2-甲氧基-5-(三氟甲基)苯硼酸 | 240139-82-6

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯硼酸系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基-5-(三氟甲基)苯硼酸
• 中文别名: 2-甲氧基-5-三氟甲基苯硼酸
• 英文名称: (2-methoxy-5-(trifluoromethyl)phenyl)boronic acid
• 英文别名: 5-trifluoromethyl-2-methoxyphenylboronic acid；2-Methoxy-5-(trifluoromethyl)phenylboronic acid；[2-methoxy-5-(trifluoromethyl)phenyl]boronic acid
• CAS: 240139-82-6
• 化学式: C₈H₈BF₃O₃
• mdl: MFCD04039222
• 分子量: 219.956
• InChiKey: PXDQUMRSSQYJSX-UHFFFAOYSA-N

物化性质

• 熔点：
  144-148℃
• 沸点：
  325.4±52.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 危险标志：
  GHS07
• 危险性描述：
  H319
• 危险性防范说明：
  P305 + P351 + P338

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Methoxy-5-trifluoromethylphenylboronic acid
Product Name:
Synonyms: 2-Methoxy-5-(trifluoromethyl)phenylboronic acid

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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.
2-Methoxy-5-trifluoromethylphenylboronic acid
Ingredient name:
CAS number: 240139-82-6

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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: C8H8BF3O3
Molecular weight: 220.0

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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, hydrogen fluoride.

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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-甲氧基-5-(三氟甲基)苯硼酸 在 双氧水 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以82%的产率得到2-甲氧基-5-(三氟甲基)苯酚
  参考文献：
  名称：

  作为多巴胺D4受体配体的新系列吗啉和1,4-恶唑烷衍生物：合成和3D-QSAR模型。

  摘要：

  自多巴胺D（4）受体亚型的鉴定和关于其可能参与精神分裂症的推测以来，选择性D（4）配体的开发已投入大量工作。这些选择性配体可能是没有锥体束外副作用的有效抗精神病药。这项工作描述了对多巴胺D（4）受体具有选择性的新系列的2,4-二取代的吗啉和2,4-二取代的1,4-恶唑酮的合成。进行了使用GRID / GOLPE方法的3D-QSAR分析，目的是更好地了解化学结构与生物活性之间的关系。通过查看系数图，我们可以确定对于亲和力至关重要的区域位于两个苯环系统（对氯苄基）周围，和属于吗啉或1，4-氧杂庚烷体系的脂族胺。另外，吗啉或1，4-氧杂庚烷环的大小对于亲和力似乎很重要。

  DOI：

  10.1021/jm031111m
• 作为产物：
  描述：

  4-三氟甲基苯甲醚 在 正丁基锂 、 硼酸三异丙酯 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 以82%的产率得到2-甲氧基-5-(三氟甲基)苯硼酸
  参考文献：
  名称：

  作为多巴胺D4受体配体的新系列吗啉和1,4-恶唑烷衍生物：合成和3D-QSAR模型。

  摘要：

  自多巴胺D（4）受体亚型的鉴定和关于其可能参与精神分裂症的推测以来，选择性D（4）配体的开发已投入大量工作。这些选择性配体可能是没有锥体束外副作用的有效抗精神病药。这项工作描述了对多巴胺D（4）受体具有选择性的新系列的2,4-二取代的吗啉和2,4-二取代的1,4-恶唑酮的合成。进行了使用GRID / GOLPE方法的3D-QSAR分析，目的是更好地了解化学结构与生物活性之间的关系。通过查看系数图，我们可以确定对于亲和力至关重要的区域位于两个苯环系统（对氯苄基）周围，和属于吗啉或1，4-氧杂庚烷体系的脂族胺。另外，吗啉或1，4-氧杂庚烷环的大小对于亲和力似乎很重要。

  DOI：

  10.1021/jm031111m

文献信息

• Discovery of Clinical Candidate 4-[2-(5-Amino-1<i>H</i>-pyrazol-4-yl)-4-chlorophenoxy]-5-chloro-2-fluoro-<i>N</i>-1,3-thiazol-4-ylbenzenesulfonamide (PF-05089771): Design and Optimization of Diaryl Ether Aryl Sulfonamides as Selective Inhibitors of Na_V1.7
  作者：Nigel. A. Swain、Dave Batchelor、Serge Beaudoin、Bruce M. Bechle、Paul A. Bradley、Alan D. Brown、Bruce Brown、Ken J. Butcher、Richard P. Butt、Mark L. Chapman、Stephen Denton、David Ellis、Sebastien R. G. Galan、Steven M. Gaulier、Ben S. Greener、Marcel J. de Groot、Mel S. Glossop、Ian K. Gurrell、Jo Hannam、Matthew S. Johnson、Zhixin Lin、Christopher J. Markworth、Brian E. Marron、David S. Millan、Shoko Nakagawa、Andy Pike、David Printzenhoff、David J. Rawson、Sarah J. Ransley、Steven M. Reister、Kosuke Sasaki、R. Ian Storer、Paul A. Stupple、Christopher W. West

