3-(三氟甲基)-2-吡唑啉-5-酮 | 401-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 3-(三氟甲基)-2-吡唑啉-5-酮
• 中文别名: 3-(三氟甲基)-2-吡唑烷-5-酮；3-三氟甲基-1H-5-吡唑酮
• 英文名称: 3-(trifluoromethyl)-2-pyrazolin-5-one
• 英文别名: 5-trifluoromethyl-2,4-dihydropyrazol-3-one；3-(trifluoromethyl)-1,4-dihydropyrazol-5-one
• CAS: 401-73-0
• 化学式: C₄H₃F₃N₂O
• 分子量: 152.076
• InChiKey: PMTWALQJNWEDLH-UHFFFAOYSA-N

物化性质

• 熔点：
  214-217°C
• 密度：
  1.70
• 溶解度：
  7.4 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933199090
• 安全说明：
  S26,S36/37/39
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	3-(Trifluoromethyl)-4 5-dihydro-1h-pyrazol-5-one Material Safety Data Sheet
Synonym:
CAS:	401-73-0

Section 1 - Chemical Product MSDS Name:3-(Trifluoromethyl)-4 5-dihydro-1h-pyrazol-5-one Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
401-73-0	3-(Trifluoromethyl)-4,5-dihydro-1h-pyr	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
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Not available.
Skin:
Not available.
Ingestion:
Not available.
Inhalation:
Not available.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
Not available.
Extinguishing Media:
Not available.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Not available.

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Section 7 - HANDLING and STORAGE
Handling:
Not available.
Storage:
Not available.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Exposure Limits CAS# 401-73-0: Personal Protective Equipment Eyes: Not available.
Skin:
Not available.
Clothing:
Not available.
Respirators:
Not available.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white - off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 214 - 217 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: C4H3F3N2O
Molecular Weight: 152.08

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Not available.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 401-73-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-(Trifluoromethyl)-4,5-dihydro-1h-pyrazol-5-one - 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 22 Do not breathe dust.
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# 401-73-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 401-73-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 401-73-0 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：

  (2-呋喃亚甲基)丙二腈 、 3-(三氟甲基)-2-吡唑啉-5-酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以31%的产率得到6-Amino-4-(furan-2-yl)-3-(trifluoromethyl)-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
  参考文献：
  名称：

  Zohdi, Hussein F.; Elghandour, Ahmed H. H.; Rateb, Nora M., Journal of Chemical Research, Miniprint, 1992, # 12, p. 3015 - 3025

  摘要：

  DOI：
• 作为产物：
  描述：

  三氟乙酰乙酸乙酯 在 溶剂黄146 、 肼 作用下， 以88%的产率得到3-(三氟甲基)-2-吡唑啉-5-酮
  参考文献：
  名称：

  一个简单且无催化剂的锅，即可进入吡唑啉酮稠合的2,8-二氧杂双环[3.3.1]壬烷†

  摘要：

  通过一锅，2-羟基查耳酮（1）与3-三氟甲基取代的吡唑酮（2）的无催化剂反应，完成了一系列新颖的芳基和杂芳基稠合的2,8-二氧杂双环[3.3.1]壬烷（3）的合成。在回流温度下在二甲苯中。通过与3-甲基取代的吡唑啉酮（2c，d）的比较研究证实了三氟甲基官能团在3的形成中的作用，并给出了结果。

  DOI：

  10.1039/c4ra07278b

文献信息

• [EN] PHARMACEUTICALLY USEFUL HETEROCYCLE-SUBSTITUTED LACTAMS<br/>[FR] LACTAMES SUBSTITUÉS PAR HÉTÉROCYCLE PHARMACEUTIQUEMENT UTILES
  申请人：CYLENE PHARMACEUTICALS INC

  公开号：WO2011031979A1

  公开（公告）日：2011-03-17

  The invention provides compounds that inhibit CK2 and/or Pim kinases and compositions containing such compounds. These compounds and compositions are useful for treating proliferative disorders such as cancer, as well as other kinase-associated conditions including inflammation, pain, infections, and certain immunological disorders.

