2,5-二(2,2,2-三氟乙氧基)苯-1-羧肼 | 50778-75-1

• 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: 2,5-二(2,2,2-三氟乙氧基)苯-1-羧肼
• 中文别名: 2,5-二(三氟乙氧基)苯甲酸肼；2,5-二(2,2,2-三氟乙氧基)苯-1-碳酰肼
• 英文名称: 2,5-di-(2,2,2-trifluoroethoxy)benzoic acid hydrazide
• 英文别名: 2,5-Bis(2,2,2-trifluoroethoxy)benzoic acid hydrazide；2,5-bis(2,2,2-trifluoroethoxy)benzohydrazide
• CAS: 50778-75-1
• 化学式: C₁₁H₁₀F₆N₂O₃
• mdl: MFCD00221192
• 分子量: 332.202
• InChiKey: WJYCMPVGQTYGSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  10

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• 海关编码：
  2928000090

SDS

Name:	2 5-di(2 2 2-trifluoroethoxy)benzene-1-carbohydrazide 95+% Material Safety Data Sheet
Synonym:
CAS:	50778-75-1

Section 1 - Chemical Product MSDS Name:2 5-di(2 2 2-trifluoroethoxy)benzene-1-carbohydrazide 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
50778-75-1	2,5-Di(2,2,2-trifluoroethoxy)benzene-1	95+%	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.

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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# 50778-75-1: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 86 - 88 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: C11H10F6N2O3
Molecular Weight: 332.2

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, acids, acid chlorides.
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# 50778-75-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,5-Di(2,2,2-trifluoroethoxy)benzene-1-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# 50778-75-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 50778-75-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 50778-75-1 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：

  2,5-二(2,2,2-三氟乙氧基)苯-1-羧肼 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 生成 2-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-5-(2-methylbenzylthio)-1,3,4-oxadiazole
  参考文献：
  名称：

  作为潜在的葡萄糖苷酶抑制剂的新型 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol 衍生物的合成

  摘要：

  背景 与标准药物相比，不同生物活性物质的混合分子可以提高亲和力和效率。因此，基于这一事实，我们预测与标准药物相比，氟、恶二唑、硫等的组合可能会增强 α-葡萄糖苷酶抑制活性。 方法 合成了一系列新型 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol 衍生物(2a-2i ) 并使用光谱技术进行表征，例如1 HNMR和LC-MS。为了评价其生物活性，进行了体外α-淀粉酶和α-糖苷酶抑制活性。使用遗传模型黑腹果蝇进行体内研究，以评估抗高血糖作用。 结果  与标准阿卡波糖 (IC 50  = 34.71 μg/ml)相比，化合物2a-2i在 IC 50 = 40.00–80.00 μg/ml范围内表现出α-淀粉酶抑制活性。 与标准阿卡波糖 (IC 50  = 34.72 μg/ml)相比，化合物2a-2i在 IC 50

  DOI：

  10.1016/j.bioorg.2021.105046
• 作为产物：
  描述：

  2,5-双(2,2,2-三氟乙氧基)苯甲酸 在 氯化亚砜 、 一水合肼 作用下， 生成 2,5-二(2,2,2-三氟乙氧基)苯-1-羧肼
  参考文献：
  名称：

  作为潜在的葡萄糖苷酶抑制剂的新型 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol 衍生物的合成

  摘要：

  背景 与标准药物相比，不同生物活性物质的混合分子可以提高亲和力和效率。因此，基于这一事实，我们预测与标准药物相比，氟、恶二唑、硫等的组合可能会增强 α-葡萄糖苷酶抑制活性。 方法 合成了一系列新型 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol 衍生物(2a-2i ) 并使用光谱技术进行表征，例如1 HNMR和LC-MS。为了评价其生物活性，进行了体外α-淀粉酶和α-糖苷酶抑制活性。使用遗传模型黑腹果蝇进行体内研究，以评估抗高血糖作用。 结果  与标准阿卡波糖 (IC 50  = 34.71 μg/ml)相比，化合物2a-2i在 IC 50 = 40.00–80.00 μg/ml范围内表现出α-淀粉酶抑制活性。 与标准阿卡波糖 (IC 50  = 34.72 μg/ml)相比，化合物2a-2i在 IC 50

  DOI：

  10.1016/j.bioorg.2021.105046

文献信息

• 2,5-Bis(2,2,2-trifluoroethoxy)phenyl-tethered 1,3,4-Oxadiazoles Derivatives: Synthesis, In Silico Studies, and Biological Assessment as Potential Candidates for Anti-Cancer and Anti-Diabetic Agent
  作者：Sathyanarayana D. Shankara、Arun M. Isloor、Avinash K. Kudva、Shamprasad Varija Raghu、Pavan K. Jayaswamy、Pushyaraga P. Venugopal、Praveenkumar Shetty、Debashree Chakraborty

  DOI：10.3390/molecules27248694

  日期：——

  In the present work, a series of new 1-5-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-1,3,4-oxadiazol-3-acetyl-2-aryl-2H/methyl derivatives were synthesized through a multistep reaction sequence. The compounds were synthesized by the condensation of various aldehydes and acetophenones with the laboratory-synthesized acid hydrazide, which afforded the Schiff’s bases. Cyclization of the Schiff bases yielded 1,3,4-oxadiazole derivatives. By spectral analysis, the structures of the newly synthesized compounds were elucidated, and further, their anti-cancer and anti-diabetic properties were investigated. To examine the dynamic behavior of the candidates at the binding site of the protein, molecular docking experiments on the synthesized compounds were performed, followed by a molecular dynamic simulation. ADMET (chemical absorption, distribution, metabolism, excretion, and toxicity) prediction revealed that most of the synthesized compounds follow Lipinski’s rule of 5. The results were further correlated with biological studies. Using a cytotoxic assay, the newly synthesized 1,3,4-Oxadiazoles were screened for their in vitro cytotoxic efficacy against the LN229 Glioblastoma cell line. From the cytotoxic assay, the compounds 5b, 5d, and 5m were taken for colony formation assay and tunnel assay have shown significant cell apoptosis by damaging the DNA of cancer cells. The in vivo studies using a genetically modified diabetic model, Drosophila melanogaster, indicated that compounds 5d and 5f have better anti-diabetic activity among the different synthesized compounds. These compounds lowered the glucose levels significantly in the tested model.

