2-(4-溴-1H-吡唑-1-基)乙醇 | 214614-81-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-(4-溴-1H-吡唑-1-基)乙醇
• 中文别名: 1-(2-羟乙基)-4-溴吡唑
• 英文名称: 2-(4-bromo-1H-pyrazol-1-yl)ethan-1-ol
• 英文别名: 2-(4-bromo-1H-pyrazol-1-yl)ethanol；2-(4-bromopyrazol-1-yl)ethanol
• CAS: 214614-81-0
• 化学式: C₅H₇BrN₂O
• mdl: MFCD06804929
• 分子量: 191.027
• InChiKey: REUWXYIZJBMWPB-UHFFFAOYSA-N

物化性质

• 沸点：
  299.2±20.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

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：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4-Bromo-1H-pyrazol-1-yl)ethanol
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: 2-(4-Bromo-1H-pyrazol-1-yl)ethanol
CAS number: 214614-81-0

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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.
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: C5H7BrN2O
Molecular weight: 191.0

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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：

  2-(4-溴-1H-吡唑-1-基)乙醇 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium [¹⁸F]fluoride 、 potassium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.58h， 生成 C₂₂H₂₂⁽¹⁸⁾FN₃O₅S
  参考文献：
  名称：

  设计，（放射）合成以及体外和体内评估高选择性和有效基质金属蛋白酶12（MMP-12）抑制剂作为正电子发射断层显像的放射性示踪剂

  摘要：

  活化基质金属蛋白酶（MMPs）的水平失调与不同的病状相关，例如癌症，动脉粥样硬化，神经炎症和关节炎。因此，用正电子发射断层扫描（PET）对MMP进行成像是诊断MMP相关疾病的有力工具。此外，为了区分单个MMP在特定病理生理过程中的独特功能和作用，必须使用放射性标记的示踪剂（例如氟18标记的MMP抑制剂（MMPI））来实现其特定的成像。因此，制备了氟化的基于二苯并呋喃磺酰胺的MMPI，其显示出对MMP-12的优异抑制作用以及对MMP-12的选择性，其优于其他MMP。MMP-12是慢性阻塞性肺疾病（COPD）和动脉粥样硬化等疾病中的关键酶。4，9和19）从该库中选择，和放射氟化类似物（[ 18 F] 4，[ 18 F] 9，和[ 18 F] 19）成功地合成。初步的体外血清稳定性和放射性标记的MMPIs与PET的体内生物分布研究表明，它们对于优选的MMP-12成像具有潜在的好处。

  DOI：

  10.1021/acs.jmedchem.8b00200
• 作为产物：
  描述：

  1-[2-(benzyloxy)ethyl]-4-bromo-1H-pyrazole 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 生成 2-(4-溴-1H-吡唑-1-基)乙醇
  参考文献：
  名称：

  Indoles

  摘要：

  一种由以下公式表示的1,4-取代的环胺衍生物或其药理学上可接受的盐： 其中A、B、C、D、T、Y和Z分别表示亚甲基或氮键合物；R1、R2、R3、R4和R5分别表示取代基；n表示0或1至3的整数；m表示0或1至6的整数；p表示1至3的整数。这些化合物具有5-羟色胺拮抗作用。因此，在临床上作为药物特别有用，用于治疗、改善和预防痉挛性瘫痪。它们还可用作中枢肌肉松弛剂，改善肌张力过高。

  公开号：

  US20020019531A1

文献信息

• Enantiomerically pure aminoheteroaryl compounds as protein kinase inhibitors
  申请人：Cui Jean Jingrong

  公开号：US20060046991A1

  公开（公告）日：2006-03-02

  Enantiomerically pure compound of formula 1 are provided, as well as methods for their synthesis and use. Preferred compounds are potent inhibitors of the c-Met protein kinase, and are useful in the treatment of abnormal cell growth disorders, such as cancers.

