2-甲基-5-羟基羰基-3-硼酸 | 170230-88-3

• 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: 2-甲基-5-羟基羰基-3-硼酸
• 中文别名: 5-羧酸-2-甲基苯硼酸；2-甲基-5-羧基苯硼酸
• 英文名称: 3-borono-4-methylbenzoic acid
• CAS: 170230-88-3
• 化学式: C₈H₉BO₄
• mdl: MFCD08061639
• 分子量: 179.968
• InChiKey: OEGYTHZGLBLPCE-UHFFFAOYSA-N

物化性质

• 熔点：
  157-167 °C
• 沸点：
  446.8±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Carboxy-2-methylphenylboronic acid
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: 5-Carboxy-2-methylphenylboronic acid
CAS number: 170230-88-3

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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, refrigerated.
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: C8H9BO4
Molecular weight: 180.0

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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

制备方法与用途

5-羧酸-2-甲基苯硼酸可用作有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程。

反应信息

• 作为反应物：
  描述：

  2-甲基-5-羟基羰基-3-硼酸 在 硫酸 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 4-甲基-3-(4,4,5,5-四甲基-1,3,2-二氧硼烷)-苯甲酸甲酯
  参考文献：
  名称：

  [EN] BORON-CONTAINING DIACYLHYDRAZINES
  [FR] DIACYLHYDRAZINES CONTENANT DU BORE

  摘要：

  公开号：

  WO2014144380A8
• 作为产物：
  描述：

  4-甲基-3-(4,4,5,5-四甲基-[1,3,2]二噁硼烷-2-基)苯甲酸 在 盐酸 、 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 2-甲基-5-羟基羰基-3-硼酸
  参考文献：
  名称：

  [EN] BCR-ABL TYROSINE-KINASE LIGANDS CAPABLE OF DIMERIZING IN AN AQUEOUS SOLUTION, AND METHODS OF USING SAME
  [FR] LIGANDS DE TYROSINE-KINASE BCR-ABL CAPABLES DE SE DIMÉRISER DANS UNE SOLUTION AQUEUSE, ET PROCÉDÉS D'UTILISATION DE CEUX-CI

  摘要：

  本文描述了一种单体，当与水性介质中的另一个、两个、三个或更多其他单体接触时，能够形成生物学上有用的多聚体。在一个方面，这种单体可能能够在水性介质（例如体内）中与另一个单体结合以形成多聚体（例如二聚体）。考虑到的单体可能包括配体基团、连接元素和连接配体基团与连接元素的连接元素。在水性介质中，这些考虑到的单体可以通过每个连接元素结合在一起，因此可以同时调节一个或多个生物分子，例如，调节Bcr-Abl酪氨酸激酶上的两个或更多结合位点。

  公开号：

  WO2015106292A1

文献信息

• Design, Synthesis, and Screening of a Library of Peptidyl Bis(Boroxoles) as Oligosaccharide Receptors in Water: Identification of a Receptor for the Tumor Marker TF-Antigen Disaccharide
  作者：Arnab Pal、Marie Bérubé、Dennis G. Hall

  DOI：10.1002/anie.200906620

  日期：2010.2.15

  Mini lectins: A new class of oligosaccharide receptors (see example) was designed by exploiting several modes of molecular recognition, including the unique ability of benzoboroxoles to complex hexopyranosides. The synthesis is modular, thus well suited to targeting specific oligosaccharides using combinatorial libraries.

  迷你凝集素：通过利用多种分子识别模式设计了一种新型的寡糖受体（参见示例），包括苯并环硼烷对复杂的吡喃吡喃糖苷的独特能力。合成是模块化的，因此非常适合使用组合文库靶向特定的寡糖。
• Phthalazine, aza- and diaza-phthalazine compounds and methods of use
  申请人：Tasker Andrew

  公开号：US20060199817A1

  公开（公告）日：2006-09-07

  The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including inflammation and related conditions. The compounds have a general Formula I wherein A 1 , A 2 , B, R 1 , R 2 , R 3 and R 4 are defined herein. The invention also comprises pharmaceutical compositions including one or more compounds of Formula I, uses of such compounds and compositions for treatment of kinase mediated diseases including rheumatoid arthritis, psoriasis and other inflammation disorders, as well as intermediates and processes useful for the preparation of compounds of Formula I.

  本发明包括一类新的化合物，用于预防和治疗蛋白激酶介导的疾病，包括炎症及相关状况。这些化合物的通用公式为I 其中A 1 ，A 2 ，B，R 1 ，R 2 ，R 3 和R 4 在此定义。该发明还包括包括一个或多个I公式化合物的药物组合物，以及使用这些化合物和组合物治疗激酶介导的疾病，包括类风湿性关节炎，银屑病和其他炎症性疾病，以及用于制备I公式化合物的中间体和工艺。
• Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation
  作者：Burcin Akgun、Dennis G. Hall

  DOI：10.1002/anie.201510321

  日期：2016.3.14

  A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m−1 s−1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2‐methyl‐5‐carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration

  新的点击生物正交反应系统设计成使快速连接（ķ ON ≈340 米-1 小号-1）一个刚性的环状二醇（nopoldiol）和仔细优化硼酸伙伴的缀合衍生物，2-甲基-5-羧甲基苯基硼酸。使用NMR和荧光光谱研究，发现对应于硼酸酯在水中低微摩尔浓度分钟内可逆地形成，从而提供亚微摩尔的平衡常数（ķ当量≈10 5 -10 6 米-1）。用模型蛋白硫氧还蛋白和白蛋白证明了在生理条件下的有效蛋白结合，并通过质谱和凝胶电泳进行了表征。
• [EN] COMPOUNDS AND METHODS FOR INHIBITION OF BAX-MEDIATED CELL DEATH<br/>[FR] COMPOSÉS ET PROCÉDÉS PERMETTANT L'INHIBITION DE LA MORT CELLULAIRE MÉDIÉE PAR BAX
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE

  公开号：WO2022051384A1

  公开（公告）日：2022-03-10

  This disclosure provides novel compounds and methods for inhibiting BAX activity and BAX-mediated apoptosis, as well as compounds and methods for treating or preventing BAX- mediated disorders.

  本公开提供了用于抑制BAX活性和BAX介导的凋亡的新化合物和方法，以及用于治疗或预防BAX介导的疾病的化合物和方法。
• Imidazo- and triazolo-pyridine compounds and methods of use thereof
  申请人：Zhang Dawei

  公开号：US20080161303A1

  公开（公告）日：2008-07-03

  The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including inflammation and related conditions. The compounds have a general Formula I wherein A, B, R 1 , R 2 , R 3 and R 4 are defined herein. The invention also comprises pharmaceutical compositions including one or more compounds of Formula I, uses of such compounds and compositions for treatment of P38 map kinase mediated diseases including rheumatoid arthritis, psoriasis and other inflammation disorders, as well as intermediates and processes useful for the preparation of compounds of Formula I.

  本发明涉及一类新的化合物，用于预防和治疗与蛋白激酶介导的疾病有关的疾病，包括炎症和相关病症。这些化合物具有通用的I式，其中A、B、R1、R2、R3和R4在此处被定义。该发明还涵盖包括I式中的一个或多个化合物的制药组合物，以及用于治疗P38地图激酶介导的疾病，包括类风湿性关节炎、牛皮癣和其他炎症性疾病的化合物和组合物的用途，以及用于制备I式化合物的中间体和工艺。