N-[2-硝基-4-（三氟甲基）苯基]哌嗪 | 58315-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: N-[2-硝基-4-（三氟甲基）苯基]哌嗪
• 中文别名: N-[2-硝基-4-(三氟甲基)苯基]哌嗪
• 英文名称: 1-(2-nitro-4-(trifluoromethyl)phenyl)piperazine
• 英文别名: 1-(2-Nitro-4-trifluoromethyl-phenyl)-piperazine；1-(2-nitro-4-trifluoromethylphenyl)piperazine；1-[2-Nitro-4-(trifluoromethyl)phenyl]piperazine
• CAS: 58315-38-1
• 化学式: C₁₁H₁₂F₃N₃O₂
• mdl: MFCD00052613
• 分子量: 275.23
• InChiKey: YOBUPGXTLFRIJD-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  370.0±42.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免接触水。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 安全说明：
  S26,S36/37/39
• 储存条件：
  在密封的贮藏器中，应放置于阴凉、干燥处避光保存。

SDS

Name:	1-[2-Nitro-4-(trifluoromethyl)phenyl]piperazine 97% Material Safety Data Sheet
Synonym:
CAS:	58315-38-1

Section 1 - Chemical Product MSDS Name:1-[2-Nitro-4-(trifluoromethyl)phenyl]piperazine 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
58315-38-1	1-[2-Nitro-4-(trifluoromethyl)phenyl]p	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 58315-38-1: 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: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 68 - 69 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: C11H12F3N3O2
Molecular Weight: 275

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acid chlorides, 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# 58315-38-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-[2-Nitro-4-(trifluoromethyl)phenyl]piperazine - 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: AMINES, SOLID, CORROSIVE, N.O.S.*
Hazard Class: 8
UN Number: 3259
Packing Group: III
IMO
Shipping Name: AMINES, SOLID, CORROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing Group: III
RID/ADR
Shipping Name: AMINES, SOLID, CORROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
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.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 58315-38-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 58315-38-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 58315-38-1 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

制备方法与用途

制备方法主要用于医药中间体、有机合成、有机溶剂，也可用于染料生产、农药生产和香料方面。

用途简介： 主要应用于医药中间体、有机合成、有机溶剂，还涉及染料生产、农药生产和香料领域。

反应信息

• 作为反应物：
  描述：

  N-[2-硝基-4-（三氟甲基）苯基]哌嗪 在 甲醇 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 3-(4-(2-nitro-4-(trifluoromethyl)phenyl)piperazin-1-yl)-1-phenylpropan-1-ol
  参考文献：
  名称：

  新型止痛药氨基甲酸1-苯基-3-（4-苯基-哌嗪-1-基）-丙基酯衍生物的合成及药理评价

  摘要：

  通过平衡基于靶点的体外筛选和表型体内筛选的发现策略，合成了一系列氨基甲酸1-苯基-3-（4-苯基-哌嗪-1-基）-丙基酯衍生物。筛选所有新合成的化合物的镇痛活性，并与标准药物吗啡进行比较。其中，化合物44r是一种有效的镇痛药，在大鼠中具有良好的药代动力学特性，最重要的是，它具有很大的安全系数。我们通过体外和体内功能分析证明了其镇痛活性可能是通过5-HT 2A拮抗作用实现的。因此，可以得出结论，在开发化合物44r方面有足够的进一步研究的空间。 作为止痛药的主要候选药物。

  DOI：

  10.1016/j.bmcl.2012.02.023

文献信息

• Piperazinyl fragment improves anticancer activity of Triapine
  作者：Marta Rejmund、Anna Mrozek-Wilczkiewicz、Katarzyna Malarz、Monika Pyrkosz-Bulska、Kamila Gajcy、Mieczyslaw Sajewicz、Robert Musiol、Jaroslaw Polanski

  DOI：10.1371/journal.pone.0188767

  日期：——

  A new class of TSCs containing piperazine (piperazinylogs) of Triapine, was designed to fulfill the di-substitution pattern at the TSCs N4 position, which is a crucial prerequisite for the high activity of the previously obtained TSC compounds–DpC and Dp44mT. We tested the important physicochemical characteristics of the novel compounds L1-L12. The studied ligands are neutral at physiological pH, which allows them to permeate cell membranes and bind cellular Fe pools more readily than less lipid-soluble ligands, e.g. DFO. The selectivity and anti-cancer activity of the novel TSCs were examined in a variety of cancer cell types. In general, the novel compounds demonstrated the greatest promise as anti-cancer agents with both a potent and selective anti-proliferative activity. We investigated the mechanism of action more deeply, and revealed that studied compounds inhibit the cell cycle (G1/S phase). Additionally we detected apoptosis, which is dependent on cell line’s specific genetic profile. Accordingly, structure-activity relationship studies suggest that the combination of the piperazine ring with Triapine allows potent and selective anticancer chelators that warrant further in vivo examination to be identified. Significantly, this study proved the importance of the di-substitution pattern of the amine N4 function.

