3-甲基苯硼酸频呐醇酯 | 253342-48-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硼烷
• 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: 3-甲基苯硼酸频呐醇酯
• 中文别名: 3-(4,4,5,5-四甲基1,3,,2-二氧杂硼烷-二基)甲苯；3-甲基苯硼酸频哪醇酯；间甲苯基硼酸频那醇酯；3-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)甲苯；4,4,5,5-四甲基-2-间甲苯基-1,3,2-二氧环戊硼烷
• 英文名称: 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane
• 英文别名: 3-methylphenylboronic acid pinacol ester；4,4,5,5-tetramethyl-2-(3-methylphenyl)-1,3,2-dioxaborolane；2-(3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；m-tolylboronic acid pinacol ester；pinacol (3-methylphenyl)boronate；3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)toluene；3-methylbenzene boronic acid pinacol ester；3-tolylboronic acid pinacol ester；4,4,5,5-Tetramethyl-2-(m-tolyl)-1,3,2-dioxaborolane
• CAS: 253342-48-2
• 化学式: C₁₃H₁₉BO₂
• 分子量: 218.104
• InChiKey: XDKYCZBGHPGKEP-UHFFFAOYSA-N

物化性质

• 熔点：
  34.0 to 38.0 °C
• 沸点：
  307.2±21.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇
• 最大波长(λmax)：
  273nm(CH3CN)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  T+,F
• 危险类别码：
  R22,R10,R28,R11,R34,R25,R20
• 安全说明：
  S1,S16,S26,S28A,S36/37/39,S45
• 危险品运输编号：
  UN 2493 3/PG 2
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险类别：
  3
• RTECS号：
  CM3150000
• 包装等级：
  II
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  0-10°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3-Tolylboronic Acid 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.
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
Precautionary statement(s) none
Supplemental Hazard none
Statements
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 : 218,11 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3-Tolylboronic Acid Pinacol Ester
Acute Tox. 4; H302 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
3-Tolylboronic Acid Pinacol Ester
Xn, R22 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
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. Consult a physician.
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. 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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
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
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
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.

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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
Strong oxidizing agents
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
H302 Harmful if swallowed.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
Further information
Copyright 2014 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  3-甲基苯硼酸频呐醇酯 在 air 作用下， 反应 16.0h， 以15.3 mg的产率得到间甲酚
  参考文献：
  名称：

  芳基卤化物的可见光光氧化还原硼化和随后的好氧氧化羟化反应

  摘要：

  开发了有效和实用的芳基卤化物的可见光光氧化还原硼化和随后的好氧氧化羟基化反应。该方案使用容易获得的芳基卤化物和双（频哪醇）二硼烷为原料，fac- Ir（ppy）3作为光催化剂，并以高收率获得了相应的芳基硼酸酯和苯酚。该方法显示出一些优点，包括简单的设备，温和的条件，容易的操作和广泛的底物范围。因此，它们应该为化学转化提供有价值的策略。

  DOI：

  10.1021/acs.orglett.6b02553
• 作为产物：
  描述：

  1-甲基-3-(甲硫基)苯 在 吡啶 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 24.0h， 生成 3-甲基苯硼酸频呐醇酯
  参考文献：
  名称：

  通过光激活的CS活化，芳基S盐的氧化还原中性硼化反应。

  摘要：

  本文报道了一种使用双（频哪醇）二硼作为硼源进行芳基sulf盐的硼化的新光诱导策略。该方法利用氧化还原中性芳基sulf在无过渡金属条件下进行光激发时通过CS键活化来获得芳基自由基。因此，它可从容易获得的芳基sulf获得具有良好性能的各种芳基硼酸酯，并伴有温和的条件，操作简便和易于扩展。

  DOI：

  10.1021/acs.orglett.9b03850

文献信息

• Suzuki–Miyaura coupling of unstrained ketones <i>via</i> chelation-assisted C–C bond cleavage
  作者：Cheng Jiang、Zhao-Jing Zheng、Tian-Yang Yu、Hao Wei

  DOI：10.1039/c8ob02075b

  日期：——

  Herein, we report that unstrained ketones can be efficiently employed as electrophiles in Suzuki–Miyaura reactions via catalytic activation of unstrained C–C bonds assist by an N-containing directing group. A wide range of aromatic ketones directly coupled with boronic ester with excellent functional group tolerance. This strategy provides an alternative and versatile approach to constructing biaryls

