4,4,5,5-四甲基-2-(4-(甲基亚磺酰基)苯基)-1,3,2-二噁硼烷 | 1016641-70-5

• 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: 4,4,5,5-四甲基-2-(4-(甲基亚磺酰基)苯基)-1,3,2-二噁硼烷
• 中文别名: 4-甲基亚磺酰基苯基硼酸,频哪醇酯
• 英文名称: 4,4,5,5-tetramethyl-2-(4-(methylsulfinyl)phenyl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-(4-methylsulfinylphenyl)-1,3,2-dioxaborolane
• CAS: 1016641-70-5
• 化学式: C₁₃H₁₉BO₃S
• 分子量: 266.169
• InChiKey: NWLRDFRSFJEVCD-UHFFFAOYSA-N

物化性质

• 沸点：
  399.2±25.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P301+P310+P330,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methylsulfinylphenylboronic acid, pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-2-(4-(methylsulfinyl)phenyl)-1,3,2-dioxaborolane

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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: 4-Methylsulfinylphenylboronic acid, pinacol ester
CAS number: 1016641-70-5

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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.
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: C13H19BO3S
Molecular weight: 266.2

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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：

  4,4,5,5-四甲基-2-(4-(甲基亚磺酰基)苯基)-1,3,2-二噁硼烷 、 ethyl 7-(4-(trifluoromethyl)phenyl)-4-(((trifluoromethyl)sulfonyl)oxy)-2-naphthoate 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 4-[4-(methylsulfinyl)phenyl]-7-[4-(trifluoromethyl)phenyl]-2-naphthoate
  参考文献：
  名称：

  [EN] SUBSTITUTED 2-NAPHTHOIC ACIDS AS ANTAGONISTS OF GPR105 ACTIVITY
  [FR] ACIDES 2-NAPHTOÏQUE SUBSTITUÉS EN TANT QU'ANTAGONISTES DE L'ACTIVITÉ DE GPR105

  摘要：

  结构式I中的2-萘甲酸替代物对GPR105蛋白的生物活性具有拮抗作用。它们可用于治疗、控制或预防对该受体拮抗有响应的疾病，如糖尿病，特别是2型糖尿病，胰岛素抵抗，高血糖，脂质紊乱，肥胖，动脉粥样硬化以及与代谢综合征相关的疾病。

  公开号：

  WO2009070873A1
• 作为产物：
  描述：

  4,4,5,5-四甲基-2-[4-(甲基硫代)苯基]-1,3,2-二氧硼烷 在 dichlorodioxobis(triphenylphosphineoxide)molybdenum(VI) 、 四丁基硝酸铵 、 copper(II) nitrate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以99%的产率得到4,4,5,5-四甲基-2-(4-(甲基亚磺酰基)苯基)-1,3,2-二噁硼烷
  参考文献：
  名称：

  钼-铜催化体系促进的硝酸盐对硫醚和硫代芳烷硼烷的选择性硫氧化

  摘要：

  钼酶催化还原硝酸盐在氮的全球生物循环中起着核心作用。然而，在合成有机化学中使用硝酸盐作为氧化剂非常有限，并且通常需要非常强的酸性和其他极端反应条件。我们已经开发出一种高度化学选择性和高效的催化方法，用于使用硝酸盐作为氧化剂对含硼酸或硼酸酯官能团的硫醚和芳基硫醚进行硫氧化。该均相催化反应在乙腈中进行，其中MoO 2 Cl 2（OPPh 3）2配合物1或配合物1与Cu（NO 3）的混合物2用作催化剂。我们使用1 H，15 N和31 P NMR技术以及18 O标记的硝酸钠（NaN 18 O 3）检查了反应机理，结果表明硫醚被硝酸盐氧化，生成亚硝酸盐。我们的工作增加了有机硼化合物现有的化学转化方法，使人们可以直接接触各种可能适用于铃木交叉偶联化学的新底物。

  DOI：

  10.1021/jo2001808

文献信息

• Synthesis of α-Aryl Primary Amides from α-Silyl Nitriles and Aryl Sulfoxides through [3,3]-Sigmatropic Rearrangement
  作者：Fan Luo、Hui Zhou、Xiao-Bei Chen、Xue-Jun Liu、Xiao-Dong Chen、Peng-Fei Qian、Xin-Ping Wu、Wei Wang、Shi-Lei Zhang

