4-(丁基甲酰氨)苯基硼酸 | 252663-48-2

• 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: 4-(丁基甲酰氨)苯基硼酸
• 中文别名: 4-(正丁基氨甲酰基)苯硼酸
• 英文名称: 4-n-butylaminocarbonylphenylboronic acid
• 英文别名: p-butylaminocarbonylphenylboronic acid；{4-[(butylamino)carbonyl]phenyl}boronic acid；4-(Butylaminocarbonyl)phenylboronic acid；[4-(butylcarbamoyl)phenyl]boronic acid
• CAS: 252663-48-2
• 化学式: C₁₁H₁₆BNO₃
• mdl: MFCD03788412
• 分子量: 221.064
• InChiKey: YPXNMPMFCXGXPU-UHFFFAOYSA-N

物化性质

• 熔点：
  206-210°C
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 储存条件：
  2-8°C，干燥且密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-(Butylaminocarbonyl)phenylboronic acid
Product Name:
Synonyms: N-Butyl 4-boronobenzamide

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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.
4-(Butylaminocarbonyl)phenylboronic acid
Ingredient name:
CAS number: 252663-48-2

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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: C11H16BNO3
Molecular weight: 221.1

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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.

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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：

  (2,4-dibromo-thiophen-3-yl)-acetic acid methyl ester 、 4-(丁基甲酰氨)苯基硼酸 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成
  参考文献：
  名称：

  Thiophene substituted acylguanidines as BACE1 inhibitors

  摘要：

  A series of thiophene-substituted acylguanidines were designed from a pyrrole substituted acylguanidine HTS lead. This template allowed a greater flexibility, through differential Suzuki couplings, to explore the binding site of BACE1 and to enhance the inhibitory potencies. This exploration provided a 25-fold enhancement in potency to yield compound 10a, which was 150 nM in a BACE1 FRET assay.

  DOI：

  10.1016/j.bmcl.2007.08.010
• 作为产物：
  描述：

  4-羧基苯硼酸 、 正丁胺 在 N,N-diethanolaminomethyl polystyrene 、 水 、 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.02h， 以63%的产率得到4-(丁基甲酰氨)苯基硼酸
  参考文献：
  名称：

  通用固相方法用于硼酸的固定化，衍生化和树脂到树脂的转移反应。

  摘要：

  含硼酸的分子广泛用于生物学，医学和合成领域。然而，这些化合物往往难以通过溶液相方法处理。在此，该问题通过用于官能化硼酸的衍生化的第一种通用固相方法的开发来解决。该方法基于使用二乙醇胺树脂锚，该锚通过避免在酯化过程中彻底去除水的需要而促进了硼酸的固定。通过在室温下在无水溶剂中简单搅拌，可以在数分钟内将多种硼酸固定在N，N-二乙醇氨基甲基聚苯乙烯（DEAM-PS，1）上。通过（1）DEAM-PS负载的对甲苯基硼酸的（1）NMR分析显示了形成具有假定的NB配位的双环二乙醇胺硼酸酯的证据。通过紫外光谱研究了DEAM-PS树脂对相同型号硼酸的水解裂解。水解和附着显示在快速达到的平衡下发生，并且需要大量过量的水（> 32当量）以实现从DEAM-PS实际定量释放硼酸。尽管它们对水和醇具有相对的敏感性，但可以用甲酰基，溴甲基，羧基或氨基官能化的DEAM-PS结合的芳基硼酸以良好或极高的收率转化成各种胺，酰

  DOI：

  10.1021/jo0106501

文献信息

• BICYCLIC COMPOUNDS AND USE AS ANTIDIABETICS
  申请人：Fang Jing

  公开号：US20100029650A1

  公开（公告）日：2010-02-04

  The present invention relates to novel compounds that are useful in the treatment of metabolic disorders, particularly type II diabetes mellitus and related disorders, and also to the methods for the making and use of such compounds.

