5-bromo-2-(piperidin-1-yl)benzonitrile | 876918-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-bromo-2-(piperidin-1-yl)benzonitrile
• 英文别名: 5-bromo-2-piperidin-1-ylbenzonitrile
• CAS: 876918-30-8
• 化学式: C₁₂H₁₃BrN₂
• 分子量: 265.153
• InChiKey: WOAHPAAQAVSBEO-UHFFFAOYSA-N

物化性质

• 沸点：
  379.9±32.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Bromo-2-(piperidin-1-yl)benzonitrile
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: 5-Bromo-2-(piperidin-1-yl)benzonitrile
CAS number: 876918-30-8

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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.
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: C12H13BrN2
Molecular weight: 265.1

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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：

  5-bromo-2-(piperidin-1-yl)benzonitrile 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 copper(l) iodide 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-(3'-cyano-4'-piperidinophenyl)-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  强力黄嘌呤氧化还原酶抑制剂1-苯基-吡唑-4-羧酸衍生物的合成及生物评价

  摘要：

  合成了多种多样的1-苯基-吡唑-4-羧酸衍生物库，并对其在体外和体内对黄嘌呤氧化还原酶（XOR）的抑制能力进行了评估，并进行了结构-活性关系（SAR）分析。大约一半的目标化合物在纳摩尔水平上表现出对XOR的抑制能力。与非布索坦相比，化合物16c，16d和16f成为最有效的黄嘌呤氧化还原酶抑制剂，IC 50值分别为5.7、5.7和4.2 nM（IC 50为5.4 nM）。稳态动力学测量表明16c是一种混合型抑制剂。进行了与XOR结合的16c的计算机分子对接研究，以深入了解其与该系列的结合模式和SAR。选择了由草酸钾-次黄嘌呤诱导的小鼠高尿酸血症模型，以进一步证实16c和16f的降尿酸作用，结果表明16c表现出与非布索坦相似的降尿酸功效。

  DOI：

  10.1016/j.ejmech.2017.08.047
• 作为产物：
  描述：

  5-氨基-2-(哌啶-1-基)苯甲腈 在 copper(I) chloride 、 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以36%的产率得到5-bromo-2-(piperidin-1-yl)benzonitrile
  参考文献：
  名称：

  Substituted compounds derived from N-(benzyl)phenylacetamide, preparation and uses

  摘要：

  本发明涉及N-(苄基)苯乙酰胺型多取代衍生物，包括含有该衍生物的药物组合物，以及其在人类和动物健康领域的治疗用途。本发明还涉及制备这些衍生物的方法。

  公开号：

  US20060079696A1

文献信息

• Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines
  作者：A. Hess、H. C. Guelen、N. Alandini、A. Mourati、Y. C. Guersoy、P. Knochel

  DOI：10.1002/chem.202103700

  日期：2022.1.3

  Aryl nitriles from oxazolines: We report a new method for for preparing highly functionalized tri-, tetra- and penta-substituted aromatic nitriles by using two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with a broad range of electrophiles followed by an efficient conversion of the oxazolyl-directing group to a nitrile function by using oxalyl chloride and catalytic

  来自恶唑啉的芳基腈：我们报道了一种制备高官能化三、四和五取代芳香腈的新方法，该方法通过在甲苯中使用s Bu 2 Mg 进行两次连续的镁化，然后与多种亲电子试剂发生捕获反应，然后使用草酰氯和催化量的 DMF（50 °C，4 小时）将恶唑基导向基团有效转化为腈官能团。
• [EN] ACYLGUANIDINES AS TRYPTOPHAN HYDROXYLASE INHIBITORS<br/>[FR] ACYLGUANIDINES COMME INHIBITEURS DE LA TRYPTOPHAN HYDROXYLASE
  申请人：KAROS PHARMACEUTICALS INC

  公开号：WO2015089137A1

  公开（公告）日：2015-06-18

  The present invention is directed to acylguanidines which are inhibitors of tryptophan hydroxylase (TPH), particularly isoform 1 (TPHl), that are useful in the treatment of diseases or disorders associated with peripheral serotonin including, for example, gastrointestinal, cardiovascular, pulmonary, inflammatory, metabolic, and low bone mass diseases, as well as serotonin syndrome, and cancer.