  设计了一类包含哌嗪的Triapine（哌嗪类似物）作为靶向铁硫簇（TSCs）的新一类化合物，旨在实现TSCs的N4位置上的二取代模式，这是先前获得的具有高活性的TSC化合物–DpC和Dp44mT的关键前提。我们测试了新型化合物L1-L12的重要物理化学特性。这些配体在生理pH下呈中性，这使得它们比亲脂性较低的配体（如DFO）更容易穿透细胞膜并结合细胞内的铁库。在多种癌细胞类型中检测了这些新型TSCs的选择性和抗癌活性。总体而言，这些新型化合物展现出最有希望作为抗癌剂，具有强效且选择性的抗增殖活性。我们更深入地研究了这些化合物的作用机制，发现它们能够抑制细胞周期（G1/S期）。此外，我们还检测到了依赖于细胞系特定遗传背景的凋亡现象。因此，构效关系研究表明，哌嗪环与Triapine的结合使得能够识别出具有强效且选择性的抗癌螯合剂，这些螯合剂值得进一步进行体内研究。值得注意的是，这项研究证明了胺N4功能的二取代模式的重要性。
• Pyrimidine A2b selective antagonist compounds, their synthesis and use
  申请人：——

  公开号：US20030162764A1

  公开（公告）日：2003-08-28

  The subject invention provides compounds having the structure: 1 wherein R 1 is substituted or unsubstituted phenyl or a 5-6 membered heterocyclic or heteroaromatic ring containing from 1 to 5 heteroatoms; R 2 is hydrogen, or a substituted or unsubstituted alkyl, —C(O)-alkyl, —C(O)—O-alkyl, alkoxy, cycloalkyl, alkenyl, monocyclic or bicyclic aryl, heteroaryl or heterocyclic moiety; R 3 is hydrogen, or a substituted or unsubstituted alkyl, —C(O)-alkyl, —C(O)—O-alkyl, alkoxy, cycloalkyl, alkenyl, monocyclic or bicyclic aryl, heteroaryl or heterocyclic moiety, or R 2 and R 3 are joined to form a heterocyclic ring; wherein the dashed line represents a second bond which may be present or absent, and when present R 3 is oxygen; R 4 and R 5 are each independently substituted or unsubstituted alkyl, —C(O)-alkyl, —C(O)—O-alkyl, alkoxy, cycloalkyl, alkenyl, monocyclic or bicyclic aryl, heteroaryl or heterocyclic moiety, or R 4 NR 5 together form a substituted or unsubstituted monocyclic or bicyclic, heterocyclic or heteroaryl moiety containing from 1 to 6 heteroatoms; R 12 is hydrogen, alkyl, halogen or cyano; and n is 0, 1, 2, 3 or 4, or an enantiomer, or a specific tautomer, or a pharmaceutically acceptable salt thereof and a method for treating a disease associated with the A 2b adenosine receptor by administering a therapeutically effective amount of the compounds of the invention.

  本发明提供具有以下结构的化合物： 1 其中R 1 是取代或未取代的苯基或含1至5个杂原子的5-6元杂环或杂芳环；R 2 是氢，或取代或未取代的烷基，—C(O)-烷基，—C(O)—O-烷基，烷氧基，环烷基，烯丙基，单环或双环芳基，杂芳基或杂环部分；R 3 是氢，或取代或未取代的烷基，—C(O)-烷基，—C(O)—O-烷基，烷氧基，环烷基，烯丙基，单环或双环芳基，杂芳基或杂环部分，或者R 2 和R 3 连接形成一个杂环；其中虚线代表可能存在或不存在第二键，当存在时R 3 是氧；R 4 和R 5 各自独立地是取代或未取代的烷基，—C(O)-烷基，—C(O)—O-烷基，烷氧基，环烷基，烯丙基，单环或双环芳基，杂芳基或杂环部分，或者R 4 和R 5 共同形成一个含1至6个杂原子的取代或未取代的单环或双环杂环或杂芳基部分；R 12 是氢，烷基，卤素或腈；且n是0，1，2，3或4，或其对应的手性体，或特定的互变异构体，或其药物可接受的盐，以及通过给药治疗与A 2b 腺苷受体相关疾病的方法。
• Inhibitors of bace
  申请人：——

  公开号：US20030095958A1

  公开（公告）日：2003-05-22

  The present invention relates to inhibitors of aspartic proteinases, particularly, BACE. The present invention also relates to compositions thereof and methods therewith for inhibiting BACE activity in a mammal, and for treating Alzheimer's Disease and other BACE-mediated diseases.

  本发明涉及天冬氨酸蛋白酶抑制剂，特别是BACE。本发明还涉及其组合物和方法，用于在哺乳动物中抑制BACE活性，并用于治疗阿尔茨海默病和其他BACE介导的疾病。
• A phase-switch purification approach for the expedient removal of tagged reagents and scavengers following their application in organic synthesis
  作者：Jason Siu、Ian R. Baxendale、Russell A. Lewthwaite、Steven V. Ley

  DOI：10.1039/b503778f

  日期：——

  In this paper we wish to report on a variety of expedient chemical transformations and purifications achieved via a generic ‘catch and release’ methodology, based on a synthetically inert bipyridyl chelating tag that can be selectively captured with a resin-bound copper(II) species. Utilising this approach we are able to derive many of the same benefits associated with both solid phase synthesis and supported reagent methods.

  本文旨在报道通过一种基于合成不活跃的双吡啶螯合标签的通用“捕获与释放”方法，实现的一系列便捷的化学转化和纯化。该方法可以选择性地利用树脂结合的铜(II)物种来捕获双吡啶螯合标签。采用这种方法，我们能够获得与固相合成和支持试剂法相关的许多相同益处。
• Design, synthesis and biological profiling of aryl piperazine based scaffolds for the management of androgen sensitive prostatic disorders
  作者：Sonal Gupta、Deepti Pandey、Dhanaraju Mandalapu、Veenu Bala、Vikas Sharma、Mahendra Shukla、Santosh K. Yadav、Nidhi Singh、Swati Jaiswal、Jagdamba P. Maikhuri、Jawahar Lal、Mohammad I. Siddiqi、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1039/c6md00426a

  日期：——

  Twenty-six piperazine derivatives were synthesized and findings revealed that compound9ais promising candidate for management of prostatic disorders.

  二十六种哌嗪衍生物被合成，研究结果显示化合物9a是治疗前列腺疾病的有希望的候选药物。