4-(3,5-二甲基-1H-吡唑-1-基)苯胺 | 52708-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(3,5-二甲基-1H-吡唑-1-基)苯胺
• 中文别名: 4-(3,5-二甲基吡唑)-苯胺；4-(3,5二甲基-1-吡唑基)苯胺
• 英文名称: 4-(3,5-dimethyl-1H-pyrazol-1-yl)aniline
• 英文别名: 1-(4-aminophenyl)-3,5-dimethylpyrazole；4-(3,5-dimethylpyrazol-1-yl)aniline
• CAS: 52708-32-4
• 化学式: C₁₁H₁₃N₃
• mdl: MFCD00661746
• 分子量: 187.244
• InChiKey: BKLODFMZXGBJAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

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:	4-(3 5-Dimethyl-1H-pyrazol-1-yl)aniline 97% Material Safety Data Sheet
Synonym:
CAS:	52708-32-4

Section 1 - Chemical Product MSDS Name:4-(3 5-Dimethyl-1H-pyrazol-1-yl)aniline 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52708-32-4	4-(3,5-Dimethyl-1H-pyrazol-1-yl)anilin	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.

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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# 52708-32-4: 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 78 - 82 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: C11H13N3
Molecular Weight: 187.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 52708-32-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(3,5-Dimethyl-1H-pyrazol-1-yl)aniline - 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# 52708-32-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 52708-32-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 52708-32-4 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-(3,5-二甲基-1H-吡唑-1-基)苯胺 在 potassium carbonate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 1-(4'-cyanoacetamidophenyl)-3,5-dimethyl-1H-pyrazole
  参考文献：
  名称：

  Patel; Vyas; Fernandes, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 836 - 842

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯肼盐酸盐 在 水 、 铁粉 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甘油 为溶剂， 反应 4.0h， 生成 4-(3,5-二甲基-1H-吡唑-1-基)苯胺
  参考文献：
  名称：

  신규한 1-페닐-1H-피라졸 유도체 및 이의 용도

  摘要：

  这项发明涉及新型1-苯基-1H-吡唑衍生物及其用途，具体而言，该发明涉及对癌细胞表现出优异抗增殖效能的1-苯基-1H-吡唑衍生物化合物，其药学上可接受的盐，其水合物或其立体异构体，以及其制备方法和包含其作为有效成分的用于预防、减轻或治疗癌转移和增殖性疾病的药学组合物，以及用于癌细胞的抗癌组合物，所述化合物表现出优异的癌细胞抑制活性和抗增殖效能，因此，癌细胞抑制不仅对抗癌细胞有效，而且对于预防癌转移和增殖性疾病或癌症治疗也是有益的。

  公开号：

  KR20210089290A

文献信息

• Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
  作者：Lixing Zhao、Chenyang Hu、Xuefeng Cong、Gongda Deng、Liu Leo Liu、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c12318

  日期：2021.1.27

  Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for

  利用 N-杂环卡宾作为非无害配体促进转化的过渡金属催化尚未得到很好的研究。我们在这里报告了具有成本效益的铬催化的环状（烷基）（氨基）卡宾（CAAC）配体促进的硝基脱氧硼氢化反应。使用 1 mol % 的 CAAC-Cr 预催化剂，将 HBpin 添加到硝基支架上会导致脱氧，从而保留各种可还原的官能团和敏感基团对硼氢化的相容性，从而提供一种温和、化学选择性和易于形成的策略苯胺，以及杂芳基和脂肪胺衍生物，具有广泛的范围和特别高的转换数（高达 1.8 × 106）。基于理论计算的机械研究，表明CAAC配体在促进HBpin氢化物极性反转中起重要作用；它用作 H 穿梭以促进脱氧硼氢化。通过这种策略制备的几种市售药物突出了其在药物化学中的潜在应用。
• Structure-Activity Relationship Refinement and Further Assessment of Indole-3-glyoxylamides as a Lead Series against Prion Disease
  作者：Mark J. Thompson、Jennifer C. Louth、Steven Ferrara、Fiona J. Sorrell、Benjamin J. Irving、Edward J. Cochrane、Anthony J. H. M. Meijer、Beining Chen