  DOI：10.1021/acs.jmedchem.7b00598

  日期：2017.8.24

  are potent and subtype selective NaV1.7 inhibitors is described. Optimization of early lead matter focused on removal of structural alerts, improving metabolic stability and reducing cytochrome P450 inhibition driven drug–drug interaction concerns to deliver the desired balance of preclinical in vitro properties. Concerns over nonmetabolic routes of clearance, variable clearance in preclinical species

  描述了一系列酸性二芳基醚杂环磺酰胺，它们是有效的亚型选择性Na V 1.7抑制剂。早期铅物质的优化集中在消除结构警报，改善代谢稳定性和减少细胞色素P450抑制性驱动的药物相互作用方面，以实现临床前体外特性的理想平衡。由于对非代谢途径的清除，临床前物种中的清除程度可变以及随后的低置信度人类药代动力学预测的担忧，导致决定进行人类微剂量研究以确定临床药代动力学。描述了临床前PK和临床人微剂量PK数据的设计策略和结果，从而发现了第一个亚型选择性Na V1.7抑制剂临床候选物PF-05089771（34），其与电压感测域中的位点结合。
• [EN] HETEROCYCLIC INHIBITORS OF THE SODIUM CHANNEL<br/>[FR] INHIBITEURS HÉTÉROCYCLIQUES DU CANAL SODIQUE
  申请人：ZALICUS PHARMACEUTICALS LTD

  公开号：WO2015130957A1

  公开（公告）日：2015-09-03

  The invention relates to compounds useful in treating conditions associated with voltage-gated ion channel function, particularly conditions associated with sodium channel activity. More specifically, the invention concerns heterocyclic compounds (e.g., compounds according to any of Formulas (l)-(ll l) or Compounds (1 )-(65) of Table 1 ) that are that are useful in treatment of conditions such as epilepsy, cancer, pain, migraine, Parkinson's Disease, mood disorders, schizophrenia, psychosis, tinnitus, amyotropic lateral sclerosis, glaucoma, ischaemia, spasticity disorders, obsessive compulsive disorder, restless leg syndrome and Tourette syndrome.

  该发明涉及与电压门控离子通道功能相关的化合物，特别是与钠通道活性相关的病症。更具体地，该发明涉及杂环化合物（例如，符合任何一种公式（l）-（ll l）或表1的化合物（1）-（65）的化合物），这些化合物可用于治疗癫痫、癌症、疼痛、偏头痛、帕金森病、情绪障碍、精神分裂症、精神病、耳鸣、肌萎缩性侧索硬化、青光眼、缺血、痉挛性疾病、强迫症、不安腿综合征和抽动症等病症的治疗。
• SUBSTITUTED ISOXAZOLOPYRIDAZINONES AND ISOTHIAZOLOPYRIDAZINONES AND METHODS OF USE
  申请人：AbbVie Inc.

  公开号：US20170073353A1

  公开（公告）日：2017-03-16

  Compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 and R 3 are as defined in the specification, are useful in treating conditions or disorders prevented by or ameliorated by positive allosteric modulation of the γ-aminobutyric acid B (GABA-B) receptor. Methods for making the compounds are described. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

  式(I)的化合物及其药用盐，其中R1、R2和R3如规范中定义的那样，可用于治疗通过或通过正向变构调节γ-氨基丁酸B（GABA-B）受体预防或改善的症状或疾病。描述了制备这些化合物的方法。还描述了式(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。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：CTXT PTY LTD

  公开号：WO2020002587A1

  公开（公告）日：2020-01-02

  A compound of formula (I), or a pharmaceutically acceptable salt thereof.

  式（I）的化合物，或其药用可接受的盐。
• Catalyst free, C-3 functionalization of imidazo[1,2-<i>a</i>]pyridines to rapidly access new chemical space for drug discovery efforts
  作者：Naresh Gunaganti、Anupreet Kharbanda、Naga Rajiv Lakkaniga、Lingtian Zhang、Rose Cooper、Hong-yu Li、Brendan Frett

  DOI：10.1039/c8cc07063f

  日期：——

  Multicomponent reactions (MCRs) are robust tools for the rapid synthesis of complex, small molecule libraries for use in drug discovery and development. By utilizing MCR chemistry, we developed a protocol to functionalize the C-3 position of imidazo[1,2-a]pyridine through a three component, decarboxylation reaction involving imidazo[1,2-a]pyridine, glyoxalic acid, and boronic acid.

  多组分反应（MCR）是用于快速合成用于药物发现和开发的复杂小分子库的强大工具。通过利用MCR化学方法，我们开发了一种协议，可通过三种组分将咪唑并[1,2-a]吡啶，乙二酸和硼酸进行脱羧反应，从而使咪唑并[1,2-a]吡啶的C-3位置官能化。