2-(4-溴丁基)-1,3,2-苯并二氧杂戊硼烷 | 142172-51-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼烷
• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 2-(4-溴丁基)-1,3,2-苯并二氧杂戊硼烷
• 中文别名: 2-(4-溴丁基)-1,3,2-苯并二氧硼烷；4-溴-1-丁基硼酸儿茶酚酯
• 英文名称: 4-bromo-1-butylboronic acid catechol ester
• 英文别名: 4-bromo-1-catecholboranylbutane；catechol 4-bromo-butaneboronate；catechol-4-bromo-butylboronate；2-(4-bromobutyl)benzo[d][1,3,2]dioxaborole；2-(4-Bromobutyl)-1,3,2-benzodioxaborole
• CAS: 142172-51-8
• 化学式: C₁₀H₁₂BBrO₂
• 分子量: 254.919
• InChiKey: OCRCQJNMXARNMQ-UHFFFAOYSA-N

物化性质

• 闪点：
  221 °F

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26
• 危险类别码：
  R34
• WGK Germany：
  3
• 危险品运输编号：
  UN 3261 8/PG 2
• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-(4-Bromobutyl)-1,3,2-benzodioxaborole
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H314: Causes severe skin burns and eye damage
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P310: Immediately call a POISON CENTER or doctor/physician

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Section 3. Composition/information on ingredients.
Ingredient name: 2-(4-Bromobutyl)-1,3,2-benzodioxaborole
CAS number: 142172-51-8

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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, under −20◦C.
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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H12BBrO2
Molecular weight: 254.9

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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, hydrogen bromide.

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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
UN Number: UN3261 Class: 8 Packing group: II
Proper shipping name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (2-(4-Bromobutyl)-1,3,2-benzodioxaborole)

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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：

  benzenediazonium tetrafluoroborate 、 2-(4-溴丁基)-1,3,2-苯并二氧杂戊硼烷 在 palladium diacetate 1,3-双-(2,6-二异丙基苯基)咪唑鎓氯化物 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以61%的产率得到4-苯基-1-丁基溴
  参考文献：
  名称：

  Palladium−Imidazolium Carbene Catalyzed Aryl, Vinyl, and Alkyl Suzuki−Miyaura Cross Coupling

  摘要：

  [GRAPHICS]N,N-Bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride with palladium(li) acetate (2 mol %) was used as catalyst, without added base, to efficiently cross couple aryl, vinyl, and alkyl boronates and boronic acids with aryldiazonium tetrafluoroborate substrates. The reactions were performed at 0 degreesC or rt, giving product in 2 to 4 h with 80 to 90% yields for isolated materials. Diazonium ions, formed in situ, also cross couple under these conditions.

  DOI：

  10.1021/ol016724c
• 作为产物：
  描述：

  4-溴-1-丁烯 、 儿萘酚硼烷 反应 18.0h， 以88%的产率得到2-(4-溴丁基)-1,3,2-苯并二氧杂戊硼烷
  参考文献：
  名称：

  新型α-链含硼酸酯的前列腺素的合成

  摘要：

  已经合成了一类新的在α链上含有硼酸酯的前列腺素。合成中的关键步骤是制备含硼酸酯的叶立德和随后使用该叶立德的Wittig反应。

  DOI：

  10.1016/s0040-4039(00)00973-4

文献信息

• Photoinduced decarboxylative borylation of carboxylic acids
  作者：Alexander Fawcett、Johan Pradeilles、Yahui Wang、Tatsuya Mutsuga、Eddie L. Myers、Varinder K. Aggarwal

  DOI：10.1126/science.aan3679

  日期：2017.7.21

  283 Light facilitates the replacement of carboxylic acids with boron esters in the absence of metal catalysts. The conversion of widely available carboxylic acids into versatile boronic esters would be highly enabling for synthesis. We found that this transformation can be effected by illuminating the N-hydroxyphthalimide ester derivative of the carboxylic acid under visible light at room temperature

