噻吩-2,5-二硼酸二频哪酯 | 175361-81-6

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 噻吩-2,5-二硼酸二频哪酯
• 中文别名: 25-双-噻吩硼酸频那醇酯
• 英文名称: 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene
• 英文别名: 2,2'-(2,5-thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane]；thiophene-2,5-diboronic acid dipinacol ester；2,5-bis-thiopheneboronic acid pinacol ester；4,4,5,5-tetramethyl-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]-1,3,2-dioxaborolane
• CAS: 175361-81-6
• 化学式: C₁₆H₂₆B₂O₄S
• mdl: MFCD09800563
• 分子量: 336.068
• InChiKey: AOJXAKMKFDBHHT-UHFFFAOYSA-N

物化性质

• 熔点：
  216-220℃
• 沸点：
  434.3±30.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Thiophene-2,5-diboronic acid bis(pinacol) ester
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 175361-81-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Synonyms : 2,5-Thiophenediboronic acid bis(pinacol) ester
2,5-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene
Formula : C16H26B2O4S
Molecular Weight : 336,06 g/mol
CAS-No. : 175361-81-6
No components need to be disclosed according to the applicable regulations.

---

SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

---

SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Sulphur oxides, Borane/boron oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

---

SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

---

SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 227 - 231 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point not applicable
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 5,325
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

---

SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-溴三苯胺 、 噻吩-2,5-二硼酸二频哪酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 tri-tert-butylphosphonium tetrafluoroborate 、 sodium carbonate 作用下， 以 水 、 甲苯 为溶剂， 生成 N,N-diphenyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl) aniline
  参考文献：
  名称：

  通过一锅四组分铃木-宫浦偶合器合成含EDOT的有机染料及其光电性能评估

  摘要：

  我们已经开发了一种一锅四组分的Suzuki-Miyaura偶联剂，用于合成用于染料敏化太阳能电池的噻吩基供体-π-桥-受体（D-π-A）染料。根据开发，快速合成了两种D-π-A染料19和20，它们在氰基丙烯酸部分旁边保留了3,4-乙撑二氧噻吩（EDOT），和一种不带EDOT的D-π-A染料21（参考化合物）。程序。的吸收光谱和合成染料的电化学特性，和使用合成的染料制备的太阳能电池的光伏性能的测量19 - 21，显示，只保留一个EDOT一氰基丙烯酸部分旁边的染料会发挥较高Ĵsc。

  DOI：

  10.1016/j.tet.2014.09.039
• 作为产物：
  描述：

  频哪醇 、 thiophene-2,5-diyl-bis-N,N-diisopropylaminoborane 在 甲醇 作用下， 以 乙酸乙酯 、 乙醚 为溶剂， 反应 5.0h， 以236 mg的产率得到噻吩-2,5-二硼酸二频哪酯
  参考文献：
  名称：

  通过使用二异丙基氨基硼烷作为硼化试剂在温和条件下将未活化的芳基氯化物硼化

  摘要：

  描述了通过使用芳基（氨基）硼烷从芳基氯化物合成芳基硼酸酯衍生物。在温和条件下，芳基氯化物和二异丙基氨基硼烷之间的钯催化偶联导致形成CB键。宽泛的官能团是可以容忍的，这使得该方法对官能化芳族化合物的硼酸酯化特别有用。

  DOI：

  10.1002/chem.201304861

文献信息

• Dithienosilole− and Dibenzosilole−Thiophene Copolymers as Semiconductors for Organic Thin-Film Transistors
  作者：Hakan Usta、Gang Lu、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ja062908g

  日期：2006.7.19

  ''-bithieno)bithiophene) (TS6T2), poly(2,5'-bis(2' ',2' ''-dioctylsilylene-1' ',1' ''-biphenyl)thiophene) (BS8T1), and poly(2,5'-bis(2' ',2' ''-dioctylsilylene-1' ',1' ''-biphenyl)bithiophene) (BS8T2). Organic field-effect transistors (OFETs) with hole carrier mobilities as high as 0.02-0.06 cm2/V s in air, low turn-on voltages, and current on/off ratios >105-106 are fabricated using solution processing techniques with

  报道了一类新的含噻吩/芳烃硅氧烷的 pi 共轭聚合物的合成和理化性质。这种新聚合物类别的例子包括：聚（2,5-双（3',3''-二己基亚甲硅烷基-2',2''-二噻吩）噻吩）（TS6T1）、聚（2,5'-双(3' ',3' ''-dihexylsilylene-2' ',2' ''-bithieno)bithiophene) (TS6T2), poly(2,5'-bis(2' ',2' ''-dioctylsilylene-1) ' ',1' ''-联苯)噻吩) (BS8T1)和聚(2,5'-双(2' ',2' ''-二辛基亚硅烷-1' ',1' ''-联苯)联噻吩) (BS8T2)。有机场效应晶体管 (OFET) 的空穴载流子迁移率在空气中高达 0.02-0.06 cm2/V s，低导通电压和电流开/关比 > 105-106是使用溶液处理技术制造的，上面的聚合物作为有源沟道层。基于此类聚合物的
• [EN] BASE METAL CATALYZED BORYLATION OF ARENES AND AROMMATIC HETEROCYCLES<br/>[FR] BORYLATION D'ARÈNES ET D'HÉTÉROCYCLES AROMATIQUES CATALYSÉE PAR UN MÉTAL DE BASE
  申请人：UNIV PRINCETON

