4-丁氧基苯硼酸 | 105365-51-3

• 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 - 苯酚醚
• 中文名称: 4-丁氧基苯硼酸
• 中文别名: 4-正丁氧基苯硼酸；4-N-丁氧基苯基硼酸
• 英文名称: 4-butoxyphenylboronic acid
• 英文别名: 4-butoxy-1-phenylboronic acid；(4-butoxyphenyl)boronic acid
• CAS: 105365-51-3
• 化学式: C₁₀H₁₅BO₃
• 分子量: 194.038
• InChiKey: QUPFQMXWFNJUNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  106-108 °C (lit.)
• 沸点：
  342.3±44.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，没有已知的危险反应，应避免与强氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保持贮藏器密封，并将其存放在阴凉、干燥处。确保工作间有良好的通风或排气装置。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Butoxyphenylboronic 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.
4-Butoxyphenylboronic acid
Ingredient name:
CAS number: 105365-51-3

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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: C10H15BO3
Molecular weight: 194.0

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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：

  4-丁氧基苯硼酸 在 双氧水 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以96%的产率得到4-正丁氧基苯酚
  参考文献：
  名称：

  二氧化硅：将芳基硼酸氧化为酚的有效促进剂

  摘要：

  这项工作报告了用于氧化芳基硼酸的简单，高效的方法。在催化量的氯化硅存在下，使用H 2 O 2作为氧化剂，将各种芳基硼酸选择性和完全转化为相应的氧化苯酚。结果表明，氯化硅是用于芳基硼酸氧化的合适且有效的促进剂。非均相催化剂，温和的反应条件，容易获得的试剂，容易的后处理，相应苯酚的优异收率，较短的反应时间和广泛的底物范围使该方案具有吸引力，并且是现有方法的一种实用替代方案。

  DOI：

  10.1016/j.tetlet.2017.07.041
• 作为产物：
  描述：

  对溴丁氧基苯 在 正丁基锂 、 硼酸三甲酯 、 盐酸 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.5h， 生成 4-丁氧基苯硼酸
  参考文献：
  名称：

  Yu, Z. N.; Tu, H. L.; Wan, X. H., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2003, vol. 391, p. 41 - 56

  摘要：

  DOI：

文献信息

• A Highly Efficient Monophosphine Ligand for Parts per Million Levels Pd-Catalyzed Suzuki-Miyaura Coupling of (Hetero)Aryl Chlorides
  作者：Pui Ying Choy、On Ying Yuen、Man Pan Leung、Wing Kin Chow、Fuk Yee Kwong

  DOI：10.1002/ejoc.202000068

  日期：2020.5.22

  A new indolylphosphine WK‐phos has been synthesized for Pd‐catalyzed Suzuki–Miyaura coupling of (hetero)aryl chlorides with (alkyl)arylboronic acids. The catalyst system with this new ligand was found to be highly effective in facilitating the reaction even at catalyst loading levels in the parts per million range (e.g. 10 ppm).

  合成了一种新的吲哚基膦WK-phos，用于Pd催化的（杂）芳基氯与（烷基）芳基硼酸的Suzuki – Miyaura偶联。发现即使在百万分之几的催化剂负载水平（例如10ppm）下，具有这种新的配体的催化剂体系在促进反应方面也是非常有效的。
• Carbohydrate Rod Conjugates:  Ternary Rod−Coil Molecules Forming Complex Liquid Crystal Structures
  作者：Bin Chen、Ute Baumeister、Gerhard Pelzl、Malay Kumar Das、Xiangbing Zeng、Goran Ungar、Carsten Tschierske

  DOI：10.1021/ja0535357

  日期：2005.11.30

  self-organization as a function of the length and position of the lateral polar chain and the length of the terminal alkyl chains. Depending on the size of the polar and lipophilic segments, a series of unusual liquid crystalline phases was detected. In three of these phases, the space is divided into three distinct periodic subspaces. In addition to a hexagonal channeled layer phase (ChL(hex)) consisting of layers

