2-氨基-4-甲氧羰基苯基硼酸盐酸盐 | 380430-55-7

• 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-氨基-4-甲氧羰基苯基硼酸盐酸盐
• 中文别名: 2-氨基-4-(甲氧基羰基)苯硼酸盐酸盐
• 英文名称: 2-amino-4-methoxycarbonylphenylboronic acid hydrochloride
• 英文别名: (2-Amino-4-methoxycarbonylphenyl)boronic acid;hydron;chloride；(2-amino-4-methoxycarbonylphenyl)boronic acid;hydron;chloride
• CAS: 380430-55-7
• 化学式: C₈H₁₀BNO₄*ClH
• mdl: MFCD02258941
• 分子量: 231.444
• InChiKey: IDUSDMZTKZZVAW-UHFFFAOYSA-N

物化性质

• 熔点：
  200-204°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  94.4
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• TSCA：
  No
• 安全说明：
  S26,S36/37/39
• 海关编码：
  2931900090
• 危险类别码：
  R36/37/38
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Amino-4-methoxycarbonylphenylboronic acid, HCl
Product Name:
Synonyms: Methyl 3-amino-4-boronobenzoate, HCl

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Amino-4-methoxycarbonylphenylboronic acid, HCl
Ingredient name:
CAS number: 380430-55-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H11BClNO4
Molecular weight: 231.4

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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, nitrogen oxides, hydrogen chloride.

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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

2-氨基-4-甲氧羰基苯基硼酸盐酸盐主要应用于实验室有机合成及化工医药研发过程。

反应信息

• 作为反应物：
  描述：

  2-氨基-4-甲氧羰基苯基硼酸盐酸盐 在 potassium phosphate 、 四(三苯基膦)钯 、 水 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 (R)-N-(1-(3-methoxyphenyl)ethyl)-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-8-carboxamide
  参考文献：
  名称：

  [EN] TRICYCLIC PYRI DO-CARBOXAM I D E DERIVATIVES AS ROCK INHIBITORS
  [FR] DÉRIVÉS PYRIDOCARBOXAMIDE TRICYCLIQUES COMME INHIBITEURS DE LA VOIE ROCK

  摘要：

  本发明提供了化合物的结构式（I）：或其立体异构体、互变异构体或药用可接受的盐，其中所有变量均如本文所定义。这些化合物是选择性ROCK抑制剂。本发明还涉及含有这些化合物的药物组合物以及使用这些药物治疗心血管、平滑肌、肿瘤学、神经病理学、自身免疫、纤维化和/或炎症性疾病的方法。

  公开号：

  WO2015002915A1
• 作为产物：
  描述：

  4-羧基苯硼酸 在 氯化亚砜 、 硫酸 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 2-氨基-4-甲氧羰基苯基硼酸盐酸盐
  参考文献：
  名称：

  合成喹啉衍生物的关键中间体 2-氨基-4-(甲氧基羰基)苯基硼酸盐酸盐

  摘要：

  通过硼酸化、氧化、硝化、酯化和加氢，开发了一种从对溴甲苯中高产率合成2-氨基-4-(甲氧基羰基)苯基硼酸盐酸盐的实用且有效的方法。

  DOI：

  10.3184/174751914x14175346572646

文献信息

• Discovery of 5-(3-Chlorophenylamino)benzo[<i>c</i>][2,6]naphthyridine Derivatives as Highly Selective CK2 Inhibitors with Potent Cancer Cell Stemness Inhibition
  作者：Yuanjiang Wang、Zhaodan Lv、Feihong Chen、Xing Wang、Shaohua Gou

  DOI：10.1021/acs.jmedchem.1c00131

  日期：2021.4.22

  concurrent CK2 along with cancer stem cell (CSC) inhibitory activities are rare in a single small molecule. Herein, a series of 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine derivatives were synthesized using a known CK2 inhibitor, silmitasertib (CX-4945), as the lead compound. Among the resulting compounds, 1c exhibited stronger CK2 inhibitory activity with higher Clk2/CK2 selectivity than CX-4945

