2-苯氧基苯硼酸 | 108238-09-1

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 2-苯氧基苯硼酸
• 中文别名: (2-苯氧基)苯硼酸
• 英文名称: 2-phenoxyphenylboronic acid
• 英文别名: (2-phenoxyphenyl)boronic acid
• CAS: 108238-09-1
• 化学式: C₁₂H₁₁BO₃
• mdl: MFCD01001592
• 分子量: 214.029
• InChiKey: AVOWPOFIQZSVGV-UHFFFAOYSA-N

物化性质

• 熔点：
  104-108 °C (lit.)
• 沸点：
  369℃
• 密度：
  1.23
• 闪点：
  177℃
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会发生分解，目前没有已知的危险反应。请避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器保持密封状态，并存放在阴凉、干燥的地方。同时，确保工作区域具有良好的通风或排气设施。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Phenoxyphenylboronic acid
Product Name:
Synonyms:

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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.
2-Phenoxyphenylboronic acid
Ingredient name:
CAS number: 108238-09-1

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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: C12H11BO3
Molecular weight: 214.0

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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.

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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-苯氧基苯硼酸 在 三(1-萘基)膦 、 palladium dichloride 盐酸 、 manganese(IV) oxide 、 tin(II) chloride dihdyrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 19.5h， 生成 4-chloro-2 (2-phenoxybenzoyl)aniline
  参考文献：
  名称：

  [EN] 2-AMINOINDOLE COMPOUNDS AND METHODS FOR THE TREATMENT OF MALARIA
  [FR] COMPOSÉS 2-AMINOINDOLES ET MÉTHODES DE TRAITEMENT DE LA MALARIA

  摘要：

  公开号：

  WO2011053697A8
• 作为产物：
  描述：

  二苯醚 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 2-苯氧基苯硼酸
  参考文献：
  名称：

  INTRACELLULAR CALCIUM CONCENTRATION INCREASE INHIBITORS

  摘要：

  一种含有活性成分的细胞内钙浓度增加抑制剂，其活性成分为（1）由化学式（I）表示的硼化合物。化学式（I）表示的化合物抑制细胞内钙浓度的增加，因此被认为可用作预防和/或治疗血小板聚集、心脑缺血疾病、免疫缺陷疾病、变态反应、支气管哮喘、高血压、脑血管痉挛、各种肾脏疾病、胰腺炎、阿尔茨海默病等的药物。

  公开号：

  EP1444981A1
• 作为试剂：
  描述：

  (E)-5-methylhex-2-enal 、 4-methyl-2-trimethylsilyloxycyclohexa-1,3-diene 、 苯甲酰氯 在 (2S,3S)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid 、 2-苯氧基苯硼酸 、 吡啶 作用下， 以 various solvent(s) 为溶剂， 生成 rel-(6R)-6-[(1R,2E)-1-benzoyloxy-5-methyl-2-hexenyl]-3-methyl-2-cyclohexen-1-one 、 [(E,1R)-5-methyl-1-[(1R)-4-methyl-2-oxocyclohex-3-en-1-yl]hex-2-enyl] benzoate
  参考文献：
  名称：

  （+）-cheimonophyllon e和（+）-cheimonophyllal的不对称全部合成。

  摘要：

  天然（+）-cheimonophyllon E（5）和（+）-cheimonophyllal（6）的高度对映体控制的总合成已完成，这在生物学上引起了人们的兴趣，它是氧化的Bisabolane型倍半萜类生物。本合成策略的特征在于使用不对称醛醇型反应在第一步合成步骤中制备旋光的6-C-取代的3-甲基-2-环己烯酮衍生物。因此，在手性（酰氧基）硼烷（CAB）型山本催化剂33存在下，1-甲基-3-甲硅烷氧基-1,3-环己二烯31与α，β-不饱和醛11的Mukaiyama羟醛反应进行得很高。非对映选择性和对映选择性的水平。通过九步序列将主要的醛醇加合物syn-9转化为γ-δ-环氧烯丙醇8，包括底物控制的烯酮syn-12的1,2-还原，

  DOI：

  10.1021/jo0203140

文献信息

• [EN] ARYL AND HETEROARYL COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSES ARYLE ET HETEROARYLE, COMPOSITIONS ET PROCEDES ASSOCIES
  申请人：TRANSTECH PHARMA INC

  公开号：WO2005014532A1

  公开（公告）日：2005-02-17

  This invention provides aryl and heteroaryl compounds of Formula (I) as described herein, and methods of their preparation. Also provided are pharmaceutical compositions made with the compounds of Formula (I) and methods for making such compositions. The compounds of Formula (I) may activate an erythropoietin receptor and thus, may be useful to induce red blood cell production. The compounds of Formula (I) and compositions including compounds of Formula (I) may be useful in a variety of applications including the management, treatment and/or control of diseases caused at least in part by deficient (or inefficient) EPO production relative to hemoglobin level.