  在本文中，我们报道，未催化反应的酮可通过含氮的导向基团催化未反应的C-C键的催化活化而有效地用作Suzuki-Miyaura反应中的亲电子试剂。多种芳族酮直接与硼酸酯偶联，具有出色的官能团耐受性。该策略提供了从未应变的酮构建联芳基的另一种通用方法。
• Visible Light-Induced Borylation of C–O, C–N, and C–X Bonds
  作者：Shengfei Jin、Hang. T. Dang、Graham C. Haug、Ru He、Viet D. Nguyen、Vu T. Nguyen、Hadi D. Arman、Kirk S. Schanze、Oleg V. Larionov

  DOI：10.1021/jacs.9b12519

  日期：2020.1.22

  photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C‒O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reac-tion exhibits excellent functional group

  硼酸是中心重要的功能基序和合成前体。可见光诱导的硼酸化可以提供结构多样化的硼酸盐，但一种广泛有效的光催化硼酸化方法可以影响包括强 C-O 键在内的多种底物的硼化，仍然难以实现。在此，我们报告了一种通用的、无金属的可见光诱导光催化硼化平台，该平台能够对苯酚和苯胺、氯芳烃以及其他卤代芳烃的富电子衍生物进行硼化。该反应表现出优异的官能团耐受性，正如一系列结构复杂底物的硼化反应所证明的那样。值得注意的是，该反应是由吩噻嗪催化的，这是一种简单的有机光催化剂，MW< 200通过质子耦合电子转移机制介导了以前无法实现的可见光诱导的苯酚衍生物单电子还原，还原电位为~-3 V vs SCE。机理研究指出了光催化剂-碱相互作用的关键作用。
• [EN] PIKFYVE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE PIKFYVE
  申请人：ACURASTEM INCORPORATED

  公开号：WO2021163727A1

  公开（公告）日：2021-08-19

  The present invention relates to compounds useful as inhibitors of phosphatidylinositol-3-phosphate 5-kinase (PIKfyve) as well as their use for treating diseases and disorders associated with PIKfyve.

  本发明涉及作为磷脂酰肌醇-3-磷酸5-激酶（PIKfyve）抑制剂的化合物，以及它们用于治疗与PIKfyve相关的疾病和紊乱的用途。
• Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation
  作者：Di Qiu、Liang Jin、Zhitong Zheng、He Meng、Fanyang Mo、Xi Wang、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo3018878

  日期：2013.3.1

  A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by

  基于芳基胺衍生物作为底物的基于Sandmeyer型转化的无金属硼化工艺已得到开发。通过优化反应条件，这种新颖的转化方法可以成功地应用于各种芳族胺，从而以中等至良好的收率获得硼酸酯化产物。通过这种无金属的转化，可以容易地获得各种难以通过其他方法获得的官能化的芳基硼酸酯。此外，在不纯化硼酸酯化产物的情况下，Suzuki-Miyaura交叉偶联后即可进行这种转化，从而增强了该方法的实用性。已经提出了可能的涉及自由基物质的反应机理。
• Palladium nanoparticle catalysis: borylation of aryl and benzyl halides and one-pot biaryl synthesis via sequential borylation-Suzuki–Miyaura coupling
  作者：Ansuman Bej、Dipankar Srimani、Amitabha Sarkar

  DOI：10.1039/c2gc16111g

  日期：——

  catalyze the reaction of bis(pinacolato)diboron with various aryl/benzyl halides to afford aryl/benzyl boronates in high yield. Arylboronates thus prepared, have been directly used in the Suzuki–Miyaura coupling reaction with different aryl halides and benzyl halides in a convenient one-pot, two-step solvent free green synthesis of unsymmetrical biaryls and diarylmethanes.

  钯纳米粒子 PEG中产生的催化剂催化 bis（pinacolato）diboron 与各种 芳基/卤代苄 负担 芳基硼酸苄基酯产率高。如此制备的芳基硼酸酯已直接用于Suzuki-Miyaura与不同的芳基卤化物和卤代苄 一锅两步 溶剂 不对称的游离绿色合成 联芳基 和 二芳基甲烷。