  T 形多亲三嵌段分子，由棒状对三联苯单元、以 1-acylamino-1-deoxy-D-山梨糖醇单元封端的亲水且柔性的侧向连接的低聚（氧乙烯）链和两个末端连接的亲脂烷基组成链，已通过钯催化的交叉偶联反应合成为关键步骤。通过偏光显微镜、差示扫描量热法 (DSC) 和 X 射线散射研究了这些化合物的热致液晶行为。我们研究了自组织模式作为横向极性链的长度和位置以及末端烷基链的长度的函数。根据极性和亲脂性片段的大小，检测到一系列不寻常的液晶相。在这三个阶段中，空间被划分为三个不同的周期性子空间。除了由极性柱穿透的层组成的六边形通道层相（ChL（hex））外，还有由方形（Col（squ）/p4mm）或五边形圆柱体（Col（方）/p4gm）。圆柱壁由由烷基链柱稠合的三联苯单元组成，内部包含极性侧链。此外，观察到六方柱状相，其中极性柱在三联苯和烷基链的连续体中组织，三联苯核在柱周围切向组织，长轴垂直于
• Sustainable Fe–ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water
  作者：Sachin Handa、Ye Wang、Fabrice Gallou、Bruce H. Lipshutz

  DOI：10.1126/science.aac6936

  日期：2015.9.4

  1087 An iron preparation substantially lowers the quantity of palladium needed to catalyze a common reaction that forms C-C bonds. Most of today’s use of transition metal–catalyzed cross-coupling chemistry relies on expensive quantities of palladium (Pd). Here we report that nanoparticles formed from inexpensive FeCl3 that naturally contains parts-per-million (ppm) levels of Pd can catalyze Suzuki-Miyaura

  铁为痕量钯提供动力 钯 (Pd) 是化学催化的支柱。贵金属具有锻造碳-碳 (CC) 键的诀窍。汉达等人。现在报告说，当与铁混合在特定制剂中时，仅百万分之一的 Pd 就足以催化形成 CC 键的 Suzuki 偶联反应。表面活性剂的加入使反应在水中进行。该协议预示着在药物和农用化学品合成中保护 Pd 是个好兆头。科学，这个问题 p。1087 铁制剂显着降低了催化形成 CC 键的常见反应所需的钯量。今天大多数过渡金属催化交叉偶联化学的使用依赖于昂贵数量的钯 (Pd)。在这里，我们报告说，由天然含有百万分之一 (ppm) 水平 Pd 的廉价 FeCl3 形成的纳米粒子可以催化 Suzuki-Miyaura 反应，包括涉及极具挑战性的反应伙伴的情况。纳米胶束用于溶解反应物并将反应伙伴传递给 Fe-ppm Pd 催化剂，从而形成碳-碳键。新形成的催化剂可以在环境温度下分离和储存。含有表面活性剂和催化剂
• Cavitand supported tetraphosphine: cyclodextrin offers a useful platform for Suzuki-Miyaura cross-coupling
  作者：Elena Zaborova、Julia Deschamp、Samuel Guieu、Yves Blériot、Giovanni Poli、Mickaël Ménand、David Madec、Guillaume Prestat、Matthieu Sollogoub

  DOI：10.1039/c1cc12241j

  日期：——

  The cyclodextrin-tetraphosphine hybrid coined α-Cytep allows turnover numbers up to 340 000 000 000 and turnover frequencies up to 1 000 000 000 h−1 to be reached in Suzuki–Miyaura reactions. These exceptional figures are clearly linked to the outstanding longevity of the reactive species induced by the ligand α-Cytep and illustrates the rising potential of cyclodextrins in catalytic applications.

  名为α-Cytep的环糊精-四膦杂化物在铃木-宫浦反应中达到了高达340万亿的周转数和高达10亿小时⁻¹的周转频率。这些卓越的数据显然与α-Cytep配体引发的活性物种的非凡寿命有关，并展示了环糊精在催化应用中日益增长的潜力。
• Synthesis and biological activity of 2-aminoimidazole triazoles accessed by Suzuki–Miyaura cross-coupling
  作者：Samuel Reyes、Robert W. Huigens III、Zhaoming Su、Michel L. Simon、Christian Melander

  DOI：10.1039/c0ob00925c

  日期：——

  A pilot library of 2-aminoimidazole triazoles (2-AITs) was synthesized and assayed against Acinetobacter baumannii and methicillin-resistant Staphylococus aureus (MRSA). Results from these studies show that these new derivatives have improved biofilm dispersal activities as well as antibacterial properties against A. baumannii. With MRSA biofilms they are found to possess biofilm inhibition capabilities at low micromolar concentrations.

  合成了2-氨基咪唑并三氮唑（2-AITs）的先导库，并对其针对鲍曼不动杆菌和甲氧西林耐药金黄色葡萄球菌（MRSA）的活性进行了评估。研究结果显示，这些新衍生物不仅对A. baumannii具有增强的生物膜分散活性，还具有抗菌特性。在MRSA生物膜方面，它们在低微摩尔浓度下表现出生物膜抑制能力。