2,5-二甲基噻吩-3-硼酸 | 162607-23-0

• 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: 2,5-二甲基噻吩-3-硼酸
• 英文名称: 2,5-dimethylthien-3-ylboronic acid
• 英文别名: (2,5-dimethylthiophen-3-yl)boronic acid；2,5-dimethylthiophene-3-boronic acid；(2,5-dimethyl-3-thiophenyl)boronic acid；2,5-dimethyl-3-thienyl boronic acid
• CAS: 162607-23-0
• 化学式: C₆H₉BO₂S
• mdl: MFCD09837620
• 分子量: 156.013
• InChiKey: RFQHMNWNEOZRLK-UHFFFAOYSA-N

物化性质

• 熔点：
  180-183 °C
• 沸点：
  311.4±52.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少量）、DMSO（轻微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：
  P305+P351+P338
• 危险性描述：
  H319
• 储存条件：
  -20°C下保存，避光且在惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2,5-Dimethylthiophene-3-boronic 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.
2,5-Dimethylthiophene-3-boronic acid
Ingredient name:
CAS number: 162607-23-0

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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, refrigerated.

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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: C6H9BO2S
Molecular weight: 156.0

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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, 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：

  2,5-二甲基噻吩-3-硼酸 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 but-2-yne-1,4-diyl dimethyl bis(carbonate) 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 以69%的产率得到2,3-[bis(2,5-dimethylthien-3-yl)]buta-1,3-diene
  参考文献：
  名称：

  New photochromic diarylethenes including P and Si atoms

  摘要：

  本文介绍了在五原子循环中包含硅原子或磷原子的新型光致变色二芳基环戊烯的制备方法。从 2 位和 3 位被噻吩基团或苯并噻吩基团取代的丁二烯开始，通过三步会聚合成法获得了目标分子，且收率相对较高。这些新颖的结构为这一化合物家族的研究开辟了一个新的领域，而这一化合物家族在光电器件和光学存储器领域的应用前景广阔。

  DOI：

  10.1039/b901277j
• 作为产物：
  描述：

  2,5-二甲基噻吩 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 为溶剂， 反应 3.75h， 生成 2,5-二甲基噻吩-3-硼酸
  参考文献：
  名称：

  光致芳香性变化促进二噻吩基苯开关的电环化

  摘要：

  近年来，激发态芳香性和反芳香性的概念越来越多地被用来使环状共轭有机化合物的光化学合理化，其长期目标是使用这些概念来提高这些化合物对不同光化学转化的反应性。在这方面，评估苯基序的存在如何影响光化学反应性尤其令人感兴趣，因为众所周知，苯在最低激发态会完全改变其芳香特性。在这里，我们研究了苯基序如何影响二噻吩乙烯（一类主要的分子开关）的光诱导电环化。具体来说，我们报告了二噻吩基苯开关的合成，其中典型的非芳香族，桥接两个噻吩基单元的类乙烯基序被苯基序取代，表明该化合物在紫外线照射下发生电环化。此外，通过详细的量子化学分析，我们证明了电环化是通过在初始光激发过程中形成反应性反芳香激发态而导致该基序中芳香性的丧失以及随后这种反芳香性的解除而共同和协同驱动的随着反应从 Franck-Condon 区域进行。总的来说，我们得出结论，光诱导的芳香性变化促进了二噻吩基苯开关的电环化。通过详细的量子化学分析，我

  DOI：

  10.1021/jacs.0c06327

文献信息

• A Dithienylethene-Based Rewritable Hydrogelator
  作者：Jochem T. van Herpt、Marc C. A. Stuart、Wesley R. Browne、Ben L. Feringa

  DOI：10.1002/chem.201304064

  日期：2014.3.10

  Dithienylethene photochromic switching units have been incorporated into a hydrogelating system based on a tripeptide motif. The resulting hybrid system provided both a photochromic response and the ability to gelate water under acidic and neutral conditions. Fluorescence spectroscopy shows that the dithienylethene units are in sufficient proximity to each other to stack in gel fibers, with the tripeptide