  照亮碳硼化的道路 硼取代基提供了多种反应性，并且它们的效用已经出现在制药领域。福西特等人。表明可见光可以诱导硼酸酯取代羧酸基团，这将有助于将它们引入各种化合物中。一旦酸被邻苯二甲酰亚胺取代基活化，它们就可以在酰胺溶剂中在光照下与儿茶酚硼烷二聚体反应，无需催化剂或其他添加剂。该反应似乎通过光引发后的自由基链增长进行。科学，这个问题 p。283 Light 有助于在没有金属催化剂的情况下用硼酯替代羧酸。将广泛可用的羧酸转化为多功能硼酸酯将非常有助于合成。我们发现，在二硼试剂双（儿茶酚）二硼存在下，在室温下，在可见光下照射羧酸的 N-羟基邻苯二甲酰亚胺酯衍生物，可以实现这种转化。简单的后处理可以分离频哪醇硼酸酯。实验证据表明，硼基自由基中间体参与了该过程。该方法通过伯、仲和叔烷基羧酸以及各种天然产物羧酸的转化来说明，从而证明其广泛的实用性和官能团耐受性。
• [EN] INHIBITORS OF ARGINASE AND THEIR THERAPEUTIC APPLICATIONS<br/>[FR] INHIBITEURS DE L'ARGINASE ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：MARS INC

  公开号：WO2013059437A1

  公开（公告）日：2013-04-25

  The inventive compounds are small molecule therapeutics that are potent inhibitors of Arginase I and II activity. The invention also provides pharmaceutical compositions of the inventive compounds and methods for using the inventive compounds for treating or preventing a disease or a condition associated with arginase activity.

  这些创新化合物是小分子治疗药物，是对精氨酸酶I和II活性的强效抑制剂。该发明还提供了这些创新化合物的药物组合物，并提供了使用这些创新化合物治疗或预防与精氨酸酶活性相关的疾病或症状的方法。
• ARGINASE INHIBITORS AND METHODS OF USE
  申请人：CHRISTIANSON DAVID W.

  公开号：US20100189644A1

  公开（公告）日：2010-07-29

  The present invention is directed to arginase inhibitor compounds of formula IA or formula IB: or a pharmaceutically acceptable salt thereof, compositions containing these compounds, and methods of their use for the treatment and diagnosis of conditions characterized by upregulation of arginase, abnormally high arginase activity, or by abnormally low nitric oxide synthase activity.

  本发明涉及化合物IA或化合物IB的抑制剂，或其药用盐，含有这些化合物的组合物，以及用于治疗和诊断由精氨酸酶上调、异常高的精氨酸酶活性或异常低的一氧化氮合酶活性所特征的疾病的方法。
• [EN] INHIBITORS OF ARGINASE AND THEIR THERAPEUTIC APPLICATIONS<br/>[FR] INHIBITEURS D'ARGINASE ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：MARS INC

  公开号：WO2011133653A1

  公开（公告）日：2011-10-27

  Compounds according to Formula I and Formula II are potent inhibitors of Arginase I and II activity : Formule (I), (II) where R1, R2, R3, R4, R5, R6, R7, R8, R9, D, M, X, and Y are defined as set forth in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use for treating or preventing a disease or a condition associated with arginase activity.

  根据式I和式II，化合物是Arginase I和II活性的强效抑制剂：式(I)，(II)中的R1、R2、R3、R4、R5、R6、R7、R8、R9、D、M、X和Y的定义如规范所述。该发明还提供了这些化合物的药物组合物以及它们用于治疗或预防与Arginase活性相关的疾病或病况的方法。
• INHIBITORS OF ARGINASE AND THEIR THERAPEUTIC APPLICATIONS
  申请人：Van Zandt Michael

  公开号：US20120083469A1

  公开（公告）日：2012-04-05

  Compounds according to Formula I and Formula II are potent inhibitors of Arginase I and II activity: where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , D, M, X, and Y are defined as set forth in the specification. The invention also provides pharmaceutical compositions of the compounds and methods of their use for treating or preventing a disease or a condition associated with arginase activity.

  根据公式I和公式II的化合物是Arginase I和II活性的有效抑制剂：其中R1，R2，R3，R4，R5，R6，R7，R8，R9，D，M，X和Y的定义如规范中所述。该发明还提供了这些化合物的制药组合物和使用它们治疗或预防与Arginase活性相关的疾病或病况的方法。