苯基磺酰胺-4-硼酸 | 214360-51-7

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 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: 苯基磺酰胺-4-硼酸
• 中文别名: 4-氨基磺酰基苯硼酸频哪醇酯；苯磺酰胺-4-硼酸频那醇酯
• 英文名称: benzenesulfonamide-4-boronic acid pinacol ester
• 英文别名: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide；4-sulfamoylphenyl boronic acid pinacol ester；4-aminosulfonyl phenylboronic acid pinacol ester
• CAS: 214360-51-7
• 化学式: C₁₂H₁₈BNO₄S
• mdl: MFCD06657806
• 分子量: 283.156
• InChiKey: XDDLLUBKOZYOMY-UHFFFAOYSA-N

物化性质

• 沸点：
  427.1±47.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应存于室温、避光且在惰性气体保护下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Boronobenzenesulfonamide, 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: 4-Boronobenzenesulfonamide, pinacol ester
CAS number: 214360-51-7

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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: C12H18BNO4S
Molecular weight: 283.2

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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, sulfur oxides.

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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

苯基磺酰胺-4-硼酸是一种广泛应用于有机合成中的硼酸衍生物，主要用于碳-碳键的形成。在Suzuki偶联反应中，芳基卤化物和硼酸芳基或乙烯基酯会使用Pd(PPb)4催化剂进行偶联。

苯基磺酰胺-4-硼酸作为羧酸类衍生物，主要用作医药中间体。

其制备方法如下：将2.5克乙酸钾（24.4毫摩尔）加入到含有2.00克4-溴苯磺酰胺（9.32毫摩尔）和2.40克双(频哪醇基)二硼（9.32毫摩尔）的20毫升DMSO溶液中，脱气45分钟。随后加入220毫克[1,1'-双(二苯膦基)二茂铁]二氯钯(II)（0.26毫摩尔），并将混合物加热至90℃反应16小时。冷却后，将反应混合物用30毫升乙酸乙酯稀释，并用水（3×30毫升）清洗，经MgSO4干燥并在真空下浓缩。残余物在50毫升乙醚和1摩尔/升盐酸中研磨，所得固体溶解于30毫升二氯甲烷中并通过硅胶垫过滤（用乙醚清洗）。最后浓缩得到灰白色固体的苯基磺酰胺-4-硼酸，产率为13%，共550毫克。

反应信息

• 作为反应物：
  描述：

  苯基磺酰胺-4-硼酸 在 sodium tetrahydroborate 、 palladium diacetate 、 caesium carbonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 水 为溶剂， 25.0~110.0 ℃ 、1.72 MPa 条件下， 反应 2.0h， 生成 4-sulfamoyl-4'-hydroxymethyl(4-nitrophenyl)-1,1'-biphenyl
  参考文献：
  名称：

  Discovery of 1,1′-Biphenyl-4-sulfonamides as a New Class of Potent and Selective Carbonic Anhydrase XIV Inhibitors

  摘要：

  New 1,1'-biphenylsulfonamides were synthesized and evaluated as inhibitors of the ubiquitous human carbonic anhydrase isoforms I, II, IX, XII, and XIV using acetazolamide (AAZ) as reference compound. The sulfonamides 1-21 inhibited all the isoforms, with K-i values in the nanomolar range of concentration, and were superior to AAZ against all of them. X-ray crystallography and molecular modeling studies on the adducts that compound 20, the most potent hCA XIV inhibitor of the series (K-i, = 0.26 nM), formed with the five hCAs, provided insight into the molecular determinants responsible for the high affinity of this molecule toward the target enzymes. The results pave the way to the development of 1.1'-biphenylsulfonamides as a new class of highy potent hCA XIV inhibitors.

  DOI：

  10.1021/acs.jmedchem.5b01144
• 作为产物：
  描述：

  4-溴苯磺酰胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 苯基磺酰胺-4-硼酸
  参考文献：
  名称：

  Syntheses of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes through Pd-catalyzed borylation of arylbromides with the successive use of 2,2′-bis(1,3,2-benzodioxaborole) and pinacol

  摘要：

  Syntheses of (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes through the Pd-catalyzed borylation of arylbromides with the successive use of 2,2'-bis(1,3,2-benzodioxaborole) and pinacol were investigated. PdCl2(dppf) and AcOK in EtOH or DMSO successfully provided (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)arenes. In particular, this method was more effective in the borylation of arylbromides bearing sulfonyl groups than the conventional Pd-catalyzed borylation using pinacolborane or bis(pinacolato)diboron. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.118

文献信息

• Catalytic Metal-free Allylic C–H Amination of Terpenoids
  作者：Wei Pin Teh、Derek C. Obenschain、Blaise M. Black、Forrest E. Michael

  DOI：10.1021/jacs.0c06997

  日期：2020.9.30

  selective replacement of C-H bonds in complex molecules, especially natural products like terpenoids, is a highly efficient way to introduce new functionality and/or couple fragments. Here, we report the development of a new metal-free allylic amination of alkenes that allows the introduction of a wide range of nitrogen functionality at the allylic position of alkenes with unique regioselectivity and no

