4-溴-1-苯基-1H-吡唑 | 15115-52-3

• 物质功能分类: 有机原料 - 杂环化合物
• 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-溴-1-苯基-1H-吡唑
• 中文别名: 1-苯基-4-溴吡唑；4-溴-1-苯基吡唑
• 英文名称: 4-bromo-1-phenyl-1H-pyrazole
• 英文别名: 4-bromo-1-phenylpyrazole；1-phenyl-4-bromo-1H-pyrazole
• CAS: 15115-52-3
• 化学式: C₉H₇BrN₂
• 分子量: 223.072
• InChiKey: DWPRPWBNLNTEFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  296.2±13.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-1-phenyl-1H-pyrazole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-1-phenyl-1H-pyrazole
CAS number: 15115-52-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
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.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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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.
Store in closed vessels, refrigerated.
Storage:

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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
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H7BrN2
Molecular weight: 223.1

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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, hydrogen bromide.

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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：

  4-溴-1-苯基-1H-吡唑 在 silver(I) nitrite 、 十二羰基三钌 、 tricyclohexylphosphine tetrafluoroborate 、 [双(三氟乙酰氧基)碘]苯 、 三甲基乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以63%的产率得到4-bromo-1-(3-nitrophenyl)-1H-pyrazole
  参考文献：
  名称：

  The ruthenium-catalyzed meta-selective C–H nitration of various azole ring-substituted arenes

  摘要：

  我们开发了一种高效且温和的钌催化的对取代芳烃的唑环进行间位-选择性的C_Ar–H硝化的方法。

  DOI：

  10.1039/c9ob01930h
• 作为产物：
  描述：

  苯肼 在 溴 、 溶剂黄146 、 苯 作用下， 生成 4-溴-1-苯基-1H-吡唑
  参考文献：
  名称：

  Balbiano, Gazzetta Chimica Italiana, 1889, vol. 19, p. 131

  摘要：

  DOI：

文献信息

• Substituted diazabicycloalkane derivatives
  申请人：Basha Anwer

  公开号：US20050101602A1

  公开（公告）日：2005-05-12

  Compounds of formula (I) Z-Ar 1 —Ar 2 (I) wherein Z is a diazabicyclic amine, Ar 1 is a 5- or 6-membered aromatic ring, and Ar 2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.

  式(I)的化合物 Z-Ar 1 —Ar 2 (I) 其中Z是一种二氮杂双环胺，Ar 1 是一个5-或6-成员芳香环，Ar 2 选自未取代或取代的5-或6-成员杂芳基环；未取代或取代的双环杂芳基环；3,4-(亚甲二氧基)苯基；咔唑基；四氢咔唑基；萘基；和苯基；其中苯基在间位或对位上取代有0、1、2或3个取代基。这些化合物在治疗由α7 nAChR配体预防或改善的病症或紊乱中有用。还公开了包含式(I)的化合物的药物组合物以及使用这些化合物和组合物的方法。
• NaBHT Generated <i>In Situ</i> from BHT and NaO<i>t</i>Bu: Crystallographic Characterization and Applications in Buchwald–Hartwig Amination
  作者：Volodymyr Semeniuchenko、Jeffrey S. Ovens、Wilfried M. Braje、Michael G. Organ

  DOI：10.1021/acs.organomet.1c00386

  日期：2021.10.11

  BHT with tBuONa in solution and in the solid state were examined, reveraling that NaBHT does not need to be prepared from pyrophoric NaH or metallic Na every time. Instead, it can be generated efficiently in or ex situ using NaOtBu in solution or with only a stoichiometric amount of solvent to assist in bringing the reactants together. Application of this methodology was demonstrated with the efficient

