二甲基4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-2,6-吡啶二羧酸酯 | 741709-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 二甲基4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-2,6-吡啶二羧酸酯
• 英文名称: dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,6-dicarboxylate
• CAS: 741709-66-0
• 化学式: C₁₅H₂₀BNO₆
• 分子量: 321.138
• InChiKey: BQULHACFOJDBBI-UHFFFAOYSA-N

物化性质

• 沸点：
  453.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,6-Bis(methoxycarbonyl)pyridine-4-boronic acid, pinacol ester
Synonyms: Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,6-dicarboxylate

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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: 2,6-Bis(methoxycarbonyl)pyridine-4-boronic acid, pinacol ester
CAS number: 741709-66-0

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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, refrigerated.
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: C15H20BNO6
Molecular weight: 321.1

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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.

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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：

  二甲基4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-2,6-吡啶二羧酸酯 在 四(三苯基膦)钯 、 caesium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Excitation- and Emission-Wavelength-Based Multiplex Spectroscopy Using Red-Absorbing Near-Infrared-Emitting Lanthanide Complexes

  摘要：

  Multiplex imaging in the red and near-infrared (NIR) should be an enabling tool for the real-time investigation of biological systems. Currently available emitters have short luminescent lifetimes, broad absorption and emission bands, and small Stokes shifts, which limits multiplexing in this region to two colors. NIR-emitting luminescent lanthanide (Ln) complexes carrying hydroporphyrin (chlorin) sensitizing antennae are excitable in the red through the narrow, intense and tunable chlorin absorptions. Both emission- and excitation-based multiplexing are possible, the former by exciting the same antenna appended to different Lns, the latter by attaching different chlorins with nonoverlapping absorptions to the same Ln. The combination of excitation and emission spectroscopies allows for the straightforward differentiation of up to four different complexes.

  DOI：

  10.1021/jacs.8b07609
• 作为产物：
  描述：

  4-氧代-1,4-二氢-2,6-吡啶二甲酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 硫酸 、 potassium acetate 、 五溴化磷 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 生成 二甲基4-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-2,6-吡啶二羧酸酯
  参考文献：
  名称：

  使用 RuII 聚吡啶基官能化吡啶二羧酸螯合物进行敏化镧系元素发光

  摘要：

  制备了一种附加有吡啶二甲酸 Ln III螯合剂的可见光吸收 [Ru II (tpy) 2 ] 2+型发色团，并与几种不同的镧系阳离子络合，形成相应的异双金属 d-f 组装体。通过1 H NMR 光谱分析的后续溶液形态显示，与母体吡啶二甲酸相比，Ln III螯合络合物稳定性意外降低，特别是对于 1:3 络合物。结果，无法分离所需的 Ln(ML) 3配合物，而是使用稳态吸收和发射光谱对 1:1 Ln III –ML 配合物进行了表征和研究。在基于 Ru II的金属配体在可见光区域约1 次MLCT 激发后，观察到 Yb III 、Nd III和 Er III配合物的敏化近红外发射。 485 纳米。使用瞬态吸收光谱的研究揭示了基本上定量的系间窜越，以形成3 MLCT 激发态，正如预期的那样，然后该激发态充当基于金属配体的天线效应的能量供体，促进 4.8、17.0 和 37 的敏化效率。Yb III

  DOI：

  10.1039/d1dt00982f

文献信息

• Design of Dipicolinic Acid Ligands for the Two-Photon Sensitized Luminescence of Europium Complexes with Optimized Cross-Sections
  作者：Anthony D’Aléo、Alexandre Picot、Patrice L. Baldeck、Chantal Andraud、Olivier Maury

  DOI：10.1021/ic8012975

  日期：2008.11.17

  2R, OR, SR, or NR 2) or the nature of the conjugated backbone (phenyl, phenylethynyl, naphtylethynyl, bis(phenylethynyl), or chalcone). The photophysical properties of related D 3 symmetric europium complexes (absorption and luminescence) were measured. Experiments using two-photon sensitized luminescence of a Eu (III) complex reveal large two-photon absorption (TPA) cross-section values (775 GM at

  描述了一系列广泛的推挽式供体-π-共轭二吡啶甲酸配体的多步合成。配体的电荷转移特性可以通过改变供体基团（CH 2R，OR，SR或NR 2）或共轭主链的性质（苯基，苯基乙炔基，萘乙炔基，双（苯基乙炔基）或查尔酮）来调节。测量了相关的D 3对称euro配合物的光物理性质（吸收和发光）。使用Eu（III）络合物的双光子敏化发光的实验显示，二氯甲烷中的大双光子吸收（TPA）横截面值（在740 nm处为775 GM）。此外，可以从该系统研究中得出一些结构-性质关系，从而可以优化镧系元素配合物的TPA性质。
• Selective Sensitization of Eu(III) and Tb(III) Emission with Triarylboron-Functionalized Dipicolinic Acids
  作者：Hee-Jun Park、Soo-Byung Ko、Ian W. Wyman、Suning Wang

