1-(4-溴苯基)哌嗪 | 66698-28-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 哌嗪类化合物
• 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: 1-(4-溴苯基)哌嗪
• 中文别名: 4-溴苯基哌嗪
• 英文名称: 1-(4-bromophenyl)piperazine
• 英文别名: 1-(p-bromophenyl)piperazine
• CAS: 66698-28-0
• 化学式: C₁₀H₁₃BrN₂
• 分子量: 241.131
• InChiKey: PJHPFAFEJNBIDC-UHFFFAOYSA-N

物化性质

• 熔点：
  91-95 °C
• 沸点：
  353.3±27.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933599090
• WGK Germany：
  1
• 储存条件：
  | 2-8°C |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-(4-Bromophenyl)piperazine
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
Wear protective gloves/protective clothing/eye protection/face protection
P280:

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Section 3. Composition/information on ingredients.
Ingredient name: 1-(4-Bromophenyl)piperazine
CAS number: 66698-28-0

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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.
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
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H13BrN2
Molecular weight: 241.1

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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

制备方法与用途

危险性

1-(4-溴苯基)哌嗪是一种危险品，具有急性毒性及腐蚀性。它可能严重刺激和灼伤皮肤与眼睛，并可能导致生命危险。因此，在使用时必须严格遵守安全操作规程并佩戴防护用品，避免直接接触和吸入。

此外，这种物质还对环境存在潜在危害。如果处理不当或随意排放到环境中，可能会污染水体和土壤，进而影响生态环境。因此，在使用及处理1-(4-溴苯基)哌嗪时，必须严格遵守环保法规，并采取必要的防护措施，以最大限度地减少其对环境的影响。

反应信息

• 作为反应物：
  描述：

  1-(4-溴苯基)哌嗪 在 Pd(Cl₂)pddf 、 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 methyl [4'-(4-methylpiperazin-1-yl)-1,1'-biphenyl-3-yl]acetate
  参考文献：
  名称：

  人组织蛋白酶K的一类新型非肽联芳基抑制剂。

  摘要：

  一种新的非肽联芳基化合物系列被鉴定为组织蛋白酶K的有效抑制剂和可逆抑制剂。已知氨基乙腈二肽1的P2-P3酰胺键被苯环取代，从而形成了与组织蛋白酶相比仍保持效力的联芳基系列K和对其他组织蛋白酶显示出改善的选择性。该系列中的结构修饰导致鉴定了化合物（R）-2，这是一种有效的人组织蛋白酶K抑制剂（IC（50）= 3 nM），相对于组织蛋白酶B（IC（50）= 3950 nM），L（ IC（50）= 3725 nM），S（IC（50）= 2010 nM）。在涉及兔破骨细胞和牛骨的体外测定中，化合物（R）-2以95 nM的IC（50）抑制骨吸收。结果表明，与某些半胱氨酸蛋白酶的肽腈抑制剂不同，组织蛋白酶K不会将（R）-2的腈部分转化为相应的酰胺3。这表明这类非肽腈抑制剂不太可能被半胱氨酸蛋白酶水解。此外，显示化合物（R）-2对组织蛋白酶K的抑制是完全可逆的，并且不是时间依赖性的。为了证明化合物（R）-2在体内的功效，将其以20

  DOI：

  10.1021/jm0301078
• 作为产物：
  描述：

  1-Boc-4-(4-溴苯基)哌嗪 在 2,6-二甲基吡啶 、 1-methoxy-4-((4-(2-methoxyethyl)phenoxy)methyl)benzene 、 erbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 生成 1-(4-溴苯基)哌嗪
  参考文献：
  名称：

  [EN] METHOD FOR REMOVING TERT-BUTOXYCARBONYL GROUPS
  [FR] PROCÉDÉ DE RETRAIT DE GROUPE TERT-BUTOXYCARBONYLE
  [JA] ｔｅｒｔ－ブトキシカルボニル基の除去方法

  摘要：

  本発明により、窒素原子上にtert-ブトキシカルボニル（Boc）基を有する化合物におけるBoc基の除去方法であって、該化合物を、トリフルオロメタンスルホン酸金属塩（金属トリフラート：M(OTf)n）または希土類金属ハロゲン化物（MXn）と塩基の存在下で処理し、Boc基をH-に変換した化合物を得ることを含む、前記方法が提供される。

