甲基硼酸频呐醇酯 | 94242-85-0

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 甲基硼酸频呐醇酯
• 中文别名: 甲基硼酸频哪醇酯；甲基硼酸频那醇酯
• 英文名称: 2,4,4,5,5-pentamethyl-[1,3,2]dioxaborolane
• 英文别名: methylboronic acid pinacol ester；methyl pinacol boronic ester；2,4,4,5,5-Pentamethyl-1,3,2-dioxaborolane
• CAS: 94242-85-0
• 化学式: C₇H₁₅BO₂
• mdl: MFCD09027082
• 分子量: 142.006
• InChiKey: FOQJHZPURACERJ-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122℃ (747 Torr)
• 密度：
  0.88±0.1 g/cm3 (20 ºC 760 Torr)
• 闪点：
  31.3±18.7℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  No
• 危险等级：
  3
• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  3
• 危险性防范说明：
  P501,P240,P210,P233,P243,P241,P242,P280,P370+P378,P303+P361+P353,P403+P235
• 危险品运输编号：
  3272
• 危险性描述：
  H225
• 储存条件：
  存放在惰性气体中，避免与空气接触和加热；温度范围为0至10°C。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methylboronic 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: Methylboronic acid pinacol ester
CAS number: 94242-85-0

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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: C7H15BO2
Molecular weight: 142.0

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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.

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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：

  甲基硼酸频呐醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium acetate 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 反应 32.0h， 生成 4-(bromomethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of new acylsulfamoyl benzoxaboroles as potent inhibitors of HCV NS3 protease

  摘要：

  HCV NS3/4A serine protease is essential for the replication of the HCV virus and has been a clinically validated target. A series of HCV NS3/4A protease inhibitors containing a novel acylsulfamoyl benzoxaborole moiety at the P1 ' region was synthesized and evaluated. The resulting P1-P3 and P2-P4 macrocyclic inhibitors exhibited sub-nanomolar potency in the enzymatic assay and low nanomolar activity in the cell-based replicon assay. The in vivo PK evaluations of selected compounds are also described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.007
• 作为产物：
  描述：

  2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 盐酸 、 甲基溴化镁 作用下， 以 乙醚 为溶剂， 生成 甲基硼酸频呐醇酯
  参考文献：
  名称：

  有机oboranes。39.制备甲基硼酸和三甲基环硼氧烷的简便程序

  摘要：

  DOI：

  10.1021/om00124a002

文献信息

• [EN] NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2017012647A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds according to Formula (I), wherein R1, R3, R4, R5, L1, and Cy are as defined herein. The present invention also provides compounds, methods for the production of said compounds of the invention, pharmaceutical compositions comprising the same and their use in allergic or inflammatory conditions, autoimmune diseases, proliferative diseases, transplantation rejection, diseases involving impairment of cartilage turnover, congenital cartilage malformations, and/or diseases associated with hypersecretion of IL6 and/or interferons. The present invention also methods for the prevention and/or treatment of the aforementioned diseases by administering a compound of the invention.

  本发明公开了根据式（I）的化合物，其中R1、R3、R4、R5、L1和Cy如本文所定义。本发明还提供了该发明的化合物、制备该化合物的方法、包括相同化合物的药物组合物以及它们在过敏或炎症症状、自身免疫疾病、增殖性疾病、移植排斥、涉及软骨周转障碍的疾病、先天软骨畸形和/或与IL6和/或干扰素过度分泌相关的疾病中的使用。本发明还提供了通过给予该发明的化合物来预防和/或治疗上述疾病的方法。
• Stereocontrolled Synthesis of 1,5-Stereogenic Centers through Three-Carbon Homologation of Boronic Esters
  作者：Phillip J. Unsworth、Daniele Leonori、Varinder K. Aggarwal

  DOI：10.1002/anie.201405700

  日期：2014.9.8

  Allylic pinacol boronic esters are stable toward 1,3‐borotropic rearrangement. We developed a PdII‐mediated isomerization process that gives di‐ or trisubstituted allylic boronic esters with high E selectivity. The combination of this method with lithiation–borylation enables the synthesis of carbon chains that bear 1,5‐stereogenic centers. The utility of this method has been demonstrated in a formal

