3-氯-4-羟基苯硼酸频那醇酯 | 629658-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-氯-4-羟基苯硼酸频那醇酯
• 英文名称: 3-chloro-4-hydroxyphenylboronic acid pinacol ester
• 英文别名: 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenol；2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS: 629658-06-6
• 化学式: C₁₂H₁₆BClO₃
• 分子量: 254.521
• InChiKey: HBKJZGOCTNRSHF-UHFFFAOYSA-N

物化性质

• 沸点：
  350.8±32.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Chloro-4-hydroxyphenylboronic 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: 3-Chloro-4-hydroxyphenylboronic acid, pinacol ester
CAS number: 629658-06-6

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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: C12H16BClO3
Molecular weight: 254.5

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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, 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

反应信息

• 作为反应物：
  描述：

  3-氯-4-羟基苯硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper diacetate 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (R)-tert-butyl 3-(4-amino-3-(3-chloro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRAZOLOPYRIMIDINES AS KINASES INHIBITORS
  [FR] PYRAZOLOPYRIMIDINES SUBSTITUÉES UTILES COMME INHIBITEURS DE KINASES

  摘要：

  本发明涉及新型吡唑吡嗪、其衍生物、药学上可接受的盐、溶剂和水合物。本发明的化合物和组合物具有对BTK和/或EGFR T790M的蛋白激酶抑制活性，可用于治疗蛋白激酶介导的疾病和病状。

  公开号：

  WO2014187319A1
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以76 mg的产率得到3-氯-4-羟基苯硼酸频那醇酯
  参考文献：
  名称：

  离子对静电相互作用引导的对位选择性、铱催化的硫酸苯酚、苯甲醇和苯胺的 C-H 硼基化反应

  摘要：

  四烷基硫酸铵和氨基磺酸盐的对位 CH 硼化 (CHB) 已使用联吡啶连接的 Ir boryl 催化剂实现。选择性可以通过四烷基铵阳离子中烷基的长度和联吡啶配体上的取代基来调节。离子对，其中阳离子的烷基屏蔽了对位离子中的间位 CH 键，被认为是对位选择性的原因。4,4'-二甲氧基-2,2'-联吡啶配体具有优异的选择性。

  DOI：

  10.1021/jacs.9b08464

文献信息

• [EN] NOVE PHENYL/PYRIDINE SERIES SUBSTITUED BY HYDROXYETHYLAMINO FOR THE TREATMENT OF CANCER<br/>[FR] NOUVELLE SÉRIE PHÉNYLE/PYRIDINE SUBSTITUÉE PAR HYDROXYÉTHYLAMINO POUR LE TRAITEMENT DU CANCER
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014106606A1

  公开（公告）日：2014-07-10

  The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and W are as described herein, compositions including the compounds and methods of using the compounds.

  本发明提供了具有通用公式(I)的新颖化合物，其中R1、R2、R3、R4、R5、R6、R7和W如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。
• <i>Para</i>-Selective C–H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation
  作者：Madalina T. Mihai、Benjamin D. Williams、Robert J. Phipps

  DOI：10.1021/jacs.9b07267

  日期：2019.10.2

  The selective functionalization of C–H bonds at the arene para position is highly challenging using transition metal catalysis. Iridium-catalyzed borylation has emerged as a leading technique for arene functionalization, but there are only a handful of strategies for para-selective borylation, which operate on specific substrate classes and use bespoke ligands or catalysts. We describe a remarkably

  使用过渡金属催化对芳烃对位的 C-H 键进行选择性官能化是非常具有挑战性的。铱催化硼化已成为芳烃功能化的领先技术，但对位选择性硼化的策略很少，它们在特定的底物类别上运行并使用定制的配体或催化剂。我们描述了一个非常通用的协议，它导致对一些最常见的芳烃构建块（苯胺、苄胺、苯酚、苄醇）产生对位选择性，并使用标准硼酸化配体。我们的策略取决于将底物轻松转化为硫酸盐或氨基磺酸盐，其中阴离子芳烃组分与四丁基铵阳离子配对。我们假设该阳离子的大部分不利于间位 C-H 硼酸化，
• Hydrazone–Palladium-Catalyzed Allylic Arylation of Cinnamyloxyphenylboronic Acid Pinacol Esters
  作者：Kohei Watanabe、Takashi Mino、Taichi Abe、Taketo Kogure、Masami Sakamoto

