3-(3-硝基苯基)-1H-吡唑 | 59843-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(3-硝基苯基)-1H-吡唑
• 中文别名: 3-(3-硝基苯基)吡唑
• 英文名称: 5-(3-nitrophenyl)-1H-pyrazole
• 英文别名: 3-(3-nitrophenyl)-1H-pyrazole
• CAS: 59843-77-5
• 化学式: C₉H₇N₃O₂
• mdl: MFCD00106146
• 分子量: 189.173
• InChiKey: RUWXJVIBNZSEQD-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128℃
• 溶解度：
  11.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(3-Nitrophenyl)pyrazole
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
3-(3-Nitrophenyl)pyrazole
Ingredient name:
CAS number: 59843-77-5

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H7N3O2
Molecular weight: 189.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-(3-硝基苯基)-1H-吡唑 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以74%的产率得到4-iodo-3-(3-nitrophenyl)-1H-pyrazole
  参考文献：
  名称：

  [EN] 3,4-DIARYLPYRAZOLES AS PROTEIN KINASE INHIBITORS
  [FR] 3,4-DIARYLPYRAZOLES UTILISÉS COMME INHIBITEURS DE PROTÉINE KINASE

  摘要：

  公开了规范中定义的式(I)的3,4-二芳基吡唑衍生物及其药用盐，其制备方法和包含它们的药物组合物；发明的化合物可能在治疗中对治疗与蛋白激酶活性失调相关的疾病，如癌症，具有用处。

  公开号：

  WO2010010154A1
• 作为产物：
  描述：

  3t-chloro-1-(3-nitro-phenyl)-propenone 在 乙醚 、 一水合肼 作用下， 生成 3-(3-硝基苯基)-1H-吡唑
  参考文献：
  名称：

  Kotschetkow et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 1181,1185; engl. Ausg. S. 1206, 1209

  摘要：

  DOI：

文献信息

• The α-Effect in Reactions of sp-Hybridized Carbon Atom:  Michael-Type Reactions of 1-Aryl-2-propyn-1-ones with Primary Amines
  作者：Ik-Hwan Um、Eun-Ju Lee、Jin-Ah Seok、Kyung-Hee Kim

  DOI：10.1021/jo050624t

  日期：2005.9.1

  mechanism. The α-effect increases as the substituent X in the phenyl ring of 2a−f becomes a stronger electron-donating group. However, the magnitude of the α-effect for the reactions of 2a−f is small (e.g., kNhydrazine/kNglycylglycine = 4.6−13) regardless of the electronic nature of the substituent X. The small βnuc has been suggested to be responsible for the small α-effect. A solvent kinetic isotope

  测量了1-（X-取代苯基）-2-丙炔-1-酮（2a - f）与一系列伯胺在H 2 O中的迈克尔型反应的二级速率常数（k N）在25.0±0.1°C下。对于1-苯基-2-丙炔-1-酮（2c）与非α-亲核胺的反应，获得了具有小的βnuc值（βnuc = 0.30）的线性布朗斯台德型图。肼比其他类似碱度的伯胺（例如，甘氨酰甘氨酸和甘氨酸乙酯）具有更高的反应活性，并且与线性布朗斯台德图呈正偏差。2a - f的反应与肼的化合物表现出线性的Hammett图，而与非α-亲核胺的化合物表现出线性的Yukawa-Tsuno图，表明取代基X的电子性质不影响反应机理。随着2a - f的苯环中的取代基X变为更强的供电子基团，α效应会增加。然而，为的反应中α-效果的大小2A - ˚F是小的（例如，ķ Ñ肼/ ķ Ñ甘氨酰甘氨酸= 4.6-13），而不管该取代基X的小β的电子性质的NUC有人认为这是造成小的α效应的原
• <i>N</i>-Phenylamidines as Selective Inhibitors of Human Neuronal Nitric Oxide Synthase:  Structure−Activity Studies and Demonstration of in Vivo Activity
  作者：Jon L. Collins、Barry G. Shearer、Jeffrey A. Oplinger、Shuliang Lee、Edward P. Garvey、Mark Salter、Claire Duffy、Thimysta C. Burnette、Eric S. Furfine

  DOI：10.1021/jm980072p

  日期：1998.7.1

  the amidine nitrogen and phenyl ring to give N-(3-(aminomethyl)phenyl)acetamidine (14) dramatically altered the selectivity to give a neuronal selective nitric oxide synthase (nNOS) inhibitor. Part of this large shift in selectivity was due to 14 being a rapidly reversible inhibitor of iNOS in contrast to the essentially irreversible inhibition of iNOS observed with 13. Structure-activity studies revealed