  本研究通过多步反应序列合成了一系列新的 1-5-[2,5-双(2,2,2-三氟乙氧基)苯基]-1,3,4-恶二唑-3-乙酰基-2-芳基-2H/甲基衍生物。这些化合物是通过各种醛和苯乙酮与实验室合成的酸酰肼缩合而得到希夫碱的。希夫碱环化后得到 1,3,4-噁二唑衍生物。通过光谱分析，阐明了新合成化合物的结构，并进一步研究了它们的抗癌和抗糖尿病特性。为了研究候选化合物在蛋白质结合位点的动态行为，对合成的化合物进行了分子对接实验，然后进行了分子动态模拟。ADMET（化学吸收、分布、代谢、排泄和毒性）预测显示，大多数合成化合物遵循利宾斯基的 5 规则。研究结果进一步与生物学研究相关联。通过细胞毒性试验，筛选了新合成的 1,3,4-恶二唑对 LN229 胶质母细胞瘤细胞株的体外细胞毒性效果。在细胞毒性试验中，化合物 5b、5d 和 5m 被用于菌落形成试验，隧道试验显示，这些化合物通过破坏癌细胞的 DNA 使细胞明显凋亡。利用转基因糖尿病模型黑腹果蝇进行的体内研究表明，在不同的合成化合物中，化合物 5d 和 5f 具有更好的抗糖尿病活性。这些化合物能显著降低受试模型的血糖水平。
• 10.1007/s13738-024-03067-x
  作者：Anjanayya, Govinda、Gani, Ramesh、Kudva, Avinash、Joshi, Shrinivas、Hiremath, Murigendra、Kavital, Apsara、Timanagouda, Karabasanagouda、Mathada, Basavarajaiah、Javeed, Mohammad、Aziz, Raifa、Raghu, Shamprasad

  DOI：10.1007/s13738-024-03067-x

  日期：——

  α-glucosidase enzyme inhibitor activity. An in vivo Drosophila melanogaster model and an in vitro system were used to investigate its antidiabetic properties, further, which were characterized by 1HNMR, MASS, and FT-IR. Spectroscopic techniques and DFT are used to calculate more geometrically optimized molecule structures using the B3LYP technique. The compounds were tested against the α-glucosidase

  目前的抗糖尿病药物具有大量有害副作用，并且大多数药物不含1,3,4-恶二唑部分。因此，有必要研究开发含有1,3,4-恶二唑部分且副作用较少的新药物。合成、表征并评估了新型掺氟 1,3,4-恶二唑衍生物 (1c-1n) 的 α-淀粉酶和 α-葡萄糖苷酶抑制剂活性。采用体内果蝇模型和体外系统研究其抗糖尿病特性，并通过 1 HNMR、MASS 和 FT-IR 对其进行了表征。光谱技术和 DFT 用于使用 B3LYP 技术计算几何更优化的分子结构。这些化合物针对 α-葡萄糖苷酶和 α-淀粉酶进行了测试。在测试的不同化合物中，化合物 1i (IC 50 = 54.83 µg/ml)、1k (IC 50 = 64.95 µg/ml)、1m (IC 50 = 64.78 µg/ml) 和 1n (IC 50 = 66.30 µg/ml) 与阿卡波糖 (IC 50 = 35.17 µg/ml) 相比显示出显着的
• US3996280A
  申请人：——

  公开号：US3996280A

  公开（公告）日：1976-12-07
• Synthesis of novel 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol derivatives as potential glucosidase inhibitors
  作者：Ramesh S. Gani、Avinash K. Kudva、Karabasanagouda Timanagouda、Raghuveer、Salma Begum Hussain Mujawar、Shrinivas D. Joshi、Shamprasad Varija Raghu

  DOI：10.1016/j.bioorg.2021.105046

  日期：2021.9

  drug. Hence based on this fact, we predict that a combination of fluorine, oxadiazole, sulfur, etc., may enhance α-glucosidase inhibition activity compared to a standard drug. Methods A series of novel 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol derivatives (2a-2i) were synthesized and characterized using spectroscopic techniques such as 1HNMR and LC-MS. In order to evaluate its

  背景 与标准药物相比，不同生物活性物质的混合分子可以提高亲和力和效率。因此，基于这一事实，我们预测与标准药物相比，氟、恶二唑、硫等的组合可能会增强 α-葡萄糖苷酶抑制活性。 方法 合成了一系列新型 5-(2,5-bis(2,2,2-trifluoroethoxy)phenyl)-1,3,4-oxadiazole-2-thiol 衍生物(2a-2i ) 并使用光谱技术进行表征，例如1 HNMR和LC-MS。为了评价其生物活性，进行了体外α-淀粉酶和α-糖苷酶抑制活性。使用遗传模型黑腹果蝇进行体内研究，以评估抗高血糖作用。 结果  与标准阿卡波糖 (IC 50  = 34.71 μg/ml)相比，化合物2a-2i在 IC 50 = 40.00–80.00 μg/ml范围内表现出α-淀粉酶抑制活性。 与标准阿卡波糖 (IC 50  = 34.72 μg/ml)相比，化合物2a-2i在 IC 50