  二噻吩基乙烯光致变色转换单元已被并入基于三肽基序的水凝胶化系统中。所得的混合系统既提供了光致变色响应，又提供了在酸性和中性条件下使水胶凝的能力。荧光光谱显示二噻吩乙烯单元彼此足够接近以堆叠在凝胶纤维中，其中三肽单元确定溶解度。TEM测量提供了对所形成的纤维的微观结构的了解。
• [EN] ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND PRODUCTION THEREOF<br/>[FR] COMPOSÉS PHOTOCHROMIQUES ROBUSTES COMPORTANT UN CYCLE HÉTÉROCYCLIQUE CONTENANT DU PHOSPHORE OU DU SILICIUM ET LEURS PROCÉDÉS DE PRODUCTION
  申请人：UNIV HONG KONG

  公开号：WO2015188790A1

  公开（公告）日：2015-12-17

  In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon-or phosphorus-containing heterocycles into the "ethene" part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.

  在一个实施方案中，提供了一种新型的含有二芳基乙烯的光致变色化合物，该化合物将含有硅或磷的杂环引入到二芳基乙烯主链的“乙烯”部分，已经显示出能够展现出可调节、稳健且热稳定的光致变色性能。同时，还提供了合成这些化合物的方法，以及这些化合物的用途，因为它们可以用作光记录材料和其他光功能设备中的光致变色层。
• Synthesis of 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione from mucobromic acid
  作者：S. V. Shorunov、F. M. Stoyanovich、M. M. Krayushkin

  DOI：10.1007/s11172-005-0126-6

  日期：2004.10

  Palladium-catalyzed cross-coupling between 2,5-dimethyl-3-thienylboronic and mucobromic acids under phase transfer catalysis (PTC) conditions gave the expected 3,4-bis(2,5-dimethyl-3-thienyl)-5-hydroxyfuran-2-one in 32% yield. The by-product was 2,2’,5,5’-tetramethyl-3,3’-bithiophene. The oxidation of the obtained hemiacylal with potassium permanganate under PTC conditions afforded 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione in high yield.

  在相转移催化（PTC）条件下，使用钯催化剂进行的2,5-二甲基-3-噻吩基硼酸与黏溴酸的交叉偶联反应生成了预期的3,4-双(2,5-二甲基-3-噻吩基)-5-羟基呋喃-2-酮，产率为32%。副产物为2,2’,5,5’-四甲基-3,3’-联噻吩。在PTC条件下，使用高锰酸钾氧化所得的半缩醛，以高产率合成了3,4-双(2,5-二甲基-3-噻吩基)呋喃-2,5-二酮。
• [EN] PHOTOCHROMIC DIARYLETHENE-CONTAINING COORDINATION COMPOUNDS AND THE PRODUCTION THEREOF<br/>[FR] COMPOSES DE COORDINATION PHOTOCHROMIQUES CONTENANT DU DIARYLETHENE ET PRODUCTION DE CEUX-CI
  申请人：UNIV HONG KONG

  公开号：WO2005003126A1

  公开（公告）日：2005-01-13

  Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower energy absorption bands characteristic of the coordination compounds, through which the excitation wavelengths for the photocyclization can be extended from lambda <= 340 nm to wavelengths beyond 470 nm. Switching of the luminescence properties of the compounds has also been achieved through photochromic reactions.

  描述了含二芳基乙烯基配体及其配位化合物。这些配体在紫外激发下显示光致变色性质，而配位化合物则在紫外区域激发和激发到特征于配位化合物的较低能量吸收带中显示光致变色性质，通过这些激发波长，光环化的激发波长可以从λ <= 340 nm延伸到超过470 nm的波长。通过光致反应也实现了化合物的发光性质的切换。
• Photochromic and Luminescence Switching Properties of a Versatile Diarylethene-Containing 1,10-Phenanthroline Ligand and Its Rhenium(I) Complex
  作者：Vivian Wing-Wah Yam、Chi-Chiu Ko、Nianyong Zhu

  DOI：10.1021/ja047446q

  日期：2004.10.1

  A versatile bis(2,5-dimethyl-3-thienyl)-1,10-phenanthroline photochromic ligand has been successfully synthesized via a Suzuki cross-coupling reaction. The excitation wavelength for photochromic reaction of the dithienylphenanthroline could be extended from lambda

  通过 Suzuki 交叉偶联反应成功合成了一种多功能的双（2,5-二甲基-3-噻吩基）-1,10-菲咯啉光致变色配体。二噻吩基菲咯啉光致变色反应的激发波长可以从λ扩展