3-醛基噻吩-2-硼酸频哪醇酯 | 632325-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-醛基噻吩-2-硼酸频哪醇酯
• 中文别名: 3-甲酰噻吩-2-硼酸频哪醇酯；2-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)-3-噻吩甲醛
• 英文名称: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-thienylcarbaldehyde
• 英文别名: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-carbaldehyde；2-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-carbaldehyde；2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-3-carbaldehyde
• CAS: 632325-55-4
• 化学式: C₁₁H₁₅BO₃S
• 分子量: 238.115
• InChiKey: VKSNHTCPMPMGNN-UHFFFAOYSA-N

物化性质

• 熔点：
  65.3-68.3 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  351.9±27.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Formylthiophene-2-boronic acid pinacol ester
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: 3-Formylthiophene-2-boronic acid pinacol ester
CAS number: 632325-55-4

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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: C11H15BO3S
Molecular weight: 238.1

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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, 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：

  3-醛基噻吩-2-硼酸频哪醇酯 在 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 4,4,5,5-tetramethyl-2-(3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-thiophen-2-yl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  寡噻吩系酞菁的液晶点击程序-自组装，对准和光电流

  摘要：

  已经成功制备了一系列具有酞菁供体核，寡噻吩触角和富勒烯受体的星形液晶（LC）。这种分层的自组装导致了最近发现的Click程序促进了纳米级分离的螺旋形施主-受主-天线LC系统的发展。该模型系统揭示了能量转换，电荷产生和传输的所有光物理前提。可以通过棒涂生产150 nm的均匀非晶薄膜。退火不仅通过点击程序诱导了色谱柱的形成，而且使非澄清样品在夹心几何结构（ITO和Ag / MoO 3）。微观研究和光电流测量已证实了这一点，在退火步骤之后，光电流增加了300倍。

  DOI：

  10.1039/d1tc00710f
• 作为产物：
  描述：

  2-溴噻吩-3-甲醛 、 频那醇硼烷 在 二(三叔丁基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-醛基噻吩-2-硼酸频哪醇酯
  参考文献：
  名称：

  Synthesis of 2,3-Substituted Thienylboronic Acids and Esters

  摘要：

  A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)(3) as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.

  DOI：

  10.1021/jo034919n

文献信息

• Addition of Bifunctional Organoboron Reagents to Strained Alkenes. Carbon−Carbon Bond Formation with Rh(I) Catalysis in Aqueous Media
  作者：Mark Lautens、John Mancuso

  DOI：10.1021/jo049874k

  日期：2004.5.1

  complex to generate a functionalized organorhodium intermediate that can cyclize onto strained olefins in good to excellent yields. The catalytic system involves the use of an electron-rich, sterically bulky ligand to stabilize the organorhodium intermediate and reduce the incidence of protodeboronation in aqueous media.

  带有侧链迈克尔型受体烯烃的芳基硼酸酯会与铑基催化络合物发生重金属化反应，生成官能化的有机铑中间体，该中间体可以良好的收率或良好的产率环化到应变烯烃上。催化体系包括使用富含电子的空间庞大的配体来稳定有机ho中间体，并减少在水性介质中原硼酸脱硼的发生率。
• DHNT MONOMERS AND POLYMER DYES WITH MODIFIED PHOTOPHYSICAL PROPERTIES
  申请人：[en]BECKMAN COULTER, INC.

  公开号：WO2024044327A1

  公开（公告）日：2024-02-29

  The present disclosure relates to dihydronaphthothiophene (DHNT), dihydrobenzodithiophene (DHBDT), and dihydronapthothienothiophene (DHNTT) monomer units and fluorescent polymers and co-polymers thereof. DHNT, DHNTT, and/or DHBDT containing water-soluble fluorescent co-polymers, water-soluble tandem fluorescent co-polymers, water-soluble fluorescent co-polymer complexes, water-soluble tandem fluorescent co-polymer complexes, and their use in methods for detecting analytes in a biological sample are also provided.
• The liquid crystal Click procedure for oligothiophene-tethered phthalocyanines – self-assembly, alignment and photocurrent
  作者：Moritz Dechant、Matthias Lehmann、Genya Uzurano、Akihiko Fujii、Masanori Ozaki

  DOI：10.1039/d1tc00710f

  日期：——

  A series of star-shaped liquid crystals (LCs) with a phthalocyanine donor core, oligothiophene antennae and fullerene acceptors have been successfully prepared. This hierarchical self-assembly results in a nanosegregated helical donor–acceptor–antennae LC-system promoted by the recently discovered Click procedure. This model system reveals all photophysical prerequisites for energy conversion, charge

  已经成功制备了一系列具有酞菁供体核，寡噻吩触角和富勒烯受体的星形液晶（LC）。这种分层的自组装导致了最近发现的Click程序促进了纳米级分离的螺旋形施主-受主-天线LC系统的发展。该模型系统揭示了能量转换，电荷产生和传输的所有光物理前提。可以通过棒涂生产150 nm的均匀非晶薄膜。退火不仅通过点击程序诱导了色谱柱的形成，而且使非澄清样品在夹心几何结构（ITO和Ag / MoO 3）。微观研究和光电流测量已证实了这一点，在退火步骤之后，光电流增加了300倍。
• Synthesis of 2,3-Substituted Thienylboronic Acids and Esters
  作者：Claus Christophersen、Mikael Begtrup、Søren Ebdrup、Henning Petersen、Per Vedsø

  DOI：10.1021/jo034919n

  日期：2003.11.1

  A noncryogenic protocol for the synthesis of 2-substituted 3-thienylboronic acids and esters as well as 3-substituted 2-thienylboronic acids and esters has been developed. Electrophiles were introduced regiospecifically in the 2-position of 2,3-dibromothiophene and in the 3-position of 2-bromo-3-iodothiophene by halogen-magnesium exchange followed by quenching with electrophiles. Palladium-catalyzed borylation of the 2,3-substituted halothiophenes with pinacolborane and P(t-Bu)(3) as ligand for Pd produced 9 and 10. The borylation protocol was tolerated by a range of functional groups; however, strongly electron-withdrawing substituents decreased the stability of the thienylboronic acids and esters.