  本发明涉及酰基胍，它们是色氨酸羟化酶（TPH）的抑制剂，特别是isoform 1（TPHl），在治疗与外周血清素有关的疾病或紊乱方面具有用处，例如胃肠道、心血管、肺部、炎症、代谢和骨量低等疾病，以及血清素综合征和癌症。
• Synthesis and bioevaluation of 1-phenylimidazole-4-carboxylic acid derivatives as novel xanthine oxidoreductase inhibitors
  作者：Haiyan Zhou、Xiaolei Li、Yuanyuan Li、Xinying Zhu、Lei Zhang、Jing Li

  DOI：10.1016/j.ejmech.2019.111883

  日期：2020.1

  As part of a continuing study, we designed and synthesized four series of 1-phenylimidazole-4-carboxylic acid derivatives as xanthine oxidoreductase (XOR) inhibitors, evaluated their in vitro inhibitory potencies against XOR and hypouricemic effects in mice, and determined their structure-activity relationships (SARs). Most of the compounds exhibited in vitro XOR inhibition at the nanomolar level.

  作为一项持续研究的一部分，我们设计并合成了四个系列的作为黄嘌呤氧化还原酶（XOR）抑制剂的1-苯基咪唑-4-羧酸衍生物，评估了它们在小鼠中对XOR和低尿酸作用的体外抑制能力，并确定了它们的结构-活动关系（SAR）。大多数化合物在纳摩尔水平上表现出体外XOR抑制作用。与非布索坦相比（半最大抑制浓度[IC50]值为7.0 nM），化合物Ie和IVa表现出最有希望的XOR抑制作用，IC50值分别为8.0和7.2 nM。在草酸钾/次黄嘌呤诱导的急性和长期高尿酸血症小鼠模型中，化合物Ie和IVa显示出明显的低尿酸潜能（P <0.05），与非布索坦相比稍弱，与之相似，分别。更有趣的是，与长期高尿酸血症小鼠组相比，这两种化合物均具有通过降低肌酐和尿素氮水平来改善肾脏损害的能力（P <0.05），而非布索坦则无明显作用。
• [EN] 2-PHENYLPYRIDINE DERIVATIVE<br/>[FR] DERIVE DE 2-PHENYLPYRIDINE
  申请人：ASTELLAS PHARMA INC

  公开号：WO2006022374A1

  公开（公告）日：2006-03-02

  A 2-phenylpyridine derivative represented by the following general formula (I) or a salt thereof. The compounds have satisfactory xanthine oxidase inhibitory activity and uric acid-lowering activity and are useful as a therapeutic or preventive agent for hyperuricemia, gout, inflammatory intestinal diseases, diabetic nephropathy, diabetic retinopathy, etc. [The symbols in the formula have the following meanings: R1: H, etc.; R2: -CO2H, etc.; R3 and R4: H, etc.; R5: -CN, etc.; R6: H, etc.; X: -O-, -N(R8)-, or -S-; (provided that the groups represented by R5 and -X-R7 are bonded in a meta position or the para position to the pyridyl group) R8: H, etc.; R7: C1-8 linear or branched alkyl, etc.; Y: a bond, etc.; and R9, R10, and R11: H, etc. (provided that when X is -N(R8)-, then R8 may be bonded to R7 to form a nitrogenous saturated heterocycle in cooperation with the adjacent nitrogen atom).]

  由以下通式（I）表示的2-苯基吡啶衍生物或其盐。这些化合物具有令人满意的黄嘌呤氧化酶抑制活性和降低尿酸活性，并可用作高尿酸血症、痛风、炎症性肠道疾病、糖尿病肾病、糖尿病视网膜病等的治疗或预防剂。【式中符号的含义如下：R1：H，等；R2：-CO2H，等；R3和R4：H，等；R5：-CN，等；R6：H，等；X：-O-，-N（R8）-，或-S-；（前提是由R5和-X-R7表示的基团与吡啶基团在间位或对位上结合）R8：H，等；R7：C1-8直链或支链烷基，等；Y：键，等；以及R9、R10和R11：H，等。（前提是当X为-N（R8）-时，那么R8可以与R7结合以与相邻的氮原子共同形成氮饱和杂环）。】
• 一种苯基咪唑类XOR抑制剂及制备与应用
  申请人：华南理工大学

  公开号：CN110078668B

  公开（公告）日：2023-03-24

  本发明属于医药化工技术领域，公开了一种苯基咪唑类XOR抑制剂及制备与应用。所述苯基咪唑类XOR抑制剂的结构如式(I)或式(II)所示，其中，R，R