4-(二苯基氨基)苯硼酸频那醇酯 | 267221-88-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(二苯基氨基)苯硼酸频那醇酯
• 中文别名: 4-(二苯氨基)苯硼酸,吡那考酯
• 英文名称: 4-(diphenylamino)phenylboronic pinacol ester
• 英文别名: N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline；4-(diphenylamino)phenylboronic acid pinacol ester；N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine；4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)triphenylamine；N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenamine；2-(4-diphenylaminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；4-(N,N-diphenylamino)phenylboronic acid pinacol ester；4-(diphenylamino)benzeneboronic acid pinacol ester；triphenylamine 4-boronic acid pinacol ester；pinacol [4-(diphenylamino)phenyl]boronate；N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-phenylbenzenamine；N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-yl)aniline；4-(diphenylamino)phenylboronic acid；triphenylamine-4-boronic acid.；triphenylamine borate；2-(4-(N,N-diphenylamino)phenyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane
• CAS: 267221-88-5
• 化学式: C₂₄H₂₆BNO₂
• 分子量: 371.287
• InChiKey: VKSWIFGDKIEVFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  93-98 °C
• 沸点：
  495.8±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境中保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(Diphenylamino)phenylboronic acid, pinacol ester
Synonyms: N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

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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-(Diphenylamino)phenylboronic acid, pinacol ester
CAS number: 267221-88-5

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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: C24H26BNO2
Molecular weight: 371.3

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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-(二苯基氨基)苯硼酸频那醇酯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 以100 %的产率得到三苯胺
  参考文献：
  名称：

  室温下用 AlCl 3 对芳基硼酸和酯进行快速原脱硼

  摘要：

  本文报道了AlCl 3介导的芳基硼酸和酯的原脱硼作用。该方法反应条件温和、反应收率高、反应时间短。基于11 B NMR 光谱的机理研究表明，它可能通过 AlCl 3与芳基硼酸或酯基团的氧原子配位的初始硼活化来进行。

  DOI：

  10.1071/ch23028
• 作为产物：
  描述：

  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 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以96%的产率得到4-(二苯基氨基)苯硼酸频那醇酯
  参考文献：
  名称：

  Organometallic Complex, Light-Emitting Element, Light-Emitting Device, and Electronic Device Including the Organometallic Complex

  摘要：

  提供了一种新型的有机金属配合物，可以轻松合成并发射磷光，或者是发射红色磷光的化合物。发明者专注于易于合成的m-氨基苯基吡嗪衍生物，该衍生物由以下通用公式（G0）表示，合成了一种有机金属配合物，其中该衍生物与第9族或第10族金属离子配位，并进一步合成了一种发射红色磷光的有用物质。

  公开号：

  US20120165523A1

文献信息

• 有機エレクトロルミネッセンス素子及び材料
  申请人：ＤＩＣ株式会社

  公开号：JP2020055768A

  公开（公告）日：2020-04-09

  【課題】 本発明が解決しようとする課題は、素子に使用した場合に低い駆動電圧、高い発光効率、高い発光の色純度及び長い発光寿命を有する青色のリン光発光性金属錯体を提供することである。さらに、当該金属錯体を含む有機エレクトロルミネッセンス素子を提供することである。【解決手段】 本願発明は下記の一般式（Ｉ）ＭＬ１ｍＬ２ｎ （Ｉ）で表される化合物を提供し、併せて当該化合物を含有する有機エレクトロルミネッセンス素子を提供する。【選択図】 図１

  本发明旨在提供一种在元件中使用时具有低驱动电压、高发光效率、高发光色纯度和长发光寿命的蓝色磷光发光性金属络合物。此外，还提供包含该金属络合物的有机电致发光元件。本申请发明提供了以下通式（I）ML1mL2n（I）所表示的化合物，并提供包含该化合物的有机电致发光元件。【选择图】图1
• Photoinduced Metal-Free Atom Transfer Radical Polymerization Using Highly Conjugated Thienothiophene Derivatives
  作者：Ceren Kutahya、Andrit Allushi、Recep Isci、Johannes Kreutzer、Turan Ozturk、Gorkem Yilmaz、Yusuf Yagci

  DOI：10.1021/acs.macromol.7b01335

  日期：2017.9.12

  Photoinduced metal-free atom transfer radical polymerization (ATRP) activated by highly conjugated electron-rich thienothiophene derivatives, namely 4-[2-(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TT-TPA), 4-[2,5-bis(4-diphenylaminophenyl)-thieno[3,2-b]thiophen-3-yl]benzonitrile (TPA-TT-TPA), 4-(2-(4-(1,2,2-triphenylvinyl)phenyl) thieno[3,2-b]thiophen-3-yl)benzonitrile (TT-TPE)