  DOI：10.1021/ic501335e

  日期：2014.9.15

  Three triarylboron- (Mes(2)BAr-) functionalized dipicolinic acids, namely, 4-(4-(dimesitylboranyl)-2,3,5,6-tetramethylphenyl)pyridine-2,6-dicarboxylic acid (H2L1), 4-(4-(4-dimesitylboranyl)-2,3,5,6-tetramethylphenyl)-1H-1,2,3-triazol-1-yl)pyridine-2,6-dicarboxylic acid (H2L2), and 4-(4-(4-dimesitylboranyl) phenyl)-1H-1,2,3-triazol-1-yl)pyridine-2,6-dicarboxylic acid (H2L3), have been designed and synthesized. Lanthanide(III) complexes with the general formula of [NBu4](3)[LnL(3)] (Ln = Eu or Tb; L = L1, L2, or L3) were obtained. The new triarylboron-functionalized ligands were found to be effective in the selective sensitization of the emissions of Eu(III) and Tb(III) ions with a high quantum efficiency (e.g., 0.54 for [NBu4](3)[TbL1(3)] in the solid state) upon excitation at similar to 330 nm. An intraligand charge-transfer (ILCT) transition from the mesityl or aryl group to the boron or boron-aryl unit was found to play a key role in the activation of the Eu(III) and Tb(III) emissions, based on TD-DFT computational data and luminescence titration experiments performed using fluoride and cyanide ions.
• Sensitised lanthanide luminescence using a Ru^II polypyridyl functionalised dipicolinic acid chelate
  作者：Divya Rajah、Michael C. Pfrunder、Bowie S. K. Chong、Alexander R. Ireland、Isaac M. Etchells、Evan G. Moore

  DOI：10.1039/d1dt00982f

  日期：——

  appended with a dipicolinic acid LnIII chelator has been prepared and complexed with several differing lanthanide cations to form the corresponding heterobimetallic d–f assemblies. The subseqent solution speciation analysed by 1H NMR spectroscopy revealed an unexpected decrease in the LnIII chelate complex stability, in particular for the 1 : 3 complex, when compared to the parent dipicolinic acid.

  制备了一种附加有吡啶二甲酸 Ln III螯合剂的可见光吸收 [Ru II (tpy) 2 ] 2+型发色团，并与几种不同的镧系阳离子络合，形成相应的异双金属 d-f 组装体。通过1 H NMR 光谱分析的后续溶液形态显示，与母体吡啶二甲酸相比，Ln III螯合络合物稳定性意外降低，特别是对于 1:3 络合物。结果，无法分离所需的 Ln(ML) 3配合物，而是使用稳态吸收和发射光谱对 1:1 Ln III –ML 配合物进行了表征和研究。在基于 Ru II的金属配体在可见光区域约1 次MLCT 激发后，观察到 Yb III 、Nd III和 Er III配合物的敏化近红外发射。 485 纳米。使用瞬态吸收光谱的研究揭示了基本上定量的系间窜越，以形成3 MLCT 激发态，正如预期的那样，然后该激发态充当基于金属配体的天线效应的能量供体，促进 4.8、17.0 和 37 的敏化效率。Yb III
• Excitation- and Emission-Wavelength-Based Multiplex Spectroscopy Using Red-Absorbing Near-Infrared-Emitting Lanthanide Complexes
  作者：Ruisheng Xiong、Dimitrije Mara、Jing Liu、Rik Van Deun、K. Eszter Borbas

  DOI：10.1021/jacs.8b07609

  日期：2018.9.5

  Multiplex imaging in the red and near-infrared (NIR) should be an enabling tool for the real-time investigation of biological systems. Currently available emitters have short luminescent lifetimes, broad absorption and emission bands, and small Stokes shifts, which limits multiplexing in this region to two colors. NIR-emitting luminescent lanthanide (Ln) complexes carrying hydroporphyrin (chlorin) sensitizing antennae are excitable in the red through the narrow, intense and tunable chlorin absorptions. Both emission- and excitation-based multiplexing are possible, the former by exciting the same antenna appended to different Lns, the latter by attaching different chlorins with nonoverlapping absorptions to the same Ln. The combination of excitation and emission spectroscopies allows for the straightforward differentiation of up to four different complexes.