4-溴-5-甲基噻吩-2-硼酸 | 154566-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 4-溴-5-甲基噻吩-2-硼酸
• 中文别名: 3-溴-2-甲基-5-噻吩硼酸
• 英文名称: 3-bromo-2-methylthiophene-5-boronic acid
• 英文别名: 3-bromo-2-methyl-5-thienylboronic acid；(4-bromo-5-methylthiophen-2-yl)boronic acid；4-bromo-5-methylthiophene-2-boronic acid；3-bromo-2-methyl-5-thiopheneboronic acid；4-bromo-5-methylthiophene-2-ylboronic acid
• CAS: 154566-69-5
• 化学式: C₅H₆BBrO₂S
• 分子量: 220.882
• InChiKey: CVCCYVWSTHTZFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromo-5-methylthiophene-2-boronic acid
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: 4-Bromo-5-methylthiophene-2-boronic acid
CAS number: 154566-69-5

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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, under −20◦C.
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: C5H6BBrO2S
Molecular weight: 220.9

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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, sulfur 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-溴-5-甲基噻吩-2-硼酸 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 1.5h， 生成 1,2-bis[2-methyl-5-(4-pyridyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  光开关铂（II）化合物的细胞毒性

  摘要：

  潜在的抗癌金属配合物的光活化是当前研究的热点，因为它可能导致开发更具选择性的药物。具有配位化合物的光活化化学疗法（PACT）通常基于在金属中心发生的（光）化学反应。在本文中，开发了一种新的策略，该策略包括“配光”与金属离子配位的配体。已从含有可光转换的1,2-二噻吩基乙烯的配体制备了铂（II）配合物，该配合物表现出两种可相互转换的光异构形式，呈现出独特的DNA相互作用特性和细胞毒性行为。

  DOI：

  10.1002/anie.201412157
• 作为产物：
  描述：

  2-甲基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 溶剂黄146 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 21.58h， 生成 4-溴-5-甲基噻吩-2-硼酸
  参考文献：
  名称：

  光致变色二噻吩基乙烯的特征在于原位辐射NMR光谱和金基底上电化学诱导的响应性

  摘要：

  已经显示出包含小分子和聚合物的光致变色化合物在用作传感器和（纳米）装置的刺激响应性材料领域中非常受关注。在这方面，二噻吩基乙烯（DTE）已被证明是特别有价值的，因为它们对化学物质的耐受性和良好的稳定性使其可以在具有不同光学特性的开放结构和封闭结构之间进行可调和可逆切换。通过利用有效的原位辐射NMR光谱法，可以确定溶液中两种DTE衍生物的光致变色能力，从而获得有关结构，DTE的化学开环和闭合的平衡以及这些分子的长期稳定性的重要信息开关。特别地，与DTE已知的不可逆环化副产物有关，全氟含硫醚的化合物显示出显着的稳定性，并且几乎没有疲劳。可以将带有硫醚的DTE脱保护并用于固定在金基底上，所述金基底的特征在于在DTE官能化之前和之后的水接触角测量。最后，通过循环伏安法研究了过氢DTE的电化学诱导转换能力，证明了它的快速性，定量和可逆环化。我们设想将这些材料用作传感器和光学开关设备。

  DOI：

  10.1039/c9tc04495g

文献信息

• Nonsymmetrical Dithienylethenes Bearing Dithieno[3,2‐ <i>b</i> :2′,3′‐ <i>d</i> ]thiophene Units with Photochromic Performance in the Crystalline Phase
  作者：Hongke Wang、Hui Lin、Wei Xu、Daoben Zhu

  DOI：10.1002/chem.201202520

  日期：2013.3.4

  Four novel nonsymmetrical photochromic diarylethene compounds containing dithieno[3,2‐b:2′,3′‐d]thiophene units were designed and synthesized to investigate their photochromic properties. All these molecules adopt a photoactive antiparallel conformation in single crystals, as revealed by X‐ray crystallographic analysis, and exhibit excellent photochromism in solution as well as in the crystalline phase

  设计并合成了四种新型的含有二噻吩并[3,2- b：2'，3'- d ]噻吩单元的非对称光致变色二芳基乙烯化合物，以研究其光致变色特性。X射线晶体学分析表明，所有这些分子在单晶中均具有光活性反平行构象，并且在溶液和结晶相中均表现出出色的光致变色现象。
• Photochromism of new unsymmetrical isomeric diarylethenes bearing a methoxyl group
  作者：Shouzhi Pu、Weijun Liu、Wenjuan Miao

  DOI：10.1002/poc.1545

  日期：2009.10

  substituent position effect of methoxyl group on their properties, including photochromism and fluorescence both in hexane solution and in PMMA film, and their electrochemical properties, were investigated in detail. These diarylethenes showed good photochromism both in solution and in PMMA film. For the same photochromic diarylethene backbone, the electron‐ donating methoxyl substituent can effectively