  提供了式1的对映纯化合物，以及它们的合成和使用方法。优选化合物是c-Met蛋白激酶的强效抑制剂，并且在治疗异常细胞生长紊乱，如癌症方面具有用处。
• Design and Synthesis of Fused Pyridine Building Blocks for Automated Library Generation
  作者：Helena Mora‐Radó、Werngard Czechtizky、María Méndez、Joseph P. A. Harrity

  DOI：10.1002/cmdc.202000852

  日期：2021.1.19

  We demonstrate that a diboration‐electrocyclization sequence provides access to a range of pyridine‐fused, small‐molecule boronic ester building blocks, and that these are amenable to high‐throughput synthesis leading to biaryl and ether‐linked compound libraries. Moreover, the implementation of an integrated physicochemical and ADME profiling workflow allows accelerated design of novel lead compounds

  我们证明了二硼化-电环化序列可以访问一系列吡啶稠合的小分子硼酸酯结构单元，并且这些结构单元适用于高通量合成，从而产生联芳基和醚连接的化合物库。此外，整合物理化学和 ADME 分析工作流程的实施允许加速设计用于药物发现项目的新型先导化合物。
• Synthesis and biological evaluation of 2-amino-5-aryl-3-benzylthiopyridine scaffold based potent c-Met inhibitors
  作者：Dengyou Zhang、Xiaowei Zhang、Jing Ai、Yun Zhai、Zhongjie Liang、Ying Wang、Yi Chen、Chunpu Li、Fei Zhao、Hualiang Jiang、Meiyu Geng、Cheng Luo、Hong Liu

  DOI：10.1016/j.bmc.2013.07.032

  日期：2013.11

  2-amino-3-benzylthiopyridines against c-Met were designed by means of bioisosteric replacement and docking analysis. Optimization of the 2-amino-3-benzylthiopyridine scaffold led to the identification of compound (R)-10b displaying c-Met inhibition with an IC50 up to 7.7 nM. In the cytotoxic evaluation, compound (R)-10b effectively inhibited the proliferation of c-Met addictive human cancer cell lines

  一系列的2-氨基Ñ -benzylpyridine -3- carboxnamides，2-氨基Ñ针对c-Met的-benzylpyridine -3-磺酰胺和2-氨基-3- benzylthiopyridines通过生物电子等排更换和对接分析来设计。对2-氨基-3-苄基硫代吡啶骨架的优化导致鉴定化合物（R）-10b，其显示出c-Met抑制，IC 50高达7.7 nM。在细胞毒性评估中，化合物（R）-10b有效抑制c-Met上瘾的人类癌细胞系的增殖（IC 50从0.19到0.71μM）和c-Met激活介导的细胞转移。在100 mg / Kg的剂量下，（R）-10b明显抑制了NIH-3T3 / TPR-Met异种移植模型中的肿瘤生长（45％）。值得注意的是，（R）-10b可以克服c-Met激活介导的吉非替尼耐药性，这表明其在药物组合中的潜在用途。综上所述，首先公开了2-氨基-3-苄基硫代吡啶
• TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS HAVING A HETEROBIARYL MOIETY, CONJUGATES THEREOF, AND METHODS AND USES THEREFOR
  申请人：Bristol-Myers Squibb Company

  公开号：US20190055246A1

  公开（公告）日：2019-02-21

  Compounds having a structure according to formula (I) or (II) where R 1 , R 2 , and Ar are as defined herein, are agonists for the Toll-like receptor 7 (TLR7) and can be used as adjuvants for stimulating the immune system. Some such compounds can be used in conjugates for targeted delivery to the organ or tissue of intended action.

  具有如公式（I）或（II）所示结构的化合物，其中R1、R2和Ar的定义如本文所述，是Toll样受体7（TLR7）的激动剂，并可用作刺激免疫系统的佐剂。某些这类化合物可用于与靶向递送到预期作用的器官或组织的结合物中。
• Regiocontrolled Synthesis of 6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazines
  作者：Peter J. Lindsay-Scott、Eloise Rivlin-Derrick

  DOI：10.1055/s-0037-1610734

  日期：2020.1

  Synthetic access to 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazines has been achieved in 3–4 steps from commercially available pyrazoles. Optimization of a protected hydroxyethyl group on N1 enabled the regiocontrolled construction of pyrazole-5-aldehydes in high yields; subsequent deprotection and reduction generated fused heterocyclic scaffolds bearing multiple substitution patterns. Moreover, the intermediate

  从市售吡唑分3至4步即可合成6,7-二氢-4 H-吡唑并[5,1- c ] [1,4]恶嗪。N1上受保护的羟乙基的优化使得能够高产地控制吡唑-5-醛的区域控制；随后的脱保护和还原生成带有多个取代模式的稠合杂环支架。此外，中间体吡唑乳醇被证明是通用的合成构件。