  烯丙基频哪醇硼酸酯对1,3-硼异向重排是稳定的。我们开发了一种由Pd II介导的异构化工艺，该工艺可产生具有高E 选择性的二或三取代的烯丙基硼酸酯。这种方法与锂化-硼化的结合可以合成具有1,5-立体异构中心的碳链。该方法的效用已在（+）-茉莉素的正式合成中得到了证明。
• Regioselective Synthesis and Photophysical and Electrochemical Studies of 20-Substituted Cyanine Dye-Purpurinimide Conjugates: Incorporation of Ni^IIinto the Conjugate Enhances its Tumor-Uptake and Fluorescence-Imaging Ability
  作者：Manivannan Ethirajan、Ping Chen、Tymish Y. Ohulchanskyy、Lalit N. Goswami、Anurag Gupta、Avinash Srivatsan、Mahabeer P. Dobhal、Joseph R. Missert、Paras N. Prasad、Karl M. Kadish、Ravindra K. Pandey

  DOI：10.1002/chem.201203867

  日期：2013.5.17

  approach to the synthesis of a variety of meso‐substituted purpurinimides. The reaction of meso‐substituted purpurinimide with N‐bromosuccinimide regioselectively introduced a bromo functionality at the 20‐position, which on further reaction with a variety of boronic acids under Suzuki reaction conditions yielded the corresponding meso‐substituted analogues. Interestingly, the free base and the metalated

  我们在这里报告了一种简单有效的方法来合成各种内消旋取代的紫嘌呤亚胺。的反应内消旋-取代紫红素与Ñ溴代琥珀酰亚胺区域选择性引入到20位，将其用各种Suzuki反应条件下，硼酸进一步反应得到相应的溴功能内消旋取代的类似物。有趣的是，游离碱和金属化类似物在光敏功效（PDT）和肿瘤成像能力方面显示出显着差异。例如，游离碱偶联物在体外具有显着的PDT功效，但在荷瘤小鼠中肿瘤亲和力有限，而相应的Ni II该衍生物不会产生任何细胞杀伤作用，但在注射后24、48和72 h，以0.3μmolkg -1的剂量显示出优异的肿瘤成像能力。Ni II类似物的PDT功效有限可能是由于其无法产生单线态氧，而单线态氧是PDT中杀死细胞所需的关键细胞毒剂。根据DMSO中的电化学和光谱电化学数据，游离碱和相应的Ni II的第一次单电子氧化（0.52 V vs. SCE）和第一次单电子还原（-0.57-0.67 V vs. S
• Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol
  作者：Colton R. Davis、Irungu K. Luvaga、Joseph M. Ready

  DOI：10.1021/jacs.1c01242

  日期：2021.4.7

  Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C–C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.

  烯基硼酸盐添加到具有高对映选择性的 Ir(π-烯丙基) 中间体。1,2-金属酸盐位移形成第二个 C-C 键并建立 1,3-立体化学关系。三组分偶联提供了可以进行多种额外功能化的叔硼酸酯。三取代烯烃的延伸设置了三个连续的立体中心。
• Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism
  作者：Qianyi Liu、Junting Hong、Beiqi Sun、Guangcan Bai、Feng Li、Guoquan Liu、Yang Yang、Fanyang Mo

  DOI：10.1021/acs.orglett.9b01951

  日期：2019.9.6

  transition-metal-free borylation of alkyl iodides. This method uses commercially available diboron reagents as the boron source and exhibits excellent functional group compatibility. Furthermore, a diverse range of primary and secondary alkyl iodides could be effectively transformed to the corresponding alkylboronates in excellent yield. Mechanistic investigations suggest that this borylation reaction

  我们描述了一种操作简单的烷基碘的无过渡金属的硼化反应。该方法使用市售的二硼试剂作为硼源，并且显示出优异的官能团相容性。此外，可以以优异的收率有效地将各种各样的伯和仲烷基碘化物有效地转化为相应的烷基硼酸酯。机理研究表明，该硼化反应通过特征在于烷基自由基中间体生成的单电子转移机理进行。