  选择性替换复杂分子中的 CH 键，尤其是萜类化合物等天然产物，是引入新功能和/或偶联片段的高效方法。在这里，我们报告了一种新的烯烃无金属烯丙基胺化的开发，它允许在烯烃的烯丙基位置引入广泛的氮官能团，具有独特的区域选择性和无烯丙基转座。该反应使用催化量的硒化膦或硒脲形式的硒。简单的磺酰胺和氨基磺酸盐可直接用于反应，无需制备分离的类氮烯前体。我们通过以高产率和区域选择性胺化大量萜类化合物来证明这种转化的效用。
• In vitro evaluation of imidazo[4,5 -c ]quinolin-2-ones as gametocytocidal antimalarial agents
  作者：Paresma R. Patel、Wei Sun、Myunghoon Kim、Xiuli Huang、Philip E. Sanderson、Takeshi Q. Tanaka、John C. McKew、Anton Simeonov、Kim C. Williamson、Wei Zheng、Wenwei Huang

  DOI：10.1016/j.bmcl.2016.04.045

  日期：2016.6

  Novel imidazo[4,5-c]quinolin-2-ones were synthesized and evaluated in asexual blood stage and late stage gametocyte assays of Plasmodium falciparum, a major causative agent of malaria. The design of these compounds is based on a recently identified lead compound from a high throughput screen. A concise synthesis was developed that allowed for generation of analogues with substitution around both the

  合成了新型咪唑并[4,5-c]喹啉-2-酮，并在疟疾的主要病原体恶性疟原虫的无性血液阶段和晚期配子细胞测定中进行了评估。这些化合物的设计基于最近从高通量筛选中鉴定出的先导化合物。开发了一种简明的合成方法，该方法可生成在喹啉和咪唑烷酮环上均被取代的类似物。通过结构-活性关系研究，鉴定了许多有效的化合物，它们对无性和有性阶段均具有优异的抗疟活性，并且在哺乳动物细胞中具有最小的细胞毒性。这是第一封描述咪唑并[4,5-c]喹啉-2-酮（一种新的用于治疗和预防疟疾的先导系列产品）的SAR和杀真菌活性的第一封信。
• [EN] N-CONTAINING HETEROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES À TENEUR EN N
  申请人：CYTOPIA RES PTY LTD

  公开号：WO2009062258A1

  公开（公告）日：2009-05-22

  The present invention relates to N-containing heterocyclic compounds that are inhibitors of protein kinases including JAK kinases. In particular, the compounds are selective for JAK1, JAK2, JAK3 or TYK2 kinases and combinations thereof such as JAK1 and JAK2. The kinase inhibitors can be used in the treatment of kinase associated diseases such as immunological and inflammatory diseases including organ transplants; hyperproliferative diseases including cancer and myeloproliferative diseases; viral diseases; metabolic diseases; and vascular diseases.

  本发明涉及N-含杂环化合物，其为包括JAK激酶在内的蛋白激酶的抑制剂。特别是，这些化合物对JAK1、JAK2、JAK3或TYK2激酶及其组合物如JAK1和JAK2具有选择性。激酶抑制剂可用于治疗与激酶相关的疾病，如免疫性和炎性疾病，包括器官移植；增生性疾病，包括癌症和骨髓增生性疾病；病毒性疾病；代谢性疾病；以及血管性疾病。
• [EN] PROTEIN KINASE MKK4 INHIBITORS FOR PROMOTING LIVER REGENERATION OR REDUCING OR PREVENTING HEPATOCYTE DEATH<br/>[FR] INHIBITEURS DE PROTÉINE KINASE MKK4 POUR FAVORISER LA RÉGÉNÉRATION HÉPATIQUE OU POUR RÉDUIRE OU PRÉVENIR LA MORT DES HÉPATOCYTES
  申请人：HEPAREGENIX GMBH

  公开号：WO2019149738A1

  公开（公告）日：2019-08-08

  The invention relates to pyrazolo-pyridine compounds which inhibit mitogen-activated protein kinase kinase 4 (MKK4) and in particular, selectively inhibit MKK4 over protein kinases JNK1 and MKK7. The compounds are useful for promoting liver regeneration or reducing or preventing hepatocyte death. They are further useful for treating osteoarthritis or rheumatoid arthritis, or CNS-related diseases.

  这项发明涉及抑制有丝分裂原活化蛋白激酶激酶4（MKK4）的吡唑啉-吡啶化合物，特别是选择性地抑制MKK4而不影响蛋白激酶JNK1和MKK7。这些化合物可用于促进肝再生或减少或预防肝细胞死亡。它们还可用于治疗骨关节炎或类风湿性关节炎，或中枢神经系统相关疾病。
• Method of preparing inhibitors of phosphodiesterase-4
  申请人：——

  公开号：US20040102472A1

  公开（公告）日：2004-05-27

  In one aspect, the present invention is directed to a one pot method of preparing intermediates of Formula V, which are useful in making inhibitors of phosphodiesterase-4: 1 The present invention is also directed to a method of preparing phosphodiesterase inhibitors comprising the Formula 2

  在一个方面，本发明涉及一种制备Formula V中间体的一锅法，该中间体在制备磷酸二酯酶-4抑制剂时非常有用： 另外，本发明还涉及一种制备磷酸二酯酶抑制剂的方法，包括Formula 2。