3-氨基-4-氟苯硼酸 | 873566-75-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯硼酸系列
• 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-氨基-4-氟苯硼酸
• 中文别名: (3-氨基-4-氟苯基)硼酸盐酸
• 英文名称: (3-amino-4-fluorophenyl)boronic acid
• 英文别名: 3-amino-4-fluorobenzeneboronic acid；3-Amino-4-fluorophenylboronic acid
• CAS: 873566-75-7
• 化学式: C₆H₇BFNO₂
• mdl: MFCD03092925
• 分子量: 154.936
• InChiKey: SYBMNJPUZMUPGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  346.0±52.0 °C(Predicted)
• 密度：
  1.34

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi,Xn
• 危险类别码：
  R22
• 海关编码：
  2916399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Amino-4-fluorophenylboronic 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: 3-Amino-4-fluorophenylboronic acid
CAS number: 873566-75-7

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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: C6H7BFNO2
Molecular weight: 154.9

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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 fluoride.

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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

3-氨基-4-氟苯硼酸

3-氨基-4-氟苯硼酸是一种硼酸衍生物，主要用于化工有机合成过程中的偶联剂。

制备方法

将63克3-硝基-4-氟苯硼酸置于500毫升单口瓶中，加入100毫升甲醇、6.3克（10%）钯碳催化剂。用胶塞封口后，使用水泵抽真空，并通过针头通入氢气。将反应瓶置于55°C油浴中搅拌反应。待氢气球不再吸收时结束反应，滤去钯碳并旋干至不流动。随后，加入正庚烷进行打浆，再进行真空干燥。

将所得固体溶于30毫升甲醇中，并加入150毫升水。此时会有大量固体析出，用旋蒸去除甲醇和一部分水分。降温至5°C后，通过布氏漏斗抽滤得淡灰色固体并进行真空干燥，最终得到42.6克产品，收率为80.7%。经1H NMR确证结构符合预期，HPLC纯度为99.1%。

3-氨基-4-氟苯硼酸的1H NMR（400 MHz, DMSO_d6, D2O）数据如下：δ ppm 7.19 (1H, d, J=9.6), 6.96(2H, q, J=5.2) ,3.15 (2H, S)。

反应信息

• 作为反应物：
  描述：

  3-氨基-4-氟苯硼酸 在 四(三苯基膦)钯 亚硝酸正戊酯 、 碘 、 sodium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[4'-fluoro-3'-iodo-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  WO2007/79186

  摘要：

  公开号：
• 作为产物：
  描述：

  对溴氟苯 在 magnesium hydroxide 、 palladium on activated charcoal 、 氢气 、 硝酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 5.5h， 生成 3-氨基-4-氟苯硼酸
  参考文献：
  名称：

  一种合成3-氨基-4-氟苯硼酸的方法

  摘要：

  本发明属于有机化学物合成领域。一种合成3-氨基-4-氟苯硼酸的方法，包括以下三个步骤：第一步将对氟溴苯制成格氏试剂，然后与硼酸三甲酯反应得到中间体对氟苯硼酸A；第二步中间体A与发烟硝酸反应生成中间体3-硝基-4-氟苯硼酸B；第三步中间体B在钯碳的催化下加氢生成产品3-氨基-4-氟苯硼酸C。本发明合成方法原料易得、操作简单，成本较低，提供一种制备3-氨基-4-氟苯硼酸的适宜路径。

  公开号：

  CN103626791B

文献信息

• Design, Synthesis, and Biological Characterization of Orally Active 17β-Hydroxysteroid Dehydrogenase Type 2 Inhibitors Targeting the Prevention of Osteoporosis
  作者：Ahmed S. Abdelsamie、Mohamed Salah、Lorenz Siebenbürger、Ahmed Merabet、Claudia Scheuer、Martin Frotscher、Sebastian T. Müller、Oliver Zierau、Günter Vollmer、Michael D. Menger、Matthias W. Laschke、Chris J. van Koppen、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1021/acs.jmedchem.9b00932

  日期：2019.8.8

  Osteoporosis is predominantly treated with drugs that inhibit further bone resorption due to estrogen deficiency. Yet, osteoporosis drugs that not only inhibit bone resorption but also stimulate bone formation, such as potentially inhibitors of 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2), may be more efficacious in the treatment of osteoporosis. Blockade of 17β-HSD2 is thought to increase intracellular