  多功能实体最近对于开发抗癌化疗药物具有吸引力。但是，在单个小分子中很少有具有并发CK2和癌症干细胞（CSC）抑制活性的实体。在此，使用已知的CK2抑制剂西米塔塞替尼（Cilmitasertib（CX-4945））作为前导化合物合成了一系列5-（3-氯苯基氨基）苯并[ c ] [2,6]萘啶衍生物。在所得化合物中，1c与CX-4945相比具有更强的CK2抑制活性和更高的Clk2 / CK2选择性。明显地，1c可以调节Akt1（ser129）-GSK-3β（ser9）-Wnt /β-catenin信号通路并抑制茎标记ALDH1A1，CSC表面抗原和茎基因的表达，显示出强大的CSC抑制活性。此外，与CX-4945钠盐相比，1c还显示出优异的药代动力学和抗肿瘤活性，且无明显毒性。1c的良好抗增殖和抗肿瘤活性，对CK2的高抑制选择性以及对癌细胞干性的有效抑制作用使该分子成为治疗癌症的候选药物。
• Structure–Activity Relationship Analysis of Imidazoquinolines with Toll-like Receptors 7 and 8 Selectivity and Enhanced Cytokine Induction
  作者：Charles E. Schiaffo、Ce Shi、Zhengming Xiong、Michael Olin、John R. Ohlfest、Courtney C. Aldrich、David M. Ferguson

  DOI：10.1021/jm4004957

  日期：2014.1.23

  Toll-like receptors 7 and 8 (TLRs) have emerged as key targets in the design of small molecule adjuvants and stimulants for use in immunotherapies. This study examines the structure–activity relationship of a series of C2- and N1-substituted C7-methoxycarbonylimidazoquinolines to gain insight to the structural basis to TLR-7 and -8 selective activity. The analysis is further applied to evaluate the

  Toll样受体7和8（TLR）已成为设计用于免疫疗法的小分子佐剂和刺激剂的关键靶标。这项研究检查了一系列C2和N1取代的C7-甲氧基羰基咪唑并喹啉的结构-活性关系，以了解TLR-7和-8选择性活性的结构基础。使用鼠BMDC和人PBMC，该分析被进一步应用于评估多种细胞因子的诱导，包括IL-10，IL-12，IL-1β，TNF-α，IFN-α和IFN-γ。结果表明，TLR-7 / 8活性与C2-烷基链长相关，其中丁基（TLR-7）和戊基（TLR-8）衍生物出现峰值活性。在IL-1β，IL-12和IFN-γ的产生中发现了类似的SAR，它们显示出既依赖于C2烷基链长，又依赖于N1位置。
• Homogenous suspension of immunopotentiating compounds and uses thereof
  申请人：Skibinski David

  公开号：US09408907B2

  公开（公告）日：2016-08-09

  The present invention generally relates to homogeneous suspensions of small molecule immune potentiators (SMIPs) that are capable of stimulating or modulating an immune response in a subject in need thereof. The homogeneous suspensions may be used in combinations with various antigens or adjuvants for vaccine therapies.

  本发明通常涉及能够刺激或调节受需要者免疫反应的小分子免疫增强剂（SMIPs）的均匀悬浮液。这些均匀悬浮液可以与各种抗原或佐剂结合在一起用于疫苗治疗。
• <i>anti</i>-Hydroarylation of Activated Internal Alkynes: Merging Pd and Energy Transfer Catalysis
  作者：Javier Corpas、Pablo Mauleón、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1021/acs.orglett.0c02281

  日期：2020.8.21

  electron-poor and electron-rich aryl reagents is reported. This selectivity is achieved through a sequential syn-carbopalladation of the alkyne by an Ar–Pd species, followed by a tandem, Ir-photocatalyzed, counter-thermodynamic E → Z isomerization. The use of ortho-substituted boronic acids enables direct access to pharmaceutically relevant heterocyclic cores via a cascade process. Mechanistic insight

  据报道，与贫电子和富电子芳基试剂均兼容的缺电子内部炔烃的一般催化抗氢芳基化反应。这种选择性是通过Ar-Pd分子对炔烃进行顺式羰基缩合，然后进行Ir串联的Ir光催化逆热力学E → Z异构化来实现的。邻取代的硼酸的使用使得能够经由级联过程直接进入药学上相关的杂环核。提供了有关Ar–Pd与Pd–H作为活性物种参与的机理的见解。
• [EN] COMPOUNDS AND COMPOSITIONS AS TLR ACTIVITY MODULATORS<br/>[FR] COMPOSÉS ET COMPOSITIONS SERVANT DE MODULATEURS DE L'ACTIVITÉ DES TLR
  申请人：IRM LLC

  公开号：WO2009111337A1

  公开（公告）日：2009-09-11

  The invention provides a novel class of compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors, including TLR7 and TLR8. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness of a vaccine (formula I) wherein: X3 is N; X4 is N Or CR3; X5 is -CR4=CR5.

  该发明提供了一类新型化合物，包括这些化合物的药物组合物以及使用这些化合物来治疗或预防与Toll样受体相关的疾病或紊乱的方法，包括TLR7和TLR8。在一个方面，这些化合物可用作辅助剂，以增强疫苗的效果（公式I），其中：X3为N；X4为N或CR3；X5为-CR4=CR5。