4-溴-2,5-二甲基苯硼酸 | 130870-00-7

• 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-溴-2,5-二甲基苯硼酸
• 中文别名: 4-溴-2,5-二甲基苯基硼酸
• 英文名称: (4-bromo-2,5-dimethylphenyl)boronic acid
• 英文别名: 4-bromo-2,5-dimethylphenylboronic acid；4-bromo-2,5-dimethyl phenylboronic acid
• CAS: 130870-00-7
• 化学式: C₈H₁₀BBrO₂
• 分子量: 228.881
• InChiKey: FUVZURQKCDUKIR-UHFFFAOYSA-N

物化性质

• 熔点：
  194-202℃
• 沸点：
  350.3±52.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT, KEEP COLD
• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Bromo-2,5-dimethylphenylboronic acid
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-Bromo-2,5-dimethylphenylboronic acid
Ingredient name:
CAS number: 130870-00-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H10BBrO2
Molecular weight: 228.9

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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 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：

  4-溴-2,5-二甲基苯硼酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 亚磷酸三乙酯 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 生成 2-bromo-1,4-dimethyl-9H-carbazole
  参考文献：
  名称：

  通过亲电环化合成功能化的椭圆形和玫瑰树碱衍生物。

  摘要：

  已报道了一种有效的方法，用于通过AgOTf或CuI催化的2-炔基-3-carbazolylaldimines的亲电环化反应，从相应的2-bromo咔唑开始合成高度官能化的椭圆形和玫瑰树碱衍生物。

  DOI：

  10.1039/c1ob05258f
• 作为产物：
  描述：

  2,5-二溴-1,4-二甲基苯 在 水 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 生成 4-溴-2,5-二甲基苯硼酸
  参考文献：
  名称：

  Side functionalization of diboronic acid precursors for covalent organic frameworks

  摘要：

  一系列取代的1,4-苯二硼酸（BDBA）被合成，并研究了它们的热性质。选择两种二硼酸作为共价有机骨架（COF）形成的构建块，即2,5-二甲氧基-1,4-苯二硼酸和2-硝基-1,4-苯硼酸。有趣的是，BDBA核心的取代导致了聚合温度的显著降低，从而形成了较为无序的结构。

  DOI：

  10.1039/c3ce26494g

文献信息

• Suzuki–Miyaura monocouplings of p-dibromobiphenyl and substituted p-dibromo(penta-p-phenylenes)
  作者：Elena Guillén、Jesús Hierrezuelo、Rocio Martínez-Mallorquín、J. Manuel López-Romero、Rodrigo Rico

  DOI：10.1016/j.tet.2011.02.025

  日期：2011.4

  electronic characteristics of the boronic derivative did not affect the selectivity of the reaction. The reaction yields observed were higher at room temperature and when arylboronic pinacol esters were used. These reactions also offer a useful method for the preparation of asymmetrically substituted terphenyls and hexa-p-phenylenes, giving good yields.

  研究了对-二溴联苯和对-二溴（戊-对亚苯基）与芳基硼酸和酯的Suzuki-Miyaura交叉偶联的单/双比率。当底物是对-二溴低聚芳烃时，偶合反应被证明对单芳基化具有高度选择性，而对p则获得选择性二芳基化-二碘代苯基。这些化合物的单/双偶合比对所涉及卤素的性质高度敏感，但是硼衍生物的位阻或电子特性不会影响反应的选择性。在室温下和使用芳基硼酸频哪醇酯时，观察到的反应产率更高。这些反应也提供了制备不对称取代的联苯和六-对-亚苯基的有用方法，具有良好的收率。
• High-Triplet-Energy Dendrons: Enhancing the Luminescence of Deep Blue Phosphorescent Iridium(III) Complexes
  作者：Shih-Chun Lo、Ruth E. Harding、Christopher P. Shipley、Stuart G. Stevenson、Paul L. Burn、Ifor D. W. Samuel

  DOI：10.1021/ja903157e

  日期：2009.11.25

  coordinates of (0.16, 0.16). The results demonstrate that dendronization of simple chromophores can enhance their properties. Single layer neat dendrimer organic light-emitting diodes (OLEDs) had an external quantum efficiency (EQE) of 0.4% at 100 cd/m(2). Bilayer devices with an electron transport layer gave improved EQEs of up to 3.9%. Time-resolved luminescence measurements suggest that quenching of triplets