  本发明涉及一种新型化合物，其在代谢性疾病的治疗中具有用途，特别是在II型糖尿病及相关疾病的治疗中，并且还涉及制备和使用这种化合物的方法。
• Bicyclic compounds and use as antidiabetics
  申请人：GlaxoSmithKline LLC

  公开号：US08101634B2

  公开（公告）日：2012-01-24

  The present invention relates to novel compounds that are useful in the treatment of metabolic disorders, particularly type II diabetes mellitus and related disorders, and also to the methods for the making and use of such compounds.

  本发明涉及一种新型化合物，可用于治疗代谢性疾病，特别是II型糖尿病及相关疾病，并且还涉及制备和使用这种化合物的方法。
• N,N-Diethanolaminomethyl Polystyrene: An Efficient Solid Support to Immobilize Boronic Acids
  作者：Dennis G. Hall、Jyoti Tailor、Michel Gravel

  DOI：10.1002/(sici)1521-3773(19991018)38:20<3064::aid-anie3064>3.0.co;2-t

  日期：1999.10.18

  The key to the efficiency of N,N-diethanolaminomethyl polystyrene (DEAM-PS), the first solid support capable of coupling to boronic acids, is the formation of a stable, resin-bound boronic ester ate adduct (see scheme). With this resin it is now possible to efficiently immobilize a wide variety of boronic acids including functionalized ones that can be derivatized by solid-phase combinatorial synthesis.
• Universal Solid-Phase Approach for the Immobilization, Derivatization, and Resin-to-Resin Transfer Reactions of Boronic Acids
  作者：Michel Gravel、Kim A. Thompson、Mark Zak、Christian Bérubé、Dennis G. Hall

  DOI：10.1021/jo0106501

  日期：2002.1.1

  amides, anilides, and ureas, respectively. Ugi multicomponent reactions on DEAM-PS-supported aminobenzeneboronic acids, derivatization of multifunctional arylboronic acids, and sequential reactions can also be carried out efficiently. These new DEAM-PS-supported arylboronic acids can be employed directly into resin-to-resin transfer reactions (RRTR). This type of multiresin process helps eliminate time-consuming

  含硼酸的分子广泛用于生物学，医学和合成领域。然而，这些化合物往往难以通过溶液相方法处理。在此，该问题通过用于官能化硼酸的衍生化的第一种通用固相方法的开发来解决。该方法基于使用二乙醇胺树脂锚，该锚通过避免在酯化过程中彻底去除水的需要而促进了硼酸的固定。通过在室温下在无水溶剂中简单搅拌，可以在数分钟内将多种硼酸固定在N，N-二乙醇氨基甲基聚苯乙烯（DEAM-PS，1）上。通过（1）DEAM-PS负载的对甲苯基硼酸的（1）NMR分析显示了形成具有假定的NB配位的双环二乙醇胺硼酸酯的证据。通过紫外光谱研究了DEAM-PS树脂对相同型号硼酸的水解裂解。水解和附着显示在快速达到的平衡下发生，并且需要大量过量的水（> 32当量）以实现从DEAM-PS实际定量释放硼酸。尽管它们对水和醇具有相对的敏感性，但可以用甲酰基，溴甲基，羧基或氨基官能化的DEAM-PS结合的芳基硼酸以良好或极高的收率转化成各种胺，酰
• Thiophene substituted acylguanidines as BACE1 inhibitors
  作者：William F. Fobare、William R. Solvibile、Albert J. Robichaud、Michael S. Malamas、Eric Manas、Jim Turner、Yun Hu、Erik Wagner、Rajiv Chopra、Rebecca Cowling、Guixan Jin、Jonathan Bard

  DOI：10.1016/j.bmcl.2007.08.010

  日期：2007.10

  A series of thiophene-substituted acylguanidines were designed from a pyrrole substituted acylguanidine HTS lead. This template allowed a greater flexibility, through differential Suzuki couplings, to explore the binding site of BACE1 and to enhance the inhibitory potencies. This exploration provided a 25-fold enhancement in potency to yield compound 10a, which was 150 nM in a BACE1 FRET assay.