 2-(pyrazol-4-yl)-1,3,4-oxadiazoles，并且它们的生物活性在体外和体内进行了系统评估。生物测定表明，一些目标化合物对三种有毒的植物病原菌表现出优异的体外抗菌活性，包括米黄单胞菌光伏。oryzae (Xoo), Xanthomonas axonopodis pv。柑橘 (Xac) 和 Pseudomonas syringae pv。actinidiae (Psa)，最低 EC50 值分别为 7.40 (7c)、5.44 (9a) 和 12.85 (9a) μg/mL。同时，化合物7c在200