2-(3-溴苯基)-5-(叔丁基)-1,3,4-噁二唑 | 957065-96-2

• 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-(3-溴苯基)-5-(叔丁基)-1,3,4-噁二唑
• 中文别名: 2-(3-溴苯基)-5-叔丁基-1,3,4-恶二唑
• 英文名称: 2-(3-bromophenyl)-5-(tert-butyl)-1,3,4-oxadiazole
• 英文别名: 2-(3-bromophenyl)-5-tert-butyl-1,3,4-oxadiazole
• CAS: 957065-96-2
• 化学式: C₁₂H₁₃BrN₂O
• 分子量: 281.152
• InChiKey: PJHHEWRHJXZUJR-UHFFFAOYSA-N

物化性质

• 沸点：
  362.4±44.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(3-Bromophenyl)-5-tert-butyl-1,3,4-oxadiazole
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: 2-(3-Bromophenyl)-5-tert-butyl-1,3,4-oxadiazole
CAS number: 957065-96-2

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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: C12H13BrN2O
Molecular weight: 281.1

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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, hydrogen bromide.

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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-(3-溴苯基)-5-(叔丁基)-1,3,4-噁二唑 、 1,3-双苯二硼酸频那醇酯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium acetate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以78%的产率得到tOXD-mTP
  参考文献：
  名称：

  Synthesis and physical properties of meta-terphenyloxadiazole derivatives and their application as electron transporting materials for blue phosphorescent and fluorescent devices

  摘要：

  合成并表征了两种基于m-三苯氧噻唑的电子传输材料，分别是双(2-tert-丁基-1,3,4-氧噻唑-5-基)-3,3′-m-三苯 (tOXD-mTP) 和双(2-(4-tert-丁基苯基)-1,3,4-氧噻唑-5-基)-3,3′-m-三苯 (tpOXD-mTP)。这两种分子均包含两个氧噻唑基团和一个m-三苯链作为核心结构，分别实现了高达2.83和2.90 eV的三重态能量间隙 (ET)。在以双(4′,6′-二氟苯基吡啶)-铱(III)吡咯酸盐 (FIrpic) 为基础的蓝色磷光发光器件中，tOXD-mTP 和 tpOXD-mTP 作为电子传输材料 (ETM) 的应用有效地限制了激发态三重态在发光层中的存在。其中一个使用FIrpic作为掺杂剂的电致发光 (EL) 器件显示出优异的电流效率为43.3 cd A−1，外量子效率 (EQE) 为23.0%，CIE（国际照明委员会）坐标为(0.13, 0.29)。基于双(4′,6′-二氟苯基吡啶)-铱(III)四(1-吡唑基)硼酸盐 (FIr6) 的更深蓝色EL器件展现出42.5 cd A−1的高电流效率和25.0%的外量子效率，CIE坐标为(0.14, 0.23)。这两种以tOXD-mTP和tpOXD-mTP为基础的器件效率是基于著名电子传输材料1,3-双[(4-tert-丁基苯基)-1,3,4-氧噻唑基]苯 (OXD-7) 的两到三倍。

  DOI：

  10.1039/c2jm33376g
• 作为产物：
  描述：

  间溴苯甲腈 在 吡啶 、 sodium azide 、 溶剂黄146 作用下， 以 正丁醇 为溶剂， 反应 72.0h， 生成 2-(3-溴苯基)-5-(叔丁基)-1,3,4-噁二唑
  参考文献：
  名称：

  Synthesis and physical properties of meta-terphenyloxadiazole derivatives and their application as electron transporting materials for blue phosphorescent and fluorescent devices

  摘要：

  合成并表征了两种基于m-三苯氧噻唑的电子传输材料，分别是双(2-tert-丁基-1,3,4-氧噻唑-5-基)-3,3′-m-三苯 (tOXD-mTP) 和双(2-(4-tert-丁基苯基)-1,3,4-氧噻唑-5-基)-3,3′-m-三苯 (tpOXD-mTP)。这两种分子均包含两个氧噻唑基团和一个m-三苯链作为核心结构，分别实现了高达2.83和2.90 eV的三重态能量间隙 (ET)。在以双(4′,6′-二氟苯基吡啶)-铱(III)吡咯酸盐 (FIrpic) 为基础的蓝色磷光发光器件中，tOXD-mTP 和 tpOXD-mTP 作为电子传输材料 (ETM) 的应用有效地限制了激发态三重态在发光层中的存在。其中一个使用FIrpic作为掺杂剂的电致发光 (EL) 器件显示出优异的电流效率为43.3 cd A−1，外量子效率 (EQE) 为23.0%，CIE（国际照明委员会）坐标为(0.13, 0.29)。基于双(4′,6′-二氟苯基吡啶)-铱(III)四(1-吡唑基)硼酸盐 (FIr6) 的更深蓝色EL器件展现出42.5 cd A−1的高电流效率和25.0%的外量子效率，CIE坐标为(0.14, 0.23)。这两种以tOXD-mTP和tpOXD-mTP为基础的器件效率是基于著名电子传输材料1,3-双[(4-tert-丁基苯基)-1,3,4-氧噻唑基]苯 (OXD-7) 的两到三倍。

  DOI：

  10.1039/c2jm33376g

文献信息

• Benchmarking of Density Functionals for the Description of Optical Properties of Newly Synthesized π‐Conjugated TADF Blue Emitters
  作者：Georgia Ivanova、Nadezhda Bozova、Nikolay Petkov、Cunbin An、Benlin Hu、Monika Mutovska、Konstantin Konstantinov、Yulian Zagranyarski、Vladimira Videva、Adelina Yordanova、Martin Baumgarten、Anela Ivanova

