2,5-二氟-1,4-亚苯基二硼酸频那醇酯 | 303006-90-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 2,5-二氟-1,4-亚苯基二硼酸频那醇酯
• 中文别名: 2,5-二氟苯-1,4-二硼酸 双(频哪醇)酯
• 英文名称: 2,2'-(2,5-difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 英文别名: 2-[2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 303006-90-8
• 化学式: C₁₈H₂₆B₂F₂O₄
• 分子量: 366.021
• InChiKey: PJCSUAIUPWCQRS-UHFFFAOYSA-N

物化性质

• 熔点：
  202-205℃
• 沸点：
  419.6±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,5-Difluoro-1,4-phenylenediboronic acid, pinacol ester
Synonyms: 2,2’-(2,5-Difluoro-1,4-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

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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: 2,5-Difluoro-1,4-phenylenediboronic acid, pinacol ester
CAS number: 303006-90-8

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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: C18H26B2F2O4
Molecular weight: 366.0

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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：

  2,5-二氟-1,4-亚苯基二硼酸频那醇酯 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-[2,5-Difluoro-4-(8-iodonaphthalen-1-yl)phenyl]-8-(2,5-dimethoxyphenyl)naphthalene
  参考文献：
  名称：

  Syntheses and ¹H NMR Spectroscopy of Rigid, Cofacially Aligned, Porphyrin−Bridge−Quinone Systems in Which the Interplanar Separations between the Porphyrin, Aromatic Bridge, and Quinone Are Less than the Sum of Their Respective van der Waals Radii

  摘要：

  Unusually rigid pi-stacked porphyrin-spacer-quinone systems have been synthesized using an approach that enables extensive control over the nature of electronic interactions between donor, aromatic spacer, and acceptor. This new class of porphyrin-based structures is distinct from related assemblies designed to probe electronic interactions between cofacial pi-stacked, aromatics: the donor (D), spacer (Sp), and acceptor (A) components of the assembly are held fixed at sub van der Waals contact distances, restricting severely the range of dynamical processes that modulate typically the magnitude of inter-ring separation and the extent of the lateral shift between juxtaposed aromatic units in the condensed phase. NMR spectroscopic studies demonstrate that these structures manifest disparate shielding environments which distribute uniformly the aromatic H-1 resonances for these diamagnetic D-Sp-A compounds over spectral windows that exceed 9.0 ppm.

  DOI：

  10.1021/ja000759a
• 作为产物：
  描述：

  1,4-二溴-2,5-二氟苯 、 联硼酸频那醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 以21 %的产率得到2,5-二氟-1,4-亚苯基二硼酸频那醇酯
  参考文献：
  名称：

  通过配位基序和连接体修饰的相互作用调节 FeII4L6 笼的自旋交叉特性

  摘要：

  尽管基于 Fe II的自旋交叉笼的数量不断增加，但在这些多核系统中配体修饰（例如配位基序取代基和接头）之间的相互作用尚未得到充分理解，限制了合理设计。在这里，我们报道了一系列基于 2,2'-吡啶基苯并咪唑的 Fe II 4 L 6自旋交叉笼，其中细微的配体修饰将 CD 3 CN 中的自旋交叉温度降低了高达 186 K。比较成对的笼，CH 3配位基序或亚苯基连接体上的取代基分别将自旋交叉温度降低了 48 K、91 K 或 186 K，这分别归因于电子效应、空间效应和两者的组合。从这项研究中获得的对配体修饰之间相互作用的理解可以用于改进自旋交叉笼的合理设计。

  DOI：

  10.1039/d3dt01569f

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2011050146A1

  公开（公告）日：2011-04-28

  Disclosed are compounds of Formula (I). Also disclosed are pharmaceutical compositions comprising the compounds, and methods for treating HCV invention by administration of the compounds.

  揭示了化合物的化学式（I）。还揭示了包含这些化合物的药物组合物，以及通过给药这些化合物来治疗HCV的方法。
• 含窒素複素環化合物及びその利用
  申请人：東洋紡株式会社

  公开号：JP2021172629A

  公开（公告）日：2021-11-01

  【課題】発光効率及び耐久性に優れた含窒素複素環化合物及びその利用に関する技術を提供する。【解決手段】含窒素複素環化合物は、式：Ｃｚ−Ｌ−Ａｒ（１）で表される化合物［式（１）中、Ｃｚは、下記式（２）：（式（２）中、Ｚは、単結合等、Ｒ２２及びＲ２７は、そ電子求引性基、Ｒ２３及びＲ２６は、電子供与性基、Ｒ２１、Ｒ２４、Ｒ２５、及びＲ２８は、Ｈ、電子求引性基、又は電子供与性基、波線は、Ｌとの結合部位）で表される基であり、Ｌは、単結合又はフェニレン基、Ａｒは、アリール基及びヘテロアリール基からなる群より選択される基。］。【選択図】なし