  公开号：

  WO2023132353A1

文献信息

• [EN] POLYCYCLIC COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF RAPIDLY ACCELERATED FIBROSARCOMA POLYPEPTIDES<br/>[FR] COMPOSÉS POLYCYCLIQUES ET MÉTHODES POUR LA DÉGRADATION CIBLÉE DE POLYPEPTIDES DU FIBROSARCOME RAPIDEMENT ACCÉLÉRÉ
  申请人：ARVINAS OPERATIONS INC

  公开号：WO2020051564A1

  公开（公告）日：2020-03-12

  The present disclosure relates to bifunctional compounds, ULM— L—PTM, which find utility as modulators of Rapidly Accelerated Fibrosarcoma (RAF, such as c-RAF, A- RAF and/or B-RAF; the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein RAF, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein, or the constitutive activation of the target protein, are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物ULM—L—PTM，其作为快速加速纤维肉瘤（RAF，如c-RAF、A-RAF和/或B-RAF；目标蛋白）的调节剂具有实用性。具体而言，本公开涉及含有一端结合到相应E3泛素连接酶的Von Hippel-Lindau、cereblon、凋亡抑制蛋白或鼠双分子同源物2配体的双功能化合物，另一端结合到目标蛋白RAF的部分，使得目标蛋白与泛素连接酶靠近，以实现目标蛋白的降解（和抑制）。本公开展示了与目标蛋白的降解/抑制相关的广泛药理活性范围。本公开的化合物和组合物用于治疗或预防由目标蛋白的聚集或积累，或目标蛋白的构成性激活导致的疾病或紊乱。
• [EN] TANK-BINDING KINASE INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE KINASES SE LIANT À TANK
  申请人：GILEAD SCIENCES INC

  公开号：WO2015187684A1

  公开（公告）日：2015-12-10

  Compounds having the following formula (I) and methods of their use and preparation are disclosed:

  揭示了具有以下化学式（I）的化合物及其使用和制备方法。
• Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor
  申请人：——

  公开号：US20040157849A1

  公开（公告）日：2004-08-12

  Compounds of formula (I) 1 are novel VR1 antagonists that are useful in treating pain, inflammatory thermal hyperalgesia, urinary incontinence and bladder overactivity.

  式（I）的化合物是新颖的VR1拮抗剂，可用于治疗疼痛、炎症性热性过敏、尿失禁和膀胱过度活动。
• Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
  作者：L. Reginald Mills、Joshua M. Graham、Purvish Patel、Sophie A. L. Rousseaux

  DOI：10.1021/jacs.9b11208

  日期：2019.12.11

  reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for

  在此，我们报告了一种 Ni 催化的还原偶联，用于从芳基（伪）卤化物和亲电氰化试剂 2-甲基-2-苯基丙二腈 (MPMN) 合成苯甲腈。MPMN 是一种工作台稳定的碳键合亲电子 CN 试剂，在反应条件下不会释放氰化物。可以以良好的收率制备多种与药用相关的苯甲腈。将 NaBr 添加到反应混合物中可以使用更具挑战性的芳基亲电试剂，例如芳基氯化物、甲苯磺酸盐和三氟甲磺酸盐。机理研究表明，溴化钠在促进这些底物的氧化加成方面发挥作用。
• Novel piperazine based compounds as potential inhibitors for SARS-CoV-2 Protease Enzyme: Synthesis and molecular docking study
  作者：Alaa Z. Omar、Tawfik M. Mosa、Samer K. El-sadany、Ezzat A. Hamed、Mohamed El-atawy

  DOI：10.1016/j.molstruc.2021.131020

  日期：2021.12

  protease enzyme using molecular docking analysis. The docking studies showed that all the ligands have been docked with negative dock energy onto the target protease protein. Moreover, Molecular interaction studies revealed that SARS-CoV-2 protease enzyme had strong hydrogen bonding interactions with piperazine ligands. The present in silico study thus, provided some guidance to facilitate drug design targeting

  合成了结构多样的基于哌嗪的化合物与噻二唑、靛红或硫/氮官能团的杂化。新化合物的结构是根据其光谱数据和元素分析确定的。使用in silico评估所有制备的配体的理化、生物活性评分和药代动力学行为计算工具。已经使用分子对接分析筛选了新的哌嗪配体对 SARS-CoV-2 蛋白酶的抑制活性。对接研究表明，所有配体都以负对接能量与目标蛋白酶蛋白对接。此外，分子相互作用研究表明，SARS-CoV-2蛋白酶与哌嗪配体具有很强的氢键相互作用。因此，目前的计算机研究为促进针对 SARS-CoV-2 主要蛋白酶的药物设计提供了一些指导。