  这项发明提供了抑制CK2和/或Pim激酶的化合物和含有这些化合物的组合物。这些化合物和组合物可用于治疗癌症等增殖性疾病，以及其他与激酶相关的疾病，包括炎症、疼痛、感染和某些免疫性疾病。
• 一种用来制造吡唑或嘧啶酮的新方法
  申请人：福建永晶科技股份有限公司

  公开号：CN110452173A

  公开（公告）日：2019-11-15

  本发明涉及胺化合物在制造环系统中含两个氮原子的氟化或非氟化的5元或6元杂环化合物(优选吡唑或嘧啶酮)的方法中的用途。本发明还涉及一种用来制造吡唑或嘧啶酮的方法，所述吡唑或嘧啶酮可以是氟化的或可以不是氟化的(非氟化的)。特别地，本发明涉及用来制造氟化吡唑或氟化嘧啶酮的方法，且具体地本发明涉及用来制造这种氟化吡唑或氟化嘧啶酮的方法，所述氟化吡唑或氟化嘧啶酮各自是制药和农业应用的非常重要的结构单元。例如，杀真菌剂是分别强烈依赖于以这种氟化吡唑作为关键结构单元的联苯吡菌胺、氟唑菌酰胺、氟茚唑菌胺、氟唑环菌胺、吡唑萘菌胺和苯并烯氟菌唑，或双氟磺草胺和氯酯磺草胺(双氯磺草胺)。
• Synthesis and Antitumor Activity of 5-Trifluoromethyl-2,4- dihydropyrazol-3-one Nucleosides
  作者：Ibrahim Abdou、Ayman Saleh、Hussein Zohdi

  DOI：10.3390/90300109

  日期：——

  2,4-Dihydropyrazole glucosides 3a-3c were prepared and tested for theirantitumor activity. The structures of these compounds were established by 1H and 13C-NMR spectroscopy. Glucoside 3b shows an in vitro IC50 value of 16.4 μM againstproliferation of the human promyelotic leukemia (HL60) cell line.

  2,4-二氢吡唑糖苷3a-3c被合成并测试了其抗肿瘤活性。这些化合物的结构通过1H和13C-NMR光谱确定。糖苷3b对人类前髓细胞白血病（HL60）细胞系的增殖显示出16.4 μM的体外IC50值。
• “On water” highly atom economical and rapid synthesis of a novel class of 3-hydroxy-2-oxindole scaffolds under a catalyst-free and column chromatography-free protocol at room temperature
  作者：Pramod B. Thakur、Harshadas M. Meshram

  DOI：10.1039/c3ra46613b

  日期：——

  An “on water” highly atom economical and rapid protocol has been developed for the synthesis of a novel class of 3-(2-pyrazolin-5-one) substituted, 3-hydroxy-2-oxindole scaffolds under catalyst-free and column chromatography-free conditions at rt. The generality of the method has been demonstrated by screening a series of isatin electrophiles as well as 2-pyrazolin-5-one derivatives. The developed method is a good example of green synthesis in which straightforward synthesis of a medicinally important 3-hydroxy-2-oxindole framework is executed by employing very mild, simple and handy procedures from readily available starting materials.

  一种“水上”高度原子经济且快速的合成新型3-(2-吡唑啉-5-酮)取代的3-羟基-2-氧吲哚骨架的方案已被开发，该方案在常温下无催化剂且无柱色谱条件下进行。该方法的普遍性通过筛选一系列异靛酮电亲体以及2-吡唑啉-5-酮衍生物得到了验证。所开发的方法是绿色合成的一个好例子，通过采用非常温和、简单且方便的程序，从易获得的起始材料中直接合成药用重要的3-羟基-2-氧吲哚框架。
• 3-Trifluoromethylpyrazolones derived nucleosides: Synthesis and antiviral evaluation
  作者：Ayman M. S. Ahmed、Reham A. I. Abou-Elkhair、Alaa M. El-Torky、Abdalla E. A. Hassan

  DOI：10.1080/15257770.2019.1591445

  日期：2019.8.3

  luoromethyl-pyrazolones, their ribofuranosyl, and 5′-deoxyribofuranosyl nucleosides were synthesized, geometry optimized using Density functional theory (DFT), and evaluated for their antiviral activity. 2-Nitrophenylhydrazonopyra-zolone derivative 5 showed significant activity against MERS-CoV (EC50 = 4.6 μM). The nucleoside analog 8 showed moderate activity against DENV-2 (EC50 = 10 μM), while the

  登革热（DENV）病毒感染是一个全球性的公共卫生问题，很少出现威胁生命的疾病，例如登革出血热（DFS）和登革热休克综合征（DSS）。中东呼吸综合征冠状病毒（MERS-CoV）是一种高致病性的人类冠状病毒，感染患者的死亡率为38％。合成了一系列的4-芳基肼基-5-三氟甲基-吡唑啉酮，其呋喃核糖基和5'-脱氧呋喃核糖基核苷，并使用密度泛函理论（DFT）进行了几何优化，并评估了其抗病毒活性。2-硝基苯基肼基no并吡喃酮衍生物5对MERS-CoV表现出显着活性（EC 50 = 4.6μM ）。核苷类似物8对DENV-2（EC 50= 10μM），而相应的5'-脱氧核糖核苷类似物消除了活性。在这项研究中确定的命中点将这类化合物设置为将来的进一步优化。