  DOI：10.1002/chem.202104411

  日期：2022.3.16

  Synthesis and computational guidelines based on benchmarking of DFT functionals for new π-conjugated TADF emitters are reported. The three target compounds were obtained by multistep synthesis, including metal-catalyzed reactions and functional-group transformations. The emitters feature electron donors and acceptors moderately coupled through a spacer. The importance of the treatment of long-range

  报告了基于新 π 共轭 TADF 发射器的 DFT 泛函基准测试的合成和计算指南。这三种目标化合物是通过多步合成获得的，包括金属催化反应和官能团转化。发射器具有通过间隔物适度耦合的电子供体和受体。明确概述了在官能团内处理远程交换的重要性以及它们平衡单独分子片段的 π-离域的能力。
• m-TERPHENYL COMPOUND DERIVATIVES AND APPLICATION FOR ORGANIC LIGHT EMITTING DIODE
  申请人：CHENG Chien-Hong

  公开号：US20110220880A1

  公开（公告）日：2011-09-15

  An m-terphenyl derivative has a structure of formula (I) or (II): wherein A and B are five-membered heterocyclic compounds containing nitrogen, each of substituents R, R 1 and R 2 is a member independently selected from the group consisting of H, halo, cyano, trifluoromethyl, amino, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, aryl and heteroaryl. The compound of the present invention may have advantages in good electron affinity, low HOMO and thereby achieving hole blocking and may be used for electron transport material and/or electron injection material.
• US8475939B2
  申请人：——

  公开号：US8475939B2

  公开（公告）日：2013-07-02
• Synthesis and physical properties of meta-terphenyloxadiazole derivatives and their application as electron transporting materials for blue phosphorescent and fluorescent devices
  作者：Cheng-An Wu、Ho-Hsiu Chou、Cheng-Hung Shih、Fang-Iy Wu、Chien-Hong Cheng、Heh-Lung Huang、Teng-Chih Chao、Mei-Rurng Tseng

  DOI：10.1039/c2jm33376g

  日期：——

  Two m-terphenyloxadiazole-based electron transporting materials, bis(2-tert-butyl-1,3,4-oxadiazole-5-diyl)-3,3′-m-terphenyl (tOXD-mTP) and bis(2-(4-tert-butylphenyl)-1,3,4-oxadiazole-5-diyl)-3,3′-m-terphenyl (tpOXD-mTP) were synthesized and characterized. These two molecules contained two oxadiazolyl groups and a m-terphenyl linkage as the core structure achieving high triplet energy gaps (ET) of 2.83 and 2.90 eV, respectively. The application of tOXD-mTP and tpOXD-mTP as the electron transporting materials (ETM) in bis(4′,6′-difluorophenylpyridinato)-iridium(III) picolinate (FIrpic)-based blue phosphorescent light-emitting devices effectively confines the triplet exciton in the emitting layers. One of the electroluminescent (EL) devices using FIrpic as the dopant showed an excellent current efficiency of 43.3 cd A−1 and an external quantum efficiency (EQE) of 23.0% with CIE (Commission International de l'Eclairage) coordinates of (0.13, 0.29). The bis(4′,6′-difluorophenylpyridinato)-iridium(III) tetra(1-pyrazolyl)borate (FIr6)-based deeper blue EL device exhibited a high current efficiency of 42.5 cd A−1 and external quantum efficiency of 25.0% with CIE coordinates of (0.14, 0.23). These two tOXD-mTP and tpOXD-mTP based devices show device efficiencies two to three times higher than that based on the well-known electron transporting material 1,3-bis[(4-tertbutylphenyl)-1,3,4-oxadiazolyl]phenylene (OXD-7).

  合成并表征了两种基于m-三苯氧噻唑的电子传输材料，分别是双(2-tert-丁基-1,3,4-氧噻唑-5-基)-3,3′-m-三苯 (tOXD-mTP) 和双(2-(4-tert-丁基苯基)-1,3,4-氧噻唑-5-基)-3,3′-m-三苯 (tpOXD-mTP)。这两种分子均包含两个氧噻唑基团和一个m-三苯链作为核心结构，分别实现了高达2.83和2.90 eV的三重态能量间隙 (ET)。在以双(4′,6′-二氟苯基吡啶)-铱(III)吡咯酸盐 (FIrpic) 为基础的蓝色磷光发光器件中，tOXD-mTP 和 tpOXD-mTP 作为电子传输材料 (ETM) 的应用有效地限制了激发态三重态在发光层中的存在。其中一个使用FIrpic作为掺杂剂的电致发光 (EL) 器件显示出优异的电流效率为43.3 cd A−1，外量子效率 (EQE) 为23.0%，CIE（国际照明委员会）坐标为(0.13, 0.29)。基于双(4′,6′-二氟苯基吡啶)-铱(III)四(1-吡唑基)硼酸盐 (FIr6) 的更深蓝色EL器件展现出42.5 cd A−1的高电流效率和25.0%的外量子效率，CIE坐标为(0.14, 0.23)。这两种以tOXD-mTP和tpOXD-mTP为基础的器件效率是基于著名电子传输材料1,3-双[(4-tert-丁基苯基)-1,3,4-氧噻唑基]苯 (OXD-7) 的两到三倍。