4-甲氧基-2-硝基苯基硼酸 | 860034-09-9

• 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: 4-甲氧基-2-硝基苯基硼酸
• 中文别名: 4-甲氧基-2-硝基苯硼酸
• 英文名称: (4-methoxy-2-nitrophenyl)boronic acid
• CAS: 860034-09-9
• 化学式: C₇H₈BNO₅
• mdl: MFCD09878340
• 分子量: 196.955
• InChiKey: PFTLRSTZYYFBNF-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: acetonitrile (75-05-8); ethyl acetate (141-78-6))
• 沸点：
  417.9±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxy-2-nitrophenylboronic acid
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-Methoxy-2-nitrophenylboronic acid
CAS number: 860034-09-9

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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: C7H8BNO5
Molecular weight: 197.0

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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.

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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-甲氧基-2-硝基苯基硼酸 在 盐酸 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 铁粉 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 氯苯 为溶剂， 反应 55.0h， 生成 8-bromo-3,9-dimethoxyphenanthridin-6-ol
  参考文献：
  名称：

  Development of potent macrocyclic inhibitors of genotype 3a HCV NS3/4A protease

  摘要：

  A series of macrocyclic compounds containing 2-substituted-quinoline moieties have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155K mutant activity while maintaining the high rat liver exposure. Cyclization of the 2-substituted quinoline substituent led to a series of tricyclic P2 compounds which also display superb gt3a potency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.106
• 作为产物：
  描述：

  硼酸三甲酯 在 苯基氯化镁 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以54%的产率得到4-甲氧基-2-硝基苯基硼酸
  参考文献：
  名称：

  WO2007/14922

  摘要：

  公开号：

文献信息

• Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed Hydroarylation and Subsequent Cadogan Cyclization
  作者：Yoshishiko Yamamoto、Erina Ohkubo、Masatoshi Shibuya

  DOI：10.1002/adsc.201700122

  日期：2017.5.17

  The copper-catalyzed hydroarylation of (trifluoromethyl)alkynes with (o-nitrophenyl)boronic acids selectively afforded trisubstituted (trifluoromethyl)alkenes bearing an o-nitrophenyl group. The obtained hydroarylation products were converted into 3-aryl-2-(trifluoromethyl)indoles in high yields via molybdenum-catalyzed Cadogan cyclization. Similarly, the hydroarylation product prepared from (o-ni

  （三氟甲基）炔与（邻硝基苯基）硼酸的铜催化加氢芳基化选择性地得到带有邻硝基苯基的三取代的（三氟甲基）烯烃。经由钼催化的Cadogan环化，将所获得的氢芳基化产物高产率地转化成3-芳基-2-（三氟甲基）吲哚。类似地，由（邻-硝基苯基）（三氟甲基）炔和（对-茴香基）硼酸制备的加氢芳基化产物也经历了Cadogan环化，尽管反应时间更长，以高收率提供了所需的吲哚产物。
• Macrocyclic Compounds As Antiviral Agents
  申请人：Harper Steven

  公开号：US20100183551A1

  公开（公告）日：2010-07-22

  A class of macrocyclic compounds of formula (I), wherein R 1 , R 3 , R 4 , R a , R b , A, Z, Y, X, M, W, n and m are defined herein, that are useful as inhibitors of viral proteases, particularly the hepatitis C virus (HCV) NS3 protease, are provided. Also provided are processes 5 for the synthesis and use of such macrocyclic compounds for treating or preventing HCV infection. Formula (I):

  提供一类宏环化合物的化学式（I），其中R1、R3、R4、Ra、Rb、A、Z、Y、X、M、W、n和m如下所定义，这些化合物可作为病毒蛋白酶的抑制剂，特别是对乙型肝炎病毒（HCV）NS3蛋白酶的抑制剂。还提供了合成和使用这类宏环化合物用于治疗或预防HCV感染的方法。化学式（I）：
• Synthesis of Unexpected trans-meso Macrocycle from Novel Unsymmetrical Tetraphenylene
  作者：Henry Wong、Chun-Lin Deng、Sam Hau、Xiao-Shui Peng

  DOI：10.1055/s-0035-1561480

  日期：——

  A highly unsymmetrical trisubstituted tetraphenylene was designed and synthesized as a novel superamolecular scaffold for an unexpected trans-meso tetraphenylene macrocycle, whose structure was unequivocally characterized by an X-ray crystallographic analysis. With the defined and electron-rich aromatic cavity, this macrocycle could be further modified to be a potential host for organic cations with

  设计并合成了一种高度不对称的三取代四亚苯基，作为一种用于意想不到的反式内消旋四亚苯基大环的新型超分子支架，其结构通过 X 射线晶体学分析得到明确表征。有了明确的和富含电子的芳香腔，这个大环可以进一步修饰成为具有生物学意义的有机阳离子的潜在宿主。
• Nickel(II)-Promoted Amide N–H Arylation of Pyroglutamate–Histidine with Arylboronic Acid Reagents
  作者：Kengo Hanaya、Mary K. Miller、Zachary T. Ball

  DOI：10.1021/acs.orglett.9b00759

  日期：2019.4.5

  Small and simple bioorthogonal reactive handles that can be readily encoded by natural processes are important for bioconjugation. A rapid nickel-promoted N–H arylation of pyroglutamate–histidine sequences with 2-nitroarylboronic acids proceeds under mild aqueous conditions. Chemoselective activation of a lactam amide N–H within a peptide or protein provides a new approach to selective conjugation

  可以通过自然过程轻松编码的小而简单的生物正交反应手柄对于生物缀合非常重要。焦谷氨酸-组氨酸序列与2-硝基芳基硼酸的快速镍促进NH芳基化反应在温和的水性条件下进行。肽或蛋白质中内酰胺酰胺N–H的化学选择性活化为聚酰胺结构的选择性偶联提供了一种新方法。
• Macrocyclic compounds as antiviral agents
  申请人：Harper Steven

  公开号：US08927569B2

  公开（公告）日：2015-01-06

  A class of macrocyclic compounds of formula (I), wherein R1, R3, R4, Ra, Rb, A, Z, Y, X, M, W, n and m are defined herein, that are useful as inhibitors of viral proteases, particularly the hepatitis C virus (HCV) NS3 protease, are provided. Also provided are processes 5 for the synthesis and use of such macrocyclic compounds for treating or preventing HCV infection. Formula (I):

  提供一类宏环化合物，其化学式为(I)，其中R1、R3、R4、Ra、Rb、A、Z、Y、X、M、W、n和m在此定义，该类化合物可用作病毒蛋白酶抑制剂，特别是乙型肝炎病毒（HCV）NS3蛋白酶的抑制剂。同时提供了合成和使用这种宏环化合物用于治疗或预防HCV感染的方法。化学式(I)如下：