  与内皮和诱导型亚型相比，可能需要选择性抑制一氧化氮合酶（NOS）的神经元亚型，以治疗由一氧化氮过量产生引起的神经系统疾病。最近，我们将N-（3-（氨基甲基）苄基）乙am（13）描述为一种缓慢，紧密结合的抑制剂，对人诱导型一氧化氮合酶（iNOS）具有高度选择性。除去the氮和苯环之间的单个亚甲基桥以得到N-（3-（氨基甲基）苯基）乙am（14）极大地改变了选择性，从而得到了神经元选择性一氧化氮合酶（nNOS）抑制剂。选择性大幅度变化的部分原因是14是iNOS的快速可逆抑制剂，而13观察到的iNOS基本上不可逆的抑制。结构活性研究表明，与芳香环相连的碱性胺官能团和空间紧凑的idine是此类NOS抑制剂的关键药效​​团。用N-（3-（氨基甲基）苯基）-2-呋喃基idine啶（77）可获得最大的nNOS抑制能力（Ki-nNOS = 0.006 microM; Ki-eNOS = 0.35 microM;
• Design, synthesis, in silico, and in vitro evaluation of 3‐phenylpyrazole acetamide derivatives as antimycobacterial agents
  作者：Nikhil B. Gaikwad、Krishna Nirmale、Santosh K. Sahoo、Mohammad N. Ahmad、Grace Kaul、Manjulika Shukla、Srinivas Nanduri、Arunava Das Gupta、Sidharth Chopra、Madhavi V. Yaddanapudi

  DOI：10.1002/ardp.202000349

  日期：2021.5

  selectivity indices (SI) of greater than 666 and 320, respectively. All derivatives exhibited excellent ADME (absorption, distribution, metabolism, and excretion) properties in silico. Also, all the derivatives were found compliant with Lipinski's rule of five, showing their druggability profile. Molecular docking insights of these derivatives have shown outstanding binding energies on the mycobacterial membrane

  结核分枝杆菌 (Mtb) 是影响全球免疫功能正常和免疫功能低下患者的最危险病原体之一。新型分子有效且可缩短抗药性菌株的治疗持续时间，是目前迫切未满足的需求。在我们目前的研究中，设计了一系列新的 2- (3-phenyl-1H-pyrazol-1-yl) 乙酰胺和 N'-benzylidene-2- (3-phenyl-1H-pyrazol-1-yl) acetohydrazide 衍生物，合成并评估了它们的抗分枝杆菌潜力。生物学评价表明，6b、6m、6l、7a 和 7k 对 Mtb 表现出选择性和有效的抑制活性。此外，发现化合物 6m 和 7h 对 Vero 细胞无毒，CC50 分别大于 20 和 80 毫克/毫升，并表现出有希望的选择性指数 (SI) 大于 666 和 320，分别。所有衍生物在硅片中都表现出优异的 ADME（吸收、分布、代谢和排泄）特性。此外，发现所有衍生物都符合 Lipinski
• Synthesis of 3-Substituted Arylpyrazole-4-carboxylic Acids
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、E. A. Kovaleva、O. L. Ustinova、I. B. Kozhevnikov

  DOI：10.1007/s11176-005-0318-7

  日期：2005.5

  3-aryl-substituted pyrazole-4-carboxylic acids, involving Vilsmeier formylation of semicarbazones of 26 available mono- and disubstituted acetophenones and 2-acetylthiophene followed by oxidation of the resulting 3-aryl-substituted pyrazole-4-carboxaldehydes under the action of potassium permanganate. The mechanism of the formylation reaction is discussed. The method successfully works even with acetophenones

  提出了一种制备以前未知的3-芳基取代的吡唑-4-羧酸的方法，该方法包括将26种可用的单和双取代的苯乙酮和2-乙酰基噻吩的半咔唑的Vilsmeier甲酰化，然后氧化所得的3-芳基取代的吡唑-。 4-羧醛在高锰酸钾的作用下。讨论了甲酰化反应的机理。该方法即使对含有烷基取代基的苯乙酮也能成功地起作用。在后一种情况下，使用另外的步骤，该步骤涉及分离吡唑-4-羧酸作为其甲硅烷基酯。
• Pyrazole amides
  申请人：The Upjohn Company

  公开号：US04072498A1

  公开（公告）日：1978-02-07

  The present invention discloses amides and thioamides substituted in the .alpha. or .beta. position with substituted pyrazoles which are useful as herbicides.

  本发明公开了取代吡唑基的酰胺和硫代酰胺，其在α或β位置上取代，可用作除草剂。