  骨质疏松症主要使用抑制由于雌激素缺乏引起的进一步骨吸收的药物治疗。然而，不仅抑制骨吸收而且刺激骨形成的骨质疏松药物，例如潜在的2型17β-羟类固醇脱氢酶抑制剂（17β-HSD2），在骨质疏松症的治疗中可能更有效。认为17β-HSD2的阻断会增加骨中的细胞内雌二醇和睾丸激素，从而分别抑制破骨细胞的骨吸收和刺激成骨细胞的骨形成。我们在这里描述了新型双环取代的羟苯基甲酮17β-HSD2抑制剂（化合物24）的设计，合成和生物学特性。化合物24是人类17β-HSD2（IC50为6.1 nM）和啮齿类动物17β-HSD2的纳摩尔强效抑制剂，体外细胞毒性较低，缺乏可检测的雌激素受体α亲和力，显示出高的水溶性和体外代谢稳定性，并且在大鼠骨质疏松症模型中具有出色的口服药代动力学特征。在大鼠骨质疏松症模型中施用24可以证明其保留骨的功效。
• [EN] DIHYDROOXADIAZINONES<br/>[FR] DIHYDROOXADIAZINONES
  申请人：BAYER AG

  公开号：WO2019025562A1

  公开（公告）日：2019-02-07

  The present invention provides dihydrooxydiazinone compounds of general formula (I) : in which R1, R2, R3, and R4, are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative diseases, as a sole agent or in combination with other active ingredients.

  本发明提供了一般式(I)的二氢氧二氮酮化合物：其中R1、R2、R3和R4如本文所定义，制备所述化合物的方法，用于制备所述化合物的中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是治疗或预防过度增殖性疾病，作为唯一药剂或与其他活性成分组合使用。
• [EN] HETEROCYCLIC COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET PROCÉDÉS D'UTILISATION
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2015058084A1

  公开（公告）日：2015-04-23

  The present application discloses compounds that are inhibitors of Btk, compounds that are inhibitors of ΡΒΚδ, and compounds that are dual inhibitors of both Btk and PI3Kδ. Also described are methods for synthesizing such inhibitors and methods for using such inhibitors for the treatment of diseases wherein inhibition of Btk and PI3Kδ provides a therapeutic benefit to a patient having the disease.

  本申请公开了抑制Btk的化合物、抑制ΡΒΚδ的化合物，以及既是Btk又是PI3Kδ的双重抑制剂的化合物。还描述了合成这些抑制剂的方法，以及利用这些抑制剂治疗疾病的方法，其中抑制Btk和PI3Kδ对患有该疾病的患者提供治疗益处。
• 3,5-(Un)substituted-1H-pyrrolo[2,3-b]pyridine, 1H-pyrazolo[3,4-b]pyridine and 5H- pyrrolo[2,3-b]pyrazine dual ITK and JAK3 Kinase Inhibitors
  申请人：Arrien Pharmaceuticals LLC

  公开号：US20140315909A1

  公开（公告）日：2014-10-23

  The present invention relates to compounds described by Formula I: salts thereof, their synthesis, and their use as ITK and JAK3 inhibitors including such compounds and methods of using said compounds in the treatment of various diseases and or disorders such disease associated with abnormal cell growth such as autoimmune, inflammation, rheumatoid arthritis, systemic lupus erythematosus, atherosclerosis, ulcerative colitis, psoriatic arthritis, psoriasis, Crohn's, metabolic and cancer diseases. The present invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions and processes for preparing the compounds of the invention.

  本发明涉及由式I描述的化合物： 其盐，它们的合成，以及它们作为ITK和JAK3抑制剂的用途，包括这些化合物以及使用这些化合物治疗各种疾病和/或疾病的方法，这些疾病与异常细胞生长有关，如自身免疫、炎症、类风湿关节炎、系统性红斑狼疮、动脉粥样硬化、溃疡性结肠炎、银屑病性关节炎、银屑病、克罗恩病、代谢和癌症疾病。本发明还提供包括本发明化合物的药学上可接受的组合物以及使用这些组合物的方法和制备本发明化合物的方法。
• [EN] 4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS<br/>[FR] DÉRIVÉS DE 4-PHÉNYL-N-(PHÉNYL)THIAZOL-2-AMINE ET COMPOSÉS ASSOCIÉS UTILISÉS COMME AGONISTES DU RÉCEPTEUR D'HYDROCARBURE ARYLE (AHR) POUR LE TRAITEMENT, PAR EX., DE TROUBLE LIÉS À L'ANGIOGENÈSE OU INFLAMMATOIRES
  申请人：IKENA ONCOLOGY INC

  公开号：WO2021127301A1

  公开（公告）日：2021-06-24

  4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

  4-苯基-N-(苯基)噻唑-2-胺和4-(吡啶-3-基)-N-(苯基)噻唑-2-胺衍生物以及相应的噻二唑、噻吩、噁唑、噁二唑、咪唑和三唑衍生物和相关化合物作为芳香烃受体（AHR）激动剂，用于治疗涉及血管生成的疾病，例如视网膜病变、银屑病、类风湿性关节炎、肥胖和癌症，或炎症性疾病。