  DOI：10.1021/jo501235w

  日期：2014.7.18

  Allylic arylation of cinnamyloxyphenylboronic acid pinacol esters 3, which have arylboronic acid moiety and allylic ether moiety, using a hydrazone 1d–Pd(OAc)2 system proceeded and gave the corresponding 1,3-diarylpropene derivatives 4 with a phenolic hydroxyl group via a selective coupling reaction of the π-allyl intermediate to the boron-substituted position of the leaving group.

  使用1d- Pd（OAc）2体系进行了具有芳基硼酸部分和烯丙基醚部分的肉桂氧基苯基硼酸频哪醇酯3的烯丙基芳基化反应，并通过选择性的反应得到了相应的带有酚羟基的1,3-二芳基丙烯衍生物4 π-烯丙基中间体与离去基团的硼取代位置的偶联反应。
• [EN] INDAZOLE COMPOUNDS AS KINASE INHIBITORS AND METHOD OF TREATING CANCER WITH SAME<br/>[FR] COMPOSÉS INDAZOLE UTILISÉS COMME INHIBITEURS DE KINASE ET MÉTHODE DE TRAITEMENT DU CANCER AVEC LESDITS COMPOSÉS
  申请人：UNIV HEALTH NETWORK

  公开号：WO2013053051A1

  公开（公告）日：2013-04-18

  The present teaching provide indazole compounds represented by Structural Formulae (I) or (I') or a pharmaceutically acceptable salt thereof. Also described are pharmaceutical compositions and methods of use thereof as protein kinase inhibitors, such as TTK protein kinase, polo-like kinase 4 (PLK4) and Aurora kinases having anticancer activity against breast cancer cells, colon cancer cells, and ovarian cancer cells.

  本教学提供了由结构式（I）或（I'）表示的吲唑化合物或其药用可接受的盐。还描述了这些药物组合物及其用作蛋白激酶抑制剂的方法，如对乳腺癌细胞、结肠癌细胞和卵巢癌细胞具有抗癌活性的TTK蛋白激酶、极化样激酶4（PLK4）和极化激酶。
• Fragment-Based Discovery of 6-Arylindazole JAK Inhibitors
  作者：Andreas Ritzén、Morten D. Sørensen、Kevin N. Dack、Daniel R. Greve、Anders Jerre、Martin A. Carnerup、Klaus A. Rytved、Jesper Bagger-Bahnsen

  DOI：10.1021/acsmedchemlett.6b00087

  日期：2016.6.9

  Janus kinase (JAK) inhibitors are emerging as novel and efficacious drugs for treating psoriasis and other inflammatory skin disorders, but their full potential is hampered by systemic side effects. To overcome this limitation, we set out to discover soft drug JAK inhibitors for topical use. A fragment screen yielded an indazole hit that was elaborated into a potent JAK inhibitor using structure-based

  Janus激酶（JAK）抑制剂作为治疗牛皮癣和其他炎症性皮肤病的新型有效药物正在出现，但其全身性副作用阻碍了它们的全部潜力。为了克服这一局限性，我们着手发现用于局部使用的软性药物JAK抑制剂。片段筛选产生了吲唑命中，并使用基于结构的设计将其精制为有效的JAK抑制剂。通过将酚部分安装在6-位上使片段生长，可以大大提高效力。对苯酚和磺酰胺基团上的取代基进行微调，得到了一组具有铅样性质的化合物，但是发现它们在光的存在下具有光毒性和不稳定性。