  DOI：10.1002/cmdc.201000383

  日期：2011.1.3

  indole‐3‐glyoxylamide series of antiprion agents have been explored further, resulting in discovery of several new compounds demonstrating excellent activity in a cell line model of prion disease (EC50 <10 nM). After examining a range of substituents at the para‐position of the N‐phenylglyoxylamide moiety, five‐membered heterocycles containing at least two heteroatoms were found to be optimal for the antiprion effect

  进一步研究了吲哚-3-乙醛酰胺系列抗pr病毒剂之间的结构活性关系，从而发现了几种在compounds病毒疾病细胞系模型中表现出优异活性的新化合物（EC 50 <10 n M）。在检查N的对位上的一系列取代基后苯乙醛基乙酰胺部分中，含有至少两个杂原子的五元杂环被认为是抗pr病毒作用的最佳选择。尽管没有很好的耐受性，但进行了许多修饰以探讨乙醛酰胺亚结构的重要性。然而，最有效的化合物确实对微粒体代谢具有很大的稳定性，并且最活跃的文库成员在单次给药后无限期地治愈了瘙痒病感染的细胞。因此，目前的结果证实了吲哚-3-乙氧基乙酰胺是有前途的铅系列，可用于继续进行体外和体内抗病毒疾病的评估。
• Fused heterocyclic compounds useful as kinase modulators
  申请人：Vaccaro Wayne

  公开号：US20070078136A1

  公开（公告）日：2007-04-05

  Compounds having the formula (1), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are usefuil as kinase modulators, including MK2 modulation, wherein one of E and F is a nitrogen atom and the other of E and F is a carbon atom, Z is N or CR 3 , and R 1 , R 2 , R 3 , X and Y are as defined herein.

  具有化学式（1）的化合物，以及其对映体、非对映体、药用可接受的盐，可用作激酶调节剂，包括MK2调节，其中E和F中的一个是氮原子，另一个是碳原子，Z是N或CR3，R1、R2、R3、X和Y如本文所定义。
• Pharmaceutical compound comprising a pyrazole derivative and methods of using the same for the treatment of calcium release-activated calcium channel associated diseases
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06348480B1

  公开（公告）日：2002-02-19

  The present invention is directed to drugs, in particular, pyrazole derivatives represented by the following general formula (I) which have a calcium release-activated calcium channel inhibitory effect and medicinal compositions, in particular, calcium release-activated calcium channel inhibitors containing the above compounds as the active ingredient, wherein each substituent is defined in the specification. The present invention also relates to a pharmaceutical composition containiing an effective amount of the compound of formula (I) and a pharmaceutically effective carrier. The present invention further relates to methods of treatment of diseases associated with calcium release-activated calcium channels, diseases associated with IL-2 production, and methods of treatment of allergic, inflammatory or auto-immune diseases.

  本发明涉及药物，特别是由以下一般式（I）表示的吡唑衍生物，其具有钙释放激活的钙通道抑制作用和药用组合物，特别是含有上述化合物作为活性成分的钙释放激活的钙通道抑制剂，其中每个取代基在规范中定义。本发明还涉及含有一定量的式（I）化合物和药效载体的药用组合物。本发明还涉及与钙释放激活的钙通道相关的疾病、与IL-2产生相关的疾病以及过敏、炎症或自身免疫疾病的治疗方法。
• Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis
  作者：David Obermayer、Desiree Znidar、Gabriel Glotz、Alexander Stadler、Doris Dallinger、C. Oliver Kappe

  DOI：10.1021/acs.joc.6b02242

  日期：2016.12.2

  allow syntheses to be performed on a 2–6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device

  提出了一种新设计的坚固，安全的实验室规模反应器，用于在密封容器条件下，最高温度250°C和最大压力20 bar的条件下进行合成。该反应器通过不锈钢加热夹套对密封的玻璃容器进行传导加热，除磁力搅拌外，还可以在线监测温度和压力。反应在10 mL硼硅酸盐小瓶中进行，并用硅胶帽和Teflon隔垫密封，并可以2–6 mL规模进行合成。在加热和冷却性能，搅拌效率以及温度和压力控制方面，将此传导加热的反应器与标准的单模密封容器微波仪器进行了比较。重要的，