  具有高发光效率的可溶液加工的蓝色磷光发光体非常适合大面积显示器和照明应用。该报告表明，当 fac-tris[1-methyl-5-(4-fluorophenyl)-3-n-propyl-1H-[1,2,4]triazolyl]iridium(III) 复合核被刚性高-三重态能量树突，物理和光物理特性都可以优化。高三重态和刚性树枝由扭曲的联苯树枝组成，扭曲是由于使用四取代的支化苯环而引起的。蓝色磷光树枝状聚合物是使用会聚方法合成的，并且被发现是可溶液加工的，并且具有 148 摄氏度的高玻璃化转变温度。 该树枝状聚合物具有 94% 的超高溶液光致发光量子产率 (PLQY)，是简单母核复合体 (27%) 的三倍多。还发现刚性和高三线态能量树突控制导致固态发光猝灭的分子间相互作用，并且发现薄膜 PLQY 为 60%，其发射具有 Commission Internationale de l'Eclairage
• Emission wavelength dependence on the rISC rate in TADF compounds with large conformational disorder
  作者：Tomas Serevičius、Rokas Skaisgiris、Jelena Dodonova、Laimis Jagintavičius、Jonas Bucevičius、Karolis Kazlauskas、Saulius Juršėnas、Sigitas Tumkevičius

  DOI：10.1039/c8cc08906j

  日期：——

  the local and charge-transfer triplet states is required for efficient reverse intersystem crossing in TADF compounds. This is ensured by low steric hindrance between donor and acceptor molecular units. However, flexible molecular cores show large conformational disorder and emission wavelength instability in solid films.

  为了在TADF化合物中进行有效的逆系统间交叉，需要在局部和电荷转移三重态之间进行大的电子耦合。供体和受体分子单元之间的空间位阻低，从而确保了这一点。但是，柔性分子核在固体膜中显示出大的构象紊乱和发射波长不稳定性。
• Synthesis of penta-p-phenylenes with oligo(ethylene glycol) side chains
  作者：J. Manuel López-Romero、Rodrigo Rico、Rocío Martínez-Mallorquín、Jesús Hierrezuelo、Elena Guillén、Chengzhi Cai、J. Carlos Otero、Isabel López-Tocón

  DOI：10.1016/j.tetlet.2007.06.167

  日期：2007.8

  We report an efficient synthesis of a series of penta-p-phenylene derivatives with four side chains of various lengths, including deca(ethylene glycol) groups. The key feature of the synthesis is that the side chains are efficiently introduced in the last step, facilitating optimization of the side chains for different applications. Raman spectroscopy study indicates a similarly high rigidity for all

  我们报告了一系列具有四个不同长度的侧链的五对苯撑衍生物的有效合成，包括十个（乙二醇）基团。合成的关键特征是在最后一步中有效地引入了侧链，从而有助于针对不同应用优化侧链。拉曼光谱研究表明，所有这些化合物都具有相似的高刚性，即使是具有长寡聚（乙二醇）侧链的化合物。十（乙二醇）取代的五对苯撑衍生物是用于构建生物应用的纳米三脚架形吸附物的多功能构建基块。
• Energy transfer from rhenium(i) complexes to covalently attached anthracenes and phenanthrenes
  作者：Mathieu E. Walther、Oliver S. Wenger

  DOI：10.1039/b809494b

  日期：——

  a series of chromophore–quencher complexes are reported. They are all comprised of a luminescent rhenium(I) tricarbonyl diimine complex that is covalently attached to anthracene or phenanthrene moieties via rigid rod-like p-xylene bridges of variable lengths. Rhenium-to-anthracene energy transfer is strongly exergonic (−ΔG0≈ 0.9 eV) and causes very efficient rhenium MLCT luminescence quenching. By contrast

  一系列化合物的合成及其光物理性质。 发色团–报告了猝灭剂复合物。它们全部由共价连接至的发光rh（I）三羰基二亚胺络合物组成。蒽或通过可变长度的刚性棒状对二甲苯桥的菲部分。hen到蒽能量转移是强烈放能（-Δ ģ 0 ≈0.9电子伏特），并导致非常有效的铼MLCT发光猝灭。相比之下，rh到菲当以足够高的能量MLCT配合物使用，因为对于这些成对层，用于能量传输的驱动力是低的（-Δ仅观察到能量转移ģ 0 ≈0.1电子伏特）。对于约15Å的供体-受体距离，弱能和强能能量传递过程的速率常数相差3个数量级以上。