  NaBHT 是一种有价值的中等强度基料，可用于许多应用，尤其是 Buchwald-Hartwig 耦合。使用单晶 X 射线衍射建立了无溶剂 NaBHT 及其与 Et 2 O、THF、t BuOH 和 THF/ t BuOH 混合物的溶剂化物的结构。[NaBHT·Et 2 O] 2采用二聚体结构并在单斜晶胞中结晶，[NaBHT·THF] 3、[NaBHT· t BuOH] 3和[NaBHT·(THF- t BuOH)] 3更喜欢三聚体结构并在立方晶胞中结晶。无溶剂 [NaBHT] n不同于溶剂化的 NaBHT 和其他已知的苯酚钠。它是一种无机聚合物，在正交晶胞中结晶，NaO 核沿 [1 0 0] 方向扩展。所有结构都证实了t Bu 基团氢与 Na 的主动相互作用，可能有助于解释 NaBHT 的还原特性。此外，研究了 BHT 与t BuONa 在溶液中和固态中的相互作用，表明 NaBHT 不需要每次都从自燃的
• Cu-Catalyzed Couplings of Heteroaryl Primary Amines and (Hetero)aryl Bromides with 6-Hydroxypicolinamide Ligands
  作者：David J. Bernhardson、Daniel W. Widlicka、Robert A. Singer

  DOI：10.1021/acs.oprd.9b00195

  日期：2019.8.16

  chemoselectivity and rate. The use of K2CO3 as the base enabled selective C–N coupling of aryl bromides over aryl chlorides with 2–5 mol % Cu at 80–120 °C. With K3PO4 as the base, aryl chlorides are capable of undergoing C–N coupling, though 5–10 mol % Cu is required at 120–130 °C. Members of the ligand family are straightforward to prepare in one step from 6-hydroxypicolinic acid and the corresponding

  已经确定了6-羟基吡啶甲酸酰胺配体家族是Cu催化的杂芳基溴化物和氯化物与杂芳基伯胺的偶联的有效支撑配体。C–N偶联是在80–120°C的DMSO或环丁砜中，以2-10 mol％CuI和支持配体的K 2 CO 3或K 3 PO 4为碱进行的。发现碱的强度对化学选择性和速率有影响。使用K 2 CO 3作为碱，可以在80–120°C的条件下，以2–5 mol％的Cu在芳基氯上进行芳基溴的选择性C–N偶联。含K 3 PO 4作为基础，芳基氯化物能够进行C–N偶联，尽管在120–130°C下需要5–10 mol％的Cu。配体家族的成员可以直接一步一步由6-羟基吡啶甲酸和相应的苯胺制备。
• [EN] METHYLAMINE DERIVATIVES AS LYSYSL OXIDASE INHIBITORS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE LA MÉTHYLAMINE COMME INHIBITEURS DE LA LYSYL OXIDASE POUR LE TRAITEMENT DU CANCER
  申请人：THE INST OF CANCER RESEARCH: ROYAL CANCER HOSPITAL

  公开号：WO2017141049A1

  公开（公告）日：2017-08-24

  Provided are compounds of the Formula (I), or a pharmaceutically acceptable salt thereof, wherein W, X, Y, Z, x, R1, R2, R3, x and n are defined in the specification. The compounds are inhibitors of lysyl oxidase (LOX) and lysyl oxidase-like (LOXL) family members (LOXL1, LOXL2, LOXL3, LOXL4) and are useful in therapy, particularly in the treatment of cancer. Also disclosed are LOX inhibitors for use in the treatment of a cancer associated with EGFR and biomarkers that predict responsiveness to a LOX inhibitor.

  提供的是Formula (I)的化合物，或其药用可接受的盐，其中W、X、Y、Z、x、R1、R2、R3、x和n在规范中有定义。这些化合物是赖氨酸氧化酶（LOX）和赖氨酸氧化酶样（LOXL）家族成员（LOXL1、LOXL2、LOXL3、LOXL4）的抑制剂，并且在治疗中很有用，特别是在癌症治疗中。还披露了用于治疗与EGFR相关的癌症的LOX抑制剂，以及预测对LOX抑制剂响应性的生物标志物。
• Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization
  作者：Song Song、Xiang Sun、Xinwei Li、Yizhi Yuan、Ning Jiao

  DOI：10.1021/acs.orglett.5b00932

  日期：2015.6.19

  efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present

  据报道，通过使用容易获得的二甲基亚砜（DMSO）和HX（X = Br，I）试剂，可对芳烃和杂芳烃进行廉价的溴化和碘化的高效实用系统。这种温和的氧化系统显示了用于合成芳基卤化物的通用协议。当与DMSO结合使用时，HX（X = Br，I）被用作卤化试剂，DMSO作为一种温和且廉价的氧化剂参与了本发明的化学反应。该氧化系统适合于天然产物的后期溴化。公斤级实验（> 95％的收率）显示出工业应用的巨大潜力。

表征谱图