  公开号：WO2015089119A1

  公开（公告）日：2015-06-18

  In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes employ bis(phosphine) or bis(imine) ligand and are operable as catalysts for borylation of arenes and aromatic heterocycles.

  在某些方面，本文描述了钴络合物。在某些实施例中，这样的钴络合物使用双(膦)或双(亚胺)配体，并且可作为芳烃和芳香杂环的硼化催化剂。
• [EN] HETEROACENES FOR ORGANIC ELECTRONICS<br/>[FR] HÉTÉROACÈNES POUR L'ÉLECTRONIQUE ORGANIQUE
  申请人：BASF SE

  公开号：WO2015128779A1

  公开（公告）日：2015-09-03

  The present invention provides compounds of formula 1 wherein X1 and X2 are independently from each other O, S or Se, and an electronic device comprising the compounds as semiconducting material.

  本发明提供了式1的化合物，其中X1和X2分别独立地为O、S或Se，以及包含该化合物作为半导体材料的电子设备。
• Synthesis and Characterization of Thiophene‐based Donor–Acceptor–Donor Heptameric Ligands for Spectral Assignment of Polymorphic Amyloid‐β Deposits
  作者：Linda Lantz、Hamid Shirani、Therése Klingstedt、K. Peter R. Nilsson

  DOI：10.1002/chem.201905612

  日期：2020.6.10

  Protein deposits are associated with many devastating diseases and fluorescent ligands able to visualize these pathological entities are essential. Here, we report the synthesis of thiophene‐based donor–acceptor–donor heptameric ligands that can be utilized for spectral assignment of distinct amyloid‐β (Aβ) aggregates, one of the pathological hallmarks in Alzheimer's disease. The ability of the ligands

  蛋白质沉积与许多毁灭性疾病有关，因此能够可视化这些病理实体的荧光配体至关重要。在这里，我们报告了基于噻吩的供体-受体-供体七聚体配体的合成，这些配体可用于不同淀粉样β（Aβ）聚集体的光谱分配，这是阿尔茨海默氏病的病理特征之一。当配体的化学组成改变时，配体选择性区分Aβ沉积物的能力被消除。我们的发现为开发新的荧光配体提供了结构和功能基础，这些荧光配体可以区分由相同肽或蛋白质组成的聚集蛋白物种。此外，
• Construction of Pinpoint-Fluorinated Benzothiophene Frameworks Using Palladium-Catalyzed Cyclization of o-(Fluorovinyl)phenyl-Substituted Thiophenes
  作者：Junji Ichikawa、Kohei Fuchibe、Nobushige Tsuda、Kento Shigeno

  DOI：10.3987/com-18-s(f)95

  日期：——

  applied to the corresponding furan systems, which led to pinpoint-fluorinated naphtho[b]furans. INTRODUCTION Sulfur-containing π-extended molecules have attracted an increasing amount of attention as organic electronic materials. In particular, oligoand polythiophenes, where every two thiophene rings are connected to each other by a single bond, have been studied from the very early stage of this chemistry

  邻-(2,2-二氟乙烯基)苯基或邻-(1,2,2-三氟乙烯基)苯基取代的噻吩在氟乙烯基部分上进行钯(II)催化的Friedel-Crafts型环化以构建区域选择性单氟化或二氟化苯并噻吩骨架(pinpoint -氟化萘并[b]噻吩）。通过添加 CuOTf 配合物有效地促进了亲核性较低的 2-取代噻吩的环化。环化也以串联工艺进行，这有助于快速合成带有噻吩环的高阶精确氟化 PAH（多环芳烃）。此外，将环化应用于相应的呋喃体系，从而产生精确氟化的萘并[b]呋喃。引言 含硫 π 扩展分子作为有机电子材料引起了越来越多的关注。特别是低聚噻吩和聚噻吩，每两个噻吩环通过一个单键相互连接，从该化学的早期阶段就开始研究（图 1）。在过去的几十年中，还研究了噻吩并苯 (TAcs) 的半导体行为，其中每两个噻吩环共享一个 C-C 双键。除了这些仅由噻吩环组成的分子外，最近还出现了由噻吩和苯环组成的并苯二噻吩 (AcDTs)、二并苯稠合噻吩噻吩