1,3,5-苯三硼酸三频哪醇酯 | 365564-05-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 1,3,5-苯三硼酸三频哪醇酯
• 英文名称: 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene
• 英文别名: 1,3,5-phenyltriboronic acid tris(pinacol) ester；1,3,5-benzenetriboronic acid tris(pinacol) ester；1,3,5-phenyltriboronic acid；1,3,5-tris(pinacolboryl)benzene；1,3,5-benzene triboronic acid tripinacol ester；2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 365564-05-2
• 化学式: C₂₄H₃₉B₃O₆
• 分子量: 456.003
• InChiKey: VKOLBYNBPONPAE-UHFFFAOYSA-N

物化性质

• 熔点：
  286-287°C
• 沸点：
  555.6±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 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

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1,3,5-Phenyltriboronic Acid, Tris(Pinacol) Ester
: BML00299
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.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 456,01 g/mol
No components need to be disclosed according to the applicable regulations.

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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

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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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting if necessary.
Further information
No data available

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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
No special environmental precautions required.
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.

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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.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
No special environmental precautions required.

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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 No data available
point
f) Initial boiling point and No data available
boiling range
g) Flash point No data available
h) Evaporation 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- No data available
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

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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
No data available
Hazardous decomposition products
In the event of fire: see section 5

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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

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
Other adverse effects
No data available

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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.

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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

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
No data available
Chemical Safety Assessment

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,3,5-苯三硼酸三频哪醇酯 在 四(三苯基膦)钯 、 potassium carbonate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,3,5-tris(3-methoxy-4-carboxyphenyl)benzene
  参考文献：
  名称：

  官能团对金属-有机骨架拓扑的影响。

  摘要：

  配体1,3,5-三（4-羧基苯基）苯（H（3）BTB）的功能已实现与甲氧基（H（3）BTB- [OMe]（3））和羟基（H（3） BTB- [OH]（3））基团。结合H（3）BTB- [OMe]（3）和Zn（II）导致形成第一个同构，功能化的MOF-177类似物（MOF-177-OMe），而结合H（3）BTB -[OH]（3）和Zn（II）生成一种稀有的，互穿的pcu-e骨架。

  DOI：

  10.1039/c2cc34938h
• 作为产物：
  描述：

  1,3,5-三氯苯 、 联硼酸频那醇酯 在 甲烷磺酸(2-二环己基膦基-2',4',6'-三-异丙基-1,1'-联苯基)(2'-氨基-1,1'-联苯-2-基)钯(II) 、 potassium acetate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 以52 %的产率得到1,3,5-苯三硼酸三频哪醇酯
  参考文献：
  名称：

  使用低熔点金属盐前体离子热合成金属有机框架**

  摘要：

  使用低熔点金属（水合物）盐作为离子热合成的前体和溶剂，可以制备一系列稳定的金属有机骨架，具有高结晶度和孔隙率，并且有机溶剂的使用最少。

  DOI：

  10.1002/anie.202218252

文献信息

• Self‐Assembly of a Purely Covalent Cage with Homochirality by Imine Formation in Water
  作者：Yixin Chen、Guangcheng Wu、Binbin Chen、Hang Qu、Tianyu Jiao、Yintao Li、Chenqi Ge、Chi Zhang、Lixin Liang、Xiuqiong Zeng、Xiaoyu Cao、Qi Wang、Hao Li

  DOI：10.1002/anie.202106428

  日期：2021.8.16

  water. When a chiral guest was recognized, the formation of one enantiomer of the cage became more favored relative to the other. As a consequence, the cage could be produced in an enantioselective manner. The tetrahedron is able to maintain its chirality after removal of the chiral guest—probably on account of the cooperative occurrence of intramolecular forces that restrict the intramolecular flipping

  通过金属-配体配位在水介质中自组装主体分子已得到很好的发展。然而，在水中制备纯共价对应物仍然是一项艰巨的任务。通过在水中缩合三胺和三甲酰基，以[4+4]方式成功地自组装了阴离子四面体笼。尽管每个单独的亚胺键都相当不稳定并且易于在水中水解，但由于多价，四面体非常稳定或惰性。四面体笼及其溶解在有机溶剂中的中性对应物具有同手性，即它们的四个螺旋桨形三甲酰基残基采用相同的旋转构象。笼子能够利用疏水作用来容纳水中的各种客体分子。当手性客人被识别时，笼的一种对映体的形成相对于另一种更有利。因此，笼可以以对映选择性方式生产。在去除手性客体后，四面体能够保持其手性——可能是由于分子内力的协同发生，限制了笼框架中苯基单元的分子内翻转。
• Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
  作者：Shun Wang、Hua Wang、Burkhard König