  提供具有优异发光效率和耐久性的含氮复杂环化合物及其应用技术。含氮复杂环化合物由以下式表示：Ｃｚ−Ｌ−Ａｒ（1）[在式（1）中，Ｃｚ表示如下式（2）：（式（2）中，Z表示单键等，R22和R27表示电子亲引基，R23和R26表示电子供给基，R21、R24、R25和R28表示H、电子亲引基或电子供给基，虚线表示与L的结合部位），L表示单键或苯基，Ar表示选自芳基和杂芳基的基。]。【选择图】无
• 一类含不同共轭桥的双核环金属铂(II)配合物近红外电致磷光材料的合成及应用
  申请人：常州大学

  公开号：CN107400147A

  公开（公告）日：2017-11-28

  本发明公开了一类含不同共轭桥的双核环金属铂(II)配合物近红外电致磷光材料及其在有机电致发光二极管中的应用。这一类双核环金属铂配合物近红外电致磷光材料是以不同共轭刚性结构(苯、1,4‑二氟苯、咔唑、芴、芘)为发光内核给体(D)单元、含氮齿共轭配体(异喹啉、蒽喹啉、菲啶)为受体(A)单元，构筑一类A‑D‑A结构为主配体、2,2,6,6‑四甲基‑3,5‑庚二酮为辅助配体以及铂离子构筑而成的环金属铂配合物近红外电致磷光材料。以这一类近红外电致磷光材料为发光层掺杂剂，以m‑MTDATA:CBP作为主体材料，制备了有机电致磷光发光器件。器件的最大发射峰为709nm、外量子效率为3.97％和最大辐照度为2354uW.Sr‑1.cm‑2的近红外有机电致磷光发光器件。
• Mechanistic Origins of Regioselectivity in Cobalt-Catalyzed C(sp2)-H Borylation of Benzoate Esters and Arylboronate Esters
  作者：Tyler P. Pabst、Linda Quach、Kaitlyn T. MacMillan、Paul J. Chirik

  DOI：10.1016/j.chempr.2020.11.017

  日期：2021.1

  Synthetic and mechanistic investigations into the C(sp2)-H borylation of various electronically diverse arenes catalyzed by bis(phosphine)pyridine (iPrPNP) cobalt complexes are reported. Borylation of various benzoate esters and arylboronate esters gave remarkably high selectivities for the position para to the functional group; in both cases, this regioselectivity was found to override the ortho-to-fluorine

  报道了双（膦）吡啶 ( iPr PNP) 钴配合物催化的各种电子多样性芳烃的 C(sp 2 )-H 硼化反应的合成和机理研究。各种苯甲酸酯和芳基硼酸酯的硼化反应对官能团的对位产生了非常高的选择性；在这两种情况下，发现这种区域选择性覆盖了之前报道的 ( iPr PNP)Co 硼化催化剂的邻位到氟的区域选择性，这是由 C(sp 2 )-H 氧化加成的热力学控制引起的。机理研究支持导致对位到酯和对位的途径分别通过动力学控制 BH 和 C(sp 2 -H) 氧化加成对硼酸酯的选择性。一种特别缺电子的氟化芳基硼酸酯的硼化导致 C(sp 2 )-H 氧化加成的加速和伴随的区域选择性反转，表明催化循环各个步骤的相对速率的细微变化可以实现独特且可切换的位点选择性。
• Selective Photocatalytic C–F Borylation of Polyfluoroarenes by Rh/Ni Dual Catalysis Providing Valuable Fluorinated Arylboronate Esters
  作者：Ya-Ming Tian、Xiao-Ning Guo、Maximilian W. Kuntze-Fechner、Ivo Krummenacher、Holger Braunschweig、Udo Radius、Andreas Steffen、Todd B. Marder

  DOI：10.1021/jacs.8b09790

  日期：2018.12.19

  B2pin2 at room temperature in excellent yields and with high selectivity. Direct irradiation of the intermediary C-F bond oxidative addition product trans-[NiF(ArF)(IMes)2] leads to very fast decomposition when B2pin2 is present. This destructive pathway can be bypassed by indirect excitation of the triplet states of the nickel(II) complex via the photoexcited rhodium biphenyl complex. Mechanistic studies

  一种高选择性和通用的光催化 CF 硼化方案，采用联苯铑配合物作为三线态敏化剂和镍催化剂 [Ni(IMes)2] (IMes = 1,3-dimesityliimidazoline-2-ylidene) 用于 CF 键活化和脱氟硼酸化过程被报告。这种串联催化剂系统在可见光（蓝色，400 nm）下运行，并在室温下以高产率和高选择性实现了多种氟芳烃与 B2pin2 的硼化。当存在 B2pin2 时，直接照射中间 CF 键氧化加成产物反式-[NiF(ArF)(IMes)2] 会导致非常快速的分解。这种破坏性途径可以通过光激发的铑联苯络合物间接激发镍 (II) 络合物的三重态来绕过。机理研究表明，用作光敏剂的 Rh 联苯配合物的超长寿命三线态激发态允许有效的三线态能量转移到反式 [NiF(ArF)(IMes)2]，从而导致 NHC 之一的解离配体。这与目前大多数采用过渡金属作为激发态单电子转移剂的光催化转化形成对比。我们之前曾报道过