  高度共轭的富电子的噻吩并噻吩衍生物，即4- [2-（4-二苯基氨基苯基）-噻吩并[3,2 - b ]噻吩-3-基]苄腈（TT ）激活的光诱导无金属原子转移自由基聚合（ATRP）-TPA），4- [2,5-双（4-二苯基氨基苯基）-噻吩并[3,2 - b ]噻吩-3-基]苄腈（TPA-TT-TPA），4-（2-（4-（ 1,2,2-三苯基乙烯基）苯基）噻吩并[3,2 - b ]噻吩-3-基）苄腈（TT-TPE）和4-（2,5-双（4-（1,2,2-三苯基乙烯基） ）苯基）thieno [3,2- b据报道有]噻吩-3-基）苄腈（TPE-TT-TPE）。甲基丙烯酸甲酯（MMA）的聚合可以有效地被光激活和失活，从而形成具有受控分子量特性，分散性和链端官能度的聚合物。聚合研究和DFT计算表明，由于具有良好的热力学性质，TT-TPA是最有效的活化剂。
• Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-<i>b</i>]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties
  作者：Recep Isci、Melis Unal、Gizem Kucukcakir、Naime A. Gurbuz、Sultan F. Gorkem、Turan Ozturk

  DOI：10.1021/acs.jpcb.1c09448

  日期：2021.12.9

  (TPA(OMe)2)-functionalized thieno[3,2-b]thiophene (TT) fluorophores, 4a–e and 5a–e, bearing different electron-donating and electron-withdrawing substituents (-PhCN, -PhF, -PhOMe, -Ph, and -C6H13) at the terminal thienothiophene units were designed and synthesized by the Suzuki coupling reaction. Their optical and electrochemical properties were investigated by experimental and computational studies. Solid-state

  一系列 10 种新型三苯胺 (TPA)/4,4'-二甲氧基三苯胺 (TPA(OMe) 2 )-功能化的噻吩并[3,2- b ]噻吩 (TT) 荧光团，4a-e和5a-e，具有不同的给电子和吸电子取代基（-PhCN、-PhF、-PhOMe、-Ph 和 -C 6 H 13) 在末端的噻吩并噻吩单元是通过 Suzuki 偶联反应设计和合成的。通过实验和计算研究研究了它们的光学和电化学性质。固态荧光量子产率记录为 20% 至 69%，最大溶液态量子效率达到 97%。此外，新型发色团的光物理表征显示出显着的斯托克斯位移，达到 179 nm 并具有红移。它们在溶液中表现出从橙色到深蓝色的调谐颜色发射，并显示荧光寿命达到 4.70 ns。三苯胺(TPA)/4,4'-二甲氧基三苯胺(TPA(OMe) 2 )-衍生的三芳胺与噻吩并[3,2- b]上不同官能团的关系] 噻吩单元进行了讨论。
• Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol
  作者：Colton R. Davis、Irungu K. Luvaga、Joseph M. Ready

  DOI：10.1021/jacs.1c01242

  日期：2021.4.7

  Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C–C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

  烯基硼酸盐添加到具有高对映选择性的 Ir(π-烯丙基) 中间体。1,2-金属酸盐位移形成第二个 C-C 键并建立 1,3-立体化学关系。三组分偶联提供了可以进行多种额外功能化的叔硼酸酯。三取代烯烃的延伸设置了三个连续的立体中心。
• Iron‐Catalyzed Fluoroalkylation of Arylborates with Sulfone Reagents: Beyond the Limitation of Reduction Potential
  作者：Zhiqiang Wei、Wenjun Miao、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.202102597

  日期：2021.6.7

  alkyl–aryl coupling reaction between sulfones and arylboron compounds has remained a challenge. We report the first iron-catalyzed radical difluoroalkylation of arylborates with N-heteroaryl sulfones. The coordination between the iron catalyst and the nitrogen atom of N-heteroaryl sulfones was identified to be important in overcoming the reduction potential limitation of sulfones in the intermolecular single-electron-transfer

  砜和芳基硼化合物之间的铁催化烷基-芳基偶联反应仍然是一个挑战。我们报告了第一个铁催化的芳基硼酸酯与 N-杂芳基砜的自由基二氟烷基化。铁催化剂与 N-杂芳基砜的氮原子之间的配位被认为对于克服分子间单电子转移过程中砜的还原电位限制很重要，这使得氟烷基 N-杂芳基砜（具有相对较高的还原电位）和非氟化烷基 N-杂芳基砜（具有低还原电位）作为强大的烷基化试剂。