  这项发明提供了如下所述的Formula (I)的芳基和杂环芳基化合物，以及它们的制备方法。还提供了使用Formula (I)化合物制备的药物组合物，以及制备这种组合物的方法。Formula (I)的化合物可能激活促红细胞生成素受体，因此可能有助于诱导红细胞的产生。包括Formula (I)化合物的化合物和组合物可能在各种应用中有用，包括管理、治疗和/或控制至少部分由于相对于血红蛋白水平缺乏（或效率低下）EPO产生而引起的疾病。
• <i>ipso</i>-Nitration of Arylboronic Acids with Bismuth Nitrate and Perdisulfate
  作者：Srimanta Manna、Soham Maity、Sujoy Rana、Soumitra Agasti、Debabrata Maiti

  DOI：10.1021/ol300325t

  日期：2012.4.6

  An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.

  的有效和一锅合成法本位的芳基硼酸-nitration已经研制成功。高效，普遍适用性以及包括杂环和官能团在内的更大的底物范围使该方法具有优势。由于其简单性，我们期望在合成中找到该方法的应用。
• Directing Group‐Promoted Inert C−O Bond Activation Using Versatile Boronic Acid as a Coupling Agent
  作者：Ram Ambre、Ting‐Hsuan Wang、Anmei Xian、Yu‐Shiuan Chen、Yu‐Fu Liang、Titel Jurca、Lili Zhao、Tiow‐Gan Ong

  DOI：10.1002/chem.202004132

  日期：2020.12.18

  strategy facilitates the efficient catalytic cross‐coupling of methoxyarenes with a variety of organoboron reagents. Directing groups facilitate the activation of inert C−O bonds in under‐utilized aryl methyl ethers enabling their adaptation for C−C cross‐coupling reactions as less toxic surrogates to the ubiquitous haloarenes. The method reported enables C−C cross‐coupling with readily available and economical

  一个简单的Ni（cod）2卡宾介导的策略促进了甲氧基芳烃与多种有机硼试剂的高效催化交叉偶联。定向基团可促进未充分利用的芳基甲基醚中惰性C-O键的活化，使它们能够适应C-C交叉偶联反应，因为对普遍存在的卤代芳烃的毒性较小。报道的方法可以使C-C与现成的经济型芳基硼酸试剂进行交叉偶联，这是前所未有的，并且可以与具有类似高反应活性的其他有机硼试剂进行比较。据报道，扩展了引导基团辅助的化学选择性的C-O键裂解，并进一步应用于合成新型双官能联芳基。
• Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions
  作者：Ming Chen、Guangbin Dong

  DOI：10.1021/jacs.9b07932

  日期：2019.9.18

  A copper-catalyzed desaturation method is reported, which is suitable for converting lactones, lactams and cyclic ketones to their α,β-unsaturated counterparts. The reaction does not require strong base/acid or sulfur/selenium reagents, and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents, exhibits excellent scalability and functional group

  报道了一种铜催化的去饱和方法，该方法适用于将内酯、内酰胺和环酮转化为它们的 α,β-不饱和对应物。该反应不需要强碱/酸或硫/硒试剂，可通过简单的一步操作进行。该协议使用廉价的催化剂和试剂，具有出色的可扩展性和官能团耐受性。值得注意的是，叔丁醇是唯一产生的化学计量副产物，并且没有观察到过度氧化。通过对照实验、氘标记、自由基钟、EPR、HRMS 和动力学研究研究了反应机理。获得的数据与涉及可逆α-去质子化的反应途径一致，Cu(II)-OtBu 物种，然后进一步氧化所得的 Cu 烯醇化物。
• Metal‐Free Synthesis of Aryl Selenocyanates and Selenaheterocycles with Elemental Selenium
  作者：Xue Zhang、Xiao‐Bo Huang、Yun‐Bing Zhou、Miao‐Chang Liu、Hua‐Yue Wu

  DOI：10.1002/chem.202004005

  日期：2021.1.13

  This work reports a green method for the synthesis of aryl selenocyanates via a three‐component reaction of arylboronic acids, Se powder, and trimethylsilyl cyanide (TMSCN) under metal‐free and additive‐free conditions. Remarkably, TMSCN acts as not only the substrate, but also the catalyst. Various selenaheterocycles can be also accessed with a catalytic amount of TMSCN.

  这项工作报告了一种在无金属和无添加剂条件下通过芳基硼酸，硒粉和三甲基甲硅烷基氰化物（TMSCN）的三组分反应合成芳基硒氰酸酯的绿色方法。显着地，TMCSN不仅充当底物，而且充当催化剂。还可使用催化量的TMSCN来获得各种硒杂环。