  在末端苯环的邻位，间位和对位具有甲氧基取代基的三个新的不对称异构二芳烃，即1-（2,5-二甲基-3-噻吩基）-2- [2-甲基-5- （2-甲氧基苯基）-3-噻吩基]全氟环戊烯（1o），1-（2,5-二甲基-3-噻吩基）-2- [2-甲基-5-（3-甲氧基苯基）-3-噻吩基]全氟环戊烯（2o）和1-（2,5-二甲基-3-噻吩基）-2- [2-甲基-5-（4-甲氧基苯基）-3-噻吩基]全氟环戊烯（3o），已经合成。详细研究了甲氧基的取代基位置对其性能的影响，包括在己烷溶液和PMMA膜中的光致变色和荧光以及它们的电化学性能。这些双芳烃在溶液和PMMA膜中均显示出良好的光致变色性。对于相同的光致变色二芳基乙烯主链，与先前报道的带有氯原子的二芳烃相比，给电子的甲氧基取代基可以有效地降低环化量子产率并提高环还原量子产率。二芳烃1o – 3o通过在己烷和PMMA膜中进行光辐照显示出清晰的荧光开关。此外
• A proton and optic dual-control molecular switch based on photochromic diarylethene bearing a rhodamine unit
  作者：Weijun Liu、Shouzhi Pu、Shiqiang Cui、Gang Liu、Congbin Fan

  DOI：10.1016/j.tet.2011.04.023

  日期：2011.6

  A novel fluorescent switch based on rhodamine B and photochromic diarylethene, 1-[2-methyl-5-(4-methoxylphenyl)-3-thienyl]-2-[2-methyl-5-(4-rhodamine B hydrazine-Schiff base-phenyl)-3-thienyl]perfluorocyclopentene (1), has been successfully synthesized through the condensation of rhodamine B hydrazine and 1-[2-methyl-5-(4-methoxylphenyl)-3-thienyl]-2-[2-methyl-5-(4-formylphenyl)-3-thienyl]perfluorocyclopentene

  一种基于若丹明B和光致变色二芳基乙烯1- [2-甲基-5-（4-甲氧基苯基）-3-噻吩基] -2- [2-甲基-5-（4-若丹明B肼-席夫碱）的新型荧光开关-苯基）-3-噻吩基]全氟环戊烯（1），已经成功地通过若丹明B色肼的缩合和1- [2-甲基-5-（4-甲氧基苯基）-3-噻吩基] -2- [2-合成甲基-5-（4-甲酰基苯基）-3-噻吩基]全氟环戊烯。UV和FL测量表明，该化合物表现出对质子和光学双输入响应良好的光致变色特性。在用297 nm光照射时，化合物1的无色溶液变为蓝色，而在用可见光（λ > 450 nm）照射后，蓝色溶液变为无色。此外，添加H +尽管二芳基乙烯为开环形式时，没有发生能量转移，但荧光共振能量从若丹明单元（FRET供体）转移至闭环二芳基乙烯单元（FRET受体）。罗丹明的发射强度可以通过质子和紫外线/可见光进行调节，并且已经建立了分子水平的信号通讯，表明该化合物在分子开关或肉眼识别系统中具有很高的潜力。
• Toward multi-addressable molecular systems: Efficient synthesis and photochromic performance of unsymmetrical bisthienylethenes
  作者：Guillaume Sevez、Jean-Luc Pozzo

  DOI：10.1016/j.dyepig.2010.03.018

  日期：2011.6

  compared to access to unsymmetrical 1,2-bisthienylperfluorocyclopentenes having one electro-withdrawing formyl group. The strategy based on key monosusbtituted cyclopentenes appears to be the most reliable and versatile synthetic approach. Applying this controlled sequential synthesis to appropriate thiophenic building blocks leads to the preparation of π-conjugated extended push–pull system where photochromic

  已经比较了各种合成途径来获得具有一个吸电甲酰基的不对称的1，2-双噻吩基全氟环戊烯。基于关键的单取代环戊烯的策略似乎是最可靠，用途最广泛的合成方法。将这种受控的顺序合成应用于适当的噻吩结构单元，可以制备出表征光致变色性能的π共轭扩展推挽系统。
• Synthesis and optoelectronic properties of unsymmetrical isomeric diarylethene derivatives having a fluorine atom
  作者：Weijun Liu、Shouzhi Pu、Gang Liu

  DOI：10.1016/j.molstruc.2009.07.012

  日期：2009.11

  that the fluorine atom and its substituted position had a significant effect on the optoelectronic properties of these compounds. For diarylethenes 1–3, the ortho-substituted derivative 1 had the biggest cyclization and cycloreversion quantum yields; while the meta-substituted derivative 2 showed the biggest extinction coefficient and the absorption maxima both in hexane and in PMMA film. The emission

  摘要 三种不对称二芳基乙烯化合物在末端苯环的邻位、间位或对位带有氟原子，即 1-(2,5-二甲基-3-噻吩基)-2-[2-甲基-5 -(2-氟苯基)-3-噻吩基]全氟环戊烯 (1o), 1-(2,5-二甲基-3-噻吩基)-2-[2-甲基-5-(3-氟苯基)-3-噻吩基]全氟环戊烯(2o) 和 1-(2,5-二甲基-3-噻吩基)-2-[2-甲基-5-(4-氟苯基)-3-噻吩基]全氟环戊烯 (3o) 已被合成。它们的结构是通过单晶 X 射线衍射分析确定的。详细研究了氟原子位置对其性能的影响，如光致变色、荧光和电化学性能。结果表明，氟原子及其取代位置对这些化合物的光电性能有显着影响。对于二芳基乙烯1-3，邻位取代的衍生物1具有最大的环化和环回复量子产率；而间位取代衍生物2在己烷和PMMA薄膜中均表现出最大的消光系数和吸收最大值。在己烷和PMMA薄膜中，二芳基乙烯1o-3o的发射峰随着氟原子从邻位