  DOI：10.1021/acs.orglett.2c00334

  日期：2022.3.4

  A simple and efficient protocol was developed for the preparation of challenging α-aryl primary amides. This metal-free coupling process was triggered by TfOH-promoted electrophilic activation of α-silyl nitrile to generate keteniminium ion species, followed by reaction with aryl sulfoxide through [3,3]-sigmatrophic rearrangement to provide the target product. To the best of our knowledge, α-silyl

  开发了一种简单有效的方案来制备具有挑战性的 α-芳基伯酰胺。这种无金属偶联过程是由 TfOH 促进的 α-甲硅烷基腈的亲电活化以产生 keteniminium 离子物质引发的，然后通过 [3,3]-σ 重排与芳基亚砜反应以提供目标产物。据我们所知，α-甲硅烷基腈很少用作亲电子试剂。计算研究证实了高度亲电的酮亚胺中间体的短暂存在。
• BIARYL DERIVATIVES AS BROMODOMAIN INHIBITORS
  申请人：Fairfax David John

  公开号：US20140140956A1

  公开（公告）日：2014-05-22

  The present disclosure relates to compounds, which are useful for inhibition of BET protein function by binding to bromodomains, and their use in therapy.

  本公开涉及一种化合物，该化合物通过结合溴结构域来抑制BET蛋白的功能，并且其在治疗中的应用。
• Development of a Ratiometric Fluorescent Probe with Two ­Reactive Sulfoxides for Monitoring the Activity of Methionine Sulfoxide Reductase A
  作者：Jiří Míšek、Nikolai Makukhin、Vladimír Nosek

  DOI：10.1055/s-0036-1591888

  日期：2018.2

  oxidation of methionine side chains in proteins is a process that affects the functions of many proteins. One of the key regulators of this signaling is the enzyme methionine sulfoxide reductase A (MsrA). MsrA is implicated in a number of diseases, but detailed understanding of its function is hindered by the lack of tools for monitoring the enzyme’s activity. We have designed and synthesized a probe named

  作为Bürgenstock专栏2017年有机化学中的未来之星的一部分发布 抽象的 蛋白质中蛋氨酸侧链的生物氧化是影响许多蛋白质功能的过程。该信号的关键调节剂之一是甲硫氨酸亚砜还原酶A（MsrA）。MsrA与许多疾病有关，但是由于缺乏监测酶活性的工具，阻碍了对其功能的详细了解。我们已经设计并合成了一种名为（S，S）-Sulfox-2的探针，该探针基于BODIPY荧光团，并且配备了两个定义立体化学的手性亚砜单元。（S，S）-Sulfox-2被显示对MsrA高度敏感，并通过荧光分布的显着变化来追踪MsrA活性。 蛋白质中蛋氨酸侧链的生物氧化是影响许多蛋白质功能的过程。该信号的关键调节剂之一是甲硫氨酸亚砜还原酶A（MsrA）。MsrA与许多疾病有关，但是由于缺乏监测酶活性的工具，阻碍了对其功能的详细了解。我们已经设计并合成了一种名为（S，S）-Sulfox-2的探针，该探针基于BODIPY荧光团，
• WO2008/37072
  申请人：——

  公开号：——

  公开（公告）日：——
• Open Source Antibiotics: Simple Diarylimidazoles Are Potent against Methicillin-Resistant <i>Staphylococcus aureus</i>
  作者：Dana M. Klug、Edwin G. Tse、Daniel G. Silva、Yafeng Cao、Susan A. Charman、Jyoti Chauhan、Elly Crighton、Maria Dichiara、Chris Drake、David Drewry、Flavio da Silva Emery、Lori Ferrins、Lee Graves、Emily Hopkins、Thomas A. C. Kresina、Álvaro Lorente-Macías、Benjamin Perry、Richard Phipps、Bruno Quiroga、Antonio Quotadamo、Giada N. Sabatino、Anthony Sama、Andreas Schätzlein、Quillon J. Simpson、Jonathan Steele、Julia Shanu-Wilson、Peter Sjö、Paul Stapleton、Christopher J. Swain、Alexandra Vaideanu、Huanxu Xie、William Zuercher、Matthew H. Todd

  DOI：10.1021/acsinfecdis.3c00286

  日期：2023.12.8