  DOI：10.1016/j.chempr.2021.04.016

  日期：2021.6

  the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive

  目前正致力于获得具有高氧化还原能力的光氧化还原催化剂。然而，将目前建立的方法应用于具有高键离解能的键的活化和具有高还原电位的基材仍然具有挑战性。在此，我们介绍了一种新的光催化策略，通过使用硫醇盐作为催化剂来活化惰性取代芳烃以进行芳基硼化。该催化体系具有很强的还原能力，可与未活化的C芳基-F、C芳基-X、C芳基-O、C芳基-N和C芳基结合-S 键用于生产性自由基硼化反应，从而扩大了可用的芳基自由基前体范围。尽管具有很高的还原能力，但该方法具有广泛的底物范围和良好的官能团耐受性。光谱研究和控制实验表明，电荷转移复合物的形成是激活底物的关键步骤。
• Cobalt(I)-Mediated Preparation of Polyborylated Cyclohexadienes: Scope, Limitations, and Mechanistic Insight
  作者：Anaïs Geny、David Lebœuf、Gabriel Rouquié、K. Peter C. Vollhardt、Max Malacria、Vincent Gandon、Corinne Aubert

  DOI：10.1002/chem.200700337

  日期：2007.6.25

  proper choice of substituents allowed the preparation of 1,3-diborylated cyclohexadienes in a highly selective manner. Alternatively, 1,4-diborylated cyclohexadienes could be prepared from diborylated diynes. The scope of this reaction has been examined and found to include electron-poor, electron-rich, linear, and cyclic alkenes. The diborylated cyclohexadienes were submitted to single or double Suzuki-Miyaura

  通过分子间CoCp介导的炔基硼酸松果酸酯与烯烃的分子间CoCp介导的[2 + 2 + 2]共环化，然后用铁进行氧化脱金属，制备了一系列1,3-和1,4-二硼基-1,3-环己二烯）氯化物。已经研究了在硼化炔烃上的取代对化学和区域选择性的影响，表明了空间控制。取代基的适当选择允许以高度选择性的方式的1,3-环己二烯diborylated制备。备选地，可以由二硼化的二炔制备1，4-二硼化的环己二烯。已经检查了该反应的范围，发现该反应的范围包括贫电子，富电子，直链和环状烯烃。将二硼化的环己二烯与卤代芳烃进行单或双Suzuki-Miyaura交叉偶联反应，得到聚芳基化体系。
• Additive- and Metal-Free, Predictably 1,2- and 1,3-Regioselective, Photoinduced Dual C–H/C–X Borylation of Haloarenes
  作者：Adelphe M. Mfuh、Vu T. Nguyen、Bhuwan Chhetri、Jessica E. Burch、John D. Doyle、Vladimir N. Nesterov、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1021/jacs.6b05436

  日期：2016.7.13

  We report herein a simple, additive- and metal-free, photoinduced, dual C-H/C-X borylation of chloro-, bromo-, and iodoarenes. The reaction produces 1,2- and 1,3-diborylarenes on gram scales under batch and continuous flow conditions. The regioselectivity of the dual C-H/C-X borylation is determined by the solvent and the substituents in the parent haloarenes.

  我们在此报道了氯芳烃、溴芳烃和碘芳烃的简单、无添加剂和金属的光诱导双CH/CX硼化反应。该反应在间歇和连续流动条件下产生克级的 1,2- 和 1,3-二硼基芳烃。双CH/CX硼化反应的区域选择性由溶剂和母体卤代芳烃中的取代基决定。
• Multicarbazole scaffolds for selective G-quadruplex binding
  作者：Arnold Ou、Aurore Guédin、Brian W. Skelton、Samir Amrane、Cameron W. Evans、Marck Norret、K. Swaminathan Iyer、Jean-Louis Mergny、Nicole M. Smith

  DOI：10.1039/c8cc03945c

  日期：——

  Herein we report a new class of G-quadruplex stabilising ligands, multicarbazoles, which display high G-quadruplex DNA selectivity in the presence of 250 times excess duplex DNA. We report the synthesis of these compounds in moderate to high yields. Ligands in the series with optimal G-quadruplex selectivity contain an N-propylamino chain length where the amino functionalities are either pyrrolidine

  在本文中，我们报告了一类新的G-四链体稳定配体，即多咔唑，在250倍过量的双链体DNA存在下，它显示出高的G-四链体DNA选择性。我们报告了中等至高收率的这些化合物的合成。具有最佳G-四链体选择性的系列中的配体包含N-丙基氨基链长，其中